Why ‘Whoever has the most fun, wins’ is a winning strategy in business

I’ve been using “Whoever has the most fun, wins”¹ for quite a while now as my motto, usually saying it multiple times with a big grin on my face. But I mean it far more seriously than it probably sounds when I use it. Somewhere along the way, business has developed this slightly peculiar idea that the more serious something looks, the more serious it must be.

Serious people attending serious meetings, with serious strategies being presented in seriously boring PowerPoints, usually using an extremely serious shade of navy blue. Everybody looking appropriately serious about the serious business of doing business, seriouslyu. And then we wonder why so many businesses end up looking, feeling exactly the same and drowning in the sea of sameness

We’ve got something backwards here. Having fun isn’t the opposite of being serious about business. In fact it is one of the ways you get seriously good at it.

Before somebody from your Finance department starts hyperventilating, let’s clear something up. I’m not suggesting we replace your Monday management meeting with a bouncy castle, although I’d definitely attend that one. And fun in business shouldn’t mean the sort of forced fun that involves compulsory karaoke or somebody from HR announcing that tomorrow is Crazy Sock Friday. In my experience, there are few things quite as effective at removing all traces of actual fun as somebody officially announcing that "AND NOW, WE ARE GOING TO HAVE FUN".

What I’m talking about is creating a business and brand that people genuinely enjoy being part of. The people who work there actually enjoy making the things and doing the stuff. The customers enjoy experiencing it. And, rather importantly, the people running it still get some enjoyment from the business they probably started because, once upon a time, they gave quite a significant shit about it.

That’s a very different idea. And commercially, it’s an incredibly powerful one, because people like things they enjoy. Revolutionary stuff, right?

If somebody enjoys dealing with you, they’re more likely to want to deal with you again. If they enjoy something you’ve created, there’s a pretty good chance they’re going to remember it. And if working with your business simply feels noticeably better than dealing with somebody else’s, that feeling starts becoming part of the value you provide your audience. It might not appear as a neat little line on the balance sheet, but trust me, it’s there.

And there are some pretty serious numbers behind this supposedly unserious idea. Oracle found that 91% of people prefer brands to be funny rather than formal, while 72% would choose a brand that uses humour over a competitor. When brands successfully use humour, 80% say they’re more likely to buy from them again. Perhaps even more interestingly, 63% say they’d spend more with them.

Now obviously fun and humour aren’t exactly the same thing and I’m not pretending they are. But they do point towards the same rather lovely human truth. People are drawn towards experiences that make them feel good. Which suddenly makes this whole idea of having a bit more fun sound considerably less frivolous.

Fun creates energy too and you can feel that energy when people are genuinely enjoying what they’re doing. Ideas get thrown around more freely because nobody is quite so terrified of suggesting something that might sound a bit ridiculous. People become more willing to try something slightly unusual and see where it goes. Customers feel that enthusiasm too and before you know it, the business starts behaving less like an organisation executing a strategy and more like a group of humans who actually want to make something brilliant.

Because businesses don’t simply run on systems or increasingly clever technology. They run on people giving a shit. You can optimise the processes until they’re beautifully efficient. You can automate enormous amounts of work and use AI to make everybody considerably more productive. But it’s becoming increasingly difficult to automate genuine enthusiasm and when a business loses that, you can bloody well feel it.

Fun also makes creativity considerably easier, because somebody has to suggest the weird idea before anybody knows whether it’s a good one. Somebody has to ask the slightly stupid question that everybody else was too sensible to ask. And at some point somebody needs to be willing to play with something, poke it around a bit and see what happens before demanding to know exactly where it’s going.

That’s how creativity works. But when every conversation has to immediately justify itself against a KPI, you start killing ideas before they’ve even had a chance to become interesting. Have a little think about your own business. You can probably picture at least one killjoy already. Not you of course.

Play creates possibilities and those possibilities are where all the joyfuelled things your competitors haven’t thought of yet, tend to be hiding.

This is where my idea of Stratejoy® matters, because the argument isn’t simply “have more fun”. That would be lovely, obviously, but it’s not really a business strategy. Stratejoy is about using joy deliberately. It’s looking at where more enerjoy could make the business not just feel better but be better, where being more human could change how somebody experiences you and where a little more playfulness might unlock something that wasn’t there before. Then actually doing something about it.

Customers can feel when you’re enjoying yourself too, because brands transmit energy whether they realise it or not. You can feel businesses that genuinely enjoy being themselves. There’s more personality in the way they speak and more confidence in the ideas they put into the world. The experience tends to contain those lovely little things that nobody technically needed to do, but somebody inside the business clearly thought, “Wouldn’t it be brilliant if we did this?”

Somebody inside the business had fun creating something and somewhere further down the line, somebody outside the business had fun experiencing it.

Put joy in. You get energy out.

And that can become a surprisingly difficult advantage for your competitors to copy.

Most businesses compete using things that can eventually be copied. Your competitor can copy a feature or decide to lower their price. They can adopt the same technology and, increasingly, use exactly the same AI tools you’re using. Give them enough time and there’s a pretty good chance they can copy quite a lot of the functional stuff that once made you different.

But your culture is considerably harder to nick. And so is genuine enthusiasm, as is the accumulated feeling customers get from dealing with a business that seems to genuinely enjoy what it does.

That emotional difference is what I call Affective Advantage™, people feeling something about your business that they simply don’t feel about the alternatives. And once you start looking at business through that lens, fun stops looking like a frivolous extra and starts looking like something considerably more commercially interesting.

I also think AI makes this whole argument more important, not less. By all means automate the boring stuff. In fact, please do. Automate the things nobody particularly enjoys doing so we have more time and energy for the things humans are actually rather good at. Coming up with ideas, building relationships and being curious enough to wonder whether there might be a better, stranger or considerably more interesting way of doing something.

Because if everybody has access to increasingly similar intelligence, simply being clever starts becoming less of an advantage. Being interesting might become one. Being properly human might become one too. But being the business people actually enjoy dealing with could become a very significant one indeed.

So when I say “Whoever has the most fun, wins,” I’m not suggesting the business with the biggest Christmas party automatically takes the market. I’m talking about businesses with oodles of enerjoy. Businesses where people still love experimenting and enjoyneering, where they actually care about the thing they’re creating and where they haven’t optimised every last bit of humanity out of themselves in the relentless pursuit of efficiency.

I’m talking about businesses brave enough to remember that commercial success and enjoying the bloody ride aren’t mutually exclusive. In fact, I increasingly think they might be quite the opposite.

Because joy isn’t simply the reward you get after you’ve won. Joy creates the kind of enerjoy, as I call it, that makes people want to do something in the first place. It gives creativity room to breathe, helps people connect with what you’re doing and creates that emotional difference that makes somebody choose you rather than the perfectly competent, perfectly sensible and perfectly joyless alternative.

Which is why I’ll keep saying it, probably far too often, with a big smile on my face and meaning every single word.

Whoever has the most fun, wins.

Sources

1. James Clear — Atomic Habits
2. Oracle & Gretchen Rubin — The Happiness Report, 2022. Research conducted by Savanta; 12,000+ consumers and business leaders across 14 countries.

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