Oooof working for a friend can be tough. You think you’re going to have a boss who’s your friend but then your friend becomes your boss. If you need to leave that situation, remember to frame it as “I love it friendship and I don’t want this to hurt it”.

As far as ball size, I guess I think I’ve been stupid so many times a Jacques Clueseau’d my way to where I am, but also I have a personality that tends to downplay risk.

Here’s a story on that:

I worked in Seattle for a start up in “chemical distribution”. It sucked. Everyone was jaded. There was no culture. I was selling something I didn’t know, but the military seemed to want a lot of it. I was there for 2 months, 26 days, and 4 hours.

On my way out, one of the charismatic smiley hot shot salesmen invited me for a farewell drink, just me and him. When we sat down, his demeanor completely changed. He slumped and stared into his glass and said “I don’t have the balls to do what you do. I wanted to be a brewer, but the market is too risky. I’m afraid if never make it so I do this instead. Maybe when I’m old I could make it happen…”

I thought “damn. I don’t have the balls to do what you do”. I mean, putting your life on hold for ~35 years!? I can die so many different ways in that time. Then I get a small window to finally live, but for how long?

Personally I decided I don’t want to retire. I want to build a life where if I knew I’d die tomorrow I’d do nothing different about my routine.