Wow. It's almost freaky what you describe as the path you have taken for your overall career... because I went and did a startup to scratch an itch and that didn't pan out so now I'm back to looking for work and in the process of zooming out and strategizing about how to get where I want to go I feel like the plan I've come up with is essentially a compressed version of that.
I really appreciate the responses here. Some very useful insights indeed!
Last piece of advise. Yeah make sure you “compress it”. Don’t make the mistake of getting comfortable like I did for a decade and not keeping up with technology. It’s really hard to get caught up once you do. Be aggressive about keeping up with technology.
I would like to think that if it ever came to it, I would always choose technology over money. Every month that you keep using older technology you’re accumulating technical debt in your own career.
I really appreciate the responses here. Some very useful insights indeed!