The Prestige
On the heels of James Bach’s Buccaneer Scholar, a new idea, book and blog where he details his experience with exploratory thinking and learning, comes my own wrestling, not only with how I learn, but what I should learn. Due to recent events I’ll make clear in a few weeks, this question has begun to capture all of my spare CPU cycles — and it won’t quit.
The crux of the question, I think, is this: When I was thirteen, I set a goal to go to college, get a degree, and work for Microsoft (then the most popular software company in existence). While in college, I latched onto open-source software and the free software movement — happily ditching Windows for Gentoo, Mandrake, then finally Ubuntu — and gleefully traded Microsoft for a slightly newer and more exciting company called Google. Google had free food, funky office chairs, and they fit the goal I previously made when I was thirteen. My sense of self was intact, no harm done.
When it came time to interview, though, things were messier than I expected. I was still trying to finish school — to graduate, move out of the dorm and wrap up all the extracurriculars that consumed most of my spare time; and I was, on the more personal side, simply trying to grasp what was happening as I made the transition from college life to real life.
It was all too fast. Not only was I not accepted by Google (that’s a story for another time), but I didn’t know where else to go from there. In magicians terms, I made all but the prestige of my childhood goals, and I was left like a confused audience member contemplating whether I should stand up and applaud.
But, prestige aside, I realized my longstanding goals ended after college, and whether or not I was employed by Big Popular Company mattered little to anything but my ego. Even if I did achieve my goal, I’d still be left with the same question: What happens next?
When I learn, I need to know the big picture. I like to know where I’m going, why I’m going there, and in general, how to get there — but not always. I know the devil’s in the details, but I like figuring out the details as I go along.
Looking back, I had more or less achieved my goal — college, degree, employment — but I didn’t have the big picture telling me where to go next. I still don’t. I’d assume even James’ Buccaneer Scholar, with his exploratory state of mind, would have some type of charter, though I can’t believe he’d always know where he is going. James, I’d like to hear you expound upon that if you haven’t already.
This leads to the more practical dilemma: Of my interests, which path do I choose? The following is a list of career paths I could be interested in taking. Though I run the risk of taking the totally incorrect approach to, well, life, of these career paths, I can’t help but be interested in their prestige. Here goes:
- Independent test consultant.
- Product Manager/Test Manager for large software engineering projects.
- Ph.D in Software Engineering or Cognitive Science, researching and teaching software engineering and/or software testing.
- Software Developer for cutting-edge, Web 2.0 technologies (I am that now).
- Entrepreneur for my own software development company. (I’ll probably need an MBA).
- Entrepreneur for my own software testing firm. (Again, an MBA).
- Tech Journalist for popular blogs and magazines. (I’ll probably need to study journalism).
- Politician. (I’ll probably need to study political science, though this brings me to my next interest…)
- Something in the arts, say, acting.
And as an aside, this whole process feels like one big game of Twister. 
This is hands-down the most interesting, fun-to-read, meaningful blog post you’ve written. We’ve been friends for 5 years now, and I never knew you were that goal-oriented, and that you’ve been so career-focused. That’s not an insult at all, as you’re more professional in more situations than any of my friends. Just, I never knew you had the goals you listed. That’s why it was cool to read.
Anyway, it’s interesting to note your outlook and questioning. It seems sooo many of my friends are experiencing the same thoughts you are having. I’m partially included as I debate which full-time job I’d truly like more. It’s hard to anticipate and measure future life enjoyment, for life is such an infinitely-multi-variable problem.
Just for fun… I’ll take a guess as to how it’s all gonna go down
I’d say that you’ll work for a non-famous company that has < 5,000 employees for a few years. You’ll do that, learn a lot, further hone in on your skills, reputation as a tester, and your articulation. You’ll be a PM during a few of those latter years with the company. Simultaneously, you’ll start to venture and attempt to make your own start-up that is unrelated to your regular day job. It’s definitely still gonna be tied w/ software, but it’s not close enough to your job because you would never dare break a non-compete agreement or whatever signing contract. After some initial work and deployment of ideas, you realize that in order for it to further blossom, you need more people and capital. So, at this point you enroll in a nearby MBA program. You finish the degree, gain some attention with your product, and after 2 years, someone buys it for a good bit of money. Nothing to make you retire on, but enough that you could definitely live comfortably for a while. Then, you become addicted to the game “twister” and nobody hears from you again 
Okay, I’m joking.
I’m with Chris. You’ve definitely touched upon an issue that I think a lot of our peers (myself included) are having. Unfortunately, I think the flash you linked to is probably the best (if totally unspecific) answer to the problem.
Really, the problem is that there is no problem. You’ve got your whole life ahead of you and opportunities in spades. If you want to change the course you’re on, you’ll have to settle on one of them. It may make you happy, it may not. Either way, life evolves. I get it, you want to optimize – choose the best possible solution, but that’s just not possible.
Here’s something I’m finally coming to grips with: Even though you see the potential for greatness in most things you do, you have to sacrifice that greatness in most endeavors so that you can actually achieve it in only a few. In other words, I’m learning to be happy with “good enough” most of the time so that every now and then I can experience “awesome.” It’s a shame that’s not something that’s taught in school. But then, I did miss a lot of classes…
One more thing — make sure you’re not over thinking things.
From “The Perks of Being a Wallflower” –
“Do you always think this much, Charlie?”
“Is that bad?”
“Not necessarily. It’s just that sometimes people use thought to not participate in life.”
“Is that bad?”
“Yes.”
Sorry, but I keep thinking about all this, and I keep running into pertinent media online.
Dan Gilbert on what makes us happy:
http://www.youtube.com/watch?v=LTO_dZUvbJA
[From Tim: That video is amazing.]
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Hi Tim – We met briefly at CAST 2008, so I feel free now to recommend stuff to you. Check out Demitri Martin’s BBC comedy special, “If I”. http://www.youtube.com/watch?v=mKnzPHtf9u4 It’s an autobiographical comedy sketch about a smart kid who could either work in his folk’s Greek diner, or be a corporate lawyer. Of course he ends up on TV telling jokes and playing guitar. It is fascinating and funny and touching.