Do you want to climb the career ladder?

Thoughts on not being a particularly goal-oriented person

A few days ago, I had a short twitter interaction, where a few people I highly respect in the industry found that, well, none of us really have career goals. Jill Wolhner started it off asking, “Am I the only one without career goals? Mine are like ‘do well, don't work too much.’”

I don’t have any 5 or 10-year plans that look like “Become a VP of Engineering at a 500 person company” or “Grow an engineering team from <10 to a few thousand.”

People often tell me that I seem like I’ve got it all figured out, but the truth is that I’m just very comfortable with figuring it out as I go, and honestly it’s been going well so far — 5 or 10 years ago, I never would have even guessed that I’d be where I am today. Extrapolate into the future, and I assume that any goals I set now for a few years out may not hit the mark either.

If I had to state my version of career goals, it might look something like this:

• Do good work that I find fulfilling and challenging, with the right balance of comfort and discomfort (the exciting kind that means I’m learning something new) for my life

• If I’m not getting the above, figure out what I want more of, and either try to get more of it in my current role, or start to think about what’s next

My non-planning approach has led me from a job at Google into the world of seed-stage startups, with a stint in leadership coaching and running a leadership development company. I’m at my third early-stage startup now as the VP of Engineering of Range, and I also host Lead Time Chats.

Every change has taught me a different set of skills, but very few transitions were made with lots of upfront planning. When I left Medium to become a coach, I had the urge to dive into the deep end of something very different. A few years later, when I returned to startups in my current role, I really missed being on a team and building things together. At each fork in the road, I chose what felt right and made sense for me and my life.

Intentions as goals

So when I had this exchange on twitter, it felt really reassuring to be in the good company of people I respect, who are by every measure “successful” in this industry, on team no-career-goals.

But it also got me thinking — am I really not a goal-oriented person, or am I just motivated by different kinds of goals?

When we talk about “career goals,” we have something specific in mind, like, “I want to found a startup,” or “I want to be a principal engineer.” I realized that it’s not that I don’t have goals, but they’re of a slightly different flavor.

While I don’t set New Year’s resolutions like “Go to the gym 3 times a week,” my attention will often gravitate towards topics of importance to me, and those start to morph into intentions.

In my personal life, I’ve been focusing on making more space for creativity (including these bi-weekly newsletters!). At work, I’ve been really drawn to the topics of remote productivity (and un-productivity), and what it would look like to have more fun personally and as a team working remotely — to bring a sense of delight and joy to my work.

Longer-term, I can feel the growing desire and intention to write more — perhaps a book or several books.

I’m happiest when I have a few things I’m circling around and making space for, even if I don’t have a lot of concrete outcome-type goals attached to the intentions. I find that when the intention is there, actions and outcomes come, even if I don’t have them totally planned out.

Do you want to climb the ladder? It’s ok if you don’t.

As part of my role, I help people on the team set annual goals. As a leadership coach who is also not conventionally “goal-oriented,” I find that I’m actually uniquely able to help people find things they’re genuinely enthused about, not just default to “become a staff engineer” (a totally legit goal if that motivates you!).

It seems like there are people who when you put a ladder in front of them, they just want to climb it. For example, I recently interviewed several sales candidates, and I met someone who said, “when I see a leaderboard, I just have to be at the top!” For those folks, structures like leveling systems may be motivation enough — when it’s in front of them, they’ll start to work through the checkboxes to get to the next level.

And then there are people like me who look at the ladder with disinterest, but feel like they’re the weird ones because they don’t want to climb it.

I left Google because the idea of spending the next 10 years of my life climbing an arbitrary ladder honestly just did not feel very appealing. At that transition, I honestly almost left tech because I wondered, is it really for me, if I’m not interested in climbing the ladder?

As an industry, we tend to assume that people want to climb the ladder. Or that people who aren’t interested in it aren’t motivated, or are happy to stagnate and coast. As one of those people, that couldn’t be further from the truth.

Supporting more people without “career goals”

Some ideas for how to make tech more inclusive by supporting people who aren’t that motivated by the standard career ladder:

Create space for people without multi-year plans. I recently talked to an early career engineer who felt overwhelmed because she didn’t have a robust career plan. It’s ok to take it one step at a time. Each new experience will give you more data about what you like that can feed into your next decision.

Share your own story and how things haven’t progressed entirely predictably on a career track. Sarah Milstein majored in gender studies and art history and is now VP of Engineering at Daily — probably not a pre-meditated career progression! Many early career people I talk to think they need to have it all figured out. As much as you can, reassure them that they don’t.

Support people who aren’t that motivated by promotions and moving from L3 to L4. Some questions you can ask them to try to understand their motivations:

• If you could have it your way, what would your role look like?

• What parts of your job most energize you?

• If you could choose between this project and this other one, which is more interesting to you?

• Of the more senior people you’ve worked with, whose role seems most interesting to you?

• When it comes time to leave this company, what would you look for next?

Make space for these conversations over time, and also let it be totally ok if they don’t have concrete answers.

Things I’ve been enjoying

• Space for creativity - handwritten morning pages (most mornings) and more crochet projects.

• My local Buy Nothing community - I’ve gotten so many great things from very local neighbors (all within a few blocks), and given away lots of things I no longer need.

• Quiet reading time - I’ve reached a glorious parenting milestone where my kids (9 and 6) are both able to lose themselves in books. So glorious!

What about you? What have you been enjoying? Do you think of yourself as a goal-oriented person? Do you have a career plan?