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The Failure Reel: 2023

2 min readJan 22, 2024

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.

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Howard Gray
Howard Gray

Written by Howard Gray

Adventures in entertainment, education and entrepreneurial endeavours. I’m an educator and executive producer based in NYC.

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