>Even if your startup / bootstrapped / micro-enterprise failed, you got tired of it, or the market shifted, you don't get to a few hundred K in revenue in a solo/micro operation without having some results, reputation, and relationships to stand on when you walk away. At least not in any situation I can think of.

Sure, but that's the thing, reputation and relationships might get you an interview, but it won't get you a individual contributor job at a top-tier company. Why do I fail those interviews? Maybe I am not technically good enough. Maybe, as a friend says, "They can tell" - they can see that I am depressed. Maybe it's a little bit of both.

My point is that you can show up to interviews at second or third tier companies (or contract gigs at first tier companies) and pretty much say "hey man, I've got hands, I can figure it out" and they hire you. And contacts and experience selling works great for that. But my experience has been that there is a ceiling on how far that takes you.

Contacts are important but they are not everything.

I'm actually fairly certain that a reasonable portion of my problem is that nobody cares about the problems I was working on, or rather, that the sysadmin role has shrunk a lot, and that's where my focus is. I need to redirect effort into SWE skills. (The path forward for me is probably SRE jobs, but the part of that I'm missing is the SWE stuff.)

That's another problem with working for a company you are majority shareholder of; the temptation is to do what you are good at and hire people who are better than you to do the things you aren't good at. When the industry moves, and the thing you are good at are no longer really in demand? well, you have a retraining problem, one you probably wouldn't have had if you had been working as an individual contributor during that time.

>I don't know you, but I'm wondering if this is more about your perception being off about what's making this next step (i.e. interviews and selling yourself) challenging for you. If it is off, maybe you're overlooking something else that is really the root cause of it, preventing you from addressing it or even asking the right questions of yourself or the community.

eh, that's possible. You could argue that my biggest problem right now is mentality. I was defeated, I feel defeated. And now I'm back contracting, which pays way better than working for a small company, and better than any of the jobs my contacts offered me, but it doesn't feel like success for a bunch of reasons; The role itself looks like what I did when I was 17 (It pays a lot better than what I did when I was 17... but it's about the same work) and it is still 1/2 to 2/3rds total comp for direct hires at places like amazon and facebook.

That's the thing, if I want to work for startup wages, sure, I could get a lot of jobs. no problem. But that's not a step up from where I was before I started this company. Hell, if I wasn't depressed as fuck, I would probably have a shot at being a co-founder somewhere funded, which possibly could be a step up, but I am depressed and exhausted and so that's not really an option right now.

I mean, as others have pointed out, I have it okay now. bills are getting paid, etc, etc, and why should I be unhappy about my current situation? Lots of people would be happy to have my job. I feel bad for feeling bad about it, you know?

but... my point that running a business (vs. working as an ambitious individual contributor) doesn't move your career forward as working as an ambitious individual contributor would, or at least that it hasn't moved my career forward.

(And yes, I'm sorry for sounding so self-pitying and bitter. That's how I feel right now; it will pass. Either I will retrain and continue my upwards career path as an individual contributor, or I will become accustomed to, you know, that path not always leading upwards. Either way requires time.)

Re-reading this... I'm painting a pretty unsympathetic picture of myself. The fact that I've spent a lot of effort on non-technical things (that, turns out, I'm not so great at) rather than moving my technical skills forward almost certainly has a lot to do with me not being able to get technical jobs that are as good as I'd like. Shock! surprise! I mean, that seems pretty obvious, no? I took a risk. I thought I could become good at business. Turns out? it's harder than it looks, and progress in that field is way harder, for me, than progress as a technical individual contributor. Now, I'm complaining because that time away from the things I'm good at is now slowing down my career progress. I reached a little too hard for that brass ring, fell off and am now whining about my bloody nose.

I'm still arguing, though, that there are costs to your technical career to taking time to try to go into business.