What Counts as a Win?

Whenever I start working with a new coaching client, I suggest they keep a simple journal. At the end of each day, I ask them to write down three things: one win, one lesson learned and one thing they might do differently.

It sounds straightforward, but I’ve noticed something interesting about the first one.

A win can mean very different things for different people. For someone who is socially anxious, it might be going to a party and staying for 20 minutes. For someone who fills every evening with plans, it might be turning down an invitation and staying home to read a book. For someone addicted to exercise, taking a rest day might be the win, while for someone who has barely moved all week, it could be going for a walk.

The point is that a win isn’t necessarily about doing more. Sometimes it is about doing something differently.

And yet, particularly among high-achieving people, I’ve noticed how readily we interpret a win as an achievement. We got the piece of work finished. We went to the gym. We had a productive meeting. We finally tackled something we’d been putting off.

Perhaps I notice this because I do exactly the same thing.

I am, I have come to realise, something of an achievement junkie.

I don’t necessarily think this is a bad thing. My drive to achieve has served me extremely well. It has helped me build a successful career, take on challenges, create things I care about and keep going when things have been difficult.

I like setting goals. I like making things happen. I like the satisfaction of moving something from an idea to reality.

But like most strengths, there is a shadow side.

If you’ve trained yourself to measure a good day by what you achieved, what happens on a day when there isn’t very much to achieve?

August is when I particularly notice this.

Work slows down. People go away. Editors disappear on holiday. The diary becomes quieter and the usual markers that tell me I am moving forwards become less frequent.

You might think I would welcome this. Part of me does.

Another part starts looking around for something to achieve.

Christmas can be even worse. While other people seem perfectly content to settle onto the sofa and watch several episodes of a Netflix series, I’m quite capable of sitting there wondering what my next project should be.

Give me an empty space and I will apparently try to put a goal in it.

I’ve noticed something else about myself during quieter periods.

I can be staying with friends, having a perfectly lovely time, and still find myself reaching for my phone.

Sometimes there is a practical reason. Often there isn’t.

What am I hoping to find?

Perhaps an editor has commissioned an article. Perhaps there’s an invitation to speak somewhere. Perhaps I’ve hit some fitness goal I’ve been tracking. Some small piece of evidence from the outside world that something is happening, that I am progressing, that I am doing well.

It is a little hit of achievement.

And the problem with relying on those hits is that they don’t last very long. There is usually another goal waiting just behind the one you’ve reached.

I see versions of this in coaching too.

When I ask highly driven people what would make life better, the answers are often somewhere in the future. The promotion. More money. The successful business. The relationship. The new house. The weight loss. The next qualification.

There is nothing wrong with wanting any of those things. Ambition can give us purpose, momentum and enormous satisfaction.

The problem comes when we make an unconscious bargain with ourselves:

When I get there, then I’ll feel good.

Because if you only permit yourself to be happy when you arrive, you can spend an awful lot of your life waiting to be happy.

This has made me rethink what I mean when I ask a client to record a win.

A win doesn’t necessarily have to be something you can put on a CV, measure on an app or tick off a list.

Perhaps today’s win was that you sat with a cup of coffee and actually tasted it.

Perhaps you had a conversation with someone you love and didn’t look at your phone.

Perhaps you went for a walk and, instead of using the time to plan, problem-solve or listen to something useful, you noticed what was around you. The air, the trees, the sounds, the feeling of your feet on the ground.

Perhaps you did something simply because you enjoyed it, with no possibility of becoming better, fitter, richer or more successful as a result.

For someone who is very achievement-driven, this can be surprisingly difficult.

Living in the moment sounds wonderfully simple until you’re a productivity freak trying to do it.

There is, of course, something faintly ridiculous about an achievement junkie turning “live in the moment” into another goal to accomplish. But perhaps some of us have to start there.

I don’t want to stop being ambitious. I don’t particularly want my clients to stop being ambitious either.

The aim isn’t to choose between achievement and enjoyment. It’s to stop asking achievement to provide everything.

There will be periods when work is exciting and goals matter enormously, and there will be August afternoons, Christmas holidays and ordinary Tuesdays when nothing particularly impressive happens.

If our sense of a life going well depends entirely on achievement, those quieter spaces can feel strangely empty.

But perhaps they aren’t empty at all. Perhaps we have simply become less practised at noticing what is already in them.

A good day doesn’t always need something to show for it.

So I’m changing my own definition of a win.

Some days, the win will still be the commission, the completed project, the fitness goal or something else I’ve been working towards.

But sometimes the win might be putting down my phone, drinking the coffee, enjoying the conversation and noticing that, for this particular moment, there is nowhere else I need to get to.