In “What Are You Going to Do With That?,” William Deresiewicz tells the freshmen class at Stanford:

In the journey toward the success that you all hope to achieve, you have completed, by getting into Stanford, only the first of many legs. Three more years of college, three or four or five years of law school or medical school or a Ph.D. program, then residencies or postdocs or years as a junior associate. In short, an ever-narrowing funnel of specialization. You go from being a political-science major to being a lawyer to being a corporate attorney to being a corporate attorney focusing on taxation issues in the consumer-products industry. You go from being a biochemistry major to being a doctor to being a cardiologist to being a cardiac surgeon who performs heart-valve replacements.

But he goes on to point out why and how these kinds of defined professional paths—the ones high school and college students students are so often told constitute “success”—might not be optimal, for either the person on the path or society in general. If you “simply go with the flow,” you can end up merely being defined by what someone else has laid out. Perhaps not surprisingly, Deresiewicz goes on to say, “There is an alternative.” He calls it “moral imagination” and defines it this way: “Moral imagination means the capacity to envision new ways to live your life.” I would call it something else: the “third way.”

Deresiewicz’s essay shows why we need more talk about the third way: there are more options out there than further advanced schooling. Stanford in particular is a good place to be reminded of this. Obviously, Deresiewicz doesn’t say you must choose grad school or the professions, but the absence of any acknowledgement about starting your own company implies that those are the two primary choices.

I’ve similar talk. In my interview with him, Tucker Max describes the primary speech he gives at colleges:

[. . . W]hen you’re an undergrad, generally you think you can do two things. You’re gonna have to get a job after you graduate or you gotta go do more school. Because everyone who’s giving you advice or telling you how to live your life are people who’ve done one of those two things.

He describes a “third way,” with his two normal paths defined a lot like Deresiewicz’s, but in a lower register:

You don’t generally have anyone in your life who has gone out on their own and done something entrepreneurial or done something artistic or truly risky or truly taken the path less traveled, because those people [. . .] don’t work in academics. And don’t become cubicle monkeys. So what I try and explain in my speeches is that there’s a third way. Because a lot of people—I think most people—want to do something besides those two things.

A lot of people want to do something else, but that something else is, in some ways, harder to do than the normal path. Yet the people who go the third way often talk about it as being more satisfying, and the people who go the “two paths” often speak wistfully of the third—despite the difficulty one is likely to encounter. A friend wrote this to me: “I know for a fact that I’d hate [Tucker] Max’s writing, but he’s dead right about how few students are aware that they can do something artistic or creative or entrepreneurial.” Too few students are aware of this—and too few people in general are. You can consider this post a very small step in the direction of increasing awareness.

So far I’ve noted two examples. Paul Graham talks about the problem of standard paths too, in “A Student’s Guide to Startups:” “Till recently graduating seniors had two choices: get a job or go to grad school. I think there will increasingly be a third option: to start your own startup.” His answer is more defined than Deresiewicz’s or Max’s, but the very language he uses is similar. But he’s also got a way of generating the “third way” by funding startups. Instead of merely telling people to find one, he’s creating a third way for people to flow, which might be the most valuable contribution of all, at least for the technically inclined.

I think all three of these disparate writers—Deresiewicz, Max, and Graham—are pointing to a more fundamental need for the imagination necessary to exit the obvious paths that so often end up going nowhere. Of the three, Graham has done the most to institutionalize this process and make it available for others by starting Y Combinator. Max has probably done the most to be a living embodiment of an unusual third way. Deresiewicz is pointing to the possibility from within the way of a well-defined path (and the same one I’m one) from undergrad to graduate school to being a professor. Taken together, they diagnose and offer treatment for the same malady that can’t quite be identified yet comes from so many sources and has so many symptoms: Dilbert, cubicles, malaise, ennui, florescent lights, midlife crises, 20-somethings with advanced degrees working as baristas, waiters, or bartenders, essay writers.

Artistic or creative activities don’t usually come prepackaged in convenient jobs that get handed to college graduates. They get created by people who are artistic and creative, who find a way to turn what they want to do, or their inchoate ideas, into something greater than the idea itself. The “inchoate idea” is important: I suspect most people don’t entirely know what they’re doing when they find a third way. Steven Berlin Johnson has a term for this in his book Where Good Ideas Come From: The Natural History of Innovation: the slow hunch. This happens when something that you’ve been gnawing on slowly develops over time. Johnson describes it much more fully, of course, but a lot of my ideas in writing novels or academic work comes from slow hunches. Writing fiction isn’t an activity that really comes packaged in convenient job form: it is made by each practitioner individually. People who succeed as writers sometimes do so not through conventional publishing, but through alternate ways—as Max did with his website, or as J.A. Konrath apparently does with his blog, “A Newbie’s Guide to Publishing.”

Like Deresiewicz and Max, I don’t really have a solution to the problem other than to encourage you to think imaginatively. But who’s against thinking imaginatively? Partners are probably telling their third-year associates the same thing, even as the associates put in soul-killing seventy hours weeks under those menacing florescent lights. The other part of my solution is to be aware of the problem. I’ll also channel Graham in “What You’ll Wish You’d Known” and encourage you to stay upwind:

In the graduation-speech approach, you decide where you want to be in twenty years, and then ask: what should I do now to get there? I propose instead that you don’t commit to anything in the future, but just look at the options available now, and choose those that will give you the most promising range of options afterward.

It’s not so important what you work on, so long as you’re not wasting your time. Work on things that interest you and increase your options, and worry later about which you’ll take.

Suppose you’re a college freshman deciding whether to major in math or economics. Well, math will give you more options: you can go into almost any field from math. If you major in math it will be easy to get into grad school in economics, but if you major in economics it will be hard to get into grad school in math.

Flying a glider is a good metaphor here. Because a glider doesn’t have an engine, you can’t fly into the wind without losing a lot of altitude. If you let yourself get far downwind of good places to land, your options narrow uncomfortably. As a rule you want to stay upwind.

“Work on things that interest you and increase your options:” the target of Graham’s essay is nominally high school students, but it’s applicable to a much broader swath of people. Maybe you’re one. If so, however, you’ll probably read this and then go back to filling out those TPS reports. Or maybe you’ll be one of the very rare people who realize there is no speed limit and react appropriately. At least you can’t say that no one told you. At least three people have: Deresiewicz, Max, and Graham. Four if you count me, writing a meta essay.

In “What Are You Going to Do With That?,” William Deresiewicz tells the freshmen class at Stanford:

In the journey toward the success that you all hope to achieve, you have completed, by getting into Stanford, only the first of many legs. Three more years of college, three or four or five years of law school or medical school or a Ph.D. program, then residencies or postdocs or years as a junior associate. In short, an ever-narrowing funnel of specialization. You go from being a political-science major to being a lawyer to being a corporate attorney to being a corporate attorney focusing on taxation issues in the consumer-products industry. You go from being a biochemistry major to being a doctor to being a cardiologist to being a cardiac surgeon who performs heart-valve replacements.

But he goes on to point out why and how these kinds of defined professional paths—the ones high school and college students students are so often told constitute “success”—might not be optimal, for either the person on the path or society in general. If you “simply go with the flow,” you can end up merely being defined by what someone else has laid out. Perhaps not surprisingly, Deresiewicz goes on to say, “There is an alternative.” He calls it “moral imagination” and defines it this way: “Moral imagination means the capacity to envision new ways to live your life.” I would call it something else: the “third way.”

Deresiewicz’s essay shows why we need more talk about the third way: there are more options out there than further advanced schooling. Stanford in particular is a good place to be reminded of this. Obviously, Deresiewicz doesn’t say you must choose grad school or the professions, but the absence of any acknowledgement about starting your own company implies that those are the two primary choices.

I’ve had similar talk. In my interview with him, Tucker Max describes the primary speech he gives at colleges:

[. . . W]hen you’re an undergrad, generally you think you can do two things. You’re gonna have to get a job after you graduate or you gotta go do more school. Because everyone who’s giving you advice or telling you how to live your life are people who’ve done one of those two things.

He describes a “third way,” with his two normal paths defined a lot like Deresiewicz’s, but in a lower register:

You don’t generally have anyone in your life who has gone out on their own and done something entrepreneurial or done something artistic or truly risky or truly taken the path less traveled, because those people [. . .] don’t work in academics. And don’t become cubicle monkeys. So what I try and explain in my speeches is that there’s a third way. Because a lot of people—I think most people—want to do something besides those two things.

A lot of people want to do something else, but that something else is, in some ways, harder to do than the normal path. Yet the people who go the third way often talk about it as being more satisfying, and the people who go the “two paths” often speak wistfully of the third—despite the difficulty one is likely to encounter. A friend wrote this to me: “I know for a fact that I’d hate [Tucker] Max’s writing, but he’s dead right about how few students are aware that they can do something artistic or creative or entrepreneurial.” Too few students are aware of this—and too few people in general are. You can consider this post a very small step in the direction of increasing awareness.

So far I’ve noted two examples. Paul Graham talks about the problem of standard paths too, in “A Student’s Guide to Startups:” “Till recently graduating seniors had two choices: get a job or go to grad school. I think there will increasingly be a third option: to start your own startup.” His answer is more defined than Deresiewicz’s or Max’s, but the very language he uses is similar. But he’s also got a way of generating the “third way” by funding startups. Instead of merely telling people to find one, he’s creating a third way for people to flow, which might be the most valuable contribution of all, at least for the technically inclined.

I think all three of these disparate writers—Deresiewicz, Max, and Graham—are pointing to a more fundamental need for the imagination necessary to exit the obvious paths that so often end up going nowhere. Of the three, Graham has done the most to institutionalize this process and make it available for others by starting Y Combinator. Max has probably done the most to be a living embodiment of an unusual third way. Deresiewicz is pointing to the possibility from within the way of a well-defined path (and the same one I’m one) from undergrad to graduate school to being a professor. Taken together, they diagnose and offer treatment for the same malady that can’t quite be identified yet comes from so many sources and has so many symptoms: Dilbert, cubicles, malaise, ennui, florescent lights, midlife crises, 20-somethings with advanced degrees working as baristas, waiters, or bartenders, essay writers.

Artistic or creative activities don’t usually come prepackaged in convenient jobs that get handed to college graduates. They get created by people who are artistic and creative, who find a way to turn what they want to do, or their inchoate ideas, into something greater than the idea itself. The “inchoate idea” is important: I suspect most people don’t entirely know what they’re doing when they find a third way. Steven Berlin Johnson has a term for this in his book Where Good Ideas Come From: The Natural History of Innovation: the slow hunch. This happens when something that you’ve been gnawing on slowly develops over time. Johnson describes it much more fully, of course, but a lot of my ideas in writing novels or academic work comes from slow hunches. Writing fiction isn’t an activity that really comes packaged in convenient job form: it is made by each practitioner individually. People who succeed as writers sometimes do so not through conventional publishing, but through alternate ways—as Max did with his website, or as J.A. Konrath apparently does with his blog, “A Newbie’s Guide to Publishing.”

Like Deresiewicz and Max, I don’t really have a solution to the problem other than to encourage you to think imaginatively. But who’s against thinking imaginatively? Partners are probably telling their third-year associates the same thing, even as the associates put in soul-killing seventy hours weeks under those menacing florescent lights. The other part of my solution is to be aware of the problem. I’ll also channel Graham in “What You’ll Wish You’d Known” and encourage you to stay upwind:

In the graduation-speech approach, you decide where you want to be in twenty years, and then ask: what should I do now to get there? I propose instead that you don’t commit to anything in the future, but just look at the options available now, and choose those that will give you the most promising range of options afterward.

It’s not so important what you work on, so long as you’re not wasting your time. Work on things that interest you and increase your options, and worry later about which you’ll take.

Suppose you’re a college freshman deciding whether to major in math or economics. Well, math will give you more options: you can go into almost any field from math. If you major in math it will be easy to get into grad school in economics, but if you major in economics it will be hard to get into grad school in math.

Flying a glider is a good metaphor here. Because a glider doesn’t have an engine, you can’t fly into the wind without losing a lot of altitude. If you let yourself get far downwind of good places to land, your options narrow uncomfortably. As a rule you want to stay upwind.

“Work on things that interest you and increase your options:” the target of Graham’s essay is nominally high school students, but it’s applicable to a much broader swath of people. Maybe you’re one. If so, however, you’ll probably read this and then go back to filling out those TPS reports. Or maybe you’ll be one of the very rare people who realize there is no speed limit and react appropriately. At least you can’t say that no one told you. At least three people have: Deresiewicz, Max, and Graham. Four if you count me, writing a meta essay.