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

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

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

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

Month 5 Recap: Be Cringe About Trying

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Month 6: Be Cringe About Being Seen

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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.

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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.

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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.

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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.

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.

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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.

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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?