Sailors and Rowers

There seem to be two distinct models people have for achieving success: sailing and rowing.


Sailors follow the wind. Do it right and they can go great distances pretty fast, often without even having to do much work. A good sailor picks the right opportunities with the right people at the right time. Sometimes they may contribute a lot. Sometimes they may be freeloaders. It’s not easy to do well, though. Most people who sail get stuck at sea or blown off course. That’s because being an effective sailor requires knowing the wind: not just how it blows now, but where it’ll blow in the future.

Rowers? They don’t care too much about the wind. They just row. Sure, current and wind still exist, but the rower keeps going when it’s easy and when it’s hard. Rowers are focused, which makes them rarer than sailors. Sometimes rowers are so good at rowing they lose sight of where they’re going in the first place. Other times they fail to realize that no matter how hard they row, the wind and the currents are keeping them in place. But being a great rower can pay off: enough hard rowing will usually get you somewhere other than the place you started.

Most people aren’t consciously aware of how they model success. But we think it’s helpful to know. Not just so you can better understand yourself, but so that you can understand how other people are likely to operate.

Who is a sailor?

Most people are sailors because most people are not particularly focused or consistent. They bounce around from one thing to the next. They are opportunistic. Try placing all of your friends into one of the two categories and there’s a great chance you view most of them as sailors.

There’s a difference between people who know they’re sailors and people who don’t. Since being opportunistic is the default for many people, it’s not uncommon to behave like a sailor (trying to chase the wind) without acting like a good sailor (being smart about it). This is how many people get stranded at dead-ends. Cryptocurrency pump-and-dump scams are a good example of this phenomenon: people chase the wind without any real knowledge of it. You should know if you’re a sailor!

Good sailors trade in status and capital. They might wind up in a field like venture capital or politics, status-driven professions in which the way you measure competency, if you even can, is by investigating someone’s ability to read the wind.

Here are some examples of how people sail:

• Bounce around at tech startups in hopes of winning it big.
• Play status and politics games at big corporations to climb the ladder.
• Join companies based on the relative hot-ness of their industry (i.e. riding the AI wave right now).
• Work in industries where perception > output (i.e. consulting).
• Constantly change their career based on what they think will help them rise fastest.
• Monetize trends (i.e. the people who make graphic tees about current events).

There’s a chance you are reading this and thinking, Oh, so these guys hate sailors. That’s not true. Being a sailor can be a viable path to becoming successful. It doesn’t have to mean being lazy and cheating your way to success. Living like a sailor can be as simple as going where the wind takes you.

If you are going to go where the wind takes you, however, it’s helpful to be smart about it. Don’t let any wind take you to any place. There is probably a whole guide to be written about living life this way (and please email us if you’ve read a good one).

Who is a rower?

You may have a friend who’s been working at the same company, or in the same field, for most of their life. Who tends to stay the course even when their employer faces rough patches, or when a flashy new opportunity comes their way. These people are rowers, and they are much harder to find. It’s impossible to know the exact number but we’d bet the ratio of sailors to rowers is something like 10:1.

You achieve success as a rower not by optimizing for the perfect opportunity, or caring a lot about your status and capital. As a rower you put in the work, ideally on the same thing, for a very long time. In many cases this consistency compounds, and in the long run you can come out successful. You might get lucky and end up making a lucky decision (imagine being a great rower early at PayPal), but your primary strategy is not to achieve success via picking well.

Most jobs are well-suited to rowers. Employers like rowers. The exceptions are jobs that revolve around status, vibes, and reading the wind (like becoming a VC or working in politics). Apart from jobs like these, you can succeed as a rower almost anywhere. And some jobs virtually require you to be a rower: most published authors, for example, spend years writing many books before landing their first book deal.

What to do with this information

Part of this essay’s intended usefulness is that you are more aware of which kind of person you are. Simply knowing how you’ll reach your goals can help you make better decisions.

This framework can also help you understand your relationships with people. If you’re a rower and you work with sailors, don’t expect them to keep rowing when the wind shifts (or to have particularly strong opinions that they will defend). They’ll just sail in another direction when things don’t work out, and if the wind ever brings them back, you’ll see them again. It can be annoying. But that’s how they view the world.

If you are more like a sailor, the decisions that rowers make may sometimes be baffling to you. Why aren’t they getting in on AI when now’s the right time? Why are they still working at that company even though it’s clearly dying a slow death? Why do they spend so much time on that project when there’s no clear evidence it is ever going to produce results? Why don’t they care about getting on our boss’ good side? [0]

You might be a little bit of both. You might be a rower and then a sailor, or vice versa. Simply being aware of the concept and mapping it onto your own behavior is a good start.



[0] This line about getting on your boss’ good side is a nice place to remind you that there can be a blurry line between these two categories. You might not be fully one or the other. Some people who are primarily rowers care (at least a little) about workplace politics and may be opportunistic. Some sailors work hard on projects even when the obvious path to success becomes less clear. We still think the distinction is useful, though, because very few people are 50% sailor and 50% rower.

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