Return on Luck: How to Actually Capitalize on Lucky Breaks

Last week I wrote about increasing your surface area for luck-putting yourself in more optional scenarios where good things can find you. But that’s only half the equation.

The other half is what happens when luck actually shows up. And here’s the uncomfortable truth: most people are terrible at capitalizing on the opportunities they create.

The Follow-Through Problem

I see this constantly. Someone goes to a conference, has great conversations, collects business cards, gets genuinely excited about potential collaborations… and then does absolutely nothing with any of it. The cards sit on their desk for three months before getting thrown away. The LinkedIn connections get sent but never messaged. The “we should definitely grab coffee” conversations never turn into actual coffee.

It’s like planting a garden and then never watering it.

I’ve done this myself more times than I care to admit. Many years ago, I met someone at a random dinner who was working on exactly the kind of problem I’d been thinking about. We had one of those conversations where both people get energized and start talking faster. He mentioned they were looking for someone with my background.

Perfect setup, right?

I never followed up. Not because I wasn’t interested, but because I got busy, then felt weird about the timing, then convinced myself it was probably not that serious anyway.

That’s not bad luck. That’s bad execution on good luck.

What Return on Luck Actually Means

Think of luck as raw material. When serendipity drops an opportunity in your lap, you still have to do something with it. The “return” is what you actually extract from that lucky moment.

Some people have incredible luck but terrible returns. They meet the right people, hear about the right opportunities, get invited to the right events-but nothing ever comes of it because they don’t know how to convert luck into outcomes.

Others might not create as many lucky moments, but they squeeze every drop of value out of the ones they get. They follow up quickly, they ask good questions, they make specific proposals, they actually do what they say they’re going to do.

The second group ends up looking much luckier than the first group, even though they might have started with fewer opportunities.

The Execution Gaps

After paying attention to my own patterns (and watching others), I’ve noticed a few common failure modes:

The Permission Problem: We wait for the other person to make the next move, or for some external validation that it’s okay to follow up. “I don’t want to seem pushy.” Meanwhile, they’re probably thinking the same thing about us.

The Perfect Timing Fallacy: We convince ourselves there will be a better moment to reach out. After this project wraps up. When we have more time to focus. When we’ve thought through exactly what we want to say. Perfect timing never comes.

The Impostor Override: We talk ourselves out of opportunities because we don’t feel qualified enough, experienced enough, or ready enough. “They probably meant someone more senior.” “I should wait until I have more to offer.”

The Analysis Paralysis: We overthink what the opportunity might lead to instead of just taking the next obvious step. “But what if this turns into a commitment I don’t want?” “What if we’re not actually a good fit?” You can’t figure that out in your head-you have to find out by engaging.

The Energy Mismatch: We’re great at creating opportunities when we’re feeling social and energetic, but terrible at following up when we’re back in normal mode. The Tuesday-morning version of yourself doesn’t want to send that email that Friday-night-at-the-event version of yourself promised to send.

My Current System

I’ve had to build explicit systems to work around these gaps, because left to my own devices, I’ll optimize for not feeling awkward in the short term, even if it costs me interesting opportunities in the long term.

24-hour rule: If I meet someone interesting, I have to take some kind of action within 24 hours. Not necessarily the full follow-up, but at least getting their contact info into my system with notes about what we discussed and what the potential next step might be.

Default to specificity: Instead of “we should grab coffee sometime,” I try to suggest actual times and places. “Are you free for coffee next Tuesday around 10am? There’s a good spot near your office.” Vague suggestions die in the coordination overhead.

Assume positive intent: When someone mentions they’re looking for help with something I could contribute to, I assume they actually want help, not that they’re just making conversation. I’d rather occasionally misread social cues than miss real opportunities.

Follow up anyway: Even when I’m not sure if it’s the right timing or if they’re still interested. The worst case is usually that they don’t respond, which isn’t actually that bad. The best case is that you revive something that might have been genuinely valuable. Sending emails is free.

The Compound Interest of Small Actions

Here’s what I’ve learned: most “return on luck” comes from small, immediate actions, not grand strategic moves.

Sending the LinkedIn message while you’re still thinking about the conversation. Texting the introduction you promised to make before you forget. Actually putting that event someone mentioned into your calendar. Sharing that article that reminded you of your conversation.

These tiny follow-ups compound in ways that aren’t immediately obvious. The person remembers that you actually do what you say you’re going to do. They’re more likely to think of you when something relevant comes up. They start including you in more conversations.

I learned this from watching someone I know who’s remarkably good at this. He’s not the most naturally charismatic person in the room, but he has this supernatural ability to turn brief conversations into lasting professional relationships. His secret turned out to be embarrassingly simple: he follows up on everything, usually within a day or two, with something specific and useful.

“Hey, here’s that article I mentioned about the supply chain issue you’re dealing with.” “I talked to my friend who’s been through a similar fundraising process-want me to intro you?” “Saw this job posting that might be relevant to your search.”

None of these are huge gestures, but they add up to him being someone people think of when opportunities arise.

When to Push and When to Let Go

The tricky part is calibrating how much to invest in uncertain opportunities. You don’t want to be the person who can’t take no for an answer, but you also don’t want to give up too easily on things that might be valuable with a little more effort.

My general rule: make it easy for people to engage, but don’t make it weird if they don’t. Follow up once or twice with specific, low-pressure suggestions. If they don’t respond or seem lukewarm, let it go gracefully. There are plenty of other opportunities to focus on.

The exception is when someone has explicitly expressed interest but just seems overwhelmed or busy. In those cases, I’ll sometimes follow up months later with a simple “still thinking about that conversation we had-any interest in picking it up again?” Sometimes the timing is just better the second time around.

The Meta-Skill

Really, maximizing return on luck is about becoming the kind of person who actually does things instead of just thinking about doing things. It’s a bias toward action, even when the action is small and the outcome is uncertain.

This extends beyond professional opportunities. The friend who mentions they’re trying to get back into hiking, and you actually text them about that trail you were discussing. The neighbor who casually mentions they’re looking for a good contractor, and you actually send them your guy’s contact info. The person at the coffee shop who’s reading a book you loved, and you actually strike up a conversation about it.

These small acts of follow-through build a reputation-both with others and with yourself-as someone who makes things happen. And people who make things happen tend to get more opportunities to make things happen.

Start Where You Are

You don’t need to overhaul your entire approach to relationships and opportunities. Just pick one area where you know you’ve been dropping the ball.

Maybe it’s actually responding to those LinkedIn messages instead of just reading them. Maybe it’s following up on conversations from events instead of just collecting business cards. Maybe it’s making those introductions you keep promising to make.

Pick one thing and get good at it. Build the muscle of turning luck into outcomes.

The opportunities are already there-most of us are just terrible at seeing them through to completion. But this is a skill you can develop, and it compounds quickly once you start practicing it.

Your future self will thank you for the follow-up email you send today.