What elite professionals get wrong about career growth
I’m taking a brief break from writing about scaling tech companies to share some advice I wish I could send to myself at the start of my career. I’ll be back to the usual stuff soon. Subscribe to join the 1,107 people who joined since my last essay:
I once fell asleep in the lobby of Disney’s Animal Kingdom Lodge at 3:00am while editing a 200-page deck about how to get people to visit more theme parks.
But contrary to the bad rap that big consulting firms get, BCG was a great place to start my career. I met a lot of ambitious people and got a bootcamp in the basics of how to write, speak, and use data in a business context.
The problem is what often takes root in people (including myself) in these “elite” professions after a few years. Many develop an incorrect mental model for how to build a successful career. I call it Generalist Disease.
The hallmark symptom of people with Generalist Disease is optimizing for optionality. In order to open as many doors as possible in the future, they chase breadth (exposure to as many industries and functions as possible) and chase prestige (logos and titles that look good on resumes).
The classic places to find breadth and prestige are fields like consulting, banking, and private equity. As tech has grown in prominence, the list now includes fields like product management and VC. Top MBA programs can be a good way to make sure Generalist Disease metastasizes.
These jobs are very good at making you feel like you’re on the right path. Your parents are impressed, and you start to make more money. You may not be enjoying the work, but you can tell yourself a story about how you’re paying your dues to generate incredible options.
But after the 3rd or 4th impressive line on the resume, where are those really good options? They often fail to materialize, and people with Generalist Disease start to feel stuck.
I had a professor who said:
"The first 10 years of your career are for learning what you want to do. The next 10 are for getting great at it. The next 10 are for making an impact and making money.”
Of course it is never that linear, and some people do it faster. But there is a kernel of truth in it: generalism is not the goal. It is just a means of goal-seeking to find what it is you really want to do. Ultimately you must specialize to build real leverage, which requires the exact opposite of increasing optionality. It means being intentional about taking options off the table.
Unless you are one of the rare few who knows what they want to do at the start of your career, chasing breadth and prestige early on is actually a good idea because it accelerates the exploration part of the journey. Breadth lets you see many potential paths, and prestige helps open the initial door to paths you might want to explore.
But they both rapidly turn counterproductive, and people with Generalist Disease don’t seem to notice. The kind of breadth you get in fields like consulting is so surface level that it can only tell you where to hunt, not cross anything off the list entirely.
The value of prestige asymptotes after one or two door-opening lines on a resume. Then it turns into a device that employers use to convince insecure people to keep working at things they probably wouldn’t otherwise.
Clearly some people work at traditionally generalist careers like consulting for a long time and love it. But let’s be clear: they are no longer generalists. They are specialists in the job of consulting. If that is what you want to do, that’s great. But if not, it’s important to get off the ride when your learning switches primarily from exploration to primarily learning the job of consulting itself, which for many people is around 2-3 years.
You ultimately need to switch to chasing aptitude and enjoyment. If you can find something you are naturally pretty good at and enjoy enough to spend a lot of time on, ultimately you will become very good at it and learn to enjoy it even more. That creates a compounding advantage.
Getting off the ride and chasing aptitude and enjoyment usually means trading a career path that goes steadily (but slowly) up and to the right, for one that is choppier at first so that you can uncover opportunities to rapidly bend the curve upward.
Hard pills to swallow
Why doesn’t everyone just take this advice? Because the only two remedies are difficult to stomach for someone who is carefully curating an elite image.
First, you must be willing to take steps that feel at best lateral and often down in order to explore widely enough to figure out what you really want to do.
The peak of my own generalist hubris was working in private equity after BCG because it was more prestigious and paid more. My colleagues were incredibly smart, and I think some of them genuinely loved it, but it just wasn’t my thing. It was hard to figure out what to do afterward because everything looked like a step down.
I ultimately decided to take my first startup role at Thumbtack. I went from private jets and a private office at the top of the Transamerica tower to making a desk out of boxes in a supply closet so that I had a quiet place to take calls. But I ended up learning that I loved startups, and I wouldn’t have had a shot at all of the things I got to do afterward if I hadn’t tried it.
Second, you have to grind. Once you narrow in on the right field, you have to find the parts of it that are the “craft”: the unsexy, manual, and repetitive tasks that you just can’t excel without.
Of course there is nothing wrong with choosing a field like product management or VC. I know many people for whom these jobs are the source of maximum impact and happiness. But the best product managers I know don’t float above the team acting like the CEO of the product. They spend an incredible amount of time talking with customers to understand what they need, and with the team figuring out how to help them move faster. And the best VCs I know are out personally pounding the pavement every day to find the best founders to work with.
My own role has “strategy” in the title, a word that people with Generalist Disease often flock to. But almost none of the job is sitting back and pontificating. I don’t know how to be good at it without spending countless hours swimming in the data and customer feedback looking for patterns.
The best of both worlds
It is initially unsettling to take a job you’re not sure is right, or to put your head down and refine the craft rather than continuing to explore options. But it will certainly make you happier to work hard at something you love and are good at. And ultimately most people that do also seem to get more of the conventional success they wanted in the first place.
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