The long and short of it is, one day the project I'm working on feels worthwhile, and the next day I'm job hunting or trying to brainstorm a new project. This is all in the context of me already having a decent remote day job, but not in an industry I care about or find meaningful (think advertising or something like that). So it pays the bills and gives some free time.
Anyways, I'm trying to take the obvious advice of getting in front of potential users/customers for the project, as their interest would certainly be a motivational boost. There's maybe a few months' lag from when I'll have something high enough fidelity (and a website) to do so. However, having just been through this process 6 months ago and getting practically no interest + rejections from customers and investors, the prospect of doing this again certainly causes a bit of dread.
After a decade of failed startups, 5 years working jobs I don't care for, it feels pretty high pressure trying to get something new going. I'm in my mid 30s now. If it goes nowhere, I've wasted time on the wrong project and I'm stuck in the dead-end job. Of course this is no reason to not try, but it's something I don't remember feeling throughout the entirety of my 20s when I pretty much just 'went for it' without regards to much else. At least back then I had conviction and consistency and shipped things. I bounced between failures much better too.
Now there's thoughts like, 'I should just be applying for better jobs', 'I should go back to school', 'I should work on something trendy like AI SaaS', etc. Yeah I'd say the lack of conviction is pretty tough lately.
Anyone experience similar, especially regarding the experience of trying startups constantly from their 20s to 30s?
Whatever you do, do it because you don't want to regret not doing it when you're on your death bed. That's how I prioritize trying the startup lottery over leet coding every evening.