the trampoline theory of opportunity

how to choose opportunities—and between opportunities—after noticing them

If you asked me to place myself on a spectrum of low risk to insanely high risk, I’d feature somewhere in the middle. I’m the kind of moderate risk-taker who is regular in life so I can be different in my work. You won’t catch me upending my life for a year of debauchery in Paris or quitting my day job to write a book I don’t even have the first sentence for. But that’s okay, because my acceptance of that has brought me to the doorsteps of opportunities that work for me. So if I had to distil how I choose between opportunities, it would be like this:

An opportunity worth chasing must have a limited downside and an open-ended upside.

What does that mean? There needs to be a floor to how bad things could get if I chose that opportunity, a contained bounded space of negative outcomes that I can stomach. On the flip side, there needs to be potential that lacks a ceiling. Not just a "big" upside, but specifically unbounded—the possibility space extends infinitely upward. When an opportunity checks both boxes, I know I have something potentially great inches away from my reach.

The Trampoline Theory of Opportunity isn’t an exact science, but it works. I think the first thing the theory unlocks is being able to see through the stories you tell yourself about risk. A lot of us tend to catastrophise, ascribe the same level of potential to any change. Make mountains out of mole hills. We also inherit some amount of our risk assessment sensibilities: from our parents, our culture, our weird experiences in middle school. So it’s our default setting to assume that what’s in our head accurately represents reality, and let that sway our decisions.

But here’s the thing about a lot of our beliefs: they are, at best, hypotheses and, at worst, completely false dogmas. Our reasoning is often only as strong as its weakest link. Seeing them for what they are makes us more likely to understand why we make the choices we do, and how we might make more attuned ones in the future. As long as we’re a little tactical about it, it’s actually quite simple to hijack this dark thought pattern.

When I notice myself feeling anxious about something, I'll ask myself: "What story am I telling myself here?" Say I’m nervous about DMing someone on X that I really admire. The story playing in my head might be: they’ll think I’m weird or that I’m trying to sell them something and it’ll go horribly. Then, I run it through my 2x2. What’s the actual downside? They reply briefly, or rudely, or not at all. That doesn’t seem unbearable. What’s the upside? It could lead to a meaningful conversation, collaboration, friendship or, at the very least, a different perspective.

The beauty of this formula is that you can apply it to almost any opportunity. Like, applying for a new job. In most of our cases, the downside of chasing the opportunity is bounded: time lost on applications, a fudged interview, maybe a “no” that, honestly, only you and the recruiter will know about. The upside, though, can be quite open-ended. You might meet people who become mentors, discover new strengths, realise something important about what you really want out of your career. It literally is a trampoline: the worst that could happen is that you bounce back to where you started. 

I think this reveals two really important things about the Trampoline Theory. The first is this: what counts as a "limited downside" is deeply personal and contextual. The same opportunity can be a safe trampoline for one person and a high-stakes gamble for another. It isn’t about being fearless, or reckless. I’ve written about this before, but opportunity-hunting is very much rooted in your personal reality. It’s about being brutally honest with yourself about the risks you can take—real ones, not the stories you tell yourself. 

The second is something you’ll run into when you have to choose between two opportunities that are differently shaped but similarly valuable. The kind where the pros and cons columns are infuriatingly equal, and the choice feels extremely hard because of that. In those cases, what’s helped me is looking at each opportunity’s bounce potential. Even if the floors are at the same level, which of the two opportunities has more space over your head? Which one might open more two-way doors in the future, has more optionality? That might well be the right choice at that moment. 

The thing about optionality, though, is that we tend to hoard opportunities without actually committing to a choice. It’s kind of like being on a dating app: swiping through a thousand profiles but not really committing to any. In such cases, it’s a cop-out to say the options aren’t good enough, because you don’t know that—you haven’t tried them. We mistake having options for having opportunity, when really, opportunity comes from engaging deeply with our choices. The worst thing you can do is not choose. 

What’s particularly sneaky is that not choosing often masquerades as wisdom ("I'm keeping my options open!"), when it's actually fear and opportunity cost anxiety stacked in a trench coat. Paths not taken are Schrodinger’s opportunities; they exist in this quantum state of perfect possibility. We romanticise them so hard that we forget every path has its own messy complexity and unexpected twists. But I’ve discovered that opportunity cost is actually impossible to calculate accurately. Each choice creates new possibilities we couldn't have seen before, and closes off others we can't really know about. So ironically, the energy we spend anxiously calculating opportunity costs is itself an opportunity cost.

What I’m getting at is that, often, the best way to create valuable optionality is to commit to something. It's when you commit to exploring one path that you see more opportunities you couldn’t have seen from the starting point. You don't get the interesting opportunities without first saying "yes" to something specific. 

There’s another side effect of the Theory that I haven’t spoken about yet: how it transforms decision-making from this heavy, anxious process into something more playful. I’ve noticed that, on top of being a lot more clear-eyed about opportunities, I’ve also started approaching them with the spirit of an experimenter rather than the caution of a catastrophist.

It’s funny: the safety of a limited downside and unbounded upside actually becomes an invitation to play, to be more willing to try unusual combinations or unexpected paths. Instead of trying to predict every possible outcome (which is impossible anyway), we're just checking if we've got a good trampoline to jump on. It's surprisingly liberating to realise we don't need perfect certainty. We just need a bouncy floor and the space over our heads to jump high.

This is part three of my series on how to spot opportunities and expand your life. In part one, I unpack getting better at spotting opportunities that lurk around us. In part two, I explore the mental and physical prerequisites for finding opportunities.

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