The Failure Reel: 2023

Howard Gray -

Tis the season for highlight reels: yes, that end of year post about how honored/excited/humbled-but-not-humbled we are. In keeping with the theme (well, kinda), here’s my 2023 reel: a compilation of my top mistakes and failures.

From what was a highly competitive pool of submissions, here's this year's top 10:

1. Writing for the algorithm vs. following my curiosity and what really interests me

2. Over investing into the nuts & bolts of producing client work, and underinvesting into biz dev and the long game

3. Not directly asking for help - especially when I most needed it

4. Eight week gaps between haircuts

5. Feeling deep shame when my income took a hit (I spent too much of the year forgetting that money is not our entire identity...)

6. Not acting on the sparks of levity & inspiration (remember, they're perishable)

7. Telling myself I'd found the others, when I probably hadn't

8. Getting caught between building two brands at the same time

9. Leaning too far into being a ‘Giver’ vs. ‘Otherish’ (per Adam Grant’s ‘Givers & Takers’)

10. Not making my first visit to CostCo until September. A true slice of life.

A few miscellaneous learnings:

  • When times are hard, you find out who your friends are
  • Most advice doesn't come with caveats - it probably needs to
  • A quick ‘No’ is underestimated
  • In person connections remain magical - and always will be
  • A key part of parenting is being able to regulate your emotions
  • A good cold email can work, but don’t bank on it
  • The Creator Economy is far more challenging than they want you to believe
  • The LinkedIn posts I delete are nearly always the ones I shouldn’t

There are a few other things I want to share, but tbh I’m not sure even this - my own space - is the place. I gotta say it’s been a tough year. In many ways, my toughest ever. 

But I’m still here. And so are you.

Onwards.