The best advice I ever got from my mentor: "Listen to your gut!" Passing it on...
I have enough savings to survive for five years.
What?!? Are you fucking crazy?!? What are you waiting for?!?
My biggest fears are: - To not stick to a schedule/routine once I am solo.
How will you know until you try? More to the point: how will you know how important "sticking to a schedule/routine" is until you try? (Probably not nearly as much as you think.)
- People's and family opinion.
Fuck. That. Shit. The first thing anyone must do when embarking on a new journey is to focus on the issues and ignore the pointless details. I can't imagine anything more pointless than "people's and family opinion".
- Failing and losing motivation. Why lump these 2 together? In my experience, failing is the best way to learn and learning is the best way to get more motivation.
Should I quit my job and work on my stuff or search for another position that would give more motivation?
YES! YES! YES! Do something, anything different! The worst thing you can do at this point in you life is stay the course. You'll just get older and more bitter. And posting the same thing on hacker news 2 years from now.
You can recapture money. You can recapture relationships. You can recapture your health. You can recapture almost anything, except for time.
Please don't make the same mistake I made by getting started in your 40's. Because you were too timid and pissed away too much of your life on what you know is the wrong thing.
I've responded to many similar questions over the years here on hn, but yours may be the clearest of them all: You already know what you must do but came here for confirmation. Now you have it. Take the next right step for yourself and please, keep us posted.
Best wishes and respect!