20 years on
Dear Me from 17 years ago,
Everything works out just fine. You move out West with Lindsay, work in the mountains for a year, settle down in Calgary, get a sweet job at a microbrewery, eventually get married, get back in IT work, buy a house, have an incredible kid, grow your career, have another incredible kid, buy a bigger house, and (so far) live Happily Ever After with your beautiful wife and kids.
So maybe ease up on the moping, yeah? You're missing the forest for all the trees.