Getting Caught Trying in Public
On lowering the bar and getting the f*ck out there!
I generally like to be mostly behind the scenes - making connections, authoring speeches/talking points, devising runs of show, making strategic plans and moving the pieces around to make them happen. In competitive sports, I was a quiet force; I scored a lot of goals at various points in my soccer career, but there wasn’t going to be a flashy celebration. This approach has suited me well - that is, until I realized that to really get where I wanted to go in career and life (i.e. I fully admitted my ambitions), I was going to need to “get caught trying” not just in little spheres - but out in public.
What’s the worst that could happen?
I used to work in politics and still like to nerd out on various issues, candidates, and races. I probably don’t need to tell you - but there was just a major upset in the NYC mayoral primary last week. In this excellent analysis by Ezra Klein and Chris Hayes of why Zohran Mamdani came out on top, they largely focus on how he wasn’t afraid to “get caught trying” trumpeting potential fixes to issues that most New Yorkers can relate to (high rent, high food prices, expensive buses, etc.). I will comment no further politically on this one - other than to say that here was someone who seemed to be saying, “These issues are so intractable - what’s the worst that could happen? I get caught trying to fix them?!”
Getting caught trying professionally?
“Self starters wanted” - we’ve all seen this in job postings, start up company culture plugs, etc. No doubt, every manager, CEO, or founder would like a team full of people who treat their job description as a loose definition of what they might do on a day to day basis and look for problems to fix and good ideas to lean into. But what does that look like in practice? Here’s what this means to me, coming from someone who has consistently built my own job description at every place I’ve worked:
You raise your hand, even when you’ve never done it before - If there’s a problem or a need, you don’t hesitate to step up. You might not have all the answers, but you want to put the work in to help make a plan, build a team, and see what could happen.
You prepare for meetings - This sounds super simple but in my experience, is a major differentiator between people who have their shit together, and those who don’t. I love Jade Boncalta’s clear and concise career advice, and she lays out her playbook for how she rose through the ranks so quickly at LinkedIn; it basically comes down to preparing for meetings with an agenda of wins, priorities, and questions. I’m sure there was much more to it than that, but I wouldn’t be surprised if this was at least 50%.
You finish projects and tie up loose ends - Again, finishing a project sounds simple but damn, if it isn’t always the norm. Being the person in a meeting asking, “so can we set a deadline to get X completed by?” might sound a bit narc-y, but it means you’re the one establishing authority and ownership over the final outcome and when it’s completed. Again, that is never a bad thing.
Getting caught trying in parenting
Real talk - at the playground, are you sitting on a bench on your phone, or are you up and playing with your kid? You could be watching what’s going on with the inter-kid dynamics or maybe making a new parent friend vs. being buried in tech. Listen, we’ve all been in both camps at various points, but I would like to be in the up and at ‘em camp more often than the other.
Parenting is rife with opportunities to get caught trying - leaning in to ask a follow up question vs. retreating from a hard moment or feeling, confronting the unearthed childhood trauma that triggers you so fucking badly instead of pushing it back down, running around on the playground like a maniac to make your kid and their friends laugh. Not always the easiest route, but always the more memorable for both parent and kid.
How I decided to lower the bar
A couple of months ago, I listened to a podcast episode by Myleik called “Lower the Bar” - if you’re interested in going deeper on this topic of getting caught trying, listening to this one (probably 2-3x) is my number one next step. I had the realization that while I was above average at getting caught trying in smaller spheres (mainly at work and in parenting), I hadn’t yet gone public in any real way with my ambitions or ideas. I liked to watch other people grow audiences, make more money, influence in areas they cared about, and generally surprise themselves with the positive power of this attention economy we live in - and I even advised some people on how to do this - but I hadn’t yet fully gotten out there myself. Enter, a deep dive on Substack and the realization that the “WORK MOM” name was available here, and I decided I had to get in the game.
I’ll share another secret of people who get caught trying from my own playbook: stating the objective/purpose of every meeting/creative brief/project up front, very concisely. For me, I realized that I would like to begin writing this Substack to:
Write consistently in a thematic area I care about (work life + parenting life)
Grow an audience of like-minded, similarly interested people who I could connect with consistently
Potentially monetize the platform and/or create professional connections that lead to more work individually and with Cohere.
So, that’s why I’m here - trying!
Where I’d like to get caught trying (other than here, duh)
If you’ve made it this far, thank you - I got going on this topic and couldn’t stop. In closing, I will tell you transparently where I would like to get caught trying over the next six months to a year, and perhaps in the comments here, you can tell me where you would like to get out there. Deal? Here’s my initial list of where I want to get caught trying:
Instagram - I would like to post 2-3x a week with content that feels in line with what I’m writing here, and un-self-consciously shares real life wins and learnings in an authentic way. I want to get out of my own head and use Instagram as an even less formal extension of what I’m doing here and see what happens!
In a new athletic pursuit/arena - We’re moving to Vermont in 2.5 weeks (more on that later) after 10 amazing years in Baltimore. A major reason for the move is to get to a place where being outside and in nature is a part of everyday life, literally out our back door. I was a competitive athlete for 20+ years and then had two kids in the course of three years. I’ve been a Crossfit gym rat for 2+ years now, but would like to find a new way to move my body competitively - maybe on a bike, on the run, or on the ski slopes - as we head north.
Signing off for this week - enjoy the holiday weekend in the U.S. and don’t be afraid to get caught trying publicly. xo.
Daring to get caught trying!! So inspiring ✨