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4 Comments

Any other serial entrepreneurs struggle with "new scheme" uncle imposter syndrome?

Always think of that uncle portrayed in the movies as the guy with a new get rich quick scheme but is never successful. 🥸

I've experimented with about 5 new products over the years. One I had a successful exit from, the rest not so much.

Nearing 4 years on my current test and it might be time to move on but feeling like I might be that uncle who always has some new "scheme". 😅

Anyone else feel this?

on March 8, 2022
  1. 2

    The uncle framing is funny but I think it mixes up two different things, trying a new scheme because the old one never worked versus running several things at once because each one earns its place. Five attempts with one real exit over the years is not scheme-chasing, that is just the actual base rate for building things, most attempts do not work and you learn which ones might. The thing I would actually check after four years on the current one is not whether you are that uncle, it is whether you are staying because the metrics say stay or because switching feels like admitting the last four years did not count. I run three very different businesses at once and the hardest personal skill has been separating sunk cost from an honest look at the numbers, those two feelings are easy to confuse from the inside.

    1. 1

      Just got this notification! That is a really great perspective! What's funny is I am now using AI to rebuild my mental health app I was referring to 4 years ago in this post. I definitely agree the numbers should dictate our decision not sunk cost! Thanks for your feedback.

  2. 2

    Sounds like there is something missing from your career that is keeping you from feeling fulfilled.

    I don't think this is about the projects but that you don't feel satisfied with the work that you done so far in your life.

    Perhaps it's time for a passion project?

    1. 1

      Not my career so much. I love it! Been 100% remote before covid and get to build meaningful products. Maybe I didn't communicate it well in the post, these feelings are more related to all the side hustles and startups I've founded over the years.