It sounds like you had held up San Francisco and a startup job as being some sort of perfect ideal. This type of thinking usually results in feeling unhappy later.<p>San Francisco is just one city among many in the world. It may or may not be right for you. Believing the hype that "NYC is the greatest city on earth" or "San Fran is the only place where smart developers go" is a surefire recipe for disappointment.<p>It's your life and it's up to you to find the balance that makes you happy. Congrats on realizing this and having the courage to do a 180.
"Getting your foot in the door" cost me a large part of my career. I did something I didn't really have my heart set on at a large financial services company and the OP is right: it's hard to work on the craft you love at night while doing your day job. I wish I'd have picked up on this years ago but that's life.
Welcome back to Chicago! We're a great city from which to operate tech companies. I still remember moving back to Chicago from San Francisco and how good it felt to be back where the leaves change color and every coffeshop in the city isn't filled with people talking about tech products.
> My problem is that I also took a job that wasn’t <i>exactly</i> what I wanted to be doing so that I could be in San Francisco, instead of staying where I was and honing my craft.<p>Nothing wrong with that. When it comes to finding a career, learning what you <i>don't</i> like about a job can be just as valuable as learning what you <i>do</i> like.<p>A lot of my friends in college already knew exactly what job they wanted the day they arrived at school (or so they thought). I don't know of a single one who got the job they'd been striving for and ended up genuinely enjoying it. Many are now in grad school and still trying to figure out what they <i>really</i> want to do.
Good luck, hopefully you find the experience that you're looking for!<p>San Francisco has only been considered a hub for startups in the past few years. Before that, very few companies made their home in the city, and it was generally down in the South Bay or the Peninsula. Before Twitter, et. al started moving to SOMA, it was mainly banks, and retail companies like the Gap, Red Envelope, etc that were up here.<p>Ever since startups have decided to move to SOMA, the rents have skyrocketed, from 2000/month for a 1 br to over $3000, all in the span of maybe 18 months.
while focusing on short-term, ego-stroking opportunities makes things exciting, i'd also recommend setting 10-year goals.<p>what do you want at 30? at 40?<p>the chain of your short-term decisions should connect to fulfill your ten year goals. this will help make whatever short-term decision you need to make not feel so aimless, soul-crushing, or rash.<p>at the end of the 10 years, you can proudly look back and see how each opportunity help fulfill a larger purpose.
"…my actions felt like they were driven mostly by ego and the desire to be known in the startup community."<p>This is not exactly unique for people working in SF as part of the current boom cycle.
<i>In the past, my actions felt like they were driven mostly by ego and the desire to be known in the startup community. If being out here has taught me anything, it is that none of that stuff matters (obviously).</i><p>Sounds like this was a great learning opportunity for him. If someone gave him that advice before he joined Twilio, it's possible he would have ignored it.<p>Sometimes it takes experiencing something first-hand to truly learn it.
I'd be a little concerned that you're abandoning the network you've built in SF. I guess it depends on the business you're starting, but when I co-founded my consulting company, all of our initial clients came from my existing network.
I don't think the "cheating" was anything unethical. I wrote about the pervasiveness of that (anti-)pattern this morning.<p><a href="http://michaelochurch.wordpress.com/2012/12/12/fundamental-subordinate-dishonesty/" rel="nofollow">http://michaelochurch.wordpress.com/2012/12/12/fundamental-s...</a><p>TL;DR: People have to <i>seem</i> more open to subordinate roles than they actually are in order to get jobs.<p>It's not always greener on the software side of the fence, though. Much of the job is dealing with bad legacy code, which seems to hurt you more if you're a good designer (cf. first and second design paradox) which your well above-average writing skills suggest you are.<p>I like Chicago a lot and think that it's a great place to live. Honestly, I think the obscene cost of living in New York and San Francisco has a <i>negative</i> overall impact on the quality of businesses that can be founded, but that's a rant for another time.<p>Good luck!
It's cool. You're still young. You'll look back at these years and realize how much you really learned with Jeff and the gang at Twilio. Keep writing and reaching out to people and above all have fun. Chicago is a pretty nice backup city. :)
How on earth does someone quitting their job and moving back home constitute news on hn??? I realize tumblr's down, but this really is a lame story. Good luck to the guy, but seriously, this is not newsworthy.