Dear SaaStr: What Has Been Your Biggest Career Mistake?

Maybe not slowing down just a little bit.

  • The week in my first real professional job when I realized I’d been there long enough and had nothing left to learn … I walked in and quit that day on the spot. I had no idea what I would do next and had zero savings. It worked out but maybe I should have found at least one person who would hire me before I did that. Just one. Staying a little longer wouldn’t have been the end of the world.
  • The moment I realized the arguably terrible idea I had for my first start-up made sense to me I dropped everything and did it — with no way to fund the company or make payroll. It worked out, but only barely, and I had to strike the worst deal in all of venture capital and sign away my house and all my savings to fund it. Maybe could have gone a little more slowly. More here: How did you fund your first startup?
  • The moment I realized I was 100.00% all-in on idea for my second start-up, I dropped everything, raised $2.5m for the team, and just started doing it. Good idea but maybe we should have mapped things out a smidge more. Going more slowly in the beginning in this case at least would have actually paid off a lot.
  • The moment I realized I had nothing left to contribute as a corporate VP I moved on. I could have just chilled for a while and maybe that would have been better for everyone including myself.  I was too burnt and didn’t have a supportive enough boss to see it.  But I should have stayed a bit longer and just played one more card.  Even if there were no great economic reasons to do so.
  • The moment I realized I would be half decent at investing I should have just chilled. I didn’t have to try so hard so quickly to take it up another notch. Didn’t really help.

So it’s tough for founders to slow down once they commit to something. I’m not saying don’t do that, per se. I am saying maybe slow down big decisions though just a little bit, maybe 11%, or something like that. Let them stew just a little longer.

Also sometimes, stay somewhere longer. You make more money that way, with less day-to-day stress. Life is short but you want to go long and deep on each journey you’re on.

I’m still trying to learn this lesson today.


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