From your comments, it seems like there's a lot of internal and external issues you're dealing with. Internally, your sense of self worth is very much tied to your compensation/wealth. The recent rejections have triggered anxiety / negative self-reflection. The lack of a job/income is really straining your confidence.
Externally ...
1) It's actually a shit job market.
2) Your startup experiences don't really help signal your skillset as an employee. There's a sorta "founder tax" you're paying.
3) COVID, remote work, and new supplies of CS grads have changed the labour dynamics to depress wages. The top 20% may be doing ok, but the bottom 80% are getting diluted.
If I were you I'd consider a few things:
- Really think about what's a good/meaningful life to you. Volunteer/do something useful for other people (ex. a non-profit) to build up confidence again.
- Recognize your technical skillset may not be as "senior" as you think, since you had to expend valuable time learning other skills as an entrepreneur. It might mean more learning, building, leetcode grinding, interview prep, etc, before you can land the role. Concurrently, you can think about how to better communicate all the other useful things you've learned at a startup.
- If you enjoyed the startup experience, but concerned about the grind, then you don't have to build high growth businesses that require the 996 mentality. Boostrapping and organically growing a niche product may be more aligned with your skillset/goals.
Agreeing with everything here, and I would add that OP likely has a decent network. Try to land some contract work, whether it's full-time or part-time, while you figure out the rest.
I didn't want to go here, but I do have direct knowledge from two final rounds I was passed over for that h1b visa holders were selected instead of me and paid less. (I knew employees at these startups)
Part of why I'm just considering doing something else is the fact that so much of this work is going to be outsourced. Most of my friends who are actively running startups don't even bother hiring inside the US and just use latam contractors.
Unfortunately, I need money. I have effectively a net zero income for 2025, this after years of entrepreneurship just isn't good enough. I find it ironic how on HN anyone advocating to push themselves into a position where they have more options (more income) is met with accusations of being "entitled" or outlandish.
Let's say my skillset isn't as "senior" as I think, how on earth do I escape the tar-pit of being a semi-junior senior (to quote DHH)? This problem is what's been tearing me apart... I genuinely don't know what to do.
I also have some medical stuff I need taken care of and I can't afford to liquidate more of my retirement. So "bootstrapping" another company is just something I'm not interested in.
It seems like the cashflow situation will rule out some options, at least for the moment, like boostrapping etc. Contracting could be a temporary option, esp for US companies that need in-person support with good language skills. This would blunt some of the competition from abroad.
Regarding learning "out of the tar-pit", it's hard to give out specifics without knowing more details about your experiences. But it might be worthwhile to reach out to other senior engineers in your network, not to ask for a job, but to ask for advice about switching from entrepreneur/founder to employee. It could be a good way to build rapport and identify what you should be learning next.
Your health obviously takes priorty over everything else. Medical problems can really push you into despair if left unaddressed. Money you can always make back later.
> I find it ironic how on HN anyone advocating to push themselves into a position where they have more options (more income) is met with accusations of being "entitled" or outlandish.
> Let's say my skillset isn't as "senior" as I think
The people from the first sentence were trying to get you to understand the content of the second sentence.
Externally ...
1) It's actually a shit job market.
2) Your startup experiences don't really help signal your skillset as an employee. There's a sorta "founder tax" you're paying.
3) COVID, remote work, and new supplies of CS grads have changed the labour dynamics to depress wages. The top 20% may be doing ok, but the bottom 80% are getting diluted.
If I were you I'd consider a few things:
- Really think about what's a good/meaningful life to you. Volunteer/do something useful for other people (ex. a non-profit) to build up confidence again.
- Recognize your technical skillset may not be as "senior" as you think, since you had to expend valuable time learning other skills as an entrepreneur. It might mean more learning, building, leetcode grinding, interview prep, etc, before you can land the role. Concurrently, you can think about how to better communicate all the other useful things you've learned at a startup.
- If you enjoyed the startup experience, but concerned about the grind, then you don't have to build high growth businesses that require the 996 mentality. Boostrapping and organically growing a niche product may be more aligned with your skillset/goals.