#7: Be Cringe about Choosing Yourself

Month 7 of our year-long commitment of living a bit more authentically (and being more cringe)

Be Cringe is a year-long experience centered on showing up more authentically — even when it feels embarrassing. Each month, I share a theme, reflect on how I’m working with it in my own life, and invite subscribers to explore it alongside me. Welcome to Month 7: Be Cringe about Choosing Yourself. Below, I’ll share insights from our sixth month, Be Cringe About Being Seen, as well as how this month will unfold.

The insights from Month 6 are free to read, and the look-ahead to what choosing yourself looks like is available for paid subscribers.

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

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Choosing yourself is difficult, and I get into that more below, but I wanted to share a very real example of me deciding to choose myself just this week. It wasn’t easy; I feel guilty, but I did it anyway.

I have a cadence and deadline I have established for this very newsletter: Be Cringe goes out on the first Monday of the month. A precedent I set and a promise I made to my paid subscribers, and one I’ve been able to follow for six months!

But this month, I missed my deadline. I knew I’d be busy on the first Monday of July after a week of travel, but I could not have anticipated being as busy as I was last week. My original plan was to prep everything ahead of my trip, but I had a whirlwind week of meetings and a few more client asks than I’d planned for.

So, it didn’t get done last week, and I sat down on the first Monday of this month, trying to get this article out. By the time 1 pm rolled around, I knew I needed to make a choice.

I could rush to the finish line to meet my deadline and check a box and share something that felt uninspired, or I could make the decision to post late.

Since the first Monday of the month is behind us, you can probably guess which choice I made!

So, thank you for being here, thank you for letting me choose myself, and I hope the fact that this is hitting your inboxes a little late doesn’t matter. Maybe you didn’t even realize it was late, but now I’ve drawn your attention to it!

Alright, enough of that! Let’s dive in.

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Month 6 Recap: Be Cringe About Being Seen

The sixth month of Be Cringe asked us all to take the work we’ve done this year so far and show it off to the world (or a few people, at least).

I’ve noticed that this month, I’ve gotten more comfortable with the way I talk about being self-employed and what I’m actually doing.

I kept up my Virtual Water Cooler Chats, and ran one to two a week. I had fun! I experimented with new times and days. Our biggest chat was five whole people, our smallest just me, with most ranging in the 1-3 people range. The growth gurus would guffaw, thinking that this can’t be worth it. But I couldn’t disagree more. Being able to engage with community, regardless of the numbers, felt important. It was a great start to my day, and while it sometimes felt uncomfortable to sit in the uncertainty of who would show up, I pushed past it.

What’s interesting is this wasn’t my loudest or most active month on places like LinkedIn or Substack Notes. I don’t think this correlation is necessarily causation, but to me it shows where I’ve chosen to show up. Because if I am being honest, posting on social media and screaming into a void can be easy for me for a few reasons.

The first reason is that posting on social media allows me to put an ask out into the world and immediately disassociate from the response. If no one likes my post or reaches out, I can blame the algorithms. But reaching out to a specific person? My brain starts to spin; I think of all the reasons why they didn’t respond, and it feels personal.

I got to meet Dylan Michael Julian for coffee (in person!) a few weeks ago, and we were talking about this. My big ‘opportunity’ is to start reaching out individually to people, something that honestly freaks me out. I have to be vulnerable, ask someone something directly, and wait for their response. Scary!!! He gave me some good perspective (perspective I’m working into another essay), but reaching out does feel less scary now.

I’d like to say I left that chat and immediately DMed 6 people on LinkedIn that I admire or want to work with, but I did not. I’ve gotten some traction from social media, and those have turned into calls or connections, but my ‘reach out’ count is currently at zero.

The second reason social media is easier for me is that I would much rather be perceived by strangers than those who know me in real life. Former co-workers, parents of my kid’s friends, a girl I knew in 2007 and haven’t seen since, yes, but also my close friends (and even family). I guess I care much more about the opinions of those that know me personally (in some way) than those who don’t know me at all.

Being seen by those in my life has always been the moment for me where I falter. From 2016-2018, I grew an Instagram following to just over 5k followers. Not quite at the level of an influencer, but enough where I was getting sent free products. I was being seen.

One day, somewhat out of nowhere, that number hit me hard. I couldn’t conceptualize what five thousand people looked like. I also started a new job, started using my personal Instagram more, and overall got really turned off by my ‘big’ account. In the moment, I told myself that it was because I didn’t like the idea of that many people knowing what I was up to, but it was a bit more complicated than that in reality. I really hated when people I knew would talk to me about my Instagram and was terrified of the idea of my coworkers ‘finding’ it.

So, I made it private for about a year, posted sporadically, and then, one day, I deleted it. Not ‘disabled’ for a time, but fully deleted it. Those 5,000 followers gone for good. The faceless followers weren’t actually the problem, though. I enjoyed sharing with that audience, getting feedback, hearing their thoughts, and interacting. It was the people I knew infiltrating that space that gave me pause.

It’s been the same with this Substack. I have no issue sending out my little newsletters to the world, but when I think about the fact that people who know me are reading my words, I get a metallic taste in my mouth. Any break I’ve taken, anything I haven’t done, any podcast I may not have started for years, isn’t because of the people I don’t know but rather because of those I do.

I’m slowly getting better at talking about what I’m doing with the people in my life. I’m welcoming all parts of my identity with open arms, and letting it be seen in multiple areas. I still sometimes try to change the subject, and it still feels very cringe, but this past month made me more aware of when I was doing that.

Something else happens when we allow ourselves to be seen. In a way, it’s the first step in choosing ourselves. We can decide how we want to be seen and what we do with that visibility.

Month 7: Be Cringe About Choosing Yourself

For some of you, choosing yourself is going to be the most difficult part of this challenge. And that’s because it is difficult.