Thanks for sharing this and I want to reiterate that it is important for a lot of people in tech to see this. I call it the "Midlife Financial Crisis for a Good Technologist Who Hasn't Cashed."
I had similar. Instead of agreeing to be on the founding team of Twitter and probably ending up with $20-40M at IPO, I started a company where I twice reported less than $25k in earnings to the IRS. And on and on.
I'm the oldest in my local entrepreneurship group (we meet every 2 months) and I can see how they, in their late 20s and early 30s, are still fine living at break even trying to thread the needle of success. And I can also predict the future.
Many will not thread that needle and then they will get severe cognitive dissonance. On the one hand, their experiences will have made them truly baller people, skilled in so many arenas. On the other hand, it'll look like they will never be able to retire. Ever. No reward for merit? It hurts and is scary and also shameful.
This feeling will happen in their late 30s (probably).
Sarah and I hit this a few years ago. The good news is that you can make money and your skills are valuable. The bad news is that you have to go decide to make it, i.e you working at Medium.
I used it to take back my company in a pretty honest renegotiation: "Unfortunately I haven't built anything that can survive without me. I'm honestly scared about dying poor, I will leave you your equity, but I need full control of cash flows, because I'm going to funnel a lot of that cash directly to myself." I.E. I'm going to run this business first to pay myself a fair wage and save for retirement, second for an exit, and I'm honestly not in a position to make any other offer than to shut the company down.
I would say, that like you, that once I started making healthier financial decisions, that things got a lot better. We bought a home in NYC, a second home upstate, I upgraded my laptop.
Also, some measure of financial health brought back the fearlessness of my youth.
The one thing I think I'm different than you on is that two of my advisor shares payed off. And that's something that I think would be really healthy for founders to consider more aggressively.
If someone worked at a FAANG they might not get this, but if you have never have done that, never made top dollar, haven't saved and have no money, "paying off" could be as simple as a $200k windfall. That can happen with tiny bits of equity on tiny acquisitions.
So imagine if you'd taken 3% of Elgg and traded 0.1% advisor stakes with your 30 closest startup friends and then done that again with Known. Would you have had any payoffs? I think so. I wish there was more of a share trading ecosystem for seed stage startups because I think it would make it financially easier for more founders to stay in the system rather than having to do stints as employees.