I Thought I’d Have a Career I Love by Now

Sterling Ringwald
6 min readDec 10, 2015

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Like most millennials, I grew up thinking that if I worked hard enough at school, I could choose a career that makes me happy. Yet here I am, 4 years into a career that so far has been unfulfilling. Not because I majored in the wrong discipline, but because it is only now that I learned what makes a job fulfilling.

Reflecting on what will be my last reflection

Sometimes I imagine myself in the (hopefully) far future, on my death bed, looking back on my life. One of the major areas of life on which I would reflect is, of course, my career. Will leave this world happy about the work I did, or will I have wasted my time all these years? As I daydream on the matter I inevitably bring myself back to the present moment: What actions am I taking or not taking now that I will regret at the end of my life?

Many of my friends are in the situation as me: We don’t like the work we do and we hope our situation is temporary. Yes, my work is challenging and rewarding at times, but mostly it’s just comfortable: It comes with a decent salary and a good work environment. However, if I continue my career doing what is comfortable yet unfulfilling, it is certain that upon my deathbed I will look at my career choices with regret. I want to be passionate about what I do and I want to feel like what I do makes a difference. Don’t we all?

The deathbed thought experiment is one we’ve all entertained at one point or another. Sometimes we might feel like we ought to redirect the course of our life and career, but to actually do something about it is daunting. And, in this age of short attention spans, I found I quickly get distracted and get busy doing much less important things. I’m not entirely against procrastinating, but when it comes to living a powerful life — one needs to act with a higher sense of urgency.

It sometimes takes something like a near-death experience to really get it. Fortunately it’s the only way. For me, an extended period of being solitary will offer me a brief period of clarity. They happen while travelling alone for work, on long rides where no movies or Wi-Fi is offered, and I have nothing to do but reflect on my life and current situation.

And every time I thought to myself, “What the hell am I doing…”

I treasure long periods of solitude. I wish they happened more often. (Oddly, I never managed to bring myself to deliberately have one, say, during a weekend. It’s like I’m addicted to being busy…)

I have acquired financial security, approval from parents and others, a comfortable routine, but these things don’t make me happy. I want more out of life. Something needs to change…

Why am I not happy yet

The problem is that we don’t really know what will make us happy. It seemed so simple at first: Get good grades at school, obtain a degree for a profession of your choice, work at a well-paying job you like. I’ve been sold on this social narrative all my life by my parents and teachers and I naively assumed it would land me a fulfilling job right out of university.

I’m realizing that things aren’t so simple. On the plus side, by taking my education seriously you could say that I covered my basic needs. The bottom of Maslow’s hierarchy of needs is taken care of, if you will, and for that I am grateful. Without this, I would not be privileged with the “first-world problem” of wanting a fulfilling career. However, I had much higher hopes and am starting to understand the difficulty in achieving this.

“Follow your passion!” some would say — We’ve all heard this advice a million times. In the excellent book So Good They Can’t Ignore You, the author Cal Newport convincingly argues that it is actually terrible advice. I won’t repeat any of his arguments, but let me add something to at least spark skepticism: Look around you for evidence of this advice being put into practice. Personally I don’t know anybody who is successfully embodying this old piece of advice. By “successfully” I mean they started with a passion, managed to make a career out of it, which subsequently filled them with a sense of fulfillment. If the advice was any good, wouldn’t I know at least a few of them?

From Newport’s research, what is much more likely is that those who are passionate about their work didn’t start that way; they developed their career and, along they way, grew passionate about their work. If that’s true, then “Follow your passion” by itself doesn’t cut it as a roadmap to lead you to work satisfaction. In fact it’s backwards…

How do I get there

In his book, Newport instead offers a different goal than “passion” and provides an actual framework to achieve it:

Build career capital to eventually find work for which you are intrinsically motivated.

Intrinsic motivation is the goal, and it boils down to 3 things:

  • Competence: The work you do must require you to use skills you’ve developed and which aren’t widespread.
  • Autonomy: You must be given the freedom to work when you want, however much you want.
  • Purpose/Relatedness: You need to see that the work you do visibly improves the life of another human being.

This is based on a 40-year-old theoretical framework known as Self-Determination Theory (SDT). This framework has been verified extensively over the decades and has been successfully applied to many domains in life other than careers, such as education and health. If you set intrinsic motivation as your goal, you cut away all ambiguity. Competence, autonomy and relatedness are all clear criteria. Compare this with “passion”, something which is nebulous for some and which can change over time.

Work that fulfills all 3 requirements is one that is valuable but also rare, unfortunately. And, by the law of supply and demand, in order to have something rare you need something in exchange. Cal Newport calls it career capital. Succinctly, Newport says:

Career capital are the skills you have that are both rare and valuable and that can be used as leverage in defining your career.

Thus, you obtain fulfilling work by following roughly this sequence: Start by building your competence so that you can one day do something that you feel has purpose (i.e. not a “Bullshit Job”, as David Graeber calls them, like being a corporate lawyer for example). This takes years of hard work but is the only way you will gain career capital. As you become more competent, you will be trusted with work that has a bigger impact on people (increased sense of purpose or relatedness). Then you cash in on your career capital: You’ve become so good that you can demand more autonomy from your employer.

Some people go through their whole careers without ever achieving all three. But with the right strategy, it should be doable long before retirement.

Where does “passion” fit in all this? Well, it is during the process of becoming valued for your rare competencies, as you make a difference in people’s lives out of your own volition, that you are likely to find your passion.

Now, I’ve only provided a gross simplification of the sequence to get there. For a more in-depth understanding, you’ll have to read his book.

On a side note, once you’re done reading it, if any parts of it speaks to you, as I’ve written before, try to actually apply its concepts to your life. You learn so much more by doing. Tell them, Tony:

I took this clip from a Tim Ferriss podcast I listened to just last night. Very timely.

So that’s what I’m doing. More on that in my next post ;)

‘Till then.

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Sterling Ringwald

Dude, suckin’ at something is the first step to being sorta good at something. — Jake, “Adventure Time”