At the end of the night that 27-year-old Matt Damon won the Oscar for Best Original Screenplay with his best friend Ben Affleck, he wasn’t able to sleep.

He sat looking at the Oscar, something that so many people in his industry spend their whole lives chasing. As he looked at it, he had a surprising realisation. The achievement was real, the sense of fulfilment he expected to come with it was harder to find.

He immediately imagined a parallel universe where another Matt Damon spent decades chasing that award, doing everything he could to get there, potentially compromising relationships, values and parts of himself along the way. Finally winning it at 80 years old and realising, too late, that achieving the goal and finding fulfilment were not the same thing.

As he said on The Graham Norton Show, “if that’s a hole you have, it won’t fill it.”

What Damon may not have realised at the time is that he had stumbled into something positive psychologist Dr Tal Ben-Shahar called the Arrival Fallacy. The Arrival Fallacy is the belief that fulfilment are waiting for us on the other side of a specific achievement. We convince ourselves that once we get the promotion, earn the pay rise, make the team, win the championship or reach the next milestone, then we will finally feel the way we have been hoping to feel.

The difficulty is that when we finally arrive, the feeling often doesn’t last as long as we expected. The achievement may be meaningful, and the moment may be special, but the deep and lasting fulfilment we imagined would come with it can be far more fleeting than we hoped.

Sport creates the perfect conditions for the Arrival Fallacy. So much of sport is built around the pursuit of a goal. Win the game. Beat your opponent. Lift the trophy.  The structure of sport constantly gives us opportunity to chase the next win. Because that chase is so clear and so visible, it can begin to feel like the purpose of the whole thing. And if we can achieve the thing ahead of us, that will finally deliver us the feeling we are after.

Scottie Scheffler, the current world number one golfer, has spoken about this with a level of honesty I find fascinating. Here is someone with 21 PGA Tour victories, four major championships and an Olympic gold medal. By almost any measure, he has reached the highest levels of his sport.

Yet ahead of The Open in 2025, he reflected on winning in a way that sounded remarkably similar to Damon.

“Why do I want to win the Open Championship so badly? I don't know because, if I win, it's going to be awesome for two minutes.”

He went on to say:

“You win it, you celebrate, get to hug my family, my sister's there, it's such an amazing moment. Then it's like, OK, what are we going to eat for dinner? Life goes on.”

Then he added:

“It feels like you work your whole life to celebrate winning a tournament for like a few minutes. It only lasts a few minutes.”

Scheffler is a competitive beast, so this isn’t someone who is philosophical on winning having never done it. Even with all his accomplishments, he seems to be separating the achievement from the meaning he once may have expected it to provide.

Listening to both Damon and Scheffler, I keep coming back to the same question. Why do achievements that matter so much often struggle to provide the fulfilment we expect them to? American philosopher C. Thi Nguyen offers a useful way of thinking about that question. Nguyen writes about games and makes a distinction between the goal of a game and the purpose of playing it.

In simple terms, the goal is what you pursue inside the game. The purpose is why you are playing the game in the first place.

In Monopoly, the goal is to be the last player with money and bankrupt everyone else. In soccer, the goal is to score more goals than the opposition. In tennis, the goal is to win the required number of points, games and sets before your opponent. In the 100-metre sprint, the goal is to get to the finish line faster than everyone else.

The goal gives the game its shape. It tells us what we are trying to do, what counts as success and how the game is won.

The purpose can be something different. You might bring out Monopoly because you want to have a fun night with friends or family. You may not win the game, but if everyone laughed, argued a little, enjoyed each other’s company and left feeling more connected, then the purpose of playing may have been fulfilled. You didn’t achieve the goal of the game, but you may have achieved the reason you played.

The reverse can also happen. You might win Monopoly, but spend the whole night frustrated, disconnected or miserable. You achieved the goal but missed the purpose.

I think this is where sport can trip us up. We lose sight of the purpose and begin treating the goal of the game as the purpose itself. Winning suddenly becomes the thing we believe will give the whole experience meaning. Which it is never going to be able to do.

Ange Postecoglou says trying to chase wins and trophies without any greater meaning or purpose behind you is like "chasing the wind." I love that phrasing because it captures the frustration at the heart of the Arrival Fallacy. You reach one milestone and another appears. The pursuit keeps moving because winning doesn’t provide all the meaning we often ask it to carry.

How do you shift from the goal of the game to the purpose?

Firstly, we have to acknowledge that within sport purpose can vary depending on who you ask. For some people, sport is a competitive outlet. For others, it is about connection. For some, it is about health, discipline, belonging, mastery, self-expression or discovering what they are capable of.

It can be personal and it’s something every coach and player has to unpack for themselves. What I find interesting is how some coaches have clearly articulated the purpose sitting underneath the pursuit of winning.

My favourite example is Pete Carroll.

Carroll, who won a Super Bowl with the Seattle Seahawks, developed his Win Forever philosophy as a way of grounding his coaching in something bigger than the result of any one game. What I like about Carroll’s framing is that it still takes competition seriously, but it places the pursuit of winning inside a broader purpose.

In his book Win Forever, he writes:

“Win Forever was never about winning every game, but rather the pursuit of being the best you can possibly be. Winning Forever is an ongoing competition to be your best while living your life to maximise the opportunities it has to offer.”

In Carroll’s framing, sport provides the opportunity to see how good you can be. It is a place to pursue mastery, test yourself, grow through challenge and become a better version of who you currently are.

Winning still matters. The goal of the game creates the challenge, and the challenge is part of what give sport the opportunity for us to be our best. But Win Forever allows the purpose to survive the scoreboard. If the deeper purpose is to pursue your best, to grow and to respond to the opportunities the game provides, then losing does not automatically make the experience meaningless. It may be painful, frustrating and disappointing, but it still sits inside the larger purpose.

That may be the deeper challenge for all of us. It is certainly the lesson Matt Damon was lucky to learn at 27. Achieving the goal does not always provide the fulfilment we imagine it will. The challenge for us all is to understand our purpose, and the purpose of the people around us, because that is what gives the pursuit its meaning.

2-for-1 today in the Deeper Dive section!

Matt Damon on The Graham Norton Show discussing the realisation he had the night he won the Oscar for Best Original Screenplay.

And here is Scottie Scheffler’s press conference ahead of The Open in 2025. A fascinating insight into his feelings about winning in the grand scheme of things.

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