> The situation you describe isn't easy to get out of until you address whatever fear is causing you to over-worry about every step.

Thanks for the reply, I think this is exactly what I needed to hear; will try to reflect on this.

From the very top of my head: I know exactly what I need to do but I feel like with every tech choice I need to either learn "how" or refresh my previous knowledge.

Wearing multiple hats in rapidly popping up and fading out tech startups didn't really help to go deep with one thing (as I managed to with objc/ios)

Don't let my blunt way of writing make you feel like it should have been easy to see or will be easy to overcome.

It sounds like you have been through the transition from a career rewarding complete knowledge and understanding to today... where a "complete understanding" and depth of knowledge is not possible in the same way.

Rolling releases, CI, and cloud dev cycles with dependencies have completely changed what is expected of you - it is OK not to know every edge case in most situations today. The answer is a google or prompt away if a problem appears.

This wasn't really true 18 years ago... even though it doesn't feel like tech has changed a ton, it has.

If you decide to keep doing a rotation of hats and languages, you have to become very comfortable with identifying the value you add as a person involved in the process, even when you don't have every answer in your head.

In other words, being able to pop in and out of various startups tells me you have the ability to learn quickly. Why not just truly sit back and ask yourself what you want? Even if it doesn't fit the HN front page expectations, doing what you want with a lucrative skillset is as close to a good work/life balance as I have ever found. Holler if you wanna talk more, but otherwise I hope others will chime in.