How I Think About My Career

In a time when so much of what we know is subject to revision or obsolescence, the comfortable expert must go back to being a restless learner.

I plucked that line from A More Beautiful Question, which was one of the best books I read in 2015. The book was centered around using questions as tools to solve problems, generate new ideas, and become better experimenters.

That last item – better experimenters – is a critical point. The author Warren Berger continued with some thoughts on a careers:

…we’ll be expected to quickly adapt to using new and unfamiliar tools, as we try to construct new businesses, new markets, new careers, new life plans – using ever-changing technology, without clear instructions, and with the clock ticking.

In the past, a career was a rigid thing written in ink and followed like a set map to a destination in the future. Now, it’s a fluid idea written in pencil with erase marks all over the page. Careers are no longer a fixed path to follow. They’re constantly evolving as Berger comments.

Automattic is a great example. Career paths at Automattic are almost non-existent, at least not in the formal sense. There isn’t a ladder to climb or formal promotions to eye every year. You don’t spend years trying to work your way up. Instead, it’s a bit like a “Choose Your Own Adventure” book. Everyone, of course, has duties and set expectations, but there’s also a large amount of flexibility.

While this freedom to experiment is liberating, it can also be a bit unnerving as my colleague Andrea illuminates:

But in other ways the lack of structure can feel chaotic and unnerving. Titles don’t matter? Leadership roles are not promotions? How, then, do we “advance”? The only model we have to go by is the traditional one: promote, get new title, climb the ladder to the top.

I recently passed my second year at Automattic, and I’ve been wrestling with this same notion in my mind since I hit year one. What do you do when the career path at your company contradicts the definition you’ve heard, seen, and imagined since you were a child?

In my case, you redefine what the term “career path” means. To me, it’s not about collecting titles or moving up any kind of organization chart. It’s about three areas.

Learn. I have a list of experiences I want to have and skills I want to grow.

Improve. The goal is to become so good at the skills mentioned above that “they can’t ignore you” (to steal from the title of Cal Newport’s latest book).

Impact. I want to feel like what I’m doing is making a positive dent in the world.

Of course, we’re looking beyond the basics of being paid fairly, treated with respect, etc. Once those basics are checked, I look at the three boxes listed above to determine if my “career” is headed in the right direction.

Am I still learning new things? Am I actively growing? Are the activities I participate in day-to-day moving me forward?

Am I receiving critical feedback on my work? Am I learning from those that are smarter than me? Have I maxed out my capacity to improve in this environment?

Am I working on something that is positively impacting the lives of others?

I’m fortunate to work at a company that ticks all of those boxes. There are dozens of learning opportunities on a daily basis. I’m put in positions where I’m forced to improve. The work I do manifests in the amazing stories our readers are sharing (like this one). Don’t just follow a set path. Take an active role, decide what is important to you, and build your own ladder.

Related: What is a career?

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