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Seeking the Messy Journey

Posted on:August 7, 2022 at 05:19 AM (3 min read)

I like watching bloopers. It tells me that nobody is perfect and that it took multiple takes to get to that lovely final shot.

I am more curious to see the execution. Behind the scenes stuff. Progress updates. The journey. Watching only the end outcome does not excite me as much. Here are some examples:

  1. One of my early idols Derek Sivers used to reply to every email. I wrote to him in March 2016 and got a reply within 24 hours. Crazy, I thought! Fast forward to today, he has quit that practice as it’s not sustainable.

  2. Pieter Levels’ hit rate is only 5% - 4 of his 70+ projects ever made money. That’s a lot, right? Someone might just see the tip of the iceberg, his top project NomadList, and say he got lucky. Nope. He increased the surface area of luck. Paid his dues.

  3. Josh Pigford’s path is long as well, having 62 projects, one of which was acquired at $4M. It’s humbling.

  4. I saw Bruce acquiring a micro-SaaS, wherein he evaluated 83 listings over 10 months to find that sweet deal. He paid $60k upfront for a product with $2k MRR. I’m following to see how it goes.

You’re not known for your losses, you’re known for your wins. You know Reid Hoffman for LinkedIn and Greylock but not SocialNet. You know Marc Andreessen for Netscape and a16z but not Ning.

This is my portfolio of motivation. I follow like 10 people for a long time, to see how different people handle different phases of life, how their thinking evolves with time, who do they emulate, their ups and downs. As an outsider, you see the steady climb or gradual decline. As an insider, you get to know that the duck gliding elegantly on the pond surface is furiously kicking underwater just to stay afloat.

I also like watching reality shows where you can see a very fast evolution of ideas - what sticks and what does not - things change in the next episode based on audience reception.

It’s easy to see someone launching a newsletter, another one starting a side project, yet another one taking a non-conventional path on social media every day. But that’s their high point. Do you know their lows? How do they react when back is against the wall? How do their values evolve?

Keeping the above in mind helps me when I’m doing something new. I also collect personal progress updates to serve as a data point for future me. Like for example, reading did not come naturally to me. I had a goal of reading 6 books in 2018 but failed. But now I’m quite comfortable reading a lot. Writing is something that has been eluding me since 2016. I hope to get better at it bit by bit. Perfection comes with practice. The rite of passage is a messy journey indeed.

What’s your favorite blooper?