Stop trying to control the arc of your career

Takeaway: It’s only possible to connect the arc of your career in hindsight. There are ways to work within this uncertainty of your future pathway, like by asking whether you’re pointed in the right direction, not worrying if you can’t figure things out, and by planning (while expecting that things will change).

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I’ve been thinking a lot about goals lately. This post is the second of three in a short series sharing a few disparate ideas I have about them.

I’ve written before about how I think five-year plans are bull$#!†. If you know exactly where you’ll be in five years, you’re probably playing things too safe, not accounting for all of the risk on the horizon, or both. Similarly, it’s impossible to know what our career will look like over the course of our lives. As Steve Jobs put it: “you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”  

In our uncertain world, it’s a wasteful exercise to plan your career too far into the future—and it’s especially pointless to predict how the arc of your career will unfold.  

As human beings, the stories we tell each other (and ourselves) are important—so it’s understandable that we want to know (and control) how our career will unfold. But just as there are countless factors that influence our career path—like privilege, unexpected opportunities, unforeseen threats, and some well-timed luck—we can’t predict the future nor can we control everything. And that’s okay. This is what makes our career trajectory so exciting: with hard work, agility, and an open mind, who knows how things will unfold? 

So what can we do to sit with this uncertainty? A few ideas have helped me navigate this unpredictable future. 

Instead of planning far into the future, ask: are you pointed in the right direction and moving at a speed that’s rewarding for you? If you are, keep it up. If not, try adjusting the projects on your plate, as well as the habits you have—or consider a different company or job that will allow for that flexibility. Developing effective work habits and taking on the right projects are two of the strongest determinants of career success. Plus, life’s too short to spend eight hours a day doing work you don’t like.  

Second, don’t worry if you can’t figure things out. The more uncertain the world becomes, the less control you have over the future—the fog of uncertainty obscures the horizon. Instead of seeing this as a bad thing, see it as a fun thing! Not knowing where you’re going or even what you’re doing are strong signals that your work is interesting and matters. If you’re a typical reader of this blog, and have done your best to map your career trajectory without much success, take solace in the fact that it’s okay to not know. 

Third: plan, but expect things to change. Especially during a global pandemic! My work is pretty unpredictable, and I plan around 12 to 18 months into the future. This is the future period when my speaking schedule fills up; planning in this chunk of time allows me to structure the other elements of my work around talks. I’ve found this timeframe works curiously well for most other knowledge workers, too.  

As a general rule, allow the duration of projects in your work to determine how far into the future you plan. If you’re chipping away on a predictable, multi-year project, you may be able to plan further into the future. If the projects are shorter in duration—or you work in a support role and don’t have projects per-se—you may not have this same freedom. 

While we can shape the immediate future, we don’t have as much control over the long arc of our career. The best we can do is take on projects that resonate and develop strong habits around our work. Even if you don’t know what comes around the next corner, at least you’re moving forward. 


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