Start-ups and Emotional Debt

By Evan Miller

December 11, 2014

Get rich, work on interesting problems, change the world — what’s not to like about doing a start-up?

Sure, you’ll hear “it’s not for everyone.” But if you’ve got time to spare, fire in your guts, and a head full of ideas, it seems like a no-brainer.

And yet occasionally a somewhat darker narrative leaks out. Maybe it’s a post on a message board from an anonymous founder at his wits’ end, or a founder-oriented blog post offering tips for dealing with depression. Or a news story about an entrepreneur with no previous health problems passing away, without explanation.

There are a number of hidden costs to doing a start-up — including costs to doing a successful start-up — which I think deserve greater awareness. Usually questions about “Should I do a start-up?” are posed as “Are you man enough to do a start-up??” by people who have a vested interest in receiving an affirmative answer. The personal and emotional costs are almost always underrepresented.

I have not done a start-up. I worked at one, briefly, and I know a few people involved in them. These are just my observations gathered from the outside — a place which, often, has a pretty decent view.

The Money Problem

The biggest cost to doing a successful start-up is the opportunity cost of not doing something else. This cost is usually underestimated because the skills you acquire in your twenties will compound and bear interest the rest of your life.

Imagine, for a moment, your life stretched out on a number line, from 0 up to 70 or so, with how hard you work in a given year represented vertically. The canonical “money problem” as described in the epistles of Paul Graham states that your work options are either a squat rectangle, covering ages 25 to 65, or a tall trapezoid, covering 4 years of your choice in your twenties and thirties. (Plus a kind of translucent rectangle beyond the tall one, in case the whole start-up thing doesn’t work out.)

Aha, you think to yourself. Everyone else is lazy and trying to minimize the height of the curve closest to them. I am smart and visionary enough to know it’s the total area of the curve that matters. Therefore I shall work my butt off in exchange for a future life of leisure.

The minimum-area algorithm makes sense here, but only if you make a fairly unrealistic assumption: that after age twenty, you’re basically the same person for the next 50 years, and your goal is to minimize the amount of time doing things other people say. But I think the picture is more complicated than that.

Your brain, and your relationships, will evolve in response to your choices. If you’ve studied physics, you’ll recognize this problem as a kind of Hamiltonian. The solution is not as simple as measuring distances and areas; you have to consider the whole path.

That is, treating “the money problem” as a strict subset of “the life problem” is a mistake. As tempting as it is for programmers, it’s impossible to divide-and-conquer the good life. Like it or not, “the money problem,” “the love problem,” “the friendship problem,” and “the true-passion-in-life problem” are all intertwined, and they develop together. That’s part of what makes life so interesting.

Developmental Debt

The good news is that if you’re smart and went to good schools, then at age 20, you possess the most wonderful asset in the world: an energetic, semi-formed brain that is capable, basically, of anything. It’s like standing at the top of a great mountain and wondering which slope to ski down.

If you ski down the Slope of Start-Ups, and successfully arrive at The Basin of Money, yes, you’ll solve “the money problem.” But you won’t be on top of the mountain any more. To get anywhere else — The River of Writing, The Sea of Sculpture, The Orchard of Architecture — you’re going to have to work for it, and it’s going to be harder than it would have been at a younger age. Getting good at anything takes a tremendous amount of work, and so taking up that Second Career will feel a lot like doing another start-up. But this time, it will feel like skiing cross-country instead of cruising down hill.

The brain, unfortunately, is a poorly understood device, so it’s not at all clear how going down one slope for a while will affect the accessibility of the others. But there are a couple of ideas that stuck with me as I planned out my own twenties. One was a graph — I can’t find it now — of the “average” person’s mathematical and verbal abilities, measured and charted over time. Mathematical abilities peak sometime in your twenties, and then decay; but the verbal skills keep sloping upwards, at least until you begin to go senile.

The second idea came from a book written by one of my professors in graduate school. It’s an almost identical idea, now that I think about it, except applied to great artists instead of average Americans. His thesis is that artists tend follow one of two developmental trajectories. Either they follow a “genius” trajectory, where they make a major conceptual breakthrough in their twenties, and keep playing the same tune after that (Picasso, Warhol). Or they follow a “master” trajectory, where their abilities slowly accumulate over a lifetime, and do their finest, most moving work relatively late in life (Rembrandt, Rothko). There just doesn’t seem to be a lot of action in between.

I don’t claim to have solved the great differential equation of life, and the results from my ongoing experiment in living aren’t in yet. I just want you to be aware that there are long-acting dynamics that shape the human brain, and that you should ignore those dynamics at your own peril. If you’re twenty, you should probably spend more time learning about your own brain, and trying to form enduring friendships, and less time worrying about money and start-ups and equity and things.

Emotional Debt

I suspect the main reason that many millennials are drawn to start-ups isn’t even the money. I recently spoke with a founder who was concerned about online comments denouncing his company’s product for (supposedly) making people lazy. It wasn’t that this founder was concerned about the negative PR, or losing customers; he just felt hurt that some people out there didn’t think that his product was an unequivocal boon for society.

The prospect of getting rich is an attractor for founders, sure, but I think there’s something else going on here. For whatever reason — maybe it’s generational — today’s founders feel the need to be the hero of their own inner narratives. For them, start-ups embody a kind of happy confluence of making a lot of money, changing the world, showing everyone how smart and wonderful they are, and, ultimately, becoming their awesome true authentic selves. This narrative thinking is reinforced by a strong oral tradition of Silicon Valley hero’s journeys (replete with the usual Campbellian tropes: The Call To Adventure, The Magical Helper, The Road of Trials, etc.), and a tech press that regards every IPO as a kind of Maslowian self-actualization event for the founding team.

These are narratives that are silently driving twenty-something founders forward, and they usually result in one of two outcomes, neither being especially happy. Either the founder will fail at their Grand Start-Up, and feel unmoored from all the achievements and structures that previously formed their sense of identity; or the founder will succeed, and without a strong and independent sense of self in place, will end up living out a life that doesn’t feel quite like their own.


I like the term emotional debt because it captures the compounding nature of feelings. If you have any niggling sense that you are on the wrong path in your twenties, those feelings will just get worse and worse over time, and the consequences will amplify with each passing year and each missed opportunity to do something else.

The term also implies that there are emotional costs to doing things. These costs are almost always left out of the rational life-calculus, and the heroic life-narrative, that lead people to become founders.

Founders with an engineering background are at a particular disadvantage because they are often unaccustomed to thinking about, and accounting for, their own feelings, in the extreme case fancying themselves as kinds of terrestrial Vulcans who live only by the lamp of reason. The uncomfortable truth is that many programmers got into programming — an activity which requires countless hours and tremendous concentration — as a kind of emotional escape: for them, programming was a world of logical order, where they could pretend that their real-world fears and feelings didn’t exist.

“Emotional accounting” is one area in which the detested jerk-MBA-sales-biz-founder-dude actually has an advantage as a founder: he’s probably more comfortable thinking about feelings, and understanding his own psychology, than the typical engineering founder, and as a result will be less likely to experience a crisis when the various emotional bills come due.

Let’s go ahead and count a few of those bills. I will indulge your natural optimism and assume that your start-up is a raging success that makes you a gazillionaire.

  1. You will probably lose at least one friendship. You need a co-founder, and your co-founder should be a friend, but you’ll probably lose that co-founder as a friend. Either one of you will force the other out of the company (Bill & Paul, Jobs & Woz), or you’ll end up as frenemies vying for control (Larry & Sergey). There are exceptions, of course, but exceptions are just that.

  2. In fact, you will probably lose most of your friends. People get weird about money. It will be obvious from their behavior. Things might be the same superficially, but they’ll feel different. That’s just the way people are. You’ll probably have to make new friends who have approximately as much money as you, so you don’t act weird around each other. But the more money you have, the smaller the friend-pool becomes. If you’ve never had money before, you’ll probably feel self-conscious about it frequently.

  3. If you’re really successful, the rich-as-me pool drops basically to zero, so your only friends left are the people at your company. I think that’s why most entrepreneurs stay with the company they founded, even if they have enough money to buy a condo on Mars. If the founder quits, all their friends will be mad at them.

  4. When you’re starting a start-up, you are going to experience strong, conflicting emotions, but you are going to have very few people to talk to about how you’re feeling. As a result, whatever internal muscle it is that articulates feelings will not get flexed and will likely atrophy. Engineering types are hit especially hard by this.

  5. If you do a start-up in your twenties, and unless you’re very headstrong, you’re probably going to undergo a serious emotional crisis. Running a start-up is all about catering to other people’s desires: customers, investors, employees, the press, the public. As a founder, your desires come last. The problem isn’t only that you have forgone the various objects of your desire for four years: by failing to give expression to what you want, during what are still formative years, you’ll come out the other end of your twenties not knowing what you actually want out of life, and you’ll question everything that you’ve done so far. That is, by suppressing your innate desires for so long, you risk losing your natural appetite for life.

  6. After the start-up, you probably won’t have any skills or interests left besides start-ups. If you spend all your time thinking about start-ups, then start-ups are the thing you’ll be really good at. Your twenties are a crucial time for developing skills that will be harder, if not impossible, to develop later on. By developing “start-up skills” for four years, you are missing an opportunity to hone your skills as a writer, musician, engineer, architect, or whatever that secret aspiration was that you had before you decided it was necessary to make a lot of money first. It will be a regret that will not go away.

A friend of mine worked at a company that was sold for a considerable sum a few years back. Now and then, he calls up his old boss; the ex-founder is a man who has supposedly “made it” in the eyes of society, but he now feels like a bored housewife casting about Berkeley for things to do. My friend said he feels kind of sorry for his former employer; he’s like the dog who caught the car.

I realize that many people who do successful start-ups say it was the best thing that ever happened to them. But they’ve also become different people, and they are not the same people they would have been if they had decided to pursue another course. They have different sets of relationships, different skills, different attitudes, and different desires. They really have no idea what kind of person they otherwise would have been become.

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