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.

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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.

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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!

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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.

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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.

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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.

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

Month 2 Recap: Be Cringe About Wanting

When I came up with the theme for the second month, I expected to face some discomfort in naming what I actually wanted out of this one precious life I get to live. I expected to have to face a few realities. I knew I’d need to take inventory and be honest about whether I was living in a way that would move me toward and away from those goals. I knew there’d be things I said I wanted that would require me to be a bit louder, a bit more unapologetic. A bit more cringe.

I expected to come to the realization that there’d be some level of sacrifice I’d need to make to get what I wanted.

But I didn’t expect how forceful naming what I wanted would be, how it would catapult me forward, shake me to my core, and not let go until I listened.

I thought I’d walk out of the month clear on what I wanted and, if I was lucky, a few small steps I could take to start getting there. In reality, this has been one of the most profound months of my life, and I’ve made some big moves.

That wasn’t the point of wanting, and if that’s not what your month looked like, that is more than okay. Whether this month led to sweeping changes or a shift within, I’d argue both are incredibly powerful.

The goal of being cringe about wanting was to allow ourselves to fully step into the things we want out of life, naming them without the qualifiers (no maybes, no some days, no “wouldn’t it be cool if I…”) and letting the dust settle.

At the start of the month, I wrote down all the things I wanted in my journal. Those included things like “I want to start a Podcast,” and “I want to write a book,” and “I want to run a marathon,” and “I want to build more of a portfolio career1 and to be my own boss.”

Once I said these things to myself, it became easier to say them out loud. At some point, I told my husband about my podcast idea. A few weeks later, he gifted me a podcast microphone. Later that day, I published my teaser episode.

The idea for my book is also becoming clearer — for starters, there are actually two books! I’ve done some outlining and have found myself able to put some pen to paper, without planning or trying. It’s really early stages — I wouldn’t expect to have anything done for a very long time, but putting my want out there really made it impossible to ignore. Small steps are very much still steps (and again, more than I expected at this stage).

I also entered the lottery for the 2026 NYC Marathon. It is notoriously difficult to get into, so I’m not expecting it, and I’m already making moves to run in ‘27 (or ‘28), but I’ve also realized if I had the chance to run it this year, I totally would.

I have a lot more to say, including one last thing I admitted to wanting and what happened after I did that, which you can read below the paywall.

But the meta-lesson here is that wanting isn’t just a passive mechanism. I thought it would be the groundwork for the rest of the year, that admitting to wanting would help me organize what to chase after, but instead, I learned that wanting forced me to act before I knew what was already happening.

So if all we need to do is admit to what we want, why does doing even that feel so hard? Why has it taken so long, and what was happening during all of those “maybe someday” moments?

And why did I find myself in this space where, once I named my wants, many of the barriers I once encountered seemed to melt away?

There isn’t one answer to this, and it likely looks different to all of us. But one thing I think is universal — we all have our blocks, things that have happened throughout our lives, beliefs we’ve picked up along the way, and unique-to-us ways we navigate the world and our own fears.

In order to figure out what that is for you, it’s time to be cringe about your blocks.

Be Cringe About Your Blocks

We all have blocks in our lives; we just don’t all know how to face them. These impact how we move through the world and affect how we see relationships, self-care, mental health, money, and our time (to name a few).

When I named the things I wanted last month, I also realized what I didn’t want, or what I wanted more than. I want to start a podcast more than I care about being embarrassed or made fun of — something that comes from my past of being bullied.

So, I started the podcast.

I want a portfolio career and to ‘be the boss’ more than I want the security and safety that comes with a W2 job — something that comes from some deeply-seated blocks I have around money and security.

I took some small steps toward an eventual life as my own boss. I spun up a new consulting offer on my website and started journaling and ideating about what it could look like to be my own boss.

Unfortunately, that didn’t feel enough, as much as I tried to bargain with myself and say it was. I wanted wanting to be enough, but I realized I was hiding behind my need for safety and security.

So I did something else, something that very well may have blown up my entire life.

Read more

I’ve discussed it in various places here — on my Notes, a brief mention in an essay, a little bit here and there in some other corners of the internet.

But I haven’t taken the time to run through (pun intended) what brought me here, how I’m feeling about it, and why this is even happening. This has been partially intentional, but also not.

I am very aware of my predisposition to sharing things before I do them, only to see the momentum I’ve built die down. I was so afraid of that happening with such a long-term goal that my first month of training was done essentially in secret, with no one but my husband and one friend knowing my big plans.

After a month, I slowly opened up but didn’t share many details. After another month passed, I started to share a few little details about a few runs, but not much else.

And now, I’ve been training for three months (and have only been back to running for four). I have three weeks to go, and I’m finally ready to put my thoughts down. Writing about something makes it real, and I think that up until yesterday, a small part of me still doubted my ability to run this half. But yesterday, I ran over 11 miles and felt great doing it. When I finished that run, a wave of knowing that I am ready washed over me. I know I’ve got this, and in the words of Olympic Gold Medalist Alysa Liu1: “That’s what I’m fucking talking about.”

This confidence is hard for me to come by. I don’t really tell myself that I can definitively do a lot of things, and instead, there’s a tiny part of me that’s always waiting for myself to fail. If I’m on a roll with keeping up with the laundry, I know I’m one weekend away from that crashing down. If I’m building up a writing streak, I’m waiting for the busyness of my life to slowly edge that out.

And over the last three months — with each sickness, tiny hip or shin twinge, busyness at work, or days (weeks!) where the weather was below-freezing — I kept waiting to find the proof I couldn’t do this. To realize that the distance set out in front of me was too much, too soon, and that it overall wasn’t for me. I could defer and run next year, I could DNS, I could show up and plan to walk part of it.

None of those are true failures, for what it’s worth, but it’s not the goal I set out for.

Yesterday’s run showed me I could. Yesterday, I traversed the longest distance I’ve run to date, weaved in and out of crowds up Flatbush and on the Brooklyn Bridge (including a protest on the bridge, where I got whacked in the face by a flag), gained over 600ft of elevation and dodged puddles (unsuccessfully) and dog shit (successfully, as far as I know).

Yesterday, I decided to change my route mid-run, once I was already in Manhattan, so I wouldn’t have to deal with the Brooklyn Bridge again (which added another 1.5 miles to the 10 I’d planned).

Yesterday, I ran what felt like a conversational pace but ended up running below my ‘goal’ half pace (and ran a negative split). I have no choice but to believe I can do this.

I have no choice but to trust myself, trust my training, and trust my ability to commit to long-term goals. Scary!

This is not the first time I’ve signed up for a half-marathon. In 2019, when living in San Francisco, I signed up to run the SF Half — but a bout of bronchitis knocked me down, and I couldn’t quite find my footing to get back to training. Between the summer of 2019 and the fall of 2025, I’d go on to run about five times. A move back east, a global pandemic, a few new jobs, a wedding, a baby, three layoffs. I told myself running was part of my old life. So what happened? How did I find myself back here?

Sometime in 2025, I decided to commit to walking outside every day for at least 30 minutes. The goal was two-fold. One, to force myself to move a bit, even when movement felt tough. And two, it made me get outside every day.

Working remotely, there are times when it can hit 7pm, and I realize I haven’t seen the outside world. It’s probably not surprising that with the winter we’ve had on the East Coast this year, I’ve been slacking for a while. But for a good chunk of 2025, my walks were a part of my daily life — something I protected.

I started this before my layoff this summer, though some of the hotter days we encountered made it impossible to get a full 30-minutes outside. This continued through fall, where the walks became longer as I was grateful to no longer be in the thick of summer (and perhaps knowing this would be a particularly tough winter, too).

Sometimes, the walks were easy to get in — I’d drop my kid off, pop in my headphones, and stroll through my neighborhood or Prospect Park. Some days I was able to take a leisurely lunch break and actually get away from my desk for a bit — something I don’t do often enough.

Other days, it felt more difficult. Deciding whether to walk or to write during nap time, bringing my husband and kid along with me for a walk after daycare pickup. Sometimes it rained. Sometimes I just didn’t want to be outside, but for about two months, I did it anyway.

One cool Saturday in October, something strange happened. It had been raining all morning, and it was one of the first days that truly felt like autumn.

I looked outside after putting my kid down for his nap and noticed the rain had stopped. My weather app confirmed — no rain for at least an hour. I started to get dressed for my walk, figuring this would be the best time to get out there. But instead, without much thought, I started getting dressed for a run.

The idea of starting to run again had been swirling around my subconscious for a few weeks at this point, but it didn’t enter my conscious brain as something I could (or even wanted to) do. I can’t quite pinpoint exactly what it was, but likely a mix of the influence of walking amongst the runners in Prospect Park, of a few YouTube videos I clicked on that forever changed my algorithm to favor ‘running content’, of the twinge of nostalgia I feel each spring and autumn for my time living in San Francisco (where the weather is essentially spring or autumn all year round, and what I think of as perfect running weather).

I grabbed my 5-year-old running shoes, downloaded the Runna app, and set out for a 2-mile walk-and-run interval session in the Return to Running plan. It was hard. It started raining within five minutes of being outside, and I could’ve turned around as soon as the first drops of cold rain hit my hat-less head. But I finished that run, felt good, and immediately checked my calendar to see when I could run next.

I tried to fight it, but I knew I was back. It felt harder than I remembered, I was slower than I remembered, new parts of my body hurt, but I knew right then and there that I wanted to continue running. I could run twice a week, I told myself. That would be enough.

I went on two more walk/runs that week, and then fell sick with my first cold of the season. The fever and fatigue had me bed-bound for a few days, and the chest cold that lingered kept me off my feet for another week.

I could’ve stopped there, but instead I hit the ‘restart’ button on the six-week plan that promised to have me 5K-ready by the end of it, by the time the mucus cleared.

On another whim (in what I can only see as a series of whims), I typed December 6 5K Brooklyn into Google, and found a race that started in Prospect Park, less than a mile from my house. I signed up right away.

My first week felt so good that I immediately upped my plan to include three runs a week (on top of the three days of strength training I’d been maintaining for most of the year). I’d run before work started during the week and during nap time on the weekends, and committed to doing so, even in rainy weather. I started figuring out how to dress as the temperature dropped further. I bought a used down running vest from Mercari and invested in a few pairs of running-specific leggings. I bought a new pair of running shoes — the same style I wore six years ago, after a gait analysis.

I went on a work trip to Florida and relished running alongside the beach (and surprised myself by keeping up the habit while traveling). I’d go to daycare dropoff underdressed for the weather so I could run right after, to maximize my time before work. I thought I’d have to skip a run during my writer’s retreat — the beautiful Catskill property was situated along a very busy interstate — but ended up running up and down the long driveway instead.

I hit every planned run during Thanksgiving Break, sacrificing other nap time activities more often than usual.

And then, a week and a half before the race, I got sick again.

With each skipped run, I felt a nagging feeling. Of course I can’t do this, I thought. There’s no way I’ll be ready now.

Despite not feeling ready, I got better just in time for the 5K. I hadn’t run in over ten days, but I knew I had to go and prove this to myself.

Because the other thing that happened in between work trips and writers’ retreats and DIY Turkey Trots?

On what I can only call the whim of all whims, I put my name into the lottery for the NYC Half Marathon, fully expecting the odds not to be in my favor, and ended up getting selected.

I knew I had to show up to this 5K. My only goal was to run the entire thing, which I wasn’t even sure I could do now, but I knew I had to try. So, on a chillier-than-usual early-December morning (hello, foreshadowing for this entire winter), I made my way into Prospect Park and completed my first race in six and a half years.

And yes, I ran the whole thing.

It wasn’t my fastest 5K, but it wasn’t my slowest either. I crossed the finish line, grabbed my bagel and hot cocoa, and walked home.

Later that night, I signed up for a 14-week half-marathon plan on Runna. 99 days to go.

I expected to keep up with my three-runs-a-week schedule, but quickly upped it to four, missing running on the days I wasn’t doing it. Week over week, my mileage slowly increased, my intervals got a little harder, and my ‘conversational pace’ got a little quicker. My long runs built on each other, and I entered the new year feeling like I was on fire.

I’ve since gotten sick two more times and have missed a few runs here and there, but overall? I’ve been reasonably consistent.

A few things helped.

First and foremost, I bought a treadmill. From the way the season had started (and having listened to my husband talk about the Farmer’s Almanac winter prediction since summer), I knew it was going to be a rough one2.

I can almost guarantee that if I did not have the financial and square-footage capital for this purchase, my training would’ve been nowhere near as successful. There’s a good chance I would’ve deferred, or even have found myself forgoing running altogether.

Sure, I could’ve joined a gym and would’ve needed much less money (and space), but I know myself. Sometimes getting dressed and filling the water bottle felt like a massive barrier on the darkest, coldest, and snowiest days, but having a treadmill right there made it possible to overcome them. And sometimes, I had exactly enough time before work or during a nap to get just the run done. If I had to get dressed for outside first? I would’ve probably made about half of the indoor runs I actually did.

But I also changed my mindset — I started (literally) embodying the phrase it’s a (half) marathon, not a sprint. It’s winter. Bad weather is inevitable. I had a toddler. Getting sick is inevitable. I am human. Other human roadblocks are inevitable. I forced myself to zoom out and focus on long-term consistency over day-to-day perfection.

So, I decided to focus on a few things3. I committed to running all my long runs first and foremost, even if that meant moving things around. One week, I felt the familiar tickle of a cold coming soon. I ran six miles on the treadmill that evening (which isn’t advice I’d give anyone else), but it helped me feel consistent when I was out for ten days in January, knowing I had that long run under my belt.

Then, I mostly focused on my weekly mileage. As long as I was roughly in line with my plan, I knew I’d be okay. My plan had two taper weeks built in, and I used them to aid recovery during the remaining two sicknesses. Maybe sheer luck, but focusing on weekly mileage and being flexible allowed me to take the recovery days I needed.

My goal for this half is to more or less just run the whole thing (though I am accounting for one bathroom break), so the first thing I let myself drop or swap out was my ‘workout runs’ — hard intervals, tempo runs, or hill repeats. Instead, I would either skip them or swap them for easy runs, again depending on what supported my weekly goals. I generally followed the rule that ‘most’ of my runs should be ‘easy’.

I didn’t sweat a missed run here or there, nor did I freak out when I needed to rest. I started embracing paces that felt too slow to be productive, and trusted the process. A way of thinking that’s traditionally difficult for me, as someone who pays way too much attention to the details and treats most other marathons like sprints.

I found joy in the act of running itself. I found fulfillment in comparing my runs and seeing the improvements. I laid the groundwork, brick by brick.

All of that is what’s brought me to today. Three weeks out from my first half-marathon, filled with a confidence I’ve not found before.

I’m nervous, I’m excited, and I know I can do it.

So, what’s next? I’ll keep running. I’ll likely get my gait re-analyzed to make sure I’m in the right shoes, since I’ve learned a lot about cadence and form and all of that over the past four months. And because I have no chill, my second half-marathon is also on the books — I entered the lottery for the Brooklyn Half in May, and will be running that too.

I don’t know if I’ll keep doing races, if I’ll start training for my inevitable try at running the NYC Marathon, if I’ll take a break, or if it’ll be another six years. I’m trying not to make too many decisions about the future in this moment, and instead hold on to the big things I’ve accomplished already and the things I already know are to come.

You Might Also Like…

I’ve wanted to start a Podcast for a while. Like, for years. And when my husband gifted me a podcast mic for Valentine’s Day, I felt I had no other choice but to jump right in.

That’s the power of wanting.

Welcome to Be Cringe, the podcast that explores what happens when you start living for yourself and stop worrying about all the other noise. This might be cringe, but we're doing it anyway.

There is something you want to do — you’ve just been letting your fear (of embarrassment, of failure, of whatever) get in your way. If that’s you, you’re in the right place.

More to come soon!

Be Cringe is available wherever you get your podcasts, including right here on Substack. If you know someone who’d make a great guest, let me know below.

Apple | Spotify | YouTube | iHeartRadio

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

Wanting something sounds easy. By just wanting something, it should be enough to set all else in motion, that plants a seed, that gets us going. Wanting is likely the reason you’re curious about joining in on this experience — after all, we know what we want to do, many of us just find it too embarrassing to actually do it.

In practice, I find it’s not that simple. Wanting does set all of this in motion, but we didn’t start there. We started with showing up.

Month 1 Recap: Be Cringe about Showing Up

Showing up allows us to evaluate what we’re already doing, and lets us see that momentum build quickly. Showing up doesn’t require a checklist or too much thought — it lets us jump into the action without getting caught up in our own brains.

Before I started this month, I naively thought that showing up would be all these little actions I planned. I thought I could pencil in all the ways I would show up, do it, and check off the box.

What I learned is that in reality, the opportunities to show up actually presented themselves as small, in-the-moment decisions, and that following the urge to do something mattered more than executing a plan.

For example, I said I wanted to share my Substack more publicly as an act of showing up, but when I looked under the hood that felt bigger than showing up. Showing up was continuing to write, when I could, amidst a particularly busy month.

But it also came up in another surprising way. I have been obsessed with the ‘This is my impression of an owl…’ trend. I’m late, I know. While watching Chicago PD, I had an idea for one. But I don’t make reels, I told myself.

But I could, I retorted back.

So, I made the Reel. And I made my instagram public to do so.

I didn’t really have an endgame here — this isn’t some grand plan to get exposure or whatever. I just wanted to participate in a silly trend, and so I decided to show up and did it.

And when I got another idea a few hours later, I did it again.

I’m not diving head-first into short-form video. This isn’t setting some big content strategy in motion, but it allowed me to show up in a way I (honestly) find really embarrassing.

Showing up was exactly what I needed to kick this off. It helped me discern in the moment what I wanted to do vs not, and gave me permission to follow through with what I wanted.

But it’s also clear that wanting itself feels cringey sometimes. And that’s why for Month 2, we’re going to be cringe about wanting.

Monthly recaps are always available to all readers, so free subscribers will be able to learn more about month two of Be Cringe, Be Cringe About Wanting, when I share my next recap (on the first Monday of March).

If you’re curious now and want to join us, we’d love to have you.

Get 30% off for 1 year

And if you’re already a paid subscriber, keep reading!

Month 2: Be Cringe About Wanting

Showing up creates space, and for me, that space reveals desires and wants — even if they are uninvited.

Read more

I’ve decided to post this all the same, and tried to scramble to add some more of the resources I’ve seen come out, but if something is missing I’d love to add it. Feel free to leave a comment below.

Also — TODAY is the National Shutdown: no shopping, no school, no working, . I reference it below, but calling it out above the fold because it’s happening now. Striking and protest is a privilege, but if you can do it, do it.

There are also protests nationwide today. You can search what’s happening in your city here.

I don’t feel the need to preface this statement so I’m just going to say it: what’s happening in Minneapolis is horrendous. Nothing shocks me any more, but that’s not a reason to just let it happen.

Defund ICE. Abolish ICE. Fuck ICE.

I have oscillated in how ‘loud’ I am politically, and feel like with each news story that leaves me more outraged than the next, I get less and less sure of what to say. I am guilty of shouting into an echo-chambery void, I often feel I don’t have anything to say that others haven’t already said, I don’t want to center myself or claim authority as this country continues to live up to its ~3001 year legacy of oppressing black and brown people.

I am also more afraid than I’ve ever been to use my voice, and I have been doing a lot of work to reconcile with that. While 10 years ago I had no problem going to protests (alone), writing publicly about my thoughts, etc, these days I second guess that a lot more. Afraid of being doxxed, of putting my family in danger, of losing my job and being put on more ‘lists’. Afraid to go to a protest because I don’t know if I’ll make it home to have dinner with my family. In a way, I feel like my outward activism has regressed, while my motivations are stronger than ever.

So first and foremost, I am grateful and feel eternally indebted to the people who are showing up, who are using their bodies and their voices and are standing up to these injustices. I’m regaining my sense of self in this regard, I am regaining my bravery. I am trying.

To quote , “you don’t have to do everything, you just have to do something. And if doing something is scary: you know what’s even scarier than doing something? Doing nothing…because something can always be done”.

To echo a point I made ~2 paragraphs ago, I’m not writing this to center my narrative, but as I sat down to plan some essays for February it felt disingenuous to just keep going as if nothing is happening. Sure, I could throw a few notes up there and keep posting graphics on my Instagram story, but none of it feels like enough.

This doesn’t either, nothing feels like enough. But amongst these times, I find comfort that there are folks who are dedicating time to report, to educate, to gather resources. So if you’re wondering ‘what the fuck can I do?’, I am too. Here’s a quick roundup of actions to take, resources to bookmark, and a list of places I’m choosing to get my news.

Necessary disclaimer to protect myself: none of this is financial, legal, political, or any other sort of advice that I would need any sort of credentials to give. This is opinion, and is a collection of things I have found that are helping me get through this. This is not financial or legal advice!!! I am not telling anyone what to do!

Also, all links and actions are recommended as of the date this article is published. If anything changes, I’ll try to keep it updated, but bear with me if I miss new news or changes to any of the below.2

Specific Actions to Take

Join in on TODAY’s National Shutdown and Strike

If you are able to, call out of work and join in on the National Shutdown happening on Friday, January 30th (that is TODAY. Better late than never, right!?!?).

There are also protests happening throughout the country. Many are happening on the 30th as a companion to the National Shutdown.

And if you are reading this after the strike is over, protests are expected to continue. And whenever you can, shop local, and divest from companies that fund ICE (more on where to find those below).

Call Your Representatives

Yesterday, the senate voted 45-55 against a six-bill government funding package — all democratic senators and seven republicans voted ‘no’ on the bill — proof that calling our representatives works (even though it might feel like we shouldn’t have to).

Calling our representatives is important even though this particular bill has not passed.

The app ‘5 calls’ organizes various issues to contact your representatives about, shows which representatives are relevant, and provides call scripts. In addition to sharing my own desire to have my senators vote ‘No’ on yesterday’s bill, I’m also using the app to ask my state leaders3 to Support Minnesota, to Stop ICE’s attacks on immigrants and citizens, and to demand we stop supporting ICE in New York.

gave some great advice on how she’s handling her communications with her representatives, since they were both decided ‘nays’ on yesterdays bill. Still applies.

Write your Representatives (After you have called them)

While calling your representatives is the best and number one way to let them know how you feel, writing also has some impact.

I like to use Resist Bot to quickly send messages via post, email, and fax. Text RESIST to 50409 to have them suggest campaigns, or take a look at state-specific letters here.

The ACLU has a general guide that gives helpful tips to consider when reaching out to your representatives.

Donate

Below, you’ll see a few roundups of guides that share ways to get involved — donating your time and money are useful ways to spread the wealth of our resources, however we can best do that.

Two of the most comprehensive resources for finding places to donate to are this Google Doc and this Reddit thread (I speak about both in more detail below).

Learn about the Tax Strike

This is not financial advice. This is not legal advice. I cannot be more clear about this! I am sharing this as something that you can learn about if you chose to, and engage with if it feels plausible to you. I am also still learning and am not at a point where I am recommending involvement (just giving you something you can learn about, should you choose to).

A friend shared this reel about engaging in a Tax Strike in a way that is legal (and without risk of retaliation). I understand this at a very surface level, and think it’s very important to talk to a tax professional if this is interesting to you.

The flyer attached attempts to explain it, but basically you’re not not paying your taxes. Instead, you’re creating a realllllly lloooonnnnnggg road for the IRS to get your funds into their hands. This is at least how I understand it. But again, please talk to a pro!

Here are a few more resources to help explain it:

• What is a tax strike:

• How to avoid penalties:

• Tax Strike Guide Links, put together by Oregon Congressional Candidate Zeva Rosenbaum. This has the forms to file, a link to the high-res Tax Strike Flyer (shared above), and resources.

Resources, Guides, and Where to get the News

Guides and resource roundups

• How You Can Help: MASTER LIST (r/minnesota). I found this list put together by u/cataloo on the r/minnesota Subreddit to be an incredibly helpful place to start. It outlines organizations and mutual aid funds to donate money to for those not local, and while the list also features a lot of in-person actions to take in Minnesota itself, I find it helpful nonetheless.

• How to Fight Back Against ICE Right Now, by . published practical guide on how to help Minnesota citizens, companies supporting ICE to boycott, and even includes a plea to members of the media to focus on how they’re framing their stories.

• If every American did 3 of these 5 things, ICE would be stopped in its tracks, by . Leona outlines five actions that would have incredible impact if we could all commit to three. Some of the resources Leona shares I’ve not seen anywhere else, and I appreciate that she includes the cost to participate — both financial, but also sharing how much time these actions cost.

• A late addition, but used ’s weekly newsletter to share a roundup of what we can do now (aptly titled the weekly: what we can do now).

Where I’m getting my news

• is probably my most-read independent journalist on Substack. His newsletter is known for leaking memos and documents when no one else will (he released Luigi Mangione’s manifesto when no one else would), and continues to report and share even when he’s under investigation himself.

• ’s News Not Noise has been an excellent source of news for me. She’s been independent for almost a decade, and I appreciate her directness. She also has published a Google Doc of resources to directly help Minnesota.

• If I’m trying to understand the core of an issue, I’ll head to Politics Made Easy first. simplifies politics, and recently what’s going on with ICE, in a way that makes it accessible without dumbing it down.

• I’ve been reading ’s newsletter, Emily in Your Phone for years now (and yes, I usually am reading it on my phone).

Is that it???

What else can be done? Showing up is always the first step. Getting involved at a national scale is important, but investing in our local communities can be just as important. Connecting with our friends and families, reaching out to folks online doing important work, and just doing something, anything.

As someone that often simultaneously feels like there’s too much to do and there will never be enough to do, I have to remind myself of that. Finding the balance of being informed and involved while also tending to myself, my home, my family.

It’s a daily and lifelong battle, but the resistance was never supposed to be easy.

If I am being honest, I just wanted to continue and keep going. I didn’t feel this sense of ‘one thing closing and another thing opening’ like I often do at the end of December. It didn’t feel necessary, and everything I tried to do — or write — felt forced.

My routines felt good. My to-do lists were more or less finding their way towards completion (though maybe sometimes more slowly than others). I started training for a March half-marathon in November, which has forced me to be on my A-game when it comes to both moving and fueling my body appropriately. I felt like I had a good balance between work and home life, and it was more or less working. I felt like I could just roll into January as if it were nothing.

Maybe there were areas of my life that could use refining, but I didn’t feel like anything needed a major overhaul. Resolutions just didn’t feel like they’d serve me. If anything, they felt distracting.

But as the end of the year marched closer, I realized I needed something. While I didn’t want a calendar that doesn’t match the reality of our seasons to dictate my goal-setting, I became hyper-aware of the goal-setting and end-of-year reflections happening all around me. The energy became infectious, and I found myself wanting to participate.

I still rejected the idea of setting resolutions, but I decided to first take inventory of what was working and what was not, and go from there.

I realized there were things that were working well that I wanted to keep, things that I wanted to let go of and re-evaluate, and things I thought I could add more of into my life.

For any tech girlies, I guess you could say I ‘stop/start/continue’-ed my New Year’s reflection.

Taking an inventory felt more aligned than having ‘resolutions’ — to be honest, I don’t feel like I have the time or energy to set (or track) proper goals in the traditional sense.

And while I jest about modeling this after the ‘Retros1’ I’ve sat through for years as a Product Manager, these buckets really did emerge organically. I wasn’t trying to fit the reflection of my personal life into an agile ceremony, it just happened.

I didn’t realize what I’d done until I listed all of this out and started bucketing my own behaviors under three headers: Let it Go, Let it Be, Let it In. Not goals, but also, not not goals.

Taking Inventory

I took inventory of what in my life was going well and what I thought could be better. From there, a natural pattern of things to keep doing, to stop doing, to start doing arose to the surface. Driven by that New Year’s desire to ‘be better’, while also allowing myself to acknowledge the parts of my life I didn’t need to overhaul.

Let It Go

The first section that emerged was all the behaviors and parts of my life that I felt I would be better off without.

These are the things that start to get in the way of the life I want to live, that make my day-to-day harder, and overall feel like they take more than they give.

For me, this looked like letting go of:

• Treating work urgency as a personal emergency

• Staying up late because I feared my ‘free time’ ending

• Justifying to myself how I spend my time…

• …but also excusing myself for not spending time on things that are important to me (like writing) because of ‘busyness.’

• Not naming my feelings publicly (and answering “fine!” when someone asks how I am)

• Worrying too much about what others think, about feeling embarrassed and how my actions are perceived — this one is what led me to launch my ‘Be Cringe’ series

Maybe some of these things worked at one point in my life, but they no longer do.

Let It Be

Arguably the most fun section — the things I am already doing well, that I want to keep doing.

For me, this meant continuing things like:

• Training consistently, even when the runs or lifts aren’t exciting (and even when winter is wintering, and I’d rather lay in bed under blankets and in my favorite sweats)

• Leaving the house every day (and allowing myself to count the short walk to and from daycare)

• Keeping up with basic housework in a way that makes the following days easier

• Feeding myself regularly and adequately (and yes, eating a bunch of protein)

• Writing when I can

These are the things that are the easiest to name because I am already doing them, but can often be hard to give myself credit for.

Let It In

Finally, I recognized the areas of my life that would perhaps improve if I added something new.

For me, this looks like letting things in, like:

• Going to bed when I say I will!

• Making more room for writing

• Organizing my work to-do list in a way that keeps me organized but also reduces the feelings of dread

• Talking more openly about the things I’m already doing (and the things I want to do!) instead of keeping them guarded

• Exploring more writing pitches, more partnerships, and more curiosity in my creative pursuits

• Finding time to read — even if it’s just a few pages a few days a week

I admittedly had to be careful here — this is the part that can really start sounding like resolutions. So, instead of making these rigid commitments or promises, I treated them like areas to explore.

Bringing it all together

With my inventory and three themes, I did some journaling and self-reflection. I made a little vision board on Pinterest and set it as the background on my iPad.

I also did a tarot spread to support this, with each card position representing one of those themes. If that’s your thing, I invite you to do the same!

I set it aside and was ready to keep moving after my brief pause to reflect. I figured things wouldn’t change too much, but I was grateful to have taken the time to take this inventory.

I had no idea what would be waiting for me in January.

Because when January started, and I went back to work, I felt my world crashing down all around me.

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Welcome to the first month of Be Cringe. I am so excited you’re here, and how appropriate that you are. Because this month’s theme is to be cringe about showing up. Which you’ve already done.

By opening this post, continuing to read, and even considering participating, you’ve already shown up.

If you want, you can stop reading now, check the box, and call Month 1 complete. Hooray! You did it.

But if you think there’s more work to be done, and more ways you want to show up (which, if you’re still reading this, I suspect there might be), keep reading.

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“Wait,” you think. “Is this too cringe or embarrassing? Does it look like I’m trying too hard? Will I regret this when people actually see it?”

And so, you don’t do The Thing™.

If you’re anything like me, this isn’t a rare occurrence but rather a cycle that has continued for years (or…decades).

I know I’ve spent way too much time thinking about how I may be perceived by others and wanting desperately to stop the cycle. This exact desire is what prompted me to rebrand my Substack to This Might Be Cringe. After writing Embarrassment is Fake, I felt inspired to show up as my authentic self, despite the cringe.

In many ways, it worked. I went from posting less than a dozen essays in 2024 to posting over 40 in 2025. This was because I committed more time to my writing, but also because I decided to stop censoring myself to comply with what I thought would be more ‘palatable’. I’ve seen immense growth in how I show up in the world, in the tough conversations I have, in sharing more of my ‘whole self’ with the people in my life.

But still, there are areas I hold back on. I do a double-take before taking a selfie in public, I try to minimize the amount of space I take up in the world, and I still self-edit more than I’d like. I’m still afraid of being cringe, and I’m ready to do something about it.

I bet some of you are too.

That’s why I’m ecstatic to introduce you to Be Cringe, a monthly practice that allows you (and me!) to take small steps to living a more authentic life (even when it feels embarrassing). I’ve been sitting on this for almost a year, and I’m so excited to finally share this with you all.

What is Be Cringe?

Be Cringe is a monthly practice about letting the person you are on the inside show up more freely in the world.

Each month, I’ll send out our new theme: Be Cringe About Showing Up, Be Cringe About Taking Up Space, etc.

These themes are intentionally open-ended and are designed to apply to your life. You’ll never see a blanket directive like “compliment one stranger each day this month,” unless that’s the way you want to embody a theme, of course.

There will be a subscriber chat to share wins along the way — more on this, and what else to expect, below.

Why Be Cringe?

It’s really easy to want to live authentically, but harder to act without a guarantee of success or approval. I truly think we’ll all shine brighter and bring more to the world if we allow ourselves to loosen the grip we have on being perceived.

Many of us have learned to protect ourselves by staying quiet, playing it ‘cool’, containing our emotions, or making ourselves smaller.

If you’ve ever felt like you’re waiting to show up with confidence, this is for you.

Why monthly?

A month is long enough to notice patterns, to practice, to fail, to try again, and to find your groove, while still being short enough to be able to see the light at the end of the tunnel. It’s meant to be non-burdensome while still having impact.

How to Join

On the first Monday of each month, I’ll publish a post introducing that month’s Be Cringe theme. I’ll share why it’s important, how I’m approaching it in my own life, and a few ideas for how you might explore it in yours. I’ll also share a recap on how the previous month went.

As a free subscriber, you’ll see the theme and get a brief overview of each month.

If you’re a paid subscriber, you get:

• the full monthly post with deeper reflections and ideas

• access to a private subscriber chat

• early access to each month’s theme in the chat before it goes live

The chat is there for sharing wins, asking questions, or just reading along. Participation is optional!

While I’ve planned a full year of themes that build gently over time, there’s no wrong time to join. Every month stands on its own, and you’re welcome to jump in wherever you are, whenever you’d like.

I’ll be doing this whether five people join or fifty — either way, I’d love the company.

If you’ve been craving a way to show up more authentically and honestly, I’d love for you to join me. Subscriptions are $5/month or $50/year, and for 2026 you can snag a full year of Be Cringe for $35 (about the cost of one OMNY tap per month, RIP, MetroCard). This will be active for all of 2026, and can only be accessed here.

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Our chat is open now, so whether you’re reading this before the challenge launches, during the first month, or halfway through the year, I’d love to have you join in.

You don’t need my permission or guidance to step into your own, full, authentic self. I believe this already exists within all of us. But I also know this work is often easier (and maybe even a bit more fun) with some structure and a supportive community.

I’ll see you for the first month of Be Cringe on January 5th, and every first Monday after that.

If you’ve made it this far, I’d love to know: what’s one way your life would improve if you released the expectations and perceptions of others? What’s the hardest thing to let go of when you think about stepping outside of your comfort zone? What scares you, and what excites you?

I realized while reading it that I’ve barely touched my sofa this week. Instead, I’ve been doing some deep cleaning, writing, keeping up with half marathon training1, connecting with friends (both in person and afar) and overall catching up on ‘life admin’ — I’m getting a much-needed haircut on Friday, and an eye exam that needs to be scheduled stat.

And despite that, I feel rested. But in an online world where I am inundated with images of people becoming one with their sofas, eating and drinking to oblivion, and wearing the same sweatsuit for 4 days, I can’t help but wonder if I am resting wrong. Should I be rotting instead? Is my desire for productivity, or am I just redefining what rest looks like for me?

The week between Christmas and New Year’s has become known as a week with no rules, a week for ‘rotting’ on the couch, and a week to lose all sense of space and time, after all. And while the idea of deep rest sounds incredibly appealing, I actually think I like knowing what day it is, I like taking a shower, I like the idea of a more nuanced pause.

I have a long history with working over the holidays. When I was in college and I’d come back to New York between semesters, I always found a job to help spend my time. One year, I babysat for a famous fashion designer and his family on the Upper East Side. When their usual nanny couldn’t go to Miami with them, they brought me. We flew private, but I was with toddlers for about 12 hours a day.

Another year, I worked at the holiday markets in Columbus Circle and Bryant Park, selling triptych photographs of NYC’s bridges or random flowers. They weren’t my taste, but I sold a lot and worked an hourly rate plus commission. I became chatty with the booths next to and around me.

After that, I was either in retail or on customer-facing teams, always working through the holidays and in that sacred time between Christmas and New Year’s. No rest, no rot.

In my time at two D2C e-commerce darlings, there was no concept of a holiday in the e-commerce world — I was managing customer support teams, and we spent the 26th gearing up for a slew of sizing questions, exchange requests for when a partner or parent inevitably bought something in Sand when they wanted it in Cloud, and the dreaded, but inevitable, “you ruined Christmas, my package is lost” emails.

My last year working for one of these companies, I worked every single day, weekends included, between Black Friday and January 5^th. That’s a long time.

But working holidays was the reality for me, and I didn’t even consider a world where I could (or would) stop doing so.

In December 2020, I had transitioned to working a proper tech job, at a company with a holiday code freeze. In my new role, I didn’t work with teams who interacted with customers, and so I was given the time between Christmas and New Year’s completely off for the first time in my working life.

It was after that holiday, when I finally got a taste of how the other half lived, that I made a promise to myself: I’d never work that week again.

Being the first holiday season of the pandemic, there was a lot of rotting. I don’t remember much, but I know we stayed home and spent a lot of time on the couch. The days blended into each other, and I relished in my rest (or rot).

I’m happy to report that since then, I’ve been able to keep this promise to myself.

The first three years, for one reason or another, I did relish in the rot. 2020 and 2021 being the height of the pandemic, so rotting was natural. Then the next year, I was pregnant and tired, so rotting became my default.

In 2023, things started to shift a bit. I had a five-month-old, and had been back at work for a month already — too much, too soon, but that’s a story for another day.

I was also mourning the death of my grandmother, who passed away the morning of Christmas Eve. I didn’t want to do anything. I canceled the New Year’s party we had planned at the house. The haze hit harder, and the rot started to take a dark turn — becoming one with the couch no longer was an act of joyful rest.

Sometime after Christmas that year but before New Year’s, I bundled my then five-month-old into his stroller and forced myself to go on a walk in our neighborhood. I didn’t realize how much I needed fresh air, movement, and a shower until the cold air — and then my sadness — made my eyes water.

After that, I vowed to take a walk every day until I went back to work. A simple act of self-care and a moment of anti-rot.

My grandmother passing has (and will) forever change the way the holidays feel. She had a love of Christmas, and the irony of her passing on the 24th of December feels too cruel, even for this cruel world. Rotting during ‘Rot Week’ no longer serves me, at least for the time being.

Last year, my parents took my son for a few days between the two holidays. What a gift!

Armed with the knowledge of how crappy rotting felt the year prior and ample free time that I didn’t need to spend parenting, I over-indexed into a different mode. I declared it my week of Getting Shit Done™.

I made a plan to clean every corner of the apartment, armed with a room-by-room to-do list and day-by-day plan2. I got a haircut, I went on walks, and I napped. I wrote. I meticulously planned these days so nothing would be lost.

I wanted to avoid the rot altogether.

This year, I’m taking a different approach — though I didn’t really plan it that way.

The days immediately following Christmas were spent mostly at home, with my husband and son. Playing in the snow, hanging out in PJs, cleaning up Magnatiles six times a day, slowly cleaning the house, running in between naps, eating food my husband has cooked.

And again, my parents have my son again for a few days.

At first, I thought I was going to do it all, just like that. I drafted the list of what needs cleaning, started to time box those tasks, and started working through the other things that need doing (the aforementioned haircut, runs, and eye exam).

Then, the first day hit. We made it back home after dropping off our kid, I started a load of laundry, did a workout, and then fell asleep.

I woke up from my nap in a stupor, not knowing how much time had passed or where it all went. I tackled the dishes in the dishwasher, ran another load, and decided I was done for the day. I laid in bed, watched a few episodes of my current show (Six Feet Under), and went out to dinner with my husband.

My time-boxed plan had already been thrown out the window, but as I tallied everything I did I still felt proud. And I knew there was always tomorrow. “Tomorrow” was the first full day, after all.

Tomorrow came. I woke up slowly, reading my book and cuddling a cat on the couch. I emptied some trash bins around the house, I cleaned out the fridge, I folded the laundry from the day prior, I went on my run. I wrote a draft of what you’re reading now3.

A warm up compared to the day I had planned, but again — I was done. I watched more Six Feet Under, read more of my book, and my husband and I went out to dinner again.

Last year, I remember feeling disappointed when I didn’t get a chance to clean out the big scary closet. I had done so much, and yet I was focused on the thing I didn’t have enough time to do.

This year, so far, these feelings haven’t come up at all. Every decision to not declutter one space is a decision to do something else for myself — it’s another chapter read, another mile run, another hour napped, another episode watched.

There is something about being an adult with a job, responsibilities, and minimal time to myself that really makes these moments not only necessary, but also incredibly joyful and rewarding. Rewarding not because I’m checking things off the list, but because I’m allowing myself to follow my own momentum and see how the days unfold.

The idea of just sitting on the couch as I used to doesn’t sound relaxing in totality, but this year I realize I do want those moments to exist, I just don’t want them to take over.

I was texting with a friend who said “vacation time is my time for doing chores and not being stressed about them,” which perfectly puts how I’m feeling into the words I couldn’t quite find.

This week is about finding the space to figure out what I want to do. I am armed with a ‘could-do’ list instead of a ‘to-do’ list, and each day is about finding the right balance of execution and stillness.

On the outside, my week probably doesn’t look like rest. But to me, the luxury of waking up at 9am, of just being responsible for myself, for being able to throw on an album while I clean out the fridge or break down boxes is in fact a form of relaxation. But so is balancing it with a slow morning spent reading, or writing at a cafe, or getting outside to run four miles in 31º F4 weather that “feels like” 17º5.

It’s taken me a long time to view taking care of my home as an act of self-care, and now that this is true for me, it feels there is no going back.

Being able to choose when I fold the laundry vs cramming it in between naps is completely different, at least for my psyche.

One is an act out of obligation and feeling time-poor. The other is something I’m choosing to do because I feel time-rich. It’s a completely different impact on my nervous system.

Choosing not to do something because I know it doesn’t have to be done just because I have free time is a gift too. If I don’t clean out the closet I have my eye on this week because I decided to do something else instead, that’s okay. It can get done another time. I don’t need to fill every moment of this week just because I can.

To me, that’s the winning formula. That is joy. That is rest. That is restorative.

I am pretty good at tending to myself, but it always feels like it is on someone else’s time — a run after daycare drop off but before work, a load of dishes done after we’ve eaten and my kid is in bed, having to make a decision every Sunday as to whether I want to use nap time to fold laundry or write.

This week is about embracing those things I do anyway, but truly doing them on my time, in the most joyful and relaxed way I can. While the internet sometimes makes me feel like I should be rotting into the couch (I’m looking at you, Wirecutter), I’ve realized for me rest is more about the absence of urgency rather than an absence of effort.