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Many great comments here which hopefully help, and I'm not going to address the anxiety/depressive side of the coin - others have done that better.

One piece of advice I got from a manager around interviewing was to be trying to interview somewhere every 3 to 6 months. He's incredibly happy in his role but he interviews to a) find out about new opportunities/products/technologies but b) so that when he finds that one job he really wants he is well versed and ready to nail the shit out of the interview.

You're clearly a smart guy. Do a little study on interview techniques + up the volume of interviews (plus reduce the stress/emphasis on any one interview) and I think you'll surprise yourself with how great you really are.

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I'll echo this. Before I went into consulting I would interview bimonthly or so. Not because I was unhappy (though sometimes I was), but because it was good to keep sharp and because sometimes you'll surprise yourself by finding a gig that really clicks. I was a lousy interview at my first job out of college. I've been a very good one since, and it's helped me get jobs I liked.

It's also helped me seriously expand my network (and Boston's a small town); you meet a lot of people.

So do you just randomly answer job listings that fit the bill or is there some better way?

Not purely randomly, I only interview at places I think I might want to work, but most of it is from inbound requests via LinkedIn. My LinkedIn profile is recruiter catnip, which helps. I've gone from Trendy Area to Trendy Area (and I'm fortunate that doing so brought me into devops/platform engineering, which I really like!) and I still get hits for mobile/Android gigs despite not touching it since before Android Studio was released.

So if a company sounds interesting, sure, I'll go talk to them. I don't actively seek them out, but they tend to find me. (And even if I don't find them particularly compelling, I might be able to sell them on consulting services.)

For me I keep a well updated Linkedin profile and recruiters will drop me a line every now and then.

I think you could apply to roles that look interesting but that's a little disingenuous if you're not seriously considering a move.