How to Let Go Gracefully as a Founder

21 Oct 2026 · 1 min

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In this reflective monologue, the speaker, a founder, shares the emotional journey of deciding to leave a venture. He describes feeling intense sadness and grief—crying, feeling like he was at a funeral—and initially interpreting those feelings as a sign that he shouldn't leave. Through deep personal learning, he realizes that the sadness actually indicates love for the company and that grieving is a natural, pure way to honor something he cherished. He frames sadness as the energy that fuels the process of letting go, suggesting that grieving is an essential, healthy step for founders transitioning away from their startups.

Chapters

I was conflating, oh, I feel really sad about leaving, that means I shouldn't leave. So I ultimately left and I cried my eyes out. I was at a funeral. I was so sad and grieving. And it was a deep learning for me of, oh, that doesn't mean that it's the wrong choice, or that at some level I don't actually want to leave. Oh, it means that I loved it. I loved being a part of it and I feel sad to leave it. Like, like, um, you know, sadness is the energy of letting go. Grieving. Grieving is the most pure way to honor something that you loved.