Tennis legend Roger Federer recently delivered the commencement address at Dartmouth university, and it’s well worth a watch. He is, as always, a class act.

Roger isn’t exactly known for his investing prowess, although let it be noted he has had considerable success on that front. Over the years he earned around $130 million in prize money, but the majority of his wealth (estimated at close to A$1 billion) was made off the court.

Endorsements, of course, make up a decent chunk of his wealth, but he’s also had good success with direct business and real estate investments and is even rumoured to be contemplating a move into venture capital.

We’ll see what, if anything, comes from that, but there was a part of his talk at Dartmouth that makes me think he likely has the proper mindset to be successful.


Perfection is impossible.

In the 1,526 singles matches I played in my career, I won almost 80% of those matches.

But what percentage of points did I win? 54%.

In other words, even top ranked tennis players win barely more than half the points they play.

When you lose every second point on average, you learn not to dwell on every shot.

You teach yourself to think:

‘Okay, I double faulted…it’s only a point.’

‘Okay, I came to the net and I got passed again…it’s only a point.’

Even a great shot, an overhead backhand smash that ends up on ESPN’s top 10 playlist – that too is just a point.

Here’s why I’m telling you this.

When you’re playing a point, it has to be the most important thing in the world. And it is.

But when it’s behind you, it’s behind you.

Perfection is impossible.

This mindset is crucial – because it frees you to fully commit to the next point with intensity, clarity, and focus.”

Roger Federer

The sentiment is reminiscent of something Michael Jordan, another sporting legend once said:

I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games.

26 times, I’ve been trusted to take the game-winning shot and missed.

I’ve failed over and over and over again in my life. And that is why I succeed.

Michael Jordan

There’s just so much wisdom in these quotes, and it’s something we as investors need to fully internalise.

Investing is a probabilistic affair. And as Howard Marks says “no one is so good that they can be right all the time, or even a high percentage of the time”. Or, to put it more plainly, you’re guaranteed to make loads of bad investments over your career – it’s unavoidable.

But those that dwell on those failures will be less receptive to the next opportunity that comes along. And there is always another opportunity ahead.

It’s a hackneyed phrase, but every mistake really is an opportunity to learn. And it is those that persevere through the rough patches that come out the other side stronger and wiser.

Smooth seas do not make skillful sailors.

In investing, as in life, it’s not about being perfect – it’s about staying in the game, learning from your mistakes, and always being ready for the next opportunity.

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