1. ADHD can come and go, like the major depressive episodes of clinical depression[1].

I had 5+ years of experience (I started programming when I was 11, in fact); my period of homelessness came after having already worked several great jobs (that I got no thanks to my parents—a retired tradesman and a gas-station attendant with a combined income of $20k/yr.) I've also built out a pretty good portfolio of work in realtime distributed systems engineering. I "burned out" of one job I had at the time, and just never looked for the next one. I lived off savings[2] for a year while trying to start a startup, until my savings ran out. Then I was homeless.

2. I was eliding a lot by saying that I was living with my parents. My parents are bankrupt, now divorced, and live in the country. (My father is bipolar, which drove much worse things to happen in their lives for decades—a string of half-baked entrepreneurial ventures each dropped after heavy investment whenever he entered his depressive phase, for just one. Moving out at 16 was a decision I still do not regret.)

I actually went to live with my grandparents, illegally, in their no-tenants-under-the-age-of-retirement condo, because they insisted that I stay with them even though they couldn't afford to support themselves, let alone me. (They certainly couldn't bail my parents out.)

This was a move that caused me to be two hours' commute from the nearest city of population greater than 10,000. While looking for a new job, I commuted that distance, both ways, nearly every day. It wasn't that I wasn't actively looking for a job; it was that each individual job application was, effectively, an arduous process it would take weeks/months to recover from. The strain I put on them was what made me finally decide I needed to see a psychiatrist.

That was only for the last few months of my "stint" at homelessness, though. Before then, I was just ducking my almost-always-absent landlord, effectively squatting in the room I had previously been renting, and trying to scape together a dollar or two each week to buy bags of rice and such.

Should I also mention that I mostly paid for living expenses while going to [community] college—for the year or two I did—by getting student loans and then avoiding spending them on anything non-essential, like textbooks?

3. I was never on welfare, or employment insurance, or on any government assistance programs of any kind. You know why? They were too much effort to get into! Also, they effectively required applications to their services to happen near-simultaneously with the loss of one's job. One of the most common effects of ADHD is putting off paperwork, homework, filing your taxes, etc. until it's far too late.

I was homeless, but I wasn't a beggar on the street. Instead, I was couch-surfing without a dollar in my bank account, tens of thousands of dollars in credit-card debt, no friends within a thousand miles of the city I lived in, and a rapidly-worsening state of health because I couldn't pay for my own healthcare.

4. I wasn't hired as CTO; the previous CTO quit, and I worked my way up. This isn't a big company, so just think "tech lead", not "guy in an expensive business suit who bosses around tech leads."

I've never mentioned having ADHD to anyone at any job I've worked at since beginning treatment for it. Medicated, I'm normal; just as a nearsighted person wearing glasses is normal. Effectively, in my mind, I don't have ADHD now—ADHD is a condition I would get (again) if I stopped taking my medication.

ADHD is a deficiency of an essential chemical my body cannot produce on its own—to wit, a vitamin deficiency. Do we say that people with scurvy always have scurvy, but were are just temporarily well as long as they continue to consume vitamin C? No; they're normal on vitamin C.

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[1] I've almost come to believe that all the talk of "burn out" in programming is because ADHD is pretty common in programmers—or rather, programming is a pretty common thing to get into for people with ADHD—and so, to someone who has undiagnosed ADHD but to a degree that's normally manageable with self-medication through things like caffeine, a stressful+unrewarding job can heighten the symptoms to the point that it can't just be managed/brushed aside, and has to be addressed as a problem. But, since it required the triggering event (a bad job), it gets blamed on the trigger-condition instead of on the vulnerability it exposed.

[2] Savings amounting to a few thousand dollars. Junior programming jobs here don't tend to pay well, nor was I very savvy about what I should charge for the contracting work I did, nor was it very easy to get hired by places with money given my lack-of-a-college-diploma. I did figure it out the general solution, in the end: working remotely for US companies, instead of accepting the local prevailing wage.