Accounting for fortune

Considering the role of fortune in success and failure, and how to make the most of it

Don’t minimize the importance of luck in determining life’s course. - Alex Trebek

I met my spouse after a chance encounter with someone that later introduced us. Even a 30-second delay would have meant me sitting next to a different person at that conference, a “sliding doors moment” leading to a totally different life. 

These kind of life-changing stories of fortune are common enough, but I think it’s clear to most people that blind reliance on fortune is still a mistake. Wise people don’t rush to play slots at a casino upon hearing about someone who had won big: the role of luck in winning at slots is too well understood. 

Nevertheless even with that common wisdom, I find people—myself included—often overlook how much fortune and luck contribute to our own success, as well as to the success of others. 

Like many people I know, I frequently catch myself comparing my achievements to others who have attained remarkable success. I strive to replicate their accomplishments, but underestimate or discount how unique the circumstances were that led to their success.

And as human beings, we love our deterministic narratives—hero X took action Y and created outcome Z—but the real world is much less certain and more probabilistic than we give it credit for, and the role of external factors is much bigger than I think most of us are comfortable with. 

Likewise, in the entrepreneurship world, successful ventures are highly studied and emulated, yet we still see a convincing majority of startups fail. This failure rate is remarkably stable, despite decades-worth of new methodologies and expert know-how that’s been developed and poured into the craft of venture creation.    

Chance and luck play a big role even here. 

But what can we do about it?

The first step is to account for chance and fortune when we study success, otherwise it is impossible to reliably learn from it… or to learn from failure.  After all, what worked for them won’t necessarily work for you, and what failed for others, might be the key to my own success. 

The second step is to make your own luck.

When I reflect on the most successful people I know—i.e. the people who can reliably recreate successful outcomes—I see people who are obsessive about “stacking the deck”.  

They look beyond the problem they are trying to solve, study the environment they are operating in and the factors that could influence success, and then they find and apply leverage to bend those conditions in their favor. 

Here are four ways in which they do so:

• Making the work worthwhile, no matter what the outcome is

• Developing an effective endurance strategy

• Deeply understanding operating context and structure

• Building capacity to generate opportunities

—Making the work worthwhile, no matter what the outcome is—

Choose to work on things that matter, something that will leave you or the world better off for having made the attempt.

For example, founder David Rogier was advised to work on an idea “that even if it fails, you would be proud of it”. Helping everyday people learn from experts was his idea that mattered, which became the core of MasterClass. 

Likewise, bestselling author Philip Roth is famously quoted as claiming “Nothing bad can happen to a writer. Everything is material.” For a writer, even failure can create opportunities. 

This is why passion for what you’re working on is so critical, but also creating ways to demonstrate and share what you have learned and to position yourself as a catalyst for others.

—Developing an effective endurance strategy—

I’ve written about the importance of endurance to innovation before, and the below applies equally well to making the most of fortune and chance.  

It takes time to build the capabilities and position to realize opportunities when they arise, either ones created directly by you or by external factors. To earn that time, you need an endurance strategy to not only keep your company “in the field” with the innovation, but to be ready to strike.

Want to be in the right place at the right time? You need to execute a strategy to allow you to endure long enough until you can find that right place, and to be ready to make the most of it when you do.

—Deeply understanding operating context and structure—

No effort exists without context, and that context creates constraints for what’s possible, whether it’s a brand new startup or a corporate innovation attempt. 

There’s a reason why both Uber and Lyft started in San Francisco, a city where it was practically impossible to find a cab. Likewise, if you’re a fintech startup, there are pros and cons to base yourself in a financial capital like New York, providing a context and constraints that could either boost your efforts or strangle them.

The point is to strive to deeply understand the context you’re operating in, so you can intentionally make a change to that context and its structure, pushing your boundaries to increase your chances of success. 

For example, the bestseller “Never Search Alone” outlines a strategy to change the underlying structure of a job search, by joining forces with other job searchers to improve your opportunities to find a new job.

—Building capacity to generate opportunities—

When something is new, quantity has a quality all of its own, specifically the quantity of opportunities you have to address real customer problems or to work meaningfully with a new capability.

Want to work on a new language learning service? Then figure out ways to maximize the opportunities you have to meaningfully engage language learners and educators, even before you’ve nailed down your solution. 

Ideally you can engineer a way to do this that both feels natural and is scalable, feeding a flywheel effect of feedback and innovation that becomes it’s own differentiation and moat. For example, Open AI built up a massive flywheel of feedback and innovation with the launch of ChatGPT, drawing in massive human engagement and training data that’s critical to the effectiveness of Generative AI services.

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In closing, whether you are reflecting on success or failure, whether that’s somebody else’s or your own, don’t forget to consider the role that fortune and chance played. And when you’re starting something new, remember to do your best to engineer as much luck for your efforts as you can.

May Make luck be on your side.

May Make fortune smile upon you.