Sounds like you came a long, long way. As a former little league baseball and musician myself, who has started my fair share of bands, and other ventures, I can totally relate to the feeling of putting so much in, and having to hang 'em up when things just aren't working out for one reason or another. For whatever it's worth, consider this: even the most talented, hardworking ballplayers never even make it to the show. Unlike those guys, there's not really an age limit in your field, and instead of needing a few hundred pros (or thousand, if you count the minors too) as a software engineer you'll have lots of time and opportunity to get back up to the plate (too many sports metaphors -- is there such a thing?)

All the best at Twilio :-)