In 2011, I interviewed with Dropbox.
Wait, that’s not far enough back.
In 2003, this one girl in high school decided she didn’t want to date me. I was also invited to apply at MIT and Yale and the like, based on my PSAT scores. Eventually I went to the University of Montana. I promptly lost my National Merit Scholarship on account of my new-found affinity for whiskey.
I got a job in tech support/dorm network administration, at the so-called “DirectConnect Office.” The DCO was great, until it wasn’t: a supervisory promotion went to exactly the wrong person, and I had to quit. I went to work at one of those body shops that calls itself an “IT Consulting” firm, and made $30,000 a year as a software engineer, until I burned out from the stress of billing clients at a rate I felt was unjust.
Being out of work wasn’t too hard. I sent emails to everyone I’d met who might be able to hire me, and I had a job less than a week later, doing DoDAF architecture for the Army’s intelligence center. Twice the salary still felt like a failure, since I was no longer a software engineer.
Through contractual weirdness, I had three different bosses at any given time, and the company on my pay stub switched even though the people I worked with stayed the same. During that period, I had interviewed at Dropbox, and they “decided not to move forward at this time:” they correctly assessed that I didn’t care about Dropbox as an app and was only in the interview hoping for a job, that I’d never be a true believer in the cause.
Eventually I managed to convince the Army and my employer to let me work remotely, and I did that for a year and a half. Then a senior developer position opened up and I decided that I needed to return to software.
Unfortunately, a few years of tech support and a year of maintenance contracts followed by four years in an unrelated industry don’t lend themselves to the “senior” title. The engineering division still hired me, but only because someone’s boss’s boss owed my boss a favor, and my boss liked me, and so I got to be a staff-level software developer, using my TS/SCI to make games in the Unity engine which would be used to train the Army and the FBI.
It was terrible. They didn’t want to let me keep working remotely. They wanted me to move to Georgia. The codebase was inscrutable. I quit. I bought a motorcycle and went rock climbing and drank too much.
Before I ran out of savings, SoFi fell into my lap. I got lucky. The interviewers liked me. I was competent enough to get the job.
If everything had worked the way I’d wanted it to, starting when I was sixteen, I’d have four kids and be working in a very small town, probably doing remodeling or cutting down trees. If I’d gotten in to MIT or Harvard, I don’t know precisely what the outcome would’ve been, but a friend of mine failed out of Brown and the Yale guy from the wrestling team was selling cars last I checked. If I’d had the supervisor promotion or if the local contracting gig had worked out, I’d still be where I was, being paid mostly in the splendor of Missoula scenery. If the Army contracting gig had worked out, I’d be making an above-average wage in Augusta, eating good food on the cheap and living an upper-middle-class existence.
SoFi just raised a billion dollars at a $4 billion valuation. I’ve got a very small piece of that. My salary is a rounding error on the value of my stock options.
Success is a local maximum. If you never fail, you can never achieve anything greater than what’s in front of you at the moment. If you always get what you want when you want it, you never have to learn to create any value. I’m not taking any credit for the good things that have happened to me; if anything, I’m doing better because i was incompetent earlier in life. Maybe I’ll continue to fail. But if I do, maybe my continued failure will allow me to find better and better things later. One can only hope.