Disdain for sales. My first exposure to a sales team was as an engineer that had to deliver on whatever requirements sales dreamed up. Several years of head-s

Disdain for sales. My first exposure to a sales team was as an engineer that had to deliver on whatever requirements sales dreamed up. Several years of head-shaking bullshit and I decided that the entire vocation was worthless. Took me ten years to figure out the better approach is to build bridges there, not burn them down. Co-founding a company without really understanding my personal exposure. Had a small consultancy that had some early success, I was personally billing and leading projects, hiring folks and managing them. CEO just stopped actually cutting checks to IRS for a few years in a row. This snowballed into a major issue that I was personally liable for. Unfucking that took 5-6 years of my life. Yes yes yes I'm sure some of you out there would have been auditing financials every quarter...I didn't. Maybe that's the second half of the mistake. Getting comfortable. After the above, I was running the show and just got comfortable. No real growth but a good salary for myself and a few other folks. Turns our there are parts of running a company that I'm just not wired for and never got good at. Decided I should let someone else do that and shut the company down (long explanation as to why selling it wasn't a good option). Worked at a FAANG for a bit then took another job. Doubled my TC in about three years and think I should have probably done this a long time ago.