Had similarly unorthodox path to tech, albeit without the drug addiction or prison.

90s early internet/BBS punk rocker/computer nerd. Hated school angry.

Dropped out to work as a bike messenger for 5 years before packing a bag and moving west randomly. Couldn't sit still. Rode freight trains around the country for a few months.

Washed dishes and landscaped to cover my cheap rent till that fell thru. Discovered shop lifting. Covered food and beer stealing from local progressive grocery store chain. Stole goods to sell on CL to cover my rent. That scam went tits up and narrowly escaped serious charges after the head of loss prevention from a regional retailer caught up to me

Was sleeping in the park--this was pre super meth/fentanyl crisis so street living was a bit more stable and low key. Didn't want to wash dishes or dig holes any more so looked around on CL. Found a small company trying to bootstrap a regional office for an established linux-related open source company. Worked for free / interned using a stolen laptop for a year or so while sleeping outside or couch surfing local punk houses.

Eventually got hired on for s but stayed for a couple years and made many FOSS connections. Eventually left to join a well known FOSS-centered company that was fully remote.

Told myself when I was young that I would never work in an office. ~15 years later and I never have ,but now work in bit tech, get paid too much, own a home and have a great family with kids who play at the same parks I used to crash at. We shop (and pay) at the same stores I used to crib from.

I'm respected and tenured at my gig but Imposter syndrome still holds me back. Nobody I work with knows where I came from and thankfully have nothing incriminating that would block a background check