02. Confession: I'm A Job Hopper

Rewind to last summer. It's August 2023, and the heat is on — and not just because it’s sweltering outside. I’m in the final round interview for a Chief of Staff role at a midsize tech company. After an initial phone screen with the recruiter, the CEO and I met for 30 minutes on Zoom, followed by two or three more conversations with members of his leadership team. Now we’re meeting again for an hour. At this point, I’ve gone through nearly 30 interview loops during my search. Thankfully there was no take-home project for this one — the amount of free work I did for startups last summer is staggering.

The CEO makes a pointed remark. It's not unfair, and it's not unexpected, but it trips me up every time: "You've had a lot of different roles."

My ego activates. I want to ask if he knows how difficult it is to take on a new role — to learn the lay of the land, build relationships, and quickly construct a mental model of what's important; to push yourself to perform, collaborate, and deliver in entirely new ways.

But I know he knows. As CEO, he does this all day long.

So I take a breath and do what I always do: I try to explain how all of the roles I've held relate to one another, and how they connect. How being a generalist has enriched my perspective, and how looking at problems through different lenses — product, engineering, operations, customer support — has made me a stronger systems thinker, a more methodical problem solver, and a more thoughtful leader.

I've built a multidimensional understanding of the ways that people, products, processes, leadership teams, and whole businesses thrive (and fail). I still have decades of learning to do, but I know enough to strategize from a few different vantage points. I'm confident I can be an effective lieutenant to the CEO.

He nods and smiles, asks a few follow-up questions, thanks me for my time. The following week I get a phone call from the recruiter: they've hired another candidate. It will be a few more months, several more interview loops, and a couple of contracts before I finally find the right role. In the meantime, I write this post.

Generalists vs Job Hoppers

Whether it's during an interview or chatting with friends, or while explaining my career at the Thanksgiving dinner table, I am frequently prompted to weigh in on this debate. While it's not exactly a holy war, it has a similar tendency to yield strong reactions and opinions from folks on all sides.

And it's a topic that has occupied prime, high-interest real estate in my brain for a long time — so I'm excited to finally share my thoughts.

My hope is that this post finds its way to two demographics in particular:

1. Generalists who struggle to own and tell their story in interviews
2. Hiring managers who struggle to properly interview and assess generalists

What sets generalists apart from job hoppers?

First, it should be noted that one cannot become a generalist by doing one job forever. To generalize is to accumulate a range of experiences and exposure, and to do that, one must make a move at some point. While the variables look a little different for every generalist (role, discipline, company, or even industry) the constant is change.

The uncomfortable truth here is that generalists and job hoppers are not mutually exclusive. But three central themes set us apart.

So the uncomfortable truth here is that generalists and job hoppers are not mutually exclusive. But three central themes set generalists apart: deliberation, dedication and depth.

1. Deliberation

I'm sure you've heard the old adage about the difference between running from and running toward. Generalists run toward. We know what we want, and while we may not have a detailed, turn-by-turn map to guide us there, we have a North Star. Generalists navigate our careers with intention and make strategic decisions about role, discipline, company and industry that move us directionally closer to our destination.

We value exposure to different contexts that allow us to build new skills or strengthen existing skillsets. Generalists recognize the difference between opportunities and shiny objects, and we strive to strike the right balance between curiosity and commitment. Purpose plays the main character in our career story.

For Interviewers:

If you're interviewing a generalist, instead of asking why they left their last role or what's missing from their current role, shift the focus to how they navigate their career decisions. Here are some questions that provide helpful signal:

1. Do you have a career North Star? What is it, and how did you discover it? Which moves have you made in order to follow that North Star?
2. When you transitioned from [prior role] to [current role], what did you hope to learn, or which skills did you hope to expand on? How have you accomplished that?

2. Dedication

Dedication means many things, but in this context it means being resilient, rolling with the punches, and rising to the occasion. If you've been in the workforce for at least a few years, you've encountered a setback of some kind: a bad manager, a challenging colleague, a team that doesn't quite click. Generalists and job hoppers handle these setbacks differently.

Generalists know — and if we don't intuitively know, we learn — how to overcome obstacles in service of our purpose. When the going gets tough, we all face the same decision to fight, flee or freeze. Job hoppers follow their impulse to jump ship, while generalists chart a path forward. We are natural problem solvers who commit to causes we care about, and we find ways to learn where others find reasons to leave.

There are, of course, exceptions to this. All the greats have left a role they were excited about because of unbearable circumstances — we've all made a bad or unlucky bet. The difference here is frequency: for generalists it's a last resort; for job hoppers it's a habit.

For interviewers:

Testing for dedication is easy if you know what it looks like. Try these prompts:

1. How do you handle setbacks at work? Tell me about a time when you encountered an obstacle that seemed insurmountable at first, and how you overcame it. What did you learn from that experience? (Don't hesitate to ask for another example if their first answer seems surface-level. A great generalist will have introspected enough to go deep here.)
2. What would make you leave a role you love?

3. Depth

In the introduction to his book Range: Why Generalists Triumph in a Specialized World (aka the generalist bible), author David Epstein writes, "We learn who we are in practice. Not in theory."

Well, dear reader, Generalists are sponges. And not the kind of sponge that sits idly on the edge of the kitchen sink — rather, the kind who lives in a pineapple under the sea. (You've made it this far, it's time to have some fun!)

Generalists don't hover on the surface or dip our toes in — we dive headfirst into the deep end, immersing ourselves in whatever we do. We make a home for ourselves wherever we land. We don't dabble — we absorb. We learn the levers of the roles we occupy, the contours and controls of the systems we reside in, and the terrain of the geography at large.

Job hoppers tend to operate one-dimensionally. They learn just enough to get by for a while, but not enough to drive sustained impact across an organization over time. They sample the subjects matter but never move beyond the knowledge of a novice before moving on.

For interviewers:

Great generalists should be able to tell you what they excel at, and articulate their overall approach to learning new skills. This is especially important for roles like Chief of Staff, where priorities evolve over time. Try asking:

1. What's one topic that you could give an impromptu 30-minute presentation about? How did you learn about this topic? Which themes would your presentation cover?
2. From what you know so far about the role here, which part of the role description do you have the least experience with? How would you go about developing the skills you need to excel?
3. Tell me about a time you were thrown into the deep end. This could be a new role, a new technology, or a new domain altogether. How did you learn to swim?

Thanks for reading!

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