Remaining Ambitious

AWM #82: On dealing with rejection, both as an applicant and as a gatekeeper 🏔

Poet on a Mountaintop by Shen Zhou (15th century/Ming period). I chose this classical painting as a nod to one of the first posts on this blog, Becoming Ambitious, in which I drew a picture of mountains to represent ambitious goals.

We tend to see ambition like a personality trait. We describe people as ambitious, or not, as if it were a fixed property of their being. But the reality is that it ebbs and flows. You can become more ambitious over time as you learn what you are capable of, and as encouraging peers push you along. Conversely, your ambition can recede when you become discouraged. You stop dreaming big. You settle for less.

Much has been written on the act of sparking ambition in a young person who hasn’t yet realized their potential. This is, of course, a hugely important undertaking. But so is the nurturing of ambition in those who already have it.

Such people probably represent only a small fraction of a given society. So if (for instance) half of them eventually get discouraged to the point of settling for less, then this would be, at the scale of that society, a great loss of potential. Can we do anything about it?

On rejection

First, what causes the destruction of ambition?

Many things can, from unsupportive family members to declining health. But assuming an ambitious person who is able and willing to challenge themselves, the answer often seems to be failure. You have some big project, like publishing a book, landing a high-status job, or disrupting an industry with a startup. You try for a while, and then you realize that it’s harder than you thought, that your writing or resumé or business ideas weren’t as good as you hoped. You decide it’s not worth pouring more time and energy into the project, and give up. When you move on to your next project, you pick something less ambitious.

But failure comes in many shapes. In some cases, it can be a catalyst for trying harder. It raises your ambition. When you climb a mountain and find that a path is blocked by some rocks, you might look for another path with renewed zeal.

What if the path is blocked not by rocks, but instead by a person? What if this gatekeeper has the power of deciding who gets to climb the mountain, based on some evaluation of your character, and refuses you access? I suspect that you would then be much more likely to give up.

Thus ambition is most vulnerable to a specific kind of failure, the one that matters socially: rejection.

People who have done a lot of job hunting — or a lot of dating — know the sting of rejection pretty well. Even when you don’t truly want a job you applied for, or when it’s clear that you don’t really get along with your date, getting rejected hurts. It chips away at your self-confidence. You begin wondering if perhaps you had aimed too high. Maybe you should apply for less prestigious jobs. Maybe you should lower your dating standards.

Notably, you tell these things to yourself even though you know, on an intellectual level, that rejection is just a normal part of life. It happens all the time. You do it yourself, too, when you need to allocate your time, money, and attention, which is always. You know, abstractly, that people reject others for the most random reasons, and that it should almost never be considered a judgment of you as a person.

But we wouldn’t insist on this point if taking rejection like a judgment of you as a person weren’t the most natural thing to do. We’re super sensitive to these things! Even the most trivial kind of rejection — losing a few anonymous followers on social media — can trigger social pain. Am I not good enough? you begin wondering. Why did they decide not to follow me anymore? Did I tweet something bad?

This number (my Twitter followers, abonné is French for follower) was 1,825 a couple of days ago, and I’m kind of ashamed to have noticed the slight decrease. Surely it’s just that a few people have deactivated their account. Right? Surely I’m still worth something as a person. I mean, 1,819 is still a large number. Right? Right??

Let me illustrate with a personal story.

In 2021, a few months after quitting my job to try out some projects and let my ambition flourish, I came up with an extremely daring plan to change the norms of scientific writing. The idea was popular, and got encouragement from many people in the form of social media approval, good conversations, a one-month residency in Texas, and even money. Things were going well. But the project, ambitious as it was, soon got muddled in the complexities of real life, and it became less and less clear what the road to success looked like. Still, I applied to a few grants so that I could keep working on it after my initial funding ran out. I was rejected from all of them.

Thus began a slow spiral of thinking that my idea wasn’t leading anywhere, and therefore not putting much energy into it, and therefore not getting anywhere, and therefore thinking that my idea wasn’t leading anywhere.

Recently, faced with the necessity of making money, I began applying to full-time jobs again. I had thought that with my skills and network, it wouldn’t be too hard to find an enjoyable job that paid well enough. But of course, the first few that I applied to rejected me right away. I could feel my ambition collapsing: half a year ago, I thought I could revolutionize some of the institutions of science, and now I am merely wondering if I’m good enough to land a regular coding job. Maybe I should go work in a restaurant or something. Am I even good enough for that?

I know, intellectually, that none of these rejections matter. I haven’t even applied to many jobs yet; with just a little more effort, I should be able to obtain some success and rebuild my ambition. But in the moment, it feels very discouraging.

One of the grants I applied to was Tyler Cowen’s Emergent Ventures. This is a program that seeks to “jumpstart high-reward ideas—moonshots in many cases—that advance prosperity, opportunity, liberty, and well-being. We welcome the unusual and the unorthodox.” A perfect fit for my idea, I thought. I was pretty confident that I could get it. So when I didn’t, it was, no matter the rationalizations I told myself, a pretty big blow.

Emergent Ventures, as it happens, is itself an interesting case study about agency and talent. It has been described as unusually good at raising the ambition of the people Tyler Cowen selects. But the other side of the coin is what it does to the people he rejects.

I have been thinking a lot about this perspective from Dwarkesh Patel (emphasis not mine):

If an applicant wins, she finds out that Tyler thinks she is promising, and her confidence increases. But if she is rejected, she finds out that Tyler does not think she has much potential, and her confidence decreases. This may be net positive, because it is much more important to raise the ambitions of the very best people, but it does come at a cost. Under this model, Emergent Ventures works by transferring ambition from the simply great to the truly excellent.

I want to say that I have felt this. I have felt the ambition leaving me when I didn’t get the grant, presumably to be bestowed to whoever did get it. (Which has included some friends and acquaintances who, to be clear, absolutely deserve the boost!)

Perhaps indeed I’m only “simply great” (or less) and it makes sense for society as a whole to transfer my ambition to the “truly excellent.” Right now, in my current low-ambition state, that seems true. But thinking that is partially a consequence of being rejected, so I can’t give an objective answer to that question.

Regardless, the cost to the rejected applicants — from Emergent Ventures, but also from every other grant, competition, and hiring process — should be taken seriously. A transfer of ambition isn’t thermodynamically perfect: some of it dissipates and is lost. We should strive to minimize the waste, both when we are climbing the mountain, and when we are responsible for gatekeeping its paths.

As an applicant: Softening the blow

How can we, as people who apply to jobs, schools, contests, funding, publishing houses, and so on, protect our own ambition? How can we soften the blow of rejection?

The answer certainly isn’t to avoid rejection altogether. That would require not asking for anything that you’re not certain to get. This is the opposite of ambition! To achieve anything impressive, you have to take risks. My project would not have benefitted from not applying to Emergent Ventures or the other grants.

“Nothing ventured, nothing gained,” supposedly uttered Benjamin Franklin

One sensible strategy is to direct most of your efforts to things that don’t require other people’s approval. Instead of trying to get hired under the promise that you’ll bloom into a talented programmer/writer/photographer when you have the job, you can just go ahead and code/write/photograph stuff on your own. But we live in a complex, specialized society, and unless you’re born rich, you will sooner or later have to apply to something. So this is good advice, but not a full solution.

Maybe, just maybe, you can be smart about what you apply to. Each time you ask for something and get told “no,” you pay a small price in ambition; so you may not want to squander your supply by asking for many things you know you’re not going to get. But… I wouldn’t really buy this piece of advice. Most of us are already too shy to ask for things. We often don’t have a good understanding of our own potential. Plus, if you carefully craft an application for a single job/grant/school/etc. and get rejected from it, the blow to your ambition can be even more damaging. It’s better to spread out the psychological cost over many small attempts.

And so the opposite piece of advice might be better: expose yourself to as much rejection as possible. Receive “no” answers so often that they don’t even register anymore. I think this mostly works, because it maximizes the chances that at least one person says “yes.” But I don’t love it as a strategy for dealing psychologically with rejection: it amounts to numbing ourselves, and I suspect that numbness can weaken the boost to ambition when we finally get a “yes.”

In practice, there isn’t any single solution. Rejection is a facet of life, and everybody needs to figure out their own strategies to cope with it. The most I can offer is that it’s better when you’re aware of how it works. It isn’t enough to know, on an abstract level, that rejection is typically random and impersonal — but it helps.

As a gatekeeper: Managing the collective supply of ambition

The previous section is about dealing with rejection as an applicant. What if you’re a gatekeeper — such as a hiring manager, a grantmaker, a publisher, or a judge in a competition? How should you yield the tremendous power of accepting or rejecting the requests of ambitious people?

If you had infinite time and money, you could craft a personalized response to each rejected applicant. Give them feedback. Tell them what they did well. Direct them to other places where their skills and talent could be used for good.

But of course, nobody has infinite time and money, so in practice you are most likely to send a generic message. (And that’s if you’re replying to the applicant at all, a low bar that isn’t even always reached.)

The art of crafting a generic rejection letter has been honed by generations of gatekeepers. To be fair, most people recognize that rejection stings, and as a result such letters are written in the most diplomatic language possible. Just for fun, let’s look at this fake example made from bits of hiring rejection emails I have received:

Thank you for giving us the chance to consider you for [role] at [company]. We really appreciate that you took the time to apply. 

(Right, I’m sure you really appreciate the extra work of sorting through a bunch of candidates who are not even a good enough fit to be interviewed.)

Your background is impressive,

(Well, clearly not enough.)

but we have chosen not to move forward with your application at this time.

(Implying that you might “move forward” at some later time, riiiight?)

We may reach out to you in the future if a position opens up that may be a good fit.

(Has this happened to anyone? Ever?)

Now, it’s very much possible that such diplomatic rejection letters are the best that most gatekeepers can do with the resources they have. Applications and submissions to (especially) well-known companies, contests, publishers, etc. can reach very high numbers, and there simply isn’t enough time to deal with them on an individual basis.

In fact, I suspect that it’s common for new organizations to try giving feedback to everyone at first, because they know it’s valuable — until they inevitably give up. For instance, this is from an email I’ve received twice to inform me that my science-fiction stories were rejected from the magazine Clarkesworld:

In the past, we've provided detailed feedback on our rejections, but I'm afraid that due to time considerations, we're no longer able to offer that service.

I’m glad that giving detailed feedback is at least seen as an ideal. But I wish we tried to uphold that ideal somewhat more. Because no matter how well-written, a generic rejection letter necessarily steals a little bit of the applicant’s ambition. There is no way for an impersonal rejection to avoid this, precisely because it is impersonal.

I have observed firsthand how much better it feels when a rejection letter is evidently personalized to you. I think it’s because it shows that the reviewer took the time to consider you as an individual, which is nice on its own, but also because it provides a bit of transparency. When you have no clue why you were rejected, you are left to speculate, and it’s all too easy to imagine the worst scenarios.

By definition, however, individualized rejection cannot scale. All attempts at scaling it up just create what we have now.

Still, I suggest that we can do better, as a civilization. We are getting wealthy enough to do things that don’t scale. Gatekeepers could see themselves not only as talent hunters for their own organization, but also as managers of society’s collective supply of ambition. We could demand that they consider it a responsibility to waste as little of their applicants’ ambition as possible. That they strive to redirect and allocate that ambition wherever it is most needed.

Instead of simply rejecting people from the mountain path, lead them, with friendliness and encouragement, to another path they can take.

Sure, that would probably require more gatekeepers. Then let’s hire more! We’re automating all the other jobs away, anyway.

It would also require a change of culture in many domains, from HR departments to funding agencies to the publishing industry. It would mean setting a new ideal. One that would often be unattainable, due to time and money constraints. But one that would be worth reaching for.

It wouldn’t be easy. But who said it had to be? After all, we are allowed to be ambitious.

More Shen Zhou: Clouds Over the River Before Rain

Thanks to Tyler Cowen for reading a version of this essay and providing encouragement.