10 things about being an actually useful "generalist"

Don't be intimidated by specialists, for one.

a painting of stem cells

Everyone’s really excited about the re-emergence of generalists, and by everyone, I really mean a certain part of Twitter. The argument goes something like, “experts are fake, smart generalists rule the world. everything is designed by people no smarter than you, and courage is in shorter supply than genius.”

Look — as the Twitter princes themselves admit, “of course our civilization works via a deep tangle of speciation and specialization.” They’re not saying that we should get rid of specialists, and of course experts are not really fake. It’s a provocative statement! It gets the people going!

The statement is trying to counter the feeling that generalists are easily dismissed in favor of specialists. Specialists have meaningful flaws: they can be hidebound, limited by their field’s orthodoxy, and artificially elevated. In order to push the work beyond the specialist-constructed confines, generalists should screw up their courage and have opinions. They should be bolder. Stop deferring to experts, and if believing “experts are fake” gives you permission to do so, great.

I do think that this statement can be taken the wrong way, which is the validation of management consulting as an industry and a mindset (no!!! no! plz!) Self importance as a service is absolutely not what I mean when I say “generalist.”

Great generalists are creative, understand the world from first principles, and aren’t afraid of just getting things done. They effectively translate skills from one domain to another. They see connections between siloed pockets of specialization. They have a strong bias to action, which makes up for their lack of expertise. A great generalist will have 2x the output and stamina of a specialist — out-working the specialists is how they learn!

I get a lot of requests on how to be a good generalist, and so I made this list so that I can send it to people who ask me for advice on the topic — if there’s anything else that’s a part of the core curriculum of generalists, comment here please!

1. A guide for getting things done in large organizations: Tom Kalil, of the Obama Administration has a nice guide to being effective. I think policy people are often extraordinarily generalist — an inch deep and a mile wide on a whole host of issues that they need to address — which makes me scared for our democracy and also triggers the development of a bunch of tactics that are surprisingly useful in most non-policy contexts. There are parts of the doc that I completely do not understand — for example, the aphorisms on the whiteboard. But most of it is exactly what I would have needed to get something done at Stripe. There are so many good ideas in this post, it should count for 4 things:

   1. “If you want someone to help you, make it as easy as possible.” —> often forgotten!

   2. Different “types” (Communicator, Diplomat, Visionary, “Tom Sawyer” etc.) and when they’re useful. I like this “when” framing, because I never think about the question of “where are we in the cycle” whilst bringing in leads for a project. For example, they deploy visionaries as leads at specific moments: “In the White House, [the ability to generate on the spot good ideas] is especially valuable in the run-up to the budget, major policy addresses, and presidential or cabinet events.”

   3. I especially liked the idea of borrowing from politics to “understand the pros and cons of multilateralism, minilateralism, and bilateralism” as a way to get things passed in the organization.

2. Giving away your Legos: This is Molly Graham’s best essay and is very famous, but I also like her essay on what she learned about work in her 20s:

   One is about collecting experiences. The other is about collecting people — finding great people and traveling with them. Both will serve you in invaluable ways over your career. Both will guide you to places you could not have imagined when you started working. 

   Focusing on people and learning about yourself is a much surer bet for success than trying to get it “right” immediately after college or trying to pick a rocketship company like Facebook to join early. It is definitely true that one stint at a well-run, fast growing company will change the trajectory of your career, but truly, those opportunities are hard to spot. I stumbled into Facebook by following Elliot Schrage. It was a lucky choice. Most people I know who have ended up at one of these “rocketships” didn’t end up there because they were a great picker, they feel like they ended up there by mistake. 

   Instead, focus on the things you can control. Follow great people. Take risks. Focus on your strengths and learning about yourself. 

   At the end of your 20s, you want to have clear lists — what you love, what you hate, what you’re good at, what you’re bad at. If you know yourself well, you will know what direction to point yourself in and what ladder to climb. You will know what makes you happy, fulfilled, and powerful at work. You also want to have a community – interesting people that you’re desperate to work with again, and wonderful people who want to help you grow and attain whatever goals you end up having. 

   Collect people and experiences – that is the magic that can set you up for a long and fulfilling career.

3. Don’t be a generalist: You can either have general interests or general skills, but not both. For example, you can be an all-round player who is really interested in Direct Air Capture. But it is very hard to “end up” as an all rounder who is interested in nothing.

4. Do not succumb to the job status cycle: Go ahead, say you want to be a chief of staff. I dare you.

5. Just tell someone they can do more: I used to get so annoyed when my managers would simply ask me to do better or do more. I’m already doing more! This was definitely good enough, and better than expected. But the push to do better usually helps. I like this Tyler Cowen statement, “At critical moments in time, you can raise the aspirations of other people significantly, especially when they are relatively young, simply by suggesting they do something better or more ambitious than what they might have in mind.  It costs you relatively little to do this, but the benefit to them, and to the broader world, may be enormous.”

6. Baby me, on work: My own take at age 21, 8 months into working at Stripe. I can’t emphasize getting into tiny details and mastering them enough. Pay attention to the small stuff!

   

7. Advanced Time Management skills: If you’re someone who constantly feels like they are running out of time, this Shreyas thread is great.

8. How to get layered: Most early career generalists get super angry when they get layered — Cristina (my former manager!) shares what to do when you get a new boss.

9. What you can do: A few years ago I was at a company where I felt urgent changes needed to be made. The changes felt so obvious to me – and it felt frustrating that it wasn’t happening sooner. Whether I was right or wrong is irrelevant.  But I felt the pain of inaction keenly – how could we not be making changes? How could we wait?

   And then a mentor of mine told me I had three options:

   1. I could write my ideas down and wait to see if I was right.

   2. I could use what skills and power I had to try to make the changes.

   3. Or I could quit.

10. Operating well: My friend Sam wrote a great post on everything he learned about operating well from his career thus far.

    Unblock psychological barriers. When something isn’t getting done, it’s because the person a) doesn’t have the time b) doesn’t have the skill or c) has some sort of psychological block. The third case is surprisingly common. After a few slips with someone I trusted, I’d just ask directly. “I noticed this work isn’t being pushed forward at the rate I expected or at the quality you normally deliver—what’s holding you back?” which would open up a conversation.