I’m remote, so the ‘drama’ around a last day isn’t what it used to be. No packing up my desk, no long lunch with my team, no romping around the office with nothing to do but to say goodbye to everyone, having my sweet ego gently stroked (I’ve always left a job that I’ve chosen to leave on good terms, what can I say?)

Instead, my last day looked like me, alone in my office bedroom, typing up loose ends and getting everything into a nice, shiny Notion doc for the team. I lost access 3 hours before I was supposed to2, and the hour-long ‘handoff’ meeting my boss scheduled ended after 10 minutes.

And then I was done.

As soon as that call ended, I started sobbing. Relief? Fear? Sadness? Reality slapping me in the face? All of the above, perhaps?

Since then, each day, I’ve tried to show up as best as I can, more or less.

So, how has it actually been going?

Three months in, and that’s still a hard question to answer. My one-liner, so far, has been: I’m happier than I’ve ever been and less stressed than I’ve ever been, but also less sure of my future and more broke than I’ve been in a long time.

It’s going well in the sense that I feel great. My brain feels like it’s fully mine for the first time in a long time, I’m decently rested, and for the most part, my stress levels are nonexistent. I’m fulfilled, I’m feeling creative, I’m getting to chat and hang with people I want to chat and hang with, and I’m overall enjoying life.

I’ve run two half-marathons, attended a writer’s retreat, and recorded my first ten podcast episodes. I’ve written a lot, signed a new copywriting client, and have landed on a loose strategy to start to go after clients in tech.

I’ve spent a lot of time chatting and connecting with folks, and have been settling into this season of life, which is another way of saying: I’m moving slowly, but that’s intentional.

I’ve spent most of the last three months with less of a plan and more of an intention: be realistic, but also don’t try to have the answers all at once. Take small steps each day, talk to interesting people, and chase ideas down as they come. That’s led me to reclaim my impulsivity, and I’ve enjoyed the permission to continue to do so.

This has allowed me to stay curious and take some pressure off of figuring it all out. I can ‘build in public,’ which is having a moment, and see what sticks. When I’m in the right mindset, this feels right and aligned. But sometimes, I lose patience, or panic, or get in my head about not having more ‘done’ by this point.

I haven’t figured out exactly what my ‘offer’ is, or how I’ll make ‘the big bucks,’ and sometimes I feel like I’m floundering. I write something, I get a little traction, I keep going, and it fades. I sometimes can’t believe that three months have already passed me by, and I’m terribly worried that I’ll wake up one morning and feel like I’ve wasted this time, time I know has an expiration date. The expiration date is fixed, based on my savings, but I also know that extending that date relies on me and my ability to ‘make this work’ (whatever that means…).

If I’m being honest, I’m also feeling very broke. I’m not at Cannes or going to Spain this summer. Heck, I might not even make it to a beach that’s not in New York City. I think about every purchase I make, justifying the hit that means my savings will take.

With my new client signed, my freelance income now just about totals a third of what I was bringing home from my last full-time job. I’m grateful for the small extension to my expiration date and to be able to dip into savings just a bit less.

I know I don’t need my old full income to survive. I’m not yet earning enough on my own to cover all of my expenses, but I’m getting closer. Still, there’s a part of me that wishes I were already there, that I could skip this uncertain bit and jump to the part where my savings can stay where it is, where the expiration date becomes a moot point. At the very least, I wish I could say I was closer to that dream.

It’s annoying (at best) to have to think about money at every turn, to not buy myself the perfect pair of summer clogs or my kid a croissant every time we pass by the coffee shop, but there’s also a level of gratitude that comes from being able to choose to have these as worries. I’m not in survival mode, and I know that it would take a lot for me to get there, even if that means re-entering the workforce.

I also have been hit with a bit of a realization: chores are still chores, and quitting my job didn’t magically make them all get done more quickly, nor did it make me enjoy them more. On the contrary, with so many irons in the fire, I find it’s been more difficult to stay on top of the laundry, dishes, and all the other things at home I thought would magically get done once my time was mine. But when the chores do get done, it feels easier and less urgent (even if, in actuality, I am more behind). I think that’s where I get to see the benefits of my time being mine.

I do have this strange feeling of knowing that, for the time being, there’s just certain information that’s not my business. Instead of trying to peek at what isn’t visible yet, I’m spending my time on what feels right. All I can do is show up every day and hope that I’ll get to see more of the path as time goes on.

I’ve noticed a personal shift that I’m going to carry forward. With what hasn’t seemed like much work, I feel like I’m a bit more confident and sure of myself. I’m defaulting less and less to what I think others want to hear, and it’s getting easier to stand firm in my beliefs. I think this is a shift that happens for many as they settle into their mid-30s, but I think all of the risks I’ve taken (and those that wait for me ahead) have almost expedited this process.

Living more closely aligned with my truth has made all of this feel easier. I don’t have to flip a switch to ‘play’ confidence, it’s just becoming a bit of a default. Conversations with others have felt easier; meeting people and connecting isn’t something I really have to psych myself up for, and talking about the things I’m doing doesn’t feel like it’s wrapped in embarrassment anymore.

I have a lot to show for these last few months, but I also acknowledge that I’ve taken the first chunk of my time off slowly. Intentionally slowly, but still, slowly.

I didn’t jump into cold outreach or force myself to create a stringent offer. I haven’t been holding myself to any sort of cadence for posting or chatting or anything else. That has served me well in these first three months, but I’m also getting to the point where I know it’s time to pick it up, even if just slightly.

This summer, I’ll be looking for ways to be more focused in how I talk about the work I’m doing — freelance writing, my work here on Substack, and yes, the work I’m hoping to do in tech and with founders. I also know that talking about it broadly isn’t enough.

The next big thing I need to chew on is the oh-so dreaded outreach part of being self-employed. I don’t want to get too deep into it, because this is an essay on its own, but the number one reason I’ve dismissed being self-employed in the past is having to be responsible for finding clients, for popping up in people’s inboxes unannounced, and putting myself out there.

But it has to be what comes next, I am starting to feel and know that deeply. I’m unwilling to reach the end of my runway and regret not reaching out to more people. I’m also unwilling to just grin and bear it. I’m committed to actually enjoying this process3.

Other than that, what lies ahead is still mostly unknown. I’ll keep walking the path, keep experimenting, and maybe I’ll finally accept I’ll never be caught up on laundry.

One day,1 while browsing Substack notes (as one does), I came across a brilliant tidbit from that I haven’t been able to stop thinking about.

“I think I just changed my life,” she says.

Anna, I think you changed mine, too.

The idea of creating a version of yourself that just does the thing you want it to feels so simple, and yet so revolutionary.

Those of us who have ADHD have probably heard someone, whether it be our doctors, therapists, friends, or other ADHDers online, talk about the importance of having a ‘toolbox’ to deal with ADHD symptoms: that is, having strategies, processes, and other ways of working when navigating the everyday feels tough. This is not novel, and is something recommended by most — awareness and medication, while monumental, are very often not enough. We need tangible ways of working.

Some of the most popular strategies that I personally have in my toolbox are: working via timers (Pomodoro timers, where you work for 25 minutes and rest for 5, are especially popular), body doubling (or working with others in community), opening the dishwasher and telling myself I only have to put one mug away when I need to empty it (or lowering the stakes of whatever is on my to do list to the most absolute bare-minimum version of it), putting my phone behind my laptop screen while working, and more. I have bare minimum workout and skincare routines, and have been known to fold one t-shirt before calling it quits.

Others store their vegetables in their refrigerator door and put the condiments in the crisper so that said vegetables don’t go bad, set automatic reminders at certain times to remind them to brush their teeth, move their hairtie from one wrist to the other when they take their meds (to remember if they’ve done it), gamifying to-do lists through apps or personal points systems, and, well, you get the point. The tools seem endless.

If you aren’t neurodivergent, this might sound absolutely foreign. Why don’t you just do the thing, you think.

I have spent far too much of my life asking myself the same question and getting frustrated when the answer wasn’t easy. For a long time, I believed there was something wrong with me, and I internalized that to mean I was lazy, lacked ambition, or was overall bad2.

But to answer your question, my sweet, well-meaning, neurotypical reader: it’s just not that simple.

Let’s work through an example together. You want to go to the gym. You need to change into gym clothes and get ready to leave the house, and then make your way to the gym.

If a neurotypical person were to write a to-do list, it might look like this:

• Get dressed

• Pack bag

• Go to gym

Or maybe, more simply, like this:

• Get ready

• Go to the gym.

And even just:

• Gym.

At most, that’s three steps. Three places where you could get caught up, three places where your motivation might wane, where you might find yourself stuck (like a Roomba, as Anna says).

For me (and I suspect for many of my ADHD buddies out there), the list looks like this:

• Plan gym outfit

• change out of home clothes

• put on gym clothes

• find headphones, hairtie, gym lock

• find bag

• put in bag

• fill water bottle

• put water bottle in gym bag

• move keys from purse to gym bag

• brush teeth

• pee before leaving

• check subway schedules (or traffic, for you drivers)

• commute to gym

• put stuff away in locker room

• put hair in pony tail

• pick playlist or podcast

• figure out today’s workout

• go workout

Breaking something like ‘go to the gym’ into microtasks is, funnily enough, one of the tools that can help you actually get there. On its own, going to the gym feels huge, because for some of us, it is. Breaking it down can help us see what’s in front of us, but is also a great illustration of just how many micro moments and decisions are involved in us ‘just doing it’.

That’s a lot more places to get stuck and caught up, and often, it plays out more like this:

• Decide to go to the gym

• figure out what time you want to go to the gym

• scroll phone for 10 minutes.

• work backwards to figure out what time you need to start getting ready and add a 15 minute buffer

• shit — that’s now

• grab gym outfit.

• change out of home pants and into gym pants

• check to see if headphones are charged.

• they’re not, so chuck them on the charger for however much time you have.

• locate hair tie. It’s not the one you want, and it’s stretched out, but it’ll have to do.

• check phone for time. see notification from email.

• open email app. your favorite brand is having a sale! Start to build a cart

• realize the card saved is expired. Realize you’re sidetracked, start to find gym bag

• your gym bag has clothes in it from the last time you were at the gym. That was 2 weeks ago. Everything smells, and now the bag needs to be washed, too.

• start laundry

• Find an alternate bag. This reusable grocery bag will have to do.

• You remember you used your water bottle last week to bring a cocktail to a friend’s picnic and never washed it. Make a mental note to buy a water bottle at a store by your house — the gym charges 5x what the bodega does.

• Pack the reusable grocery bag. You realize your gym lock is now in the wash. You leave anything valuable at home.

• brush teeth, use the bathroom, run out the door

• arrive at gym. you forgot to buy water. you save your $5 and rely on the water fountains

So yeah. A lot of steps. A lot of places to get sidetracked, to get decision fatigue, to just give up.

This video also explains it really well, if you prefer a visual.

@atypicaltokerHaPpY wEdNeSdAy 😵‍💫 This feels accurate. Also, Srry I’ve been gone; I won’t be for much longer ☺️🫶 #executivedysfunction #reltable #adhd #adultadhd #neurodivergent #adhdtok

Tiktok failed to load.

Enable 3rd party cookies or use another browser

This isn’t the first time I created an alter ego. In grade school, I got in trouble for something homework-related. In order to get my work done, I created a new persona, Kimberly, and did my homework as her. I played ‘school’ at home, pretending I was Kimberly. Kimberly had great handwriting and neat notebooks. Kimberly used a fuzzy pink pencil.

I even wrote the name ‘Kimberly’ at the top of my homework. Now, this is a ~25-year-old memory, so I don’t know if I handed this in or if this was practice homework, so bear with me. But I do know that, as Kimberly, my handwriting was impeccable. I finished my homework early, put it neatly in a folder, and moved on with my day.

One night in 8th grade, while not studying for a history test the next day, I looked at the stack of flashcards, wondering why I couldn’t bring myself to flip through them. Without studying, I knew I could probably get a B+, maybe even an A-. But for some reason, the memory of Kimberly popped into my head. Kimberly would study, I thought.

And so I studied. And so I got a 99% on that test. Is that how easy it is to get good grades? I remember thinking.

The next ~8 years of school would prove that statement right and wrong. If I just applied myself, I thought, this is easy. I just couldn’t understand why applying myself was so difficult. Kimberly lost her name over time, but whenever I needed to really buckle down, I would think what would they do? They, being whichever type-A, good-student friend or peer that popped into my head that day.

And so I would do what they’d do; I’d write the paper, I’d make the study guide, and the gains were there.

I’m making it sound much simpler than it was. Because for every success, there was also an all-nighter, a paper that fell just short of the length it needed to be, for an email sent to a professor humbly asking for an extra 4 to 24 hours to finish something I knew I had more than enough time to do.

A big part of what I get hung up on as a person with ADHD is not just the languishing between tasks and the inability to ‘get up and do it,’ as Anna says, but the ensuing guilt that follows.

So why does this happen?

For most humans, in order to get something done we start with the intention to do it. The space between that intention and actually doing it is where our motivation lives.

An analogy I love to use to describe this comes from How to ADHD’s theory on ‘Motivation Bridge’.

Her theory is that motivation is just a bridge between intent and doing. We all have this bridge, and our bridge is made up of various planks to help us get there. All bridges have gaps — even the most type-A, neurotypical person you can think of doesn’t have perfect motivation all of the time.

But those of us with ADHD have bigger gaps in our bridges. Like, half the bridge is missing. Finishing something can be just as important to us as it is to a neurotypical person on the bridge next to us. We can try as hard as we can, but if the planks aren’t there to physically support us, it’s not going to happen.

In the following video, Jessica explains this theory better than I did and goes on to talk about how to add more planks. I highly recommend giving it a watch.

We can build planks as long as they are stimulating. Which is why the idea of creating an alter ego is so appealing.

And so, I’m bringing Kimberly back. Kind of.

Last year, I wrote about being in my ‘Just Do It’ era. Of wanting something and going for it. I think I’ve done a pretty good job at that, at least professionally.

I got a job, quit a job, started a podcast, started a paid series on my Substack, signed a new freelance client, and much, much more in the last six months.

Part of ‘being cringe’, I find, almost requires me to dissociate from my body a bit. To take a birds-eye view and detach from what I’m doing. To observe as if it’s someone else.

But I still get stuck. Laundry piles up, I procrastinate the dishes, and I put off a run for too long that I end up skipping it. I do my freelance work at the last minute more often than not. The possibilities and to-dos on my list feel endless, and so I stand there, like a Roomba, and sometimes accomplish nothing.

So now, I’m going to actively name my alter ego and bring her in to help.

Kimberly doesn’t worry about making the perfect choice. If there’s laundry to fold and dishes to be done, she just picks one.

I’ll be thinking about Kimberly in the moments where the dirty water bottle would be enough to keep me home from the gym (but also thinking about her in the moments where I bring the water bottle home and decide whether or not to wash it right away). I think about what she’s allowed me to do so far, and where that will take me.

Armed with awareness (and medication), life has gotten easier. I have the tools to get things done, even when all of my planks from Motivation Bridge have gone missing.

Tools will never cure me, even this one, who’s been with me for longer than I knew I needed ‘tools’. The novelty may wear off (it will). But it’s a tool in the box, a plank for the bridge, and one more thing I can try when I’ve had enough of those damn Pomodoro timers. When I feel stuck, I can think, ‘What would Kimberly do?’

And I’ll tell you what — Kimberly would finally get caught up on the damn laundry.

In this conversation, we talk about:

• Why a portfolio career is artistry by another name

• His grandfather, who ran an ice cream shop, manufactured children’s dresses, and robo-traded from his Upper East Side apartment, and what Max learned from him

• What it feels like to leave a job and watch years of work relationships disappear

• Why he built 500+, and what “real community” looks like online

• His dream of owning a store on Court Street

Huge thanks to Max for appearing on the podcast. I really appreciated our conversation and always love chatting with folks who are actively trying to build community. I also had a podcast first when he shared his phone number on air. He’s currently on parental leave (BIG congrats to him and the family), so he may be slower-than-usual to respond.

Find Max:

• 500+ Community: whop.com/500-plus

• Substack: readmaxos.substack.com

• LinkedIn: linkedin.com/in/max-nimaroff/

• Text him: (516) 660-7269 (his idea, not mine)

Thanks for listening to ‘Be Cringe’! Find us online:

• Instagram: @becringepod

• Substack: thismightbecringe.com

• Listen to the pod: becringe.riverside.com

Welcome to All of the Above, a place where Generalists, folks-of-all-trades, and the wearers of many hats are finally at home. In this column, I explore how those of us who do it all (and love to do it all) can make it work in a world that is obsessed with fitting us into boxes.

I love a personality test. I love the insights they bring and the personal understanding that comes to light. Discernment and decisiveness have historically been difficult for me, and answering a series of questions and seeing an answer spit out has always felt comforting. Here are the answers I couldn’t see myself, the ideas and traits that could only come to light by answering a series of questions (or inputting my birthday, time, and location).

Because, like many others, my interest in personality tests started with Astrology. As a kid (and tween), I’d read my horoscope in Teen Vogue and loved buying shirts, bags, and other merch branded with my sun sign from Claire’s or Wet Seal. Even my first AIM screen name mentioned my zodiac sign (and if you want to know what that screen name actually was, you’ll have to listen to my recent podcast episode with ).

I got more into Astrology, learned what a birth chart was, and dove in. I learned about Human Design, another system that uses your birthdate and time and place.

Throughout college and various jobs, I’ve taken half a dozen personality tests (Myers-Briggs, Enneagram, StrengthsFinder, to name a few). They all tell slightly different stories, as is their point, but I found them comforting all the same.

One throughline across them all is my adaptability and my ability to connect with others (and to connect others). It’s sometimes described in other words — an ability to fit in, to blend, to synthesize and arrange, to manage ambiguity, to finish tasks with little context, etc., but overwhelmingly, these tests (and my Astrology) point to the way in which I can easily fit in and rise to many occasions.

I used to get frustrated by results like these. I wanted to be the achiever, the natural leader, to be seen as organized, to have the elusive Woo pop up on one specific test.

Instead, these tests tell me I am adaptable (also: empathetic, customer-focused, someone who acts without much thought, sensitive, and able to connect people to one another). I found these strengths to be soft and not well-suited for the low-stress, high-earning career I craved.

I also found that where all these tests differed was in the variety of careers they recommended. Many of these tests give you a variety of careers, but I found that if I compared one test to another, my results were really different. A teacher, a social worker, a career in the arts, PR and marketing, HR, law, project management, mediation, “your work should be structured”, “your work should not be structured or traditional”, consulting, finance, operations, leadership, change management, and broadcasting, just to name a few.

None of these felt particularly resonant or interesting, but neither did any of the other jobs.

I kept getting such different results, I ignored them all. I still held on to the results of these tests, but told myself the career advice didn’t fit me and my working style, and for a long time, accepted that as truth. But the writing on the wall for being a generalist was there; I was just too focused on picking the right capital-C Career to see it.

It wasn’t until I stepped back and really looked at the various careers, job titles, industries, and companies (and eventually, my pivot into self-employment), that I started to see this differently.

The Projector in Human Design guides systems and tells me that I work best outside of traditional 9-5 frameworks, but my Taurus Sun/Capricorn Rising craves structure and predictability. The INFP centers values above all else, and my Enneagram 9 speaks to my ability to be easy-going and adaptable. The traits that came out of the other tests I’ve taken speak to my adaptability and humanness, and make it really obvious that I am meant to work in the way I am working right now. It just doesn’t make sense to everyone.

These tests have been trying to tell me something valuable all along: that I can do all of the above, and may even be good at that. There’s a reason why marketing and HR and social work and rigidity and flexibility all came to the surface.

Every test, chart, framework, and set of questions I’ve answered points to different sides of me. I hold complexity, connect systems, and make sense of them for myself and others. I lead with empathy, understanding, and love to manage ambiguity. What I once saw as soft now presents to me as the job itself. A job I don’t have a name for.

Instead of forcing a name, I find comfort in figuring out what the specific actions are. Doing something with my career in startups and tech, honoring each step of the journey, and also acknowledging that I can’t just be one thing anymore.

It’s writing this newsletter and struggling to fully niche down for the last three years. It’s the freelance work I’m paid to do, copywriting, community management, and social media strategy, and I’m having a hard time painting the picture of how that fits into the tech consulting work I know is where the ‘money’ is. I created a discipline, Customer Product Ops, to try to make sense of my decade-plus experience, but it still doesn’t feel like a big enough box to shove my experience into.

It’s hard to articulate all I do (and all I can do that I haven’t had the chance to do yet) to myself, and it’s even more difficult to articulate it to companies and founders. Companies want generalists, but they don’t want to hire them.

What if I stop trying to be hireable and instead focus on all of the things I know I am good at? What if that’s what leads to figuring out how to do All of the Above while highlighting my strengths? Yes, because of tests and charts, but also because I’ve been me for thirty-five years, and while I used to think I wasn’t too good with discernment, it turns out I know myself pretty well.

Over the last two-and-a-half decades, Seth has found his place on the Internet, through places like his 2001 heavy-metal blog (Buzz Grinder), his AOL music blog (Noise Creep), and being an early adopter of places like Twitter (he was user number 2,700, or so), Flickr, and something called ‘IRC’, a text-based platform where he used to make plans with people before going to local shows.

In this conversation, we talk about:

• The early internet in all its glory (including a little trip down memory lane).

• How he accidentally discovered SEO

• How spending time away from social media can allow you to spend more time on your craft

• Why most of us wouldn’t know what to do with virality, even if growing more slowly is, well, slow

• The fact that spending time away from social media is not anti-Internet (in fact, you could argue it’s done out of love for the World Wide Web).

• Why 50 subscribers can be more impactful than 5,000 followers

This conversation was such a delight. I’d been wanting to talk to Seth for a while, since I first watched one of his lives here on Substack, and I’m so glad he agreed to come join me on the podcast. I say this often, but I really felt like I could’ve kept the conversation going for another hour. We’ve got more to talk about, so hopefully more to come there soon.

I can’t wait for you all to listen!

Find Seth

• Social Media Escape Club: socialmediaescape.club

• Substack: socialmediaescapeclub.substack.com

• Seth’s Blog: sethw.xyz

Thanks for listening to ‘Be Cringe’! Find us online:

• Instagram: @becringepod

• Substack: thismightbecringe.com

• Listen to the pod: becringe.riverside.com

Be Cringe is available wherever you get your podcasts. Thanks for listening, and for supporting these conversations.

Apple | Spotify | YouTube | iHeartRadio | RSS Feed

Welcome to Month 6: Be Cringe About Being Seen. It’s time to show the world all that is you (or maybe, it’s time to show one person one thing that makes you you).

Below, I’ll share insights from our fifth month, Be Cringe About Trying, as well as how our sixth month will unfold. I can’t believe that, after this month, we’ll be halfway through the challenge!

The insights from the previous month are free to read, and the full Be Cringe experience is available for paid subscribers.

Get 30% off for 1 year

You can read about Be Cringe, and learn how to join us, here:

Month 5 Recap: Be Cringe About Trying

Month 5 was the first month where the ‘work’ of this challenge happened outside of just reflection, questioning, and inner work. While in other months, a lot of that has led to action (both from myself and what I’m hearing from some of you), being cringe about trying asked you to try something tangible, in the real world, beyond the page.

Over the last five months, a lot of the other themes led me to take specific action — being cringe about my why led me to start my All of the Above column and being cringe about wanting exposed the fact that I really did want to give self-employment a real go and was the catalyst that had me finally start my podcast (after wanting to do so for so long).

None of the prior themes actually required any action, but I found that when I set my specific intentions and uncovered my inner reasoning, I couldn’t not take action. So this past month, I felt I was faced with something I wanted to personally distinguish: how is being cringe about trying different than all of the other ways I’ve been trying all year?

I decided I would do more trying with a little less thinking. A lot of what I’ve done this year has been the result of thinking, of journaling, of reflecting. For month five, and in order to really be cringe about trying, I decided to be more impulsive and try things that sounded good in the moment, even if I didn’t know why I felt that way.

There was a good deal of reflection this month, too, but it came after the action, after the trying, and that helped me understand how I felt.

So, the first thing I tried was to adjust how I tried. To reclaim my impulsivity, a character trait I used to see as a flaw and am now seeing as a strength.

This brought a lot of good, and I’m realizing that leaning into impulsivity makes sense at this stage in my life. I’m trying to get a self-employed practice off the ground, and while ignoring impulsivity and embracing strategic planning is what listening to the business people would have me do, I’m realizing that’s not where I am right now. If I were to try to plan, I’d be looking out into space, thinking, and maybe getting a spark or an idea, but nothing firm could take root. I just can’t see that far out in front of me right now.

So, I embraced impulsivity. And one day, a phrase popped into my head, I bought a domain, and a week later, I’d fully launched Customer Product Ops, my consulting offering after not being able to figure it out for the last few months. This isn’t a business per se, and it doesn’t actually change some of what I was hoping to put out into the world on that front, but it allows me to experiment with the positioning and labeling and give it a go.

While I’m convinced that Customer Product Ops is a gap, I’m not convinced it is a gap that founders and startups are willing to pay for — the level of suffering that comes from when your customer-facing teams and product teams are out of sync is pain that a lot of us are just expected to deal with (and are often handled in the background). But I won’t know until I try.

I also launched what I’m calling a Virtual Water Cooler Chat, a low-stakes way for remote folks to ease into their days with the company of others. It’s not co-working, it’s not really anything I’ve seen anyone ask for, but so far I’ve led two sessions that have had FIVE unique guests.

I have no idea if this is something that’s just novel up front and will lose its steam, but I’m going to keep trying as we enter June. If you’d like to join us, you can check out the event calendar here (which will be kept up to date for as long as trying here makes sense).

There’s also an unexpected cost of trying that I realized when I was reflecting on my month: when the things I try stick, that creates more work, more time spent doing those things, and less time in my day for everything else. I recorded quite a few podcast episodes in April, but was only able to fully edit and share one (partially due to some platform issues, but also due to myself struggling to find the time). I also launched my All of the Above column. I posted one essay for that column in May, and I haven’t gotten my act together to share the article I’ve been teasing since that launched.

I’m excited about that column, and I want to see where it goes, but I found myself having to pick and choose between too many options. What happens when all the things you try work out? The downside to leaning into what impulsively comes to me is that the newer thing is often the shiny thing I want to work on, so I’m going into this next month trying to find a way to be a bit more balanced. Impulsive and willing to try, yes, but also with an understanding of what happens if I want to keep trying, and what that means for the other things in my life.

A final note about trying — for me, what I tried in month five demanded I be seen almost immediately after trying. I shared about my consulting work on LinkedIn, and the very nature of a virtual water cooler chat is that people need to show up (and so, they need to see me doing so).

In a way, I got a head start on Month 6 and got to flex my ‘being seen’ muscle a bit. In other ways, I know I’ve just scratched the surface. I also tried things that stayed more ‘private’, like a new workout routine, a calendar embed I secretly added to my website to see if anyone even wanted to book a call, and a new way of journaling. These didn’t immediately go anywhere, and I kept them to myself after trying. So if you tried but haven’t been seen yet, that’s okay. That’s what Month 6 is for.

Month 6: Be Cringe About Being Seen

Read more

Regardless of where my career takes me, I feel this in my bones to be true. Before the pandemic, I’d only known a world where I went into the office every day and worked 8-to-10 (and in some cases, 12) hour days. I’d relish in the occasional work-from-home moment, dreaming of a life without commutes or ‘hard pants’, where I could properly fuel myself with the food from home. Those were my most productive days, by far, too.

But there’s something to be said about being in an office, amongst others, and for me, it’s being able to hang, chat, and otherwise engage in antics.

TL;DR: I created something called the ‘Virtual Water Cooler’ chat. We meet remotely to settle into the work day (or enjoy a well-deserved lunch). It’s not a place for quiet work (those exist, and they’re great, more below).

This is to reclaim the connection I used to feel in the office and connect with my ‘co-workers,’ other people working remotely who want company while crafting their to-do lists or avoiding sending that overdue Slack message to Peter.

If you’d like to join us, you can sign up here. If you want to learn more about the backstory and what to expect, keep reading.

JOIN US AT THE WATER COOLER

The Backstory

When the pandemic hit, I leaned into remote work. It took me a while to find my groove (and finally pushed me to get an ADHD diagnosis, which I was able to ignore for the previous three decades), but when I leaned into it, I loved it.

When the job I had during the pandemic opened its offices, I was considered ‘non-essential,’ and so I had the choice whether I wanted to go in or not. I went into the office once. I embarked on the arduous commute to Hudson Yards, enjoyed the comfort of our multi-level flagship office, and spent most of the day in a phone booth, getting work done and joining all my meetings remotely. I met no one I worked with, and otherwise felt alone. It was fun, I enjoyed the free snacks and Diet Cokes (I drank three), but it felt unnecessary.

The job I had after that had a twice-weekly office requirement, with some people only going in once and others going in 4-5 days (freaks1). It was fine, but I didn’t have a child at this point, and a lot of my time was still spent doing heads-down work or in meetings that didn’t benefit from being in person.

But it did remind me of what I did miss about remote work: the culture. My boss would bake scones for the office, we put together a Thanksgiving potluck and holiday ‘white elephant2’, and we’d take turns on the metaphorical aux (connecting to the Bluetooth speaker and playing tunes in the office). It was fun, but the obligation still took a bit of a toll.

I haven’t been in an office in earnest since then. I’ve gone on off-sites, worked from WeWorks in an ad-hoc way, and overall have gotten to know those former coworkers in person in a way that allowed me to optimize the ‘culture’ while maintaining the flexibility of remote work. There’s definitely something nice about getting work done with others in person, but I prefer it to be the exception to the rule, not the norm.

And overall, I do kind of miss the connection (on my own terms, of course). If there were a way to just emulate the culture and antics without the commute, the stress, the schedules, I’d do it.

I love co-working (but I need something else)

I’ve been a big fan of virtual co-working, or body doubling, for a while. For the uninitiated, body doubling is a popular concept that’s particularly helpful for neurodivergent minds, but can benefit anyone who works better amongst others. I, for one, do my best writing at coffee shops, and when I look at why, it’s because I’m surrounded by people and taken away from my usual distractions. Working in front of others is a great motivator and accountability partner.

I’ve been co-working for over a year, when I started joining the co-working sessions put on by and when they were running (RIP, miss you so much <3). I currently co-work with one of the other gals3 I met on those calls, and while the body doubling aspect is the motivator for those calls, I do also love that we get to chit chat before and after our work is done.

of runs his ‘CO-WORK ESCAPE POD’ sessions weekly. I’ve been a few times, and Seth does a great job at giving everyone ten minutes or so to settle in and share what they’ll work on. There’s a mid-session check-in, and one at the end. Again, a few moments to step away, look up, and connect with freaking people.

Co-working has become a mainstay in my weekly schedule, and when I was without it for a few months at the start of the year, I found myself lost and immediately less productive than usual.

There are other options for co-working out there. So why a water cooler? How is that different? Why the need for co-working that’s not co-working?

The Virtual Water Cooler Chat

One morning, while settling into my day and trying to get work done during the 9 o’clock hour, I found myself constantly distracted by Substack (as one does). I fired off a few notes, left a few comments, and noticed my notification bell was more active than usual.

Substack was buzzing, and instead of getting my work done, I just wanted to sit and chat with the fellow Substackers who were also online (the closest thing I have to co-workers these days).

I sent this off, opened up some work, and was immediately pulled away by another notification. A reply from of came flooding in, and confirmed what I’d kind of been feeling all morning:

This is my water cooler. I thought to myself.

I quickly replied, “gives me an idea for a ~9a zoom ‘get settled into work and shoot the shit’ call at some point” and left it at that.

But I kept thinking about the idea of getting ready for work, avoiding my email, and chatting with others over coffee as we settled into our days.

Impulsively, I opened Luma and scheduled a WATER COOLER COFFEE CHAT for the next day.

The description read:

​It’s time to clock in!

​Your work is remote. Maybe you work for yourself, maybe your co-workers are across the globe.

​You love remote work. But you miss the office antics: pretending to check emails while catching up with coworkers, grabbing coffee, keeping track of what time Peter actually gets to the office, submerging the new guy’s stapler in jello, standing by the proverbial water cooler (an aside: I’ve never had a water cooler at my office jobs — have you?)

​Come join a casual video call where we hang out virtually, drink our coffees (or tea, or Red Bull if you must), and get settled into the day.

​Multitask, check your calendar, plan your to-dos, pretend to check your email, or just shoot the sh*t. It’s like co-working, without the pressure to get any work done.

​It doesn’t solve for the stapler-in-jello (and similar) pranks or ganging up on Peter for being late, but maybe with how fast AI is moving, we can get there in a few years.

​Hope to see you there <3

---

​A note: If you are looking for a quiet space to get your work done, this isn’t the space for that. Unless you want to join and turn the volume down on all of us, and honestly — that’s okay! We’d love to see your face while you work quietly and ignore us, that’s part of the office experience.

Three other people joined, and for an hour I made my to-do list while chatting about whatever we wanted — our plan for the day, whether you can actually be a ‘cat’ or ‘dog’ person ( — I have a Subway Take about this), interesting people we met and spoke to, and our plans for the long weekend.

When the call ended, I jumped into work refreshed and ready to go. Nothing like shooting the shit for an hour at the water cooler, except this time, I hadn’t come off of an hour-long commute, and I was still in my sweatpants.

I’ve scheduled two more, and I’d love for you to join. You can check out the details on my Luma, which will always be kept up to date.

These calls are free to join and have very few rules. Join when you can, stay as long as you want, and just be ready and open to wherever the morning takes us. I’m also experimenting with time zones, format, and length, so I’d love to hear any and all feedback!

If you go heads down for a moment to send that Slack you’ve been avoiding, no one will bat an eye. If you want to go heads-down the whole time and just miss being around chatty people, that’s fine too.

But I want to be very clear: this is not co-working. It’s not a quiet, focused space where you’re committing to get work done in a specific amount of time; it’s not meant to increase productivity in the moment (though after the fact, you may find yourself more productive).

As I said in the comments of one of ’s most recent lives: it’s not co-working because it is not quiet! Cameras on, mics on!

I love co-working and love that I can engage with it weekly, but I started these virtual water cooler chats to solve a different personal problem. And if you think this could solve a problem of yours, I’d love to have you.

JOIN US AT THE WATER COOLER

2

Gifts were to be under $20, and included a hidden Smirnoff Ice (and so the receiver did in fact get ‘Iced’), pre-rolled joints, and a pair of Airpods via the CEO (who definitely pulled a Michael Scott)

My impulsivity got me in trouble as a kid, whether I was shouting out an answer instead of raising my hand, blurting something out that was easy to make fun of, or otherwise reacting before thinking. It took a while, but I learned that my impulsivity was a problem that needed addressing.

I’ve been caught between two realities for most of that time. On the one hand, I like to know what is coming, I like to have a plan, I like to be predictable. On the other hand, I like to follow urges in the moment, need space to let parts of my life unfold, and find a too-rigid to-do list stifling.

There are days when this feels impossible to navigate. It’s part of what makes (and has always made) the typical institutions in our society so difficult for me to hold myself to.

Give me a sheet of math homework every day, I might struggle to turn in all five (or might be doing them in my time between classes). Give me five sheets of math homework due Friday, I’ll knock them out when my brain says “it’s math time”. Sometimes that would be on Monday, sometimes scattered across the week, and yes, sometimes on the ride to school Friday morning.

The same patterns held for my full-time work and even my Substack. I love the predictability of certain tasks, but loathe anything that needs to be done at a specific time. I try to create a content calendar, but by the time I’m “supposed” to write an essay I was excited about three weeks ago, the excitement is gone and nothing gets published.

I fight the impulsivity even though it’s so obvious that my best work is done when I follow those pulls. And so, I am reclaiming my impulsivity. That doesn’t mean following it blindly, but it means following thoughts and ideas that do seem to be serving me, and discerning when I need to take a beat, when I should plan, and when I should ignore an impulse altogether.

This duality within me is one of the things that has made me so nervous to go out on my own, but it’s also the thing that I think will make me successful (if I am successful). I quit my job with an idea, but not a plan. “I want to use my experience in some way and consult”. Great idea, shit plan.

Deep down, I knew the idea would come to me (or it wouldn’t and that would mean it’s not the right idea). But I also knew it would not come to me if I didn’t give myself the space to experiment, think, test ideas, and yes, dream. I knew I had to quit my job first — a job that took a little too much out of me and left little room at the end of the day for said dreams.

It has been two months and a week since my last day of work, and I’ve finally been able to narrow my focus on what I want to offer. I was only able to do that because I listened to the ideas that popped into my head, that seemed random, and let them fester. I followed the impulsivity when it showed up, but didn’t force it when it waned. I trusted the process.

I’ve felt like I’ve been in a (literal, actual) fog for the past two months. I can see my feet and the brick I am standing on, but I have no idea where the rest of the path leads. All I know and have known is that there is a path in front of me, a path which will reveal itself in time, brick by brick. Sometimes I get lucky and can see two bricks at once, sometimes I have to take a step without seeing anything, the only thing I know is that there is a brick to catch my step.

It feels like I have a need-to-know relationship with my future right now, which is terrifying and exciting. A more practical-minded person might shove down that reality and might force a path, but they might also not see the other paths out there. Fortunately, I’m not a more practical-minded person and am leaning into that identity more. Thankfully, I’m embracing my impulsivity.

A few weeks ago, while on a run or journaling or staring into space, three words popped into my head. Customer Product Operations.

“Ok…” I thought to myself. “Those are the things I’ve done. And??”

I didn’t understand why those words popped into my head. I’ve been trying to figure out my place in this world as a generalist, someone who’s had a career in Product but also in CX and who’s worn all the hats in between. I’ve been touting my ability to help ‘fix things’ and work in ‘product, comms, cx, operations, and special projects’ at startups, which is admittedly bad self-marketing. It’s not niche enough, it’s a mouthful, and I’m asking people to decide what they need, instead of sharing what I can actually offer.

Customer Product Operations. It echoed again. I Googled it, thinking I’d uncover a discipline or niche I could latch on to. Instead, I got a lot of information about Product Ops, a discipline that has always felt like something I could do but felt too limiting, and two outdated job postings: one for a “Customer and Product Operations Associate,” based in Singapore, and one for a “Customer/Product Operations Lead”.

I was admittedly frustrated. I know what I’ve done, I thought. But that’s not a thing.

Another lightbulb, another impulse. Before thinking, my fingers zoomed to my trackpad and placed my cursor in the address bar.

I type as quickly as I can: customerproductops.com.

“This domain cannot be reached”.

I sprint to GoDaddy and buy the domain. I do nothing else.

Worst case, I’ve wasted $12.99. I can still call it a tax write-off.

I think about this domain and about this phrasing time and time again over the next few weeks, but nothing else comes to me. I know there is something there, and the fact that it hasn’t come to me feels frustrating. But I decide to stop forcing it, stop spinning my wheels. Que sera, sera.

Until yesterday.

I’m settling into my day, doing some freelance work, when I suddenly remember my domain. Again, without thinking, I open a blank note on my laptop and start typing:

your cx and product strategy don’t need to be separate. in fact, i’d argue they shouldn’t be. yet organizations everywhere have two distinct functions, at best these teams are meeting 1x a week, and usually it’s a similar format: product shares updates or anything that might cause customers issues (and things customers might see or ask about), cx shares trends, reports, feature requests, and bug reports. but what would a more symbiotic relationship between the two look like? what if your cx informed your product strategy and vice versa? what if you had a system that gave equal weight to both, that deeply understood these needs? that wasn’t secretly in favor of one over the other, that didn’t have a favorite child?

enter customer product ops.

More lightbulbs, more impulses, and a few hours later, I launched a website and figured out my offer.

I hit publish, posted on LinkedIn, and shared on Substack. I’ll be honest — if someone books a call with me tomorrow, I have no idea how it’ll go. I haven’t given much thought to pricing, other than what I roughly want my net hourly rate to be. But again, I followed the impulse and trust that I know everything I need to know right now.

I have thoughts of where this can go beyond just consulting, but I’m going to let them come to me organically, like everything else has. Right now I’m throwing my idea at the wall and seeing what resonates. Is this a problem? I think so, but having been in these spaces, I also know it’s something teams just deal with. I worry about getting buy-in, and am unsure if this is a problem people want to spend money on. But I won’t know what’s next unless I take a first step.

I’m going to write more on what Customer Product Ops actually is soon, in hopes that next time someone Googles the phrase, my words come up.

But this essay isn’t about the discipline. It’s about reclaiming my impulsivity.

Impulsivity is what made me launch my Substack three years ago. It’s what led me to, on a whim, rebrand my Substack to “This Might Be Cringe” a year and a half later, and is how most of the essays I’ve written were born (including this one — I was working on a whole other draft when this one started to come out, and I realized it was its own essay).

It gave me my year-long Be Cringe series, which boosted paid subscribers. It’s what (coupled with a gift from my husband), finally kicked me in the pants to start my podcast, and what gave it its name (also Be Cringe, which is sometimes confusing, but it works for now1).

Impulsivity is what made me start running after very much not being a runner for most of my life (and what made me sign up for two half marathons, which in turn kept me running). It’s what made me finally admit that I wanted to quit my job (obviously, that one took planning…but even getting to the planning felt impulsive). It’s what made me start posting on LinkedIn and Threads2 — most of the posts that are my best performing fly into my mind, and I post them as soon as they arrive.

My impulsivity led me to schedule what I’m calling a WATER COOLER COFFEE CHAT, after realizing Substack was abuzz at 9 am, wanting to just chat with my friends, and reading a reply from that confirmed — we’re all just settling into work as we would in an office, and I realized I want to do that in community.

Taking a moment to break the fourth wall! If you want to join us at the water cooler, we’re meeting Friday, May 22nd (tomorrow) at 9am EST. If I have a good enough time, I’ll do it again. Maybe a lunch hour too, so the PST folks can join. We’ll see where the impulsivity takes me. Sign up here →

The part of my identity I used to think was something to fight or change is now the thing I am trying to embrace the most. It has given me so much, and everything I’ve described is mostly in the personal<>professional development space. Impulsivity helps me figure out what I want to eat, guides me to text our daycare group chat to let them know we’re headed to the playground (which sometimes turns a sleepy Saturday morning into a playdate with 5 kids), and leads to my most productive cleaning blocks.

Sure, sometimes it keeps me up past my bedtime to watch one more episode, or is what causes me to drink a 2 pm cup of coffee I’ll later regret, but I am realizing I can lean into impulsivity while also being more discerning about it at the same time.

I still have a desire to plan and to know how things will work out. I’m still uncomfortable in the unknown, but leaning into my impulsivity (and yes, my intuition) makes what I don’t know feel intentional, and it’s what makes it almost bearable. I’ve accepted I am an ‘impulsive planner,’ an identity that feels like it is at odds, but if I squint, I can see that they’re just two sides of a scale needing to be balanced.

Being in a need-to-know relationship with my future sometimes takes a toll on me. There are moments when I want all the fog to lift, where I want to see every brick, where I want to meticulously plan and figure out how I’ll get to the end, where I want clarity of what each stop along the way looks like.

But I’ve started to understand that I’m not that person. Right now, I don’t get to see the bricks or the stops, and I need to exist within the fog. I can fight it, like I have in the past, but that will leave me standing on the same brick until frustration forces me to create a new path, one that I can see, without knowing what I’m leaving behind.

Or, I can lean into the impulsivity, allow the path to unfold for me, and trust that each step builds off of what came before and is in support of what’s coming. Some bricks are big moves, some are lessons in what doesn’t work or feel right, but all deserve their place on my path.

She is working on her YA novel set at theater camp, while navigating the many swim lanes of her career and finding comfort in being able to go back and forth between in-house roles and working for herself (while writing her book)

In this conversation, we talk about:

• Giving ourselves the permission to define our own success in our career.

• Going back in-house, and seeing that as part of a larger career ecosystem.

• Being theater kids (I promise, we move on quickly).

• Writing a novel, using the ‘author’ label before it’s published, and having big dreams for where it can go.

• Being brave enough to examine your career and ask “do I like this or am I just good at it?”

I am really, truly, so excited about this one. I’ve admired Lia on Substack for a while, since reading her How to recharge without quitting your job essay (and then quitting my job anyway, oops).

the recharge

🔌 How to recharge without quitting your job

Oh my goodness, a lot of new faces this week. 🥹 (Which means the pressure is on…

Read more

10 months ago · 528 likes · 39 comments · Lia Zneimer

There are just some people you come across and immediately know they’re kind, good, passionate, and incredibly capable of whatever they want to do. Lia is one of those people, and I’m so glad our paths crossed when they did. I’m honored she came on the pod after I called her cringe (always a bit of an awkward sell, I wonder if I’ll ever get over that…).

I can’t wait for you to listen and hear from Lia. If you know her, you know you’re in for a treat. And if this is your first time coming across her, you have no idea how big of a treat you’re in for!

Find Lia

• Substack: getrecharged.substack.com

• LinkedIn: linkedin.com/in/liazneimer/

What Lia Shared:

• ’s Pie Chart1, referenced here

  Quite Contrary

  2 Years After Leaving Tech, Here’s What I’ve Learned

  Read more

  a year ago · 283 likes · 49 comments · Mary Jantsch

• A plot twist… by

  Lia talks about standing in front of three opportunities, and which one she ended up choosing

  the recharge

  🔌 A plot twist...

  I posted this Note last week with zero context… and then immediately started second-guessing myself…

  Read more

  3 months ago · 52 likes · 51 comments · Lia Zneimer

• The tech dream is a nightmare by

Good Enough

The tech dream is a nightmare

Working in tech used to be fun, not because of the cold brew kegs or ping-pong tables, but because it felt like we were moving toward something together…

Read more

9 months ago · 57 likes · 33 comments · Max Pete

• Can’t Even: How Millennials Became the Burnout Generation by Anne Helen Petersen

  

Thanks for listening to ‘Be Cringe’! Find us online:

• Instagram: @becringepod

• Substack: thismightbecringe.com

• Listen to the pod: becringe.riverside.com

Welcome to All of the Above, a place where Generalists, folks-of-all-trades, and the wearers of many hats are finally at home. In this column, I explore how those of us who do it all (and love to do it all) can make it work in a world that is obsessed with fitting us into boxes.

After my last layoff1 last summer, I have a distinct memory of looking at the Product jobs on LinkedIn and feeling a pit in my stomach. I don’t want to do that, I thought, or that, or that, or that.

Did I even want to be a Product Manager anymore?

While I was sorting through that very question, I wrote an essay originally titled I don’t want to be a Product Manager anymore, later titled I might not want to be a Product Manager anymore. I never ended up publishing that essay — I probably didn’t want to say those out loud, because there was something I really loved about Product work. Today, I am revisiting that topic with a new perspective.

It’s not that I don’t ever want to be a PM, it’s that at this point in my life, I don’t just want to be a PM. It’s a role that requires you to wear a lot of hats, but it still boxes me in. I’m not only ready to say that, but I’m ready to publish that.

But back then, I wasn’t. I wasn’t ready to close the door, even though I knew in my gut a traditional PM role just wasn’t aligned with what I wanted.

But I felt like I’d worked so hard for that career, and there was still more to do. I wanted the ‘Senior’ tacked on to my title (badly). I had — and still have — this deep desire to solve problems for people, and I became a PM because I think software is a compelling way to do that. I’d placed a target on that title early in my career, told myself, ‘I think I’d like to do that one day,’ and let my career unfold. And eventually, five years after that initial thought, I was stepping into a Product role.

PMs will tell you “Product is different everywhere,” and that’s true, but it’s also an established discipline. There are books written about it, ‘rules’ and best practices to follow, podcasts and newsletters about it, and most importantly, it’s a specific title that, when you see it, you more or less know what to expect.

So when, after five years, I realized there was a chance I wanted to forgo the title and career I worked hard for and that finally helped me fit into a neat box, I’ll admit it — I was scared.

I realized there was a lot about Product work I liked, but also a lot about the work I didn’t like. And there was also a lot of experience I had before becoming a PM, leveraging skills I liked leveraging, that I felt like I wasn’t using anymore (or when I tried to use them, that I faced resistance).

Last summer, while laid off, I joined a Job Search Council after reading the book Never Search Alone. I met weekly with other folks looking for employment, and part of the program is creating a detailed two-pager that takes your strengths, likes, dislikes, and market-fit into account.

While working through this exercise, I started to face the reality that a lot of the things I ‘liked’ and ‘disliked’ didn’t quite match a traditional PM job description. I started to say things like “I want to maybe explore other paths while I also look at Product jobs,” but had never allowed myself to say “I don’t want to be a Product Manager anymore”, even if that is what I had felt.

During a round of revisions, someone on my council noted that everything in my “Strengths” section were very ‘PM-coded’, and pushed me to think of whether I had other strengths (spoiler: I did). Even as I was trying to push myself outside of my box, I found it difficult to actually do so until I was given permission by someone else.

I think I am a decent PM, but is ‘decent’ enough to build my career on? That’s the wrong question, because yes, it is enough. But I, maybe unfortunately, want more than just doing something I’m good at.

When I started actually mapping what I liked and didn’t like, a pattern emerged that had nothing to do with Product, though I think it’s part of what helped me in those roles. I like people, writing, fixing things, and seeing how all the pieces fit together when no one else can. I like the early stages of a problem — whether it’s a user problem, a need for operational improvements, or an issue within a team, working incredibly cross-functionally, and I like making language say exactly what it needs to. What I don’t love is being judged entirely on outcomes I can’t fully control, doing everything right and having it not matter because the numbers didn’t move, and living and breathing data analysis.

None of that is inherent to Product work, but it’s also not not Product work. It doesn’t quite fit in a box, and if it does, I haven’t found the right box yet.

So where does this leave me? On paper, I'm doing this backwards. I quit my job, and now I'm figuring it out. If I were giving responsible advice, it wouldn't be that.

But the first thing I needed to do was to take a step back. Having clarity on what I want and don’t want is a great step, too, but the space between my full-time product role and what I have now is necessary. You might argue that I had this back in June, but I needed to choose this.

What I do know is that being a fixer is at the core of what I want to do. I like seeing what’s a bit messy and helping make sense of it (whether that’s in a product, on a team, or apparently, in my own career).

So far, I haven’t seen any roles on LinkedIn for ‘Fixer,’ and I believe that’s by design. The work I want to do at this time isn’t joining an organization full-time. The problems I want to solve shouldn’t be problems forever, but rather something I can shape and send off to its permanent home when it’s all fixed.

Leveraging the skills in Product, ops, and working with teams in customer-facing roles will lead me down the right path. After all, there’s a lot in those domains I enjoy, and that is where my experience is — the next step is to figure out how to do that on my own terms. That’s the ticket to success.

I know I am not the only one who’s spent far too long chasing titles and a linear career path only to find that it mostly, but not quite, fits. That is, after all, the plight of the generalist.

Next week, I’ll be sharing more about that plight with a wider aperture. If that is you and you have something to share — a feeling, advice for others, a question you’re wrestling with, or advice you need — I’d love to hear it below, and perhaps share it in next week’s issue of All of the Above.

1

I’ve written a lot about my feelings and experiences with layoffs — I’ve been laid off three times, my husband twice, and now we’re both self-employed. If you want more on that, the linked collection is for you.

Welcome to Month 5: Be Cringe About Trying. Yes, we actually get to do something this month!

Below, I’ll share insights from our fourth month, Be Cringe About Your Why, as well as how our fifth month will unfold, for those that want to follow along in real time.

The insights from our previous month are free to read, and the full Be Cringe experience is available for paid subscribers.

Get 30% off for 1 year

You can read about Be Cringe, and learn how to join us, here:

Month 4 Recap: Be Cringe About Your Why

There is a version of this challenge where figuring out your why could’ve been one of the first things I had you do. Figuring out why you want to do something is often the core to success, and can be more illuminating than knowing what it is you want to do, showing up for it, or knowing what’s stopped you in the past.

One of my favorite TEDx talks is Simon Sinek’s Start with Why — and I’d reckon many of you have seen this one at least once, too.

I watched it in multiple college classes, at various trainings while I was at Apple, and have had teams I’ve worked on and with watch it as well.

Sinek explains his ‘golden circle’. He takes the angle of business, but this can be applied to us as people too. We all know what we do, some of us know how we do it, and only a few of us really take the time to figure out why.

So when I was designing this challenge, my gut was to have us start with the why — our purpose, our beliefs, our reason for doing. But I also wanted the why to be impactful, and in order to really get to the true core of our why, I knew we needed to define our what and go through what has blocked us in the past (or else we’d have started with why and would’ve probably needed a ‘Be Cringe About your Why Again’ month). You probably started this challenge with a loose idea of your why, anyway. Month 4 is just when we really were able to focus in.

My focus for this month was to get really clear on embarking on a journey of self-employment. As much as I know this is the right path now (my what), and I am experimenting with different ways of going about it (my how), I’ve been struggling to articulate why. I’ve been struggling to figure out what exactly I wanted to do, too, beyond a very loose shape, and I think not settling into my why absolutely contributed to that.

I spent the month reflecting, writing, and figuring out why I wanted to be self-employed. I paid attention to the feelings I wanted to evoke and why, the types of tasks I like doing and why, and why having some more freedom and autonomy around my time is so important.

Once I did that, I had secretly hoped that the perfect career would fall out of the sky. It didn’t, but what I found was much more profound.

I’ve realized that my journey to being self-employed is a bit more nuanced and layered, and that I am close to hitting on something. I don’t know what it is yet, but this month gave me the clarity to visualize what my perfect days look and feel like, how I define success, and to overall really get curious. For a while, every time I’d ask and answer the question why, I’d ask why again.

And through all of that, a few ideas were born. Most notably, I’ve launched a new column on my Substack called All of the Above, which is a space where I’m going to dig into all of the various whats I want to do and how I think I can get there, when it comes to my career. That would not have been possible without understanding my why — it’s also the thread I know I will carry as I work through that column, and keeps me honest as my foggy future unfolds.

Month 5: Be Cringe About Trying

Now that you know why you’re chasing after something (and also — what you want to do, showing up to that, and understanding what may be blocking you), it’s easier to actually try to go after what you want to go after.

Read more

Welcome to All of the Above, a place where Generalists, Jacks-of-all-trades (not to mention Jills and Jaxes), and the wearers of many hats are finally at home. I’ve found I have a lot to say about career, purpose, and how people like us can fit into a corporate world that so desires to box us in. All of the Above is my attempt at making sense of all of that.

I’ve had this idea for awhile, but haven’t quite known how to start it. Should it be a new newsletter, or just a section? A new newsletter may make sense one day, but for now, I’ve decided to stick with this being a section under my current brand. As this grows, that may change! But for now, this is the way I can give this a go without overthinking it too much (and if you know me, you know I already have the newsletter created…)

Do I need a new logo? I decided I did, and I created this placeholder myself in Canva, which I am stating in case anyone reading this is familiar with my husband’s work and thinks “did he create that monstrosity?”. He didn’t — this is all me, but if this takes off I’ll enlist his help soon enough. Visual arts are not my strength, but I am allowed to do things I am bad at, an idea that I am trying to embrace more and more since it came up in podcast interview with .

I have a lot to say about career, but also don’t want it to take over what I’m doing on This Might Be Cringe. So, I’m carving out a section of that space (for now) called All of the Above. I know there are other Generalists and ‘All of the Above-ers’ out there – so this one is for you.

I originally titled this essay The Plight of the Generalist, but as I wrote this evolved into me reckoning with why I’m even starting a new project now and how it fits into my career history and evolution. Yes, it’s an introduction post. The seemingly throw-away ‘welcome to this new thing!’ essay. But it felt important to write (and don’t worry — The Plight of the Generalist is coming).

Two months ago, I gave two-weeks’ notice at a job I’d only been at for six months. Since I left, I’ve been exploring a self-employed path for myself. I’ve talked about why I quit at length here, but I’ll walk through the situation I found myself in and where I went from there at a high level here.

I’ve been laid off three times since 2022, and since then I feel like I’ve been treading water from one role to the other, trying to grow a career in a niche I put a target on, and then fell into. During my last layoff, I started to explore what being self-employed would look like, and things were unfolding. I snagged a three-month contract in a Product Management role, and really started to see how I could make a career in this space. I found I enjoyed having a set amount of time to go in, figure out a set of problems, and know I’d leave at the end of a set period, having left things better than before.

Six weeks in, my manager asked if I wanted to extend my contract. And instead of just saying yes, I asked about whether or not a full-time role at the company was possible. If I am being honest, that question came from fear I didn’t know I had until I blurted it out. I negotiated a title I’d been working towards, a salary that felt comfortable, and I was converted to full-time. All along, there was a tiny nagging voice telling me to stop this process. To extend my contract, to keep working, to figure it out later.

But my ego kept seeing the LinkedIn layoff posts, the large companies getting rid of employees en masse, and I thought I was doing the right thing for me (and my family).

Unfortunately, that nagging voice wouldn’t shut up. As soon as I converted to full-time, I felt a visceral shift within me. I started to see the work differently. I felt less ownership of my time and my energy — even if the work didn’t change all that much, my psyche knew I was working for someone else now. I tried to push through, but I felt extremely un-aligned from what I knew I wanted and it took a deep toll on me. It’s so hard to articulate what was so difficult now that I am on the other side of it, but ultimately, I think straying so far from my surface made a lot of ‘little’ things difficult for me to manage. Staying in that role accelerated my burnout and zapped my energy in a way that was, frankly, a bit terrifying.

Build your freelance offer on the side, and figure it out while you still have a paycheck, the conventional wisdom reads. And that is wisdom — if I were giving anyone advice, this is what I would say too.

But wisdom is not black and white, and unfortunately often doesn’t understand the nuance and gray areas of our situations. The energy I was giving to my job felt like it was triple the energy I’d given to any other — even though the work wasn’t that different, I got to work from home, and on paper it was a dream! I was in the thick of the worst periods of seasonal depression I’ve experienced (which I can only now see in hindsight) while training for a half marathon, parenting a toddler, and attempting (and honestly, failing) to keep up with all that it takes for adults to keep their homes running smoothly (I’m talking to you, laundry). This created a perfect breeding ground for burnout to infiltrate my life, and made it so that I had no energy at the end of the day to even think about what my next steps could be.

To use the analogy so eloquently shared in our recent podcast interview: I was on a treadmill that was not stopping, and I knew sooner or later I’d have to make the choice whether or not I would fall off or step off gracefully. So, I took some time to get my bare-minimum finances in order, put in my notice, and opened a door without having any clue where it leads.

I am stepping out into a fog, only able to see one step in front of me at a time, but trusting that following the inspiration I feel will open up the world of possibilities.

I’ve been in tech and startups for TEN YEARS (fourteen years if I am allowed to count my experience in Apple Retail), and while I’ve sat on many different teams and have in fact worn those many different hats I’ve spoken about, I find it really hard to articulate that experience. But surely, there’s something there that someone wants, right? I threw together a basic offering on my website that I know needs work. Right now, I’m trying to sell people on the fact that I can do it all, while everyone is begging for me to pick a niche.

I don’t want to pick a niche and I want to do it all, but I also know I need to really spend some time thinking about that and figuring out what that positioning looks like. My hope is that this space can help me (and hopefully you) get closer to what that is.

I am pretty clear on the fact that I do not want to just be a product manager anymore — in my five years in product, I’ve picked up a lot of other skills that are useful, and have found things I enjoy more than some of the more traditional PM work. I’ve been sitting on an essay draft called I Never Want to Be a Product Manager Again since August, that I quickly put on the backburner when I did in fact become a Product Manager again. I’m excited to revisit that here, too.

There’s also an essay I could write where I walk through each step of my career, how it all seemed to unfold without a plan in front of me, and how that led me to where I am today. In fact, this essay started to take that shape, but what I think is important to communicate now is this: in fourteen years, I went from working at Apple Retail to becoming a Senior Product Manager in a very non-linear career path. I refuse to believe that the work I did before stepping into product is irrelevant, and I know there’s a way to leverage it.

In between that time, I slowly figured out what I was good at, what I enjoyed, and the fact that those aren’t always the same. I managed teams, supported users, and implemented new systems. The word ‘operations’ was thrown onto a few titles I had, to capture the fact that I did the things that didn’t fall neatly under other disciplines. I’ve done a lot, worn those hats, and carry that experience with me in everything I do today.

I’ve also learned that employers and companies love having the person who can do it all on their team, but when hiring need to box people in. I became skilled in interviews at connecting the work I did to the slightly different work the next role would require of me, and between doing that well and coming off as ‘likable’ in interviews (their words, not mine, I promise!), I was able to forge a career path in a non-traditional way, that often doesn’t make sense until you look at it in hindsight.

And once I’m hired in my boxed-in role, I become the person who can do all of the above. And because I know that it’s possible, I’m on a mission to figure out how to convince companies they need a fixer, a generalist, an ‘All of the Above-er’ to [insert job here].

Can I do everything? No. I’m not saying I want to do it all, but I want to do more than a box would traditionally allow. And I know there are other people out there who do too. Maybe, even, that’s you.

And if that’s you too, welcome to All of the Above. I’m excited to dig in, to figure out what ‘career’ even means, and to do it alongside all of you.

All of the Above is for you if:

• You’re finding yourself standing in a fog and not sure where everything you’ve done up until this point will lead.

• You’re letting the path unfold as you walk it.

• You’ve answered the questions “what do you do” (or “what do you want to do”) with a series of words and sentences that don’t feel like they make sense together.

• You wish job applications came with an ‘All of the Above (and more)’ checkbox.

• You’ve been laid off or have found yourself in a similar career pause and want to use that as a forcing function to figure out what’s next.

• You know you’re more than a job title, career path, or corporate box but don’t know how to articulate that yet.

• You’d rather pull all your hair out than ‘pick a niche’, and you believe deep down you shouldn’t have to.

• You’re figuring out how to sell ‘I do it all’ without sounding unfocused, unambitious, or confused.

• You feel like you’re alone in a world where everyone around you seems to fit so nicely into their boxes and niches.

Thanks for reading — I am excited to see where this goes, and looking forward to connecting with others who relate to being ‘All of the Above-ers’. Your ‘All of the Above’ might look different than mine. Maybe you’re a designer who’s been looped into research and go-to-market conversations, or a Chief of Staff who somehow started running analytics and product marketing for a company, or the social media manager who also writes internal communications briefs for the company (and holds the keys to all the PR contacts).

If you have a story to share, I’d love to hear it. You found this for a reason, and hopefully made it this far because this resonates.

Welcome to your new community.

All of the Above is a publication by of . If you already subscribe to This Might Be Cringe, you’re all set and will receive these updates — nothing else to do here.

You can subscribe to get updates on everything I do, and if you only want All of the Above emails, you can manage your preferences here. And if that’s all confusing — just let me know what you want and I’ll help sort it out.

Subscribe now

She went to a good school, snagged a business degree, became a CPA, and spent the better half of a decade at a Big 4 firm. She checked promotions off one by one in a career that felt predictable, until one day, she chose to step off the treadmill.

In this conversation, we dig into what apathy at work tells us, why the fear of making the wrong choice keeps people stuck longer than the wrong choice itself ever would, and what happened when Devon finally gave herself permission to want more (and allowed herself to be seen doing it).

We get into:

• Why passion fall-off is a signal worth listening to (and why pushing through isn’t always the answer)

• What burnout leave looks like (spoiler: it’s not a bubble bath)

• The difference between an opportunity finding you and working your ass off to be in the right place for it, and how they often coexist and seem to intermingle

• Why publishing her writing was more difficult for her than the writing itself

• Why fashion and aesthetics deserve intellectual rigor

I loved this conversation with Devon, and have been so excited to share it with you all. She’s self-aware, confident, fun to talk to, and has a way with words (both spoken and written). She cites Bourdieu in essays about fashion and somehow makes it feel completely natural, and has recently started sharing her journey in doing The Artist’s Way on her Substack.

What I keep coming back to from this episode is her framing of apathy as the canary in the coal mine. I know I’ve felt this, and at various stages in my life have either ignored the signs or pushed through. Devon talks about what happened when she listened to those warning signs, took a step back, and what she’s found since. I think many others can relate as well.

Find Devon

Substack: closet brain rot

closet brain rot

CBR is a study of personal style as a way of living, through clothing, spaces, and objects, and an exploration on how to build a more intentional, visually rich life through what we surround ourselves with—delivered around the first of the month.

By Devon Hunt

Be Cringe is available wherever you get your podcasts. If you know someone who’d make a great guest on the pod (yourself included), fill out this form!

Apple | Spotify | YouTube | iHeartRadio

Not because the company was going to rocket to the moon and would IPO and I would be a rich bitch. I mean, maybe I thought that, but that wasn’t what made me feel like I’d made it.

But before I get into why I felt like I made it, I’m just going to say this now. Both in case someone from the Allbirds legal team is reading this (whom I no longer know) and also in case someone reading this really loves a story about a fallen darling (a la WeWork2). That this essay, maybe much to your chagrin, isn’t an exposé or a peek under the cloth. I know, lame. I’m sorry!

This isn’t going to be where I tell you the writings were on the wall, that leadership walked around barefoot (again, a la WeWork), that the reason I left the company after 11 months was because of a reason other than the fact that I wanted to move back east.

The writings were not on the wall because there wasn’t anything to be written on the wall. No one walked around barefoot, although we did gather at 4pm every day to do a series of pushups3. The only reason I left the company after 11 months was that I got a job at another former D2C darling that would move me back east, my ultimate goal, because San Francisco just wasn’t the city for me (it’s not you, SF. It’s me).

When I take a step back, this essay isn’t even about the current state of Allbirds at all. But the darling hath fallen, and therefore is now relevant. I’m not going to cover the downfall or retell a story that can easily be found within the archives of Business Insider or WaPo. I’m not really going to talk about the AI pivot at all, at least not in a grand ‘what it means for the industry’ sense.

I’m not a tech reporter, and I don’t care to be. But I did spend 11 months with the brand, and those 11 months shaped me more than makes sense.

Oh, you’re still here after all of that? Okay, let’s get into it4.

To really tell this story, we need to go back a little further in time, to October 2017. I was visiting New York after living in the Bay Area for just over a year — at the time, we were still in San Jose. I was overwhelmed with emotion and nostalgia for my East Coast life, but I hadn’t yet thought about moving back any time soon (though crying in Central Park should’ve been a sign? I digress again…).

I brought a pair of Birkenstocks5 with me and a pair of Nike Frees that had far too many miles on them. I cannot remember the events leading up to this moment, except that I’d walked a lot on a particular day during this trip (like, 30,000 miles) and my feet hurt.

While walking in Soho, I spotted an Allbirds sign in the distance. I don’t know what made me walk in — I guess I’d seen them around, or had heard about them (I was living in the Bay Area, after all), and something about spotting that sign while my feet ached made me walk in to that small storefront on Prince Street.6

I could’ve walked half a mile in any direction and have been met with any other shoe store — the Nike store on Broadway, the Adidas store on Houston, the David Z on Broome. But I found myself walking into an Allbirds.

At that point, the brand was selling one shoe — the Wool Runner (the one you probably think of when you think Allbirds). I walked out with the quintessential gray shoe with white sole. Yeah, you know the one.

The store employee assured me that, even though I was a true half-sizer, I’d find myself at home in the half size down. We carry whole sizes only, but wool stretches7.

And stretch it did, I guess, because I wore the fuck out of those shoes. One of the first in my Mountain View office to own a pair, with the exception of an engineer or two, I fit right in. They went with nothing and yet I wore them with almost everything.

Coming from a gal who, just a few years earlier, had a shoe collection that included canvas platform sneakers, Doc Martens, black jelly sandals, desert boots, clogs, and aforementioned Birkenstocks (to name a…few), this was, well, a departure. I’m not saying I was the personification of fashion, to be clear, but still.

Fast forward six months later and I realize how much I want to move to San Francisco proper. I also know that the commute to Mountain View on CalTrain will get old fast, and so I set out to find an apartment and a job up in the city.

I could go into detail about how I stumbled across a job as CX Manager at Allbirds, how I went through a lengthy interview process, how I questioned whether I should wear my (at this point, beat up) Allbirds to my in-person interviews, that I’d also managed to move to a tiny apartment in Hayes Valley in May and had been doing the CalTrain commute for months.

But what’s important to know is that in August of 2018 I was walking into the doors of 730 Montgomery Pl8 for the first time (an address still saved with a select few online retailers).

And yeah, I’d felt like I’d made it. I was making not one cent more than I had in my last job — I negotiated as far as I could, and that led me to taking neither a pay cut nor a pay raise and breaking criminally even. I was granted stock options, but nothing that even in the event of a ‘to the moon’ IPO would make me a multimillionaire (though, it could’ve been a down payment).

My commute on Muni was fine on paper but painful in reality. I didn’t really ever feel like I had ‘extra’ money but found ways to spend it anyway. So how, after all of that, had I made it?

Because I fell for the darling. And darling she was.

When I think back to what made me purchase Allbirds in the first place, it wasn’t the look. I don’t think I thought they necessarily looked good, though I didn’t necessarily think they looked bad, either. What brought me into the store in the first place was the fact that they were familiar enough that I had some trust in them, but new enough to be interesting. The promise of comfort, too.

But what kept my interest wasn’t the shoes. It was the intentionality of the store design, the copy, and the illustrations. Everything had a purpose, and that purpose was wrapped in whimsy and delight.

The feelings of purpose and intentionality I felt as a consumer were solidified and strengthened when I became an employee. The chairs at the stores were designed to optimize the try-on experience, from their height to the fact that they could fit a shoe box underneath9. The whimsy was intentional, and made it easy to not question why a shoe made from wool would be named after birds?

Throughout my 11 months, I learned the commitment to sustainability was not just a message the brand used as a marketing tactic but also was deeply engrained in how the company operated. I have fond memories of team lunches, of making waffles for my team (and then leaving my waffle iron there for months on end), the email we got from a colleague asking us to not feed his dog (no matter how much said dog begged).

The feelings I had as a 27-year-old manager, to people close in age to me (and older) were something I had to wrestle with, but ultimately gave me more confidence than I realized at the time.

I remember our ski trip to Tahoe, eating crumpets when we launched in the UK, and all of the small corners of the office I used to work from.

When we ran out of coffee, whoever found the empty pot would just make it. If you forgot to recycle or compost or left the toilet seat up in the bathroom, know that you’d hear about it on Slack (often, from me).

And overall, I remember the people. The inside jokes that formed naturally, the stapler-in-jello level antics (yes, a stapler in jello did in fact happen). The true experts I got to work alongside daily. I’ll never say anyone, especially leadership, at any company is infallible, but by and large, we wanted to do good, and the love for the product, the materials, the customer, the innovation, and the potential ran deep.

In May of 2019, I took another trip to New York. My desire to return to my hometown slapped me in the face, and I started to casually apply for jobs in New York. One of those casual applications became an incredibly fast interview and offer, and I felt this was the nudge from the universe I needed.

It wasn’t a decision I made lightly, and leaving was hard. I had been there for less than a year, I loved the work, I loved the team, and I loved the potential. I loved the brand and everything it stood for. I was a part of it, and leaving would mean I would become a blip in the company’s history.

And after 11 months, that should be expected, and they should be more of a blip on my history too. But for some reason, the time I spent there has stuck with me in such a vivid way. It marks a real shift in my career, made me understand what I want from a workplace culture, and set a bar for my workplace experiences from here on out.

Before I left, one of my co-workers sent me a message informing me that I was in fact leaving behind a legacy. That in my short 11 months at the company, I held the record for the most Slack messages sent per day (when averaged against the number of days worked at the company).

I hope that in the almost 7 years since I’ve left, someone else has beaten that record.

Once I left, I was cheering on the company from the wings. Each new store opening, product launched, headline about a big partnership and eventually, an IPO, all had me wondering what life would be like if I had stuck around. Those moments did also have me beaming with pride. Even while writing this essay, I’ve had to fight the urge to say ‘we’ many times.

I never regretted leaving, because I knew I wanted to come back to New York (and coming back to New York is what set the rest of my career in motion), but there was a lingering feeling of what if, that I was watching a parallel path unfold in real time.

At some point, the company IPOed, and the headlines went from giving the brand positive accolades to worrying about shareholder value and whatnot.

To be honest, I didn’t follow this much. I didn’t want to remember the brand for its “fallen” status, and that wasn’t part of my story. I don’t even know if I can really articulate what happened — and this essay isn’t really about what happened10.

But what the headlines and media did tell me is that the brand never recovered, the company was acquired, and now they’ve announced a pivot to AI. It’s okay if you need to do a double take, I did too.

When I first read the headline, I thought it was satire. I looked around for confirmation, and even when I saw ‘CNBC’ plastered in the address bar, I thought oh wow, they have a humor section now?

I can’t tell you what this means. I’m not a tech reporter or a market predictor, nor do I ever want to be (God, no).

But the pivot from Silicon Valley’s favorite shoe to AI might be the exact move we could expect from a shoe company turned apparel company turned back to a shoe company in 2026.

It makes no sense, and therefore, it’s perfect.

Do I understand the logistics of this move? No. From warehouse to data warehouse? From serving the feet of the tech bro to serving their AI GPU needs? I feel like I am reaching.

Do I understand the motivation? Kind of. Do I think this will become an HBS case study or Hulu documentary? Maybe.

Time will tell what the future of Allbirds New Bird AI11 will look like. The CNBCs and Business Insiders of the world will keep us posted on that, but not me.

After being there less than a year, I don’t have that authority, nor do I want it. I was a small blip on the company’s history, and the success or current state of the company has nothing to do with me — without me, I don’t see the company having any different of an outcome. And yet, here I am.

My story ended when I got on a plane to New York in 2019. What happened after was news. Sometimes exciting, sometimes sad, and now, apparently, AI news. News that shaped the company more than my 11 months there ever could. But that news will never shape me more than that time did. And for that, I guess I am grateful.

2

This footnote is for my mother who I am guessing does not know about the rise and fall of WeWork, and in case anyone else finds themself in the same boat, here’s a fairly good summary thanks to the New Yorker (though, you can and should just watch the Apple TV series ‘WeCrashed’, staring Jared Leto and Anne Hathaway in performances I’ll never forget.

In this conversation, we get into:

• Why it’s okay (and encouraged) to have hobbies we’re not immediately good at

• The lessons she brought to the ice after watching this classic Disney Channel Original Movie

• What it means to ‘donate your talents’ to a corporate job as a creative, and what that often leads to

• The power of creating in community and being willing to move through projects, even if you don’t quite know where they’ll lead

• How being yourself in front of teenagers will humble you quickly

I immediately knew that I wanted Amanda on the podcast when I read her responses to my call on Substack Notes. She’s in a season of transition and experimentation and I find her entire ethos and approach to be relatable and refreshing. She exudes creativity and I feel like in many ways offers me some proof on would happen if I let some of the hobbies I’ve let die in their proverbial graveyard live on — I may even pick up a sketchbook again after this chat.

I hope you all get as much out of this as I did. I appreciate Amanda and her perspective, and can’t wait for you all to listen!

Find Amanda:

• Substack: Mandaroo Stack

• LinkedIn: Amanda Jackson

And if you have read this far, I did in fact find Amanda’s first venture into podcasting. Listen here.

Be Cringe is available wherever you get your podcasts. If you know someone who’d make a great guest on the pod (yourself included), fill out this form!

Apple | Spotify | YouTube | iHeartRadio

Anyone who has been on these ‘rising’ charts knows how fleeting and fickle they can be. In this case, I got three paid subscribers in a day. In others, it’s one. In one case, it was a trial that never converted.

So I know not to read too deeply into it — that at this point, it just doesn’t take much.

But even so, each time I make it onto the ‘rising’ charts, a few things always happen.

First, I glance at the word Rising. I get a little dopamine boost (and we all know how much I love my dopamine). It feels good. I’m being rewarded for my efforts, and I like that. Finally. I think. After three years, maybe now I’ll break the seal on [insert arbitrary number of subscribers I’m chasing today].

Then, my eyes shift to the word Parenting. It’s a self-selected category, but I think, “am I a major fraud? Parenting?? Is that what this Substack is truly about?”.

In many ways, yes, and in many ways, no.

I started my Substack three years ago when I was laid off from a job at 23 weeks pregnant. I’d been gearing up for this profound identity shift (becoming a parent for the first time) and found myself in a situation that I can only describe as unfortunate, stressful, and distracting.

Being unemployed at a time when I craved certainty and wanted to reject the unknown was tough. I needed to channel that energy into something (anything!) while I navigated that space.

And that something was Substack.

At first, it was a place where I navigated pregnancy and job loss. Then, I ended up getting hired while I was 28 weeks pregnant. That job flew me out to LA, and between new employment and getting ready to give birth, I found myself with limited time to write. I laugh at that statement now, because I now understand that I had so much time, but the way I viewed free time before becoming a parent and the way I view it now has shifted so profoundly that I truly believe that if I had the time now that I had then, I could take over the world.

That is the cruel beauty of hindsight (and perhaps something we can dig into more another day).

I told myself that when the baby came, I’d use my free time to write. I figured I’d have so much to say, and a lot of time to write it. Babies nap, after all. And my new job came with eighteen weeks of parental leave!

L-O-fucking-L.

I gave birth in July of 2023, wrote a little bit in September, and then abandoned this newsletter for the better part of 2024.

Time was a factor, but I also found writing while in the thick of it to be impossible. I had so much to say, and yet I couldn’t find the words to actually say it. And as I did slowly but surely come back to writing, I found myself writing more broadly about myself. I guess I assumed writing about myself would also mean writing about motherhood, but as time went on it just wasn’t happening.

Because parenting is the lens through which I see the entire world. Every action I take is clouded by the identity of being a mom. But that doesn’t mean everything is about being a mom.

It’s taken me a long time to be able to even scratch the surface on articulating this feeling. That my identity has shifted in a way that has impacted every fiber of my being: I am ‘Mom,’ but I am also deeply still me. My identity can’t be separated from being a parent, and yet my identity is not being a parent.

In many ways, motherhood has deepened my sense of self, has made me understand parts about me I didn’t know existed, has forced me to look at my life microscopically.

Being a parent has impacted my way of moving through the world. It is not a ‘topic’ to talk about. It’s not a hobby, it’s not a subject matter, but it is deeply ingrained in who I am without being who I am. The more I write about it, the more clarity I gain. But also, the more I confuse myself.

And this makes me feel like a bad Mommy Blogger. Not worthy of the parenting charts. But where else would I go?

When I’m in spaces with other parents — both digital and in person — I see two distinct viewpoints that like to say they are at odds with one another.

On one side, I see the groups who shout from the rooftops that they are MOM and MOM is them. Parenting here is an identity, sometimes the identity. Yes. This is true. I agree.

On the other side, I see the groups who stand firm in the fact that parenthood hasn’t changed them, and will never be their identity. That we are people and parenting is just something to do. And I agree with this, too.

So how is it possible to stand here, admitting that being a parent is both very much my identity but very much not? I love nuance, but even I’ve struggled with this one (so much so, that I’ve been writing this particular essay for over a year).

Being a parent touches everything I do, every word that moves through me. It informs how I show up in my work, how I schedule my time, how I engage in hobbies, how I take care of myself. It is deeply ingrained in me, which makes it something always present but not something I always feel I need to talk about. Because it’s always there, always a truth.

My podcast has nothing to do with being a parent. But what pushed me to start was my desire to do the things I’ve always wanted to do. And what’s made that so important to me is that I want my child to know that they shouldn’t make themselves smaller because they’re afraid of what someone might think, and the only way I could think to do that is to finally practice what I preach and face this head-on.

I can talk about sitting in a coffee shop or missing my life in San Francisco, and my perspective is being colored by being a parent now. Because it’s impossible for me to sit somewhere or reminisce about a past life without motherhood being in the background.

And sometimes there’s an experience that is actually directly linked to my experience as a parent, like when I talk about breastfeeding or how getting four colds a winter is my new normal.

It’s impossible for me to do anything, think anything, write anything without motherhood being in the background.

The longer I’ve had this Substack, the more it has become clear that I am not a ‘Mommy blogger’. I am not writing about the ins and outs of parenting regularly. I am not posting product roundups of the top ten bath toys. If you’re not paying close enough attention, you might miss the fact that I’m even a mom.

I probably could do that, but it’s not what feels natural. It isn’t my truth, and I’m happy to leave the niche to those who feel that way — in many ways, I envy them.

I think that if I were just able to stick to this ‘niche’, to write throughout my maternity leave and my return to work, to focus on the ups and downs of each stage, that this would all be easier. I see folks who’ve done that, who’ve been on this platform for 1/3rd or 1/6th of the time that I have, who’ve seen exponential growth because of that.

If I could just be a damn Mommy Blogger, maybe I’d see that too. Because sometimes it feels like I’ve alienated myself and carved out a place that no one really wants to be a part of. I don’t talk about parenting enough to take off with the other parents, but I also talk about it just enough to alienate those who don’t have children, who don’t want this content.

Where does that even leave me?

When I examine these thoughts, I know they’re not totally true. I believe that sticking to our true, authentic paths will help us find our “people”. I also believe we can create our own niches; it might just take more time.

So yeah, I’m a bad Mommy Blogger, and sometimes I’m not sure I deserve to be “Rising in Parenting”.

But then I remember parenting looks different on all of us, and I know there are others juggling the profound shift that takes over, with the acknowledgment that, under all of that, we’re still people.

Our perspectives may have shifted, our priorities may have changed one way or another, but I believe this is informed by who we were and who we are. As humans, we are always evolving, and for me, motherhood has accelerated that evolution in a way I didn’t know was possible.

I can’t separate motherhood from who I am because it’s not an entity in itself. It’s not a part of my being that I can extract and analyze under a microscope. It’s not just a part of who I am. It’s not my entire identity. It’s something that lives between and amongst those two paradigms. A consistent thread. A low hum.

Maybe that makes me a bad Mommy Blogger.

I think I’m okay with that.

The insights from Month Three are free to read, and the full Be Cringe experience is available for paid subscribers.

Get 30% off for 1 year

You can read about Be Cringe, and learn how to join us, here:

Month 3 Recap: Be Cringe About Your Blocks

I’ll be honest. I did not want …Your Blocks to be the theme for Month 3 when I first created this plan. It felt a bit too deep, too much, too soon. Frankly, I wasn’t in the mood. Surely we can deal with this later, when we’re really warmed up, right?

My reaction was visceral, and this resistance told me everything I needed to know — I need to do this now in order to set the course of the rest of the year. Whatever was coming up for me likely was one of my blocks in action, and starting to tackle it now is how I can ensure I am able to approach the rest of the year as open and honest as I possibly can.

Hopefully, you feel the same. I mean, I did give us two months to warm up, after all. What’s to come can’t unfold the way I know it can if we don’t know what’s holding us back.

I knew the first block I needed to tackle was that reaction — why was I so resistant to going through this exercise, even when I knew it was right? What can I learn about how I resist other situations?

The answer came to me instantly. I don’t like dealing with hard stuff around other people, even those closest to me. I don’t exactly suppress my emotions — on the contrary, I feel them deeply, try to work through them, spend time thinking, ruminating, etc. But I do so alone, privately, and maintain an air of everything being “all good”.

But why?

Again, a few things came up immediately.

Loudly and at the forefront was my history in social situations growing up. I don’t want to say I was an outcast or a black sheep, because I always had some sort of grouping of friends. But I also was often made fun of, bullied, and through those experiences learned to wear a mask.

I am very lucky that my bullying was rarely physical or extreme (except for the one time on a bus ride in 6th grade when a girl1 slapped me, seemingly for no reason, while everyone was singing Hey, Juliet) and that I largely existed before cyberbullying was a term that was well-known. I wasn’t psychologically tortured, but man, I dealt with a lot of assholes.

It was mostly being excluded on the playground, being made fun of for something I wore, said, or did, etc. It got to the point where it felt like no matter what I did, something would be taken the wrong way and there was no way out of it. It felt like something I was destined to go through, and I felt it would go on forever.

The fear of saying or doing the ‘wrong thing’ is something that lives deep within me.

In my American History class, I raised my hand and asked, “Where did the Boston Massacre take place?”

I assumed it was very obvious that the Boston Massacre took place in, well, Boston, so I didn’t feel I needed to specify that I had actually just come back from a trip to Boston, and I wanted to know precisely where in Boston this historic event took place.

My classmates also thought it was obvious that it took place in Boston, but did not understand that I knew that. Laughter erupted throughout the classroom, and my face turned instantly red.

“No, I mean where,” I tried to interject. “In Boston, but where?” It kept not landing, and the joke kept going.

The words I couldn’t get out were, “Obviously it took place in Boston, you fucking twelve-year-old asshole morons. I want to know the location within the city of Boston where this particular event took place, because I was just there and I am trying to orient my lived experience with the historical one”.

But I couldn’t find those words, and I kept asking variations of “where?” to try to explain myself further. I’m pretty sure this infamous question was referenced in my yearbook.

This is only one example of how the fear of saying the wrong thing started. It illustrates my worry of not looking ‘smart,’ and is one of many origin stories to my belief that I’m bad at spoken communication.

As I kept writing and working through my blocks, dozens of these stories poured out of me from all walks of life. It was deeply uncomfortable to go through, but sitting with it was healing and important. But letting these stories pour out onto the page2 was illuminating.

I don’t know how dealing with that type of scrutiny for over a decade would have any other result, to be honest. Of course I keep things close to my heart now. Of course I second-guess the way I show up and how what I’ll do will be perceived. Even as I work through this particular block, I don’t know if I’ll ever move past it.

Other blocks also appeared — blocks around money and not having what other people have (and how I fear I’ll be in the same position with my child), around not being diagnosed with ADHD until I was 29, and how that has deeply impacted how I view my intelligence, my ambition, and my overall ability.

The way I dealt with these experiences was to put on a mask and hide how I was really feeling in an attempt to be less noticed and take up less space. I realize I’ve been wearing it for so long that it started to feel glued to my face. I’m in the process of prying that glue off.

So, I was cringe about my blocks. I faced them head on, and tried to understand as much as possible why these things came up in regard to the things I wanted to do in my life.

Another thing I learned this month is that it’s okay to have something come up and not know what to do with it immediately. I knew this when I picked this theme — this one isn’t going to be wrapped up in a bow in 30 days, and it’s okay to know that something is a block, not be able to really figure out why yet, and take action and push through despite that.

I’ve launched the podcast and quit the job, even though I don’t have all my blocks figured out. Just knowing they’re there allows me to continue to explore and push back as time goes on.

There are always people who are going to have something to say — who are going to see what you’re doing and have a comment. I’ve realized my life isn’t for them, and now that I understand some of the reasons why I gave this group so much power in the past, I’m finding it so much easier to be unapologetic.

Month three was powerful. I’d love to have you join us. And honestly? Even if the full series isn’t for you, I think there’s a lot to be learned from peeling back our own layers and understanding what stops us from reaching our full potential.

Be Cringe About Your Why

Throughout the first quarter of this year, you’ve shown up and named what you wanted. You’re thinking and taking action, and you’ve reflected on what’s stopping you and your blocks (and why they exist). You’ve started to cast those blocks aside and maybe you’re getting clearer on the things you want.

But maybe you still feel a little disconnected from those wants in the first place. Or, you know you want them but are finding it hard to have real momentum in going after those goals.

It’s time to define your why.

Read more

In this conversation, we dig into how he got there, the ways ego and identity can help us make decisions, and why being yourself is often the scariest option (but for Max, it’s the only option).

We get into:

• How his experiences growing up shape how he shows up with others today

• How to know when it’s finally time to let something go, even if it’s something that is seemingly doing well and that other’s enjoy

• What it means to build community without it being a strategy

• Scarcity vs. trust as decision drivers

• Career growth and thoughts on living for retirement

I am truly so excited, honored, humbled, etc. that Max joined me, and I couldn’t think of a more perfect guest. Max and I connected on Substack (where he write’s ), and then LinkedIn, and then he was just everywhere, connected to everyone, and one of those personalities that instantly attract. He’s the ultimate hype man, will send you $10 for a coffee when you’re having a not-so-great day, and is overall the guy you want in your corner (the way he talks about his wife and family is just the absolute sweetest, too 😭🥹).

I can’t wait for you all to listen to this one. As I was editing, I was laughing and nodding along as if I was hearing it for the first time. 😅

Find Max:

• Substack:

• LinkedIn: Max Pete

Be Cringe is available wherever you get your podcasts. If you know someone who’d make a great guest on the pod (yourself included), fill out this form!

Apple | Spotify | YouTube | iHeartRadio

Which is understandable. When I see other people quit their jobs, I have questions. Do they have something lined up? Did something happen? Are they switching careers? Is this temporary? In this economy?!

How can they afford it?

So when I quit my job, I guess I should’ve expected an onslaught of questions and to explain myself time and time again. But I didn’t, and it took me by surprise.

I’m not saying I mind the questions, nor do I find them rude, off-putting, or otherwise invasive — I very much not only understand it, but have so far welcomed them. But it did surprise me.

I’ve retold the story again and again — to my former boss and colleagues, to my partner, to my friends, to my parents, to my kid, to acquaintances, to the LinkedIn universe — and I realize everyone has gotten a slightly different version of the story.

The core of my message has stayed the same, and to answer a question you may also (rightfully so) want answered, it’s this:

I quit because I needed to, and because I finally felt like I could. Yes, logistically, but also emotionally.

To me, the more interesting question is why it took me so long to quit in the first place. Why am I driven by having a job, and why does financial security feel like it’s the only thing that matters sometimes?

The short answer is that working and making money is what I’ve known for two-and-a-half decades, and this is the first time in that time that I’ve chosen to not have a job.

I got my first babysitting job when I was 11. It wasn’t consistent, but it was a source of income. Since then, if I wanted spending money, I needed to earn it. In high school, I continued babysitting. I still had my normal gigs, working as an occasional date-night sitter, but I also had regular after-school jobs that would involve me picking a kid up from school and taking them to an after-school activity or back home. I was really good at navigating babysitting ads on Craigslist, and even maintained my own listings1.

When I was 17, I became a counselor at the summer camp I’d gone to since I was 11.

Within the first three weeks of my first semester of college, I realized the money I’d made at camp that summer was almost completely gone. I quickly assembled every resource I had available to find a job.

My roommate sold vintage clothes on Etsy (in 2009! How innovative!) and I handed her a stack of my clothes, asking what would sell.

“I can probably sell this one,” she said, pulling a single red and white polka-dot romper out of the pile.

With my plan to ride her coattails foiled, I looked at the campus job board, hoping to find a job opening at the Gopher Hole cafe or at the Help Desk or the library, but what I found were scraps — there was a job fair during orientation, but I slept in that day. My two options were to either take a job as the college mascot, a Gopher named Mortimer, or to work the front desk in the Comptroller’s office.

What the hell is a Comptroller? I thought, as I applied for both. They were both work study jobs, both paid $7.25 an hour.

I got an email to audition as the Gopher almost immediately. This is my last resort, I thought. This is my rock bottom.

I picked the date and time furthest away, praying I could figure something else out by then.

I logged into Craigslist and quickly posted an ad College Student available in Towson for Babysitting!

I thought I could find someone who lived within walking distance of campus, not realizing most of the houses there were occupied by college students. Requests flooded my inbox to pick the kids up from school (“don’t worry,” the responses would read, “you can use our car!”), but I realized I would not be able to babysit in this town without my driver’s license.

As my Mortimer audition came closer and closer, I realized I was fresh out of options. I took myself to the campus gym for the first time, and spent 20 minutes on the elliptical — surely, if I’m going to be wearing a mascot costume, I’ll need to be in shape, I thought.

The day before my audition, I received an email with the subject: COMPTROLLER INTERVIEW.

I quickly skimmed the email and responded, Yes, I am still interested! and sent over a few times I was available to interview. By the end of that day, I had the job and cancelled the fateful Gopher audition.

The Comptroller’s office job was boring but easy, and it was my first glimpse of what working in an office was really like — one of the only places on campus completely devoid of students. I would sit at the front desk and do my homework and pretend I was Pam from the Office. Sometimes, they’d have me do some filing. I’d work a few hours in between classes, and come out the end of the week with just enough to join my friends for a movie or Chipotle burrito or whatever else we may be getting up to.

Throughout my college years, I picked up tutoring and mentoring jobs as well, both for middle school students in the area, but also for our very own impressionable freshmen. Eventually, I scored an interview at the Gopher Hole, the ‘cool’ cafe on campus where everything was either made in a blender or a toaster oven.

When I moved off campus my senior year, I realized everything off campus was more expensive. One afternoon, I opened the directory for the Towson Town Center, the mall next to campus, and got to work sending off applications.

The Apple Store was the only interview I scored from that effort, and I ended up working there for four years — I realized I’d make about the same going full-time at the store as I would have as a teacher in Baltimore City, my original post-graduation plan, and the benefits were better. So I stayed.

Four years later, we moved to California. I got my first job in tech, and then another, and another. And here we are, ten years later.

That history is to say: I’ve spent a lot of time working, and for me, working has always been a means to an end. From that first job at 11, I’ve had some sort of employer ever since.

That was twenty-four years ago, which is a long time to build an identity around having an income. Long enough that quitting a job, even one that wasn’t a fit, felt like it needed a reason good enough to justify all of it.

If you’ve spent any period of time around me or around here, you know this isn’t my first time being unemployed or without consistent, reliable income. I’ve been laid off three times since 2022. It’s just my first time choosing this.

Which, maybe, begs more questions. Because up until this year, I never would’ve imagined I’d willingly put myself in a situation where I don’t know where my next paycheck is coming from, draining the savings I’ve so meticulously built for an ‘emergency’ or a rainy day.

In many ways, quitting is neither an emergency nor a rainy day. But in many ways, it is both.

The last time I was laid off, I felt a strong pull to try to pick up some consulting work or figure out another path, after realizing the things I like and don’t like about work don’t actually line up with a traditional Product Manager job description.

I became disillusioned by the industry in general — is this my last job in tech? Unsure. Is this my last job as a traditional Product Manager? Also unsure, but honestly? Probably.

As much as I wanted it to work, it was hard to believe it was possible. It felt like everyone in my corner was so focused on me finding the next JOB (well-intentioned as they were) that I, too, started chasing it down.

But then a contract role landed in my lap, and I was comfortable in the unknown for quite awhile.

Slowly but surely, as news of layoffs at other companies and a tanking economy inundated me, the fear of job insecurity set in. Instead of just extending my contract, I negotiated a full time offer.

I could not have anticipated how quickly that decision would unravel, and how it would lead me to where I am today — unemployed, with no backup.

All of the reasons I’ve shared so far are true, but they’re also not the whole story.

The true, full, and real reason I quit my job is this:

Read more

In this solo episode, I lay the foundation for what I hope we’ll all get out of this podcast. I also share some pretty big news (and I do it suspiciously casually…).

This is actually the second version of this intro episode. When I first decided to launch the podcast, I wrote out what I wanted to talk about in this first episode and turned it into a script. It was polished, it didn’t ramble or go off on tangents, and overall, it sounded clean.

Too clean, if you asked me. I published it just moments after I put up the trailer, but took it down after listening again. It sounded scripted, and it didn’t sound like me.

It sounded like I wrote something for This Might Be Cringe, set up my mic, and recorded it to be enjoyed while reading on Substack. There’s definitely a time and place for that — I’ve always wanted to add recordings to my essays, but if that were the goal, I wouldn’t need a podcast.

I want the podcast to be different. I want the conversations I have and learnings and insights that come out of those conversations to happen authentically and organically, and I knew I had to lead by example with this solo episode. It’s less polished, and that feels important for me.

One of the reasons starting a podcast has felt so difficult for me (besides it being totally cringe) is that I’ve sold myself a narrative that I’m not a speaker but a writer — that written communication just isn’t my jam, that I talk in circles and ramble, and that I don’t have a voice for radio. And if I am being self-aware, that all might be true! But I know it won’t get easier unless I try.

Also, we’re allowed to do things we’re bad at. We’re allowed to have fun while learning, figuring it out, and making mistakes along the way.

I’ll be back in a few weeks’ time with our first guest! I’m really excited about the conversation we’re going to have, and can’t wait for you to follow along.

Thanks for listening to Be Cringe.

Share

Be Cringe is available wherever you get your podcasts, and this episode will be available on all platforms very soon. If you know someone who’d make a great guest, let me know in the comments below.

Apple | Spotify | YouTube | iHeartRadio