What I Learned About Decisions Playing Tennis With Richard Branson

The four-step process that changed how I think about everything

Jan 22, 2026

When I was living in the Caribbean teaching tennis, I got to play with Richard Branson on Necker Island.

This was right after we sold our first company. I took five years off to teach tennis in the Caribbean, Dubai, and Maui. That weekend with Branson stands out for two reasons: he was way better at tennis than I expected, and he had a story for everything.

He didn’t care about pithy definitions of words or perfect social media soundbytes that the modern TikTok-addicted world salivates over. He had this endless repository of stories to help you see the world differently without making you feel like an idiot.

Back to tennis… we’d just finished two sets of doubles. I’d been rehearsing a question for two hours. As he was taking a sip of his carrot juice, I finally asked him how he thought about making decisions.

Of course, he answered with a story. But that story came with a good point. He explained that every person makes decisions differently but the biggest mistake is not knowing your own process for making decisions.

As you can imagine, he was too much of a gentleman to put me on the spot and ask me for my decision making process, as clearly the reason I asked the question showed that I didn’t have one.

I spent the next year deconstructing how I make decisions in conversations, in meetings, or anytime the answer is not pre-made, like your favorite ice cream flavor.

Here is mine:

Understand the context
Isolate the issue
Accept the risk
Map the decision

While this is mostly self-explanatory, let me explain a few of the nuances for you.

First, amateurs just jump to attacking the issue while the pros know there are a lot of nuances at play.

You will see the best of the best zoom out and ask contextual questions to orient themselves with the overall situation. In fact, I like forcing myself to ask a context revealing question just to ensure I am tracking the situation well.

Then comes the skill of isolating the issue, which is also known as the constraint, that needs to be resolved.

This takes practice, reps and the development of the analytical eye, as this is extremely nuanced. And the more context you have, the less you hallucinate about the constraint.

The third component is where most people miss the beat and that is protecting the downside.

After working on wall street and running a public company, risk management gets drilled into your operating DNA. The untrained eye calls this judgment but in all practical respects this is understanding what the tradeoffs are and where things can go wrong, and then you accept it. Otherwise you get stuck in an eternal loop of second guessing yourself on whether you made a good decision.

And finally the job is to map the decision.

What did we actually decide? What are the next steps? If you can’t answer both clearly, you haven’t finished the decision.

If you hang with me, you will see that this is kinda hard-coded into how I think, work and communicate as it provides a starting point to make decent decisions.

Maybe you can use this framework. Maybe you have your own.