Why None of my Past Successes Felt Like Successes; or Annoying Google Interview Questions

So here we are. A decade after college, I realized I wasn't getting any closer to anything. I had given up on several big, sustained projects that were actually very successful by traditional standards:

  • My musical aspirations that has taken me from self-teaching guitar to playing shows in two college bands in 3 years
  • The blog I had been posting to daily from 2009 to 2013 which culminated in an ebook launch
  • Learning the contractor-gig lifestyle well enough to become a 50% owner of a web marketing agency
  • Teaching myself to code and two years later landing a senior developer job at a billion-dollar startup

None of these made me happy. They all felt like distractions from what I really wanted to do, which was...never figured out. I think by the time I left the startup, I had become fairly obsessed with space and mathematics, so I thought maybe that would make me happy. I figured I was picking goals that were too small, and that if I just picked bigger goals, attaining them might be more fulfilling. Astronaut seemed like an appropriately unreasonable goal, though I guess becoming a genre fiction author might be similarly unreasonable, at least by my dad's reckoning. Ha...ha...ha.

I realize now that bigger goals are probably not the solution. The right goals might be more fulfilling.

Large and Hollow

I used to want the biggest and the best of everything. I wanted tons of money, like, historically significant sums of money. I wanted the most exclusive cars. I wanted to be the best of all fantasy AND sci-fi authors. I also wanted to win the CrossFit games, while also becoming a master traceur and a blackbelt in everything. Not surprisingly, I never accomplished any of those things, and eventually was so wrapped up in only doing the best that I didn't even try, because I realized how unattainable all of it was.

In retrospect, I realize that most of those things are out of my control. I can probably make a lot of money if I really wanted to, but that amount of money relies on a lot of luck and other factors out of my control. Some of the others are less out of my control, but to be the best of the best requires some luck. Especially if I'm not even doing the basics.

But even the big goals that I did attain didn't make me feel fulfilled. I just felt like it had been a waste of time. The taste of success was bitter, so why would I even want to pursue the even higher levels of success that I was aiming for?

Happy in the Doing

The things that make me happy in the doing are not particularly fancy or ground-breaking. I love flying. I keep coming back to that. Adventuring, spending time in nature and feeling exposed and tired and exultant in my physical endurance feels good. Spending time with my family. Writing feels good in the doing. Just putting the words down on the page/screen is lovely. I don't know why. But I don't think I'm supposed to question that.

I also enjoy coding and constructing math proofs actually. Not just understanding math, but building a math thing to solve a problem in my head. Ah, now that is true bliss! Haha, I never realized that I liked that about math. That's why I feel like some math is like learning .NET, with all its hidden and arbitrary methods that I didn't know existed, why they exist and what they do (oh, well how was I supposed to know that was the right way to do that thing?). While other math is more like my familiar JavaScript: I know it well enough that I can build anything I want. Though of course, it too has its own foundational building blocks...though they feel much less arbitrary and black-boxy than .NET. On the other hand, .NET allows you to spin up a much more complex tool from the get go, without needing to write everything yourself.

Building a thing to solve a problem. Building a solution. Designing and executing a plan to make a thing a reality.

The Level of Performance

I don't know why I never really felt challenged in these various endeavors. I felt frustated, sure, but they all felt like small time gigs. Nothing felt big, or matterful. But I don't think anything really would ever be, especially in 2-5 years, which is the timeframe we're talking about here.

I wanted something that would challenge me, something that I might fail at a few times before I finally succeeded. But if I look back on these things, I failed plenty of times. I was rejected from several job interviews before I landed the coding job that really got things rolling. I bombed so many public performances on guitar before I had any sort of success in a college band. I published plenty of flops, and a few real bad articles, before I saw any success with my blog. How many pitches did I make as a contractor that I didn't land? How many clients did I have that went nowhere?

I don't know why I only tell the stories of the easy-success. Maybe that's the one that is consistent with my image of myself as naturally gifted. But oddly, that's really hurting me, because it causes me to devalue the struggle I went through in order to attain the successes that I did. They don't feel worthwhile because in my memory, I didn't have to pay anything to attain them.

I was once asked at a big-time coding interview (Google) to recount a time in my life when I had failed. I couldn't come up with anything. I have certainly failed at big goals and projects, but I don't frame setbacks as failures, and if it's something I really want to do, which I try to make everything I pursue, then I just come back and try again. I can't really imagine a situation in which I would just walk away from a failure and leave it at that. Unless I didn't really want to succeed, in which case, why would I even bother in the attempt?

That's just me. I don't know if that's what they meant. I am still not sure the question makes a lot of sense, because I don't think I had the same definition of failure as they did. Even in analysis, I can't really pin down what they were talking about.

Someone said, if you're not making mistakes, you're not working on something hard enough. I don't feel like I ever really make big mistakes, and I wanted to be in a situation where I wouldn't find things so easy to learn. This sounds very arrogant, and I don't want to present false modesty about my abilities; I know I am a fast learner of skills and have an adaptable mindset that I have found able to take on a variety of persepctives and mental models. But I also want to recognize that I have always played things safe, and avoided risks. I have always been careful to weigh my current abilities against a proposed challenge, considered whether I would grow fast enough to master it, and thought about the resources being provided. If it was too much, I waited until I felt I was ready. But since I've never overreached, I don't actually know what that looks like. Where is the limit of my ability? I have never been able to answer that question to my satisfaction.

I would say that most of my math classes in the last year have been beyond my ability, from my personal standards of understanding. I have earned A's, but if you asked me today what I learned, I wouldn't be able to give you much. By my standards, that's not really success. On the other hand, that is exactly the question the interview at Google found so inadaquate. I gave a story in which I had failed by my own standards, but had apparently succeeded by his. Thus, I didn't answer the question.


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