5 Intentionally Cringey Things I Did (or Didn't Do) This Week
11/25 - 12/1 | Shameless self-promotion, missed coffee shop opportunities, unreciprocated conversations
Welcome to this week’s edition of 5 Intentionally Cringey Things I Did This Week, where I catalog the moments I stepped outside my comfort zone and leaned into things that I might’ve once avoided due to feelings of embarrassment, discomfort, or vulnerability. This helps me embrace and celebrate the growth and mark the moments that felt brave, scary, or otherwise human. It’s a practice in owning my choices as I try to live more authentically—and maybe inspiring you to own yours too. Please share with a friend if this resonates <3
Before diving in, a little bit of honesty: this is my second week of trying to do things that make me uncomfortable and, well, I failed. I played it safe, and there were more opportunities I didn’t take than I did.
I guess this is a good reminder that stepping outside of my comfort zone takes some intentionality, as much as I hate to admit it. I wish I could just effortlessly float through my days, finding big BOLD things to do, but it seems that might not always be the case.
So, we’ll see how this continues to go. This week, I’m sharing the ways I stepped outside my comfort zone, but also the moments where I maybe played it a bit safe. We’ll see what the future of this feature holds, but there very well could be a world where I share both the wins and misses weekly. And if that happens, I’ll be sure to update the intro ;)
Shamelessly self-promoted my newsletter more than I was comfortable with. I shared every piece I’ve written recently on my (private) instagram account, threads, and have started dabbling in Bluesky. I also shared some relevant essays with relevant people that may or may not have been mentioned in them, specifically my ‘Embarrassment is Fake’ and ‘Burden of relatability’ essays. I did think about sharing my most recent ‘We’ve been laid off 4 times’ piece on LinkedIn but I can’t bring myself to do that yet. I can’t do everything in the same week and need to save something to write about going forward! I’m just not ready for the LinkedIn people to be here, in this space.
Noticed someone working on their own Substack when I was working from a café and didn’t say anything. On Monday, I decided to drop off my son at daycare and go to a nearby coffee shop right after. "I planned to spend the first hour in Substack-land, wrapping up a draft about the early newborn days (set to go live next week), and the second hour on my work work—setting to-dos for the week, reviewing some data, yada yada yada. At some point in my little couple-hour stint at the coffee shop, I look over and notice a woman next to me doing some writing. I take a closer look (but not too obviously) and notice she, too, is on Substack. In the moment, I wanted to say something, but just couldn’t get it out. I mean what would I even say? “Hey, while I’m over here not minding my business, I just wanted to let you know that I, too, have a Substack”? The words were in my head but I just couldn’t get them out. Part of it felt like a missed opportunity in hindsight, but part of me also enjoyed my ‘solo time’, not talking to anyone, being independent. It brings me to a larger question to be honest — is pushing myself outside my comfort zone always the right answer? I think the verdict is still out on that one.
Recognized a mom at the park and didn’t do a great job of keeping the conversation going (despite her best efforts). We said hi politely, she did a good job at asking a few questions and I just didn’t reciprocate. It wasn’t intentional. Sometimes I get so focused on the task at hand (in this case, keeping an eye on my very wobbly 16 month old) that I get hyper focused on that and forget how to engage with people in a normal way, lol. Next time I see her I’ll try to make appropriate small talk though.
Reached out to a neighborhood parent group to see if anyone happened to have a high chair we could borrow for Thanksgiving. We went to a friend’s house for Thanksgiving. I didn’t want to bring our highchair from our house, so checked a local group to see if someone had something portable I could maybe pick up on the way. I got a few hits for boosters and what not and was ready to pick one up, when a woman responded, “I’ll have two Tripp Trapps sitting in my apartment, unused. I live at [the same corner I was heading to for the holiday]. DM me”. I did, and she ended up being right upstairs. Easy peasy. This one, honestly, felt a little lame to write about. I needed something, I asked for it, someone delivered. In some ways this doesn’t feel super intentionally cringey, but it was also a moment I was overthinking and something I almost didn’t do. The serendipitous nature of it all was a good reminder to take action.
Didn’t do a bunch of big, bold, cringey things—but wrote this post anyway. Can I tell you how much I didn’t want to write this post? Because I really didn’t want to write this post, and didn’t feel like I had much to say. I had just, seven days prior, committed to doing five things outside of my comfort zone every week and quickly realized this was easier said than done. So when faced with another Sunday where this needed to be written and I realized I didn’t have five brave things to write about, I almost just gave up and moved on (which would’ve been just so typically me). But I decided to somewhat pivot and give this piece a shot. Is this my favorite piece I’ve written here? No, it’s not. But I also think sometimes it’s good to make myself do things I don’t think are perfect or particularly good. idk. one of those ‘personal growth’ things, just from another angle.
So there we go — 5 things I did this week, whether they were embracing intentional cringe or actively not. I’m reminded every moment, to some extent, is a choice. I think part of this journey is about acknowledging the way I move through these moments, being honest, and reflecting on what maybe I can try next time.
I’d love to hear from you — did you do any intentionally cringey things this week? Were there moments you maybe weren’t as bold as you could’ve been?