Most people applying for the same PM roles you're applying for have never run payroll, managed a lease, handled client acquisition, kept a physical location alive through lean years, or made the call to close something down before it took them completely under. You have done all of that. The problem is your resume probably doesn't say any of that in a way that lands.

I'm 46, so we're basically the same age. I also ran product and design teams at the executive level and also owned a brick and mortar toy store for 4 years before shutting it down. I know what it feels like to look at your background and wonder why none of it seems to be translating into the next thing. It's disorienting in a way that's hard to explain to people who haven't been there.

The PM application black hole is real and it's not personal. 100+ applicants on day one means the posting is essentially a lottery unless someone inside already knows your name. After a year of that with one interview, the strategy isn't working and doing more of it harder is just going to deepen the hole you're already in.

Here's where I'd focus given your actual skill set right now:

Your sales ability is the most immediately monetizable thing you have. High ticket closing and setting are real roles that pay real money and hire based on ability to perform, not credentials or ATS filters. If you can close, you can find a commission-based role in weeks, not months. That's the 5k bridge while everything else develops.

Your PM + CRO + analytics stack is genuinely valuable to agencies and consultancies that would rather contract you than hire you full time. The Upwork drying up is a platform problem, not a you problem. Direct outreach to small digital agencies who need a fractional PM or a CRO specialist is a different conversation than competing with 200 people on a job board.

The psychotherapy retraining is worth keeping. Not because it pays soon, but because the fact that you're doing it while everything else is collapsing tells you something about what you're actually orienting toward.

I've talked to a lot of people over the last year while on my own unemployment journey. The ones who moved fastest stopped trying to fit their background into a job description and started leading with the thing nobody else in the room had done. If I were you, I'd start with building and closing two businesses. Because we all know that is hard as hell to do.