The best mistake I ever made

I originally wrote this as an answer on Quora to the question “How did one small decision change your entire life?

In 1990 I was applying to colleges. I had a love of computers and writing, but I decided to abandon computers because being a geek in high school was so unrewarding. I applied to three ‘big name’ schools (Harvard, Stanford, and MIT), UC schools (Berkeley, UCLA, UCSD), and three small liberal arts colleges (Oberlin, Swarthmore, and Carleton). Carleton was far and away my first choice. I’d visited the campus and found the small but focused liberal arts culture to be exactly what I was looking for. Located about 40 miles south of Minneapolis/St. Paul in Northfield, Minnesota, I thought I’d also find an experience very different than the life I had in the San Fernando Valley.

I asked two of my favorite teachers to write my college recommendations. Teaching English and Calculus, they were also the coaches of my Academic Decathlon team (and they eventually dated and got married, but that’s probably outside the scope of this post).

When I handed them the recommendation forms, they looked at each other and she asked, “Are you sure you want us to write your recommendations?” I instantly knew this was one of those moments that required a definitive answer, right off the bat. Either take that feedback along with the forms, thank them, and find other teachers to write my recommendations, or acknowledge that these were the two teachers who knew me best, and tell them with certainty “Absolutely. You two know me better than any other teachers,” counting on that vote of confidence to reflect positively in the recommendations they were to write. I chose the latter.

Okay, a bit of background here is needed. In high school I was a fantastic test-taker, and a horrible procrastinator. I would learn everything the class had to teach, but usually on my own in the final weeks of the class, or immediately before each unit test. Assignments were chores to be avoided or rushed through, and test were the saviors that would buoy my grades. If not for teachers using tests to comprise the majority of their courses grades, I would have done more assignments, and done them better. I just did the math and saw that if I aced tests I wouldn’t have to work hard on the rest. And so while in the top 5% of my class and with SAT scores in the 99th percentile, I was still considered a poor student.

Over the next several months college applications were filled out, recommendations were written, paperwork was submitted, and we entered the long cold winter of expectations and anticipation. My two teachers had the custom of giving their students copies of the recommendations they wrote, a tradition they broke with in my case. This was my first (though clearly should have been my second) clue that my college plans might not be as bright as I had hoped.

To cut to the chase, of the nine schools I applied to, six of them required teacher recommendations and those were the six schools I was rejected from. The three schools I was accepted to (UC Berkeley, UCLA and UCSD), relied almost entirely on mathematica formulas, which made me a shoo-in.

In the end I went to UC Berkeley, intending to major in either Physics, English, or Dramatic Arts (yeah, I know, a lot of people have no idea what they want to do when they start college though). Within the first two weeks there I met folks from the Berkeley Mac Users Group, started volunteering on their helpline a few weeks later, got a job as their campus liaison a few months later, got an internship at MacWEEK magazine a few months after that, started independently developing software for the Apple Newton, then moved over to web development (back in 1995 when the web was in its dark ages), spent as many years out of school as I had in, taking a year or two out here and there to work for SoMa web companies, and finally returned to Berkeley to finish my degree when their Cognitive Science department had fully taken root and I realized that was exactly the education I was looking for, blending my liberal arts and scientific interests into a greater whole.

I finally graduated from Berkeley 10 years after I started, firmly entrenched in the technological world. I spent a year designing at Yahoo before leaving to get a masters degree in HCI at Carnegie Mellon where I met my wife, and then came back to the Bay Area to design UX for Google in 2003. My life is completely different than it would have been if I spent the first four years of my post-secondary life in Northfield, Minnesota studying literature and creative writing.

I’ll never know what that life would have held, but the life I have now is so different and so much more fulfilling than the fears I had as a graduating senior about pursuing computer science. Every aspect of my life can be traced back to that one moment when I made a snap decision in answering the question “Are you sure you want us to write your recommendations?” In the short term I thought I gave the worst possible answer to that question, but in the long term it was the best mistake I ever made.


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