How to burn your resume and build a new career

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3 min readSep 26, 2024

📺 On this day 64 years ago, JFK faced off with Nixon in the first-ever televised presidential debate. JFK agreed to wear makeup at the last minute; Nixon (who was getting over a knee injury) didn’t. Most viewers agree Nixon looked haggard; he later lost the election by 0.17%.
Issue #172: don’t call it “aging,” yodeling in Walmart, and the power of “yet”
By
Harris Sockel

I’ve worked at three startups by now, and I’ve gotten to know their founders pretty well. I’ve Slacked with them late at night. I’ve left the office at 7 while they’re still there, hunched over their (standing) desks. It’s an all-consuming job. It’s also one that’s misunderstood.

Podcaster Harry Stebbings, who’s made a career of interviewing VCs, got some pushback on Sunday after writing: “we have made entrepreneurship too safe a career path.” Really? Maybe from the comfort of a podcast studio, or if you’re only speaking to a narrow subset of founders who’ve already raised a ton of cash (to say nothing of female and underrepresented CEOs). But most founders (and freelancers) I know spend most of their time worrying about runway, minutiae, and whether it will all matter in the end.

They do it because, like writers, they question things deeply. They’re dissatisfied with the tools or stories that exist and want to make better ones.

Neela, an entrepreneur on Medium, literally burned her resume (and set off a smoke alarm) because she was so dissatisfied with her career before building her own business. If you’re thinking of going it alone, here are a few of Neela’s hard-won lessons:

  • Book “worry time”. If you’re getting sucked into an obsessive spiral, put time on your calendar to mull it over later that day. (I’ve started doing this and I’m not even freelance… it works wonders.)
  • Find mentors who won’t sugarcoat reality, because in a crisis the best thing someone can do is bluntly tell you what you’re doing wrong.
  • The 80/20 rule of stress: Most of your stressors boil down to just a few problems or people. Identify what those are and focus on making them better.

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