The Game Theory of Pointy Things: Careers, Catastrophes, and Missing Well

I was twenty-four when I turned down the dream job. Not the job I dreamed about as a kid (nobody dreams about enterprise software sales) but the dream job in the sense of what every ambitious twenty-something supposedly wants: prestigious company, six-figure salary, corner office trajectory, the whole aspirational package.¹ My college friends thought I'd lost my mind when I took the lower-paying position at a company they'd never heard of.

The fancy job offered everything I'd been told to optimize for. Salary maximization. Prestige maximization. LinkedIn-profile-impressiveness maximization. If career planning were archery, I'd been taught there was only one sensible target: aim for the ten-ring, always, forever, without exception. Because if you aim for the ten and miss, you get a nine. Miss the nine, you get an eight. The mathematics are straightforward, unassailable, obvious.

Except I'd spent enough time in my own head to know something nobody mentions about the archery model of ambition: I am not, actually, a particularly good archer.

The Game Theory of Pointy Things

Here's what I mean. In archery, the scoring rings are concentric circles radiating outward from a center point. Ten at the bullseye, nine in the ring around it, eight in the next ring, and so on down to one at the outer edge. The geometry creates a simple optimization problem: aim for the center. If your arrow flies slightly left, slightly right, slightly high, slightly low, it doesn't matter. You still score well. Nine points, eight points, seven points. The system rewards precision but forgives near-misses with graceful degradation.²

In darts, the board operates on different principles entirely. The scoring zones aren't concentric—they're wedge-shaped segments radiating from the center. The twenty segment sits at the top of the board, worth twenty points. But directly adjacent to it? The one segment and the five segment. The highest-scoring target on the board shares borders with the two lowest-scoring targets.³

This creates an entirely different strategic calculation. If you're skilled enough to hit the twenty reliably, then yes, aim for the twenty. But if you're not (if your accuracy is questionable, if you're tired, if you've had a drink, if you're playing casually) then aiming for the twenty means you're essentially gambling. Hit or miss. Big score or catastrophic failure. No middle ground.

The optimal strategy for an amateur? Aim for the southwestern quadrant of the board, where the 8, 12, 7, and 19 segments cluster. You won't hit the triple-twenty, but you also won't hit the one or the five. You'll score moderately, consistently, and without catastrophic failures.⁴

It's the same activity: throwing a pointy object at a board. But entirely different strategic implications based on how the scoring system distributes risk and reward.

Predictable Mediocrity

Behavioral economists have spent decades documenting what regular humans knew intuitively: we hate losses more than we love equivalent gains. Losing fifty dollars hurts worse than finding fifty dollars feels good. Getting fired feels worse than getting promoted feels good, even if the salary change is identical. This asymmetry they call >loss aversion shapes nearly every decision we make, whether we're aware of it or not.⁵

But there's another layer. It's not just losses versus gains. It's about the magnitude of worst-case scenarios. A ten percent chance of catastrophe often outweighs a ninety percent chance of moderate success, because catastrophe isn't just another point on the continuum. Catastrophe is the game ending. Catastrophe is having to rebuild from scratch, or worse, not being able to rebuild at all.

When you're hungry in an unfamiliar city, do you gamble on the hole-in-the-wall place with three Yelp reviews, or do you choose the golden arches? The hole-in-the-wall might be transcendent. It might also be a coin flip between brilliance and food poisoning. McDonald's offers guaranteed mediocrity. And humans, despite our pretensions about optimizing for excellence, often choose guaranteed mediocrity over risky excellence.⁶

This was the calculation I was making at twenty-four, though I didn't have the vocabulary for it yet. The prestigious job was aiming for the triple-twenty—maximum possible score, but with the one and the five lurking on either side. Seventy-hour weeks. A manager whose leadership style could be generously described as Darwinian. The potential for burnout, relationship collapse, health deterioration. The job I chose instead? The southwestern quadrant. Not spectacular, but reliably decent. Forty-five hours maximum. A boss who believed people had lives. Thirty percent less money, but also thirty percent less risk of complete collapse.

Nobody claims McDonald's makes the world's best hamburger. Nobody's last meal request includes a Big Mac. Yet McDonald's remains the most successful restaurant chain on Earth because it has mastered the art of not being awful. Wherever you are, whatever you're craving, a McDonald's hamburger will be... fine. Not transcendent. Not memorable. But definitely not food poisoning, not a two-hour wait, not a surly server having the worst day of their life.

If you're not very good at darts, the optimal strategy is not to aim for the bullseye. Aim for the southwestern quadrant. You won't hit the triple twenty, but you also won't hit the one or the five. You'll score moderately, consistently, without catastrophic failures.

So: Which boards in your life are you treating as archery, and which as darts?⁷

Your career: Are you aiming for maximum possible achievement, or are you hedging against burnout, unemployment, obsolescence? Your relationships: Are you holding out for the perfect partner, or are you choosing someone who's good enough, unlikely to be terrible, and currently available? Your health: Are you optimizing for peak performance, or are you just trying to avoid falling apart?

I've watched friends aim relentlessly for the ten-ring in relationships, holding out for someone who checks every box on an impossible list, rejecting perfectly good partners because they're nine-ring material, not ten-ring material. Meanwhile, years pass. The archery competition ends. The board gets put away.

I've watched other friends (and myself, if I'm being honest) stay in six-ring situations far too long because at least it's not a one or a five. At least it's not a disaster. At least nobody's getting hurt beyond the slow erosion of time and possibility.

Neither strategy is obviously superior. Instead, the superiority depends entirely on context, on skill level, on what you're optimizing for, and on what you can afford to lose.

The Question You're Not Asking

When you evaluate an opportunity, a job, a relationship, a move to a new city, a shift in career direction, you probably ask yourself: What's the best possible outcome here? What do I stand to gain? How good could this get?

Fine questions. Important questions. But insufficient questions.⁸

The question you're probably not asking, or not asking with enough weight: What's the worst possible outcome? Not the worst likely outcome, but the worst possible outcome. And more importantly: If the worst happens, can I recover? Will I be able to draw the bow again? Or does this potential disaster have the power to end the game entirely?

This isn't pessimism. This is strategy. This is the difference between archery thinking and darts thinking.

When you frame it this way, choices clarify. But only in retrospect, only after making the decision. At the time, everyone's framing was archery-based: aim for the ten. Maximize salary. Maximize prestige. Accept no substitutes.⁹

The Trap of Optimization

Personal and Professional Development culture is drowning in archery thinking. Maximize your productivity. Maximize your network. Maximize your skills, your salary, your influence, your impact. Aim for the ten. Aim for the ten. Aim for the ten.

But here's what the optimization gurus rarely mention: Maximizing one variable often means accepting catastrophic failure in others. The person who maximizes career success might minimize family relationships. The person who maximizes social life might minimize financial security. The person who maximizes creative output might minimize physical health.¹⁰

You can't hit the ten-ring on every board simultaneously. You probably can't hit the ten-ring on even one board, at least not consistently, at least not without turning yourself into a highly specialized instrument with zero tolerance for variation or error.

What if the goal isn't to be the best? What if the goal is to be consistently good enough across multiple domains, with low probability of catastrophic failure in any single domain?¹¹

There are no universal right answers. The person with robust health, strong support systems, and a financial cushion can afford to aim for the ten in their career. The person one car transmission emergency away from bankruptcy cannot.

The person who's already found a solid relationship might optimize other areas. The person who's deeply lonely might rationally decide to aim for the southwestern quadrant in career choices to create space for relationship-building.

The tragedy is when we don't realize we're making these choices. When we follow someone else's strategy—usually archery strategy, because archery strategy makes better motivational content—without asking whether it's appropriate for our actual situation, our actual skill level, our actual capacity for recovering from disaster.¹²

Most important life decisions don't work this way. You don't get to choose careers a thousand times to see how the expected value plays out. You don't get to marry a thousand people to average out the results. You get a few shots, maybe just one shot, and if you blow it badly enough, you don't get another turn.

When was the last time you asked yourself: What am I optimizing for? Maximum possible gain, or minimum possible regret? Peak performance, or sustained functionality? The chance of hitting the ten, or the certainty of avoiding the one?

And the follow-up question, the one most people never ask: Given my actual skill level, my actual resources, my actual tolerance for catastrophic failure, which strategy actually makes sense?

Not which strategy sounds impressive. Not which strategy you could Instagram-quote. Not which strategy your parents or peers or society expects. Which strategy matches your reality, your constraints, your actual situation rather than your idealized situation.¹³

Where You're Actually Aiming

Most people are playing darts with archery strategy, then wondering why they keep hitting ones and fives. Or playing archery with darts strategy, then wondering why they never hit anything remarkable.

The first step isn't choosing the right strategy. The first step is recognizing you're making a choice at all. Recognizing when you're playing archery, when you're playing darts, and which game your current approach is suited for.

Maybe you look at your career and realize you've been aiming for the ten in a situation where you should have been playing defensive. Maybe you look at your relationships and realize you've been hedging when you could afford to aim higher. Maybe you look at your whole life and realize you've been following someone else's strategy, optimized for their constraints, not yours.

The prestigious job I turned down? Someone else took it. Someone with different constraints, different goals, different tolerance for worst-case scenarios. For them, maybe it was the right choice. For me, choosing the southwestern quadrant meant I could keep playing. Could keep growing. Could avoid catastrophic failure long enough to develop the skills and resources to aim higher later.

Which is maybe the real point: Your strategy shouldn't be static. The person who can only afford to play defensively right now might develop skills, resources, resilience to play offensively later. The person burning themselves out aiming for the ten in every domain might need to shift to strategic defense before complete collapse.

You're already aiming somewhere. The dart is already leaving your hand, has been leaving your hand every day for years. You've been scoring points on boards you didn't know you were playing, racking up ones and fives while aiming for twenties, or settling for sixes when you had the skill for tens all along. The strategy you think you're using and the strategy you're actually using might be two entirely different games.

The board is in front of you. The score is being kept whether you're paying attention or not.