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Not too long ago, I was reading Charlie Kindel’s “You’re Thinking of Your Career Trajectory Wrong” and it reminded me of yet another trope that somehow is very commonplace, at least in the tech industry - your career is not a sprint, it’s a marathon. It comes from a well-intentioned desire to communicate the fact that careers should be looked at through the long-term lens, which makes sense - we rarely hear the story of someone being right out of college and then becoming a Vice President of Product at a Fortune 500. It’s all about the long game. But it also sets a lot of folks for failure early on.
The marathon analogy is deeply flawed. First - running a marathon is by no better than sprinting. Neither is sprinting excluded from a marathon, despite the fact that you need to keep a sustainable long-term pace. The analogy in question puts forward the idea that thinking of your career means that you need to be constantly running to some kind of “finish line” - an end goal. You’re told that a career is analogous to a race - you have to keep going to some destination to be successful. But here’s the kicker - careers are not races. They have no map. There is no finish line. As a matter of fact, you can freely drop out and still be successful. The end goal is no goal at all - it’s entirely up to you what that is or isn’t.
Conventional advice will tell you that you should be mapping out your career over the long term - set milestones, and then execute against those. Lifehacker went as far as put it this way:
At the expense of sounding like a corporate consultant or corny stock broker, you should try imagining your career track like a graph that shows short-term versus long-term investment gains—it looks volatile in the short-term, but when you zoom out you can see the upward trend.
In theory, this sounds a-okay. In practice, this once again binds us to the same “go up and to the right” model. I was guilty of this thinking too. Up until the point when I realized that careers are not as “up and to the right” as corporate mantra books teach you. Building a map for something that I have no understanding of and mistaking it for the territory is a terrible waste of time and a sure-fire way to be disappointed over the same very long timeframe.
When you work at a big company, there is a very crisply defined career ladder that is handed to you that is tailored to the role that usually maps to impact but more often than not is associated with time in role in conjunction with impact. That leads folks to believe that in five years, based on the team or organization average, they can be a senior product manager, and in ten - they should be at a partner role, and so on. Once you have this model in your mind, you start thinking about ways to climb that ladder and start chasing the title. In your mind - there is a linear path that you have to follow to be successful, and by golly you better start running in that direction lest you be passed over for promotion by someone who had a better map. The danger in this kind of thinking is that you’ll be missing the forest for the trees. Careers, and specifically careers in tech, are almost never a linear path. Career planning, in its traditional sense, is a load of baloney.
As Marc Andreessen said:
The world is an incredibly complex place and everything is changing all the time. You can’t plan your career because you have no idea what’s going to happen in the future.
So - you can’t assume that your career path will be linear, and you can’t assume that you are in some kind of race to be the top dog. What’s the alternative?
A Different Mental Model #
The way I was thinking about my career early on was flawed, and for what I thought was a race to the top in reality was more like a drive through the mountains. Sometimes you’ll be driving and seeing beautiful peaks, other times you’ll be in the middle of a snowstorm with your view entirely obstructed, while on occasion you might even turn back and take a completely different route because the one you were on was getting boring. Or, if you are adventurous - you could ditch the car and start climbing up some hill you saw in the hopes that you’ll get an even better view from there. You have many options. You’re not competing against anyone. There’s nobody behind you or in front of you. It’s all about your own path that is determined by what you want.
Your own path can be carved in many ways, depending on what you are optimizing for at your stage in life, none of them better than others. It can be financial gains, satisfaction from building world-changing technology or solving complex puzzles, or simply because you have an interest in the domain. This list is, of course, not exhaustive. The motivation, just like anything else, can also change with time. When you’re young, you have a higher tolerance for risk than when you’re supporting a family with two kids. This means that as time goes on, you can take a different class of opportunities.
At my current career stage, I am personally optimizing for opportunity. I talked about this on a podcast with @hellomayuko, and it’s once again something you can find in Marc Andreessen’s writings. For me, at this point in time I am interested in figuring out ways to open doors to faster and more abundant learning. In a number of years that can change, depending on where my wife and I will be and what needs we’ll have around our shared lifestyle. I started learning a lot about graphics programming and CUDA, and who knows - maybe in some distant future I’ll be designing video games, or helping some biotech team build the next virus analysis framework. I don’t know, but I am also comfortable with this degree of not having a plan. It’s not that I don’t know what I am doing - I do, but I also leave the door open for a more fulfilling life for me and my family.
I don’t know what opportunities or obstacles will pop up in six months or three years. If bad project planning taught me anything, is that software engineering planning past 6 months in advance is a well-organized Kanban board of lies everyone agrees around, but secretly know that it will never happen. I believe careers are the same way. Pace yourself, figure out what you care about most, and start carving a path in that direction. If you realize that you were going the wrong way, no big deal - just take bit of a detour back, and go in a different direction. As Bob Ross used to say:
We don’t make mistakes, just happy little accidents.
And for the love of everything, don’t forget to tweak any mental model, framework, or guide you read somewhere and adjust it to your own situation. There is no “one size fits all” when it comes to personal growth.