I stayed at my second job for nine years from 1999-2008. By 2008, I became an expert beginner. I asked myself for years why I stayed there so long. The current me, would have left April 2003 when I closed on the house I was having built.

If I do a retrospective, it is kind of clear:

I worked with most of the same people all nine years. My coworkers became my friends and they were the only constant in my life.

My managers were shady as hell though.

I was going through a horrible marriage (2002-2006) a horrible financial mess because by 2006 I had $500K worth of mortgages making $70K a year (because you could back then).

My skillset was outdated. I was maintaining VB6 code in 2008 - 7 years after it had been discontinued (and some old school C++/MFC/COM).

As bonuses got cut and raises were meager, I only made $8K more in 2008 than I did in 2001.

My head wouldn’t have been in the game enough for another job.

I learned my lesson with my next six jobs. I do resume driven development. I only worked at companies that were using in demand technologies. I jumped ship after two meager raises or when the bullshit/pay ratio got too high.

I kept my network strong.

But on the other hand, I’m going to “stay put” at my current job at $BigTech until at least my initial 4 year initial vest (and an interim refresher) is done and see what else is out there.