Life (and Business) is a Game Worth Playing

I’ve always been drawn to the idea that life is a game. Not in a trivial way, like nothing matters. More like: the rules keep changing, the terrain shifts, and the best players stay curious instead of rigid. They experiment. They try things. They don’t get so attached to outcomes that they forget to enjoy the process.

That mindset has served me well over 25 years, though I’ll admit I lose touch with it sometimes. When things get heavy and I’m caught up in worry, or ego, or just the sheer weight of responsibility, the game starts feeling like a grind. That’s usually a signal. Not that something’s wrong with the business, but that I need to adjust my grip or tone.

The framing we choose to move through life matters. If you see business as a war, everything becomes survival and beating the competition. See it as a performance and you get stuck worrying about how you look. But when you see it as a game? You stay lighter. You focus on making the next good move. You’re willing to try things that might not work. You learn faster because failure is just feedback.

Some of my best decisions at Smart Dolphins came from that playful energy. Not reckless, but experimental. Willing to test an idea, adjust, and move on. The managed services model we built wasn’t linear. We tried things. We borrowed from others. We iterated. That’s how games work. You don’t start with all the answers. You figure it out as you go as the world tells you what has value.

I see this in the parts of my work that light me up most right now. AI is a great example. Over the past year or two, diving into what’s possible with AI has felt like rediscovering an old game made new. It’s not just about efficiency or staying competitive (though those matter). It’s about curiosity. About playing with new tools and seeing what happens. That’s the feeling I want more of, not just for me, but for the whole team.

We’ve created space for play at Smart Dolphins before. The quarterly “mini games” we used to run where we would pick a metric or theme, make it ridiculous, and build some competition around a priority would lift the work behind the metric. Those worked because they gave us permission to not take ourselves so seriously. We got away from that for a while. I think there’s something worth bringing back there.

Play also shows up in smaller ways. The newer Dolphin contingency who’ve brought lunch time Mario Kart battles and ping pong back into the office, brought fresh energy through this play. The way a well-timed joke can shift the tone in “another meeting”. The “will this matter in a year?” question that reminds us most things aren’t as serious as they feel. These aren’t distractions. They’re part of how we stay engaged.

Nature reminds me of this (probably another Insight to write about). I’ll see birds flying for what seems like no reason beyond the joy of it, and it pulls me back. We came from all this natural world. The schedules, the metrics, the pressure… these are human constructs. Underneath, we’re still just here to move, to explore, to be alive to the experience. Remembering that helps.

Alan Watts has a concept he calls “work as play”: the idea that we should approach life not as something we’re trying to win or survive, but as something to engage with fully and lightly. That doesn’t mean being careless. It means not gripping so tight that you can’t adjust when things shift. Which they always do.

I’m not always good at this. There are seasons when I get too serious, too caught up in the weight of it all. When I lose that sense of play, everything gets harder. Decisions feel heavier. Creativity dries up. The team mirrors that energy (and vice versa). But when I remember to lighten up and I can see the challenge as interesting instead of threatening and when I see uncertainty as possibility, things open up again.

Heading into 2026, I want more of that. Not as some forced positivity or denial of real challenges. Just a commitment to staying engaged with the game instead of grinding through it. Bringing curiosity and experimentation back to the front. Creating space for the team to play, not just execute.

Business is important work and it can be difficult. But it doesn’t have to feel heavy all the time. When you remember it’s a game worth playing well, with people you care about, toward something meaningful, the whole experience changes. That’s when the best work happens and isn’t that what we’re all looking for?

What’s this 25/25 stuff about?: 25 YEARS, 25 INSIGHTS – Reflections on Growth, Leadership and Resilience | Smart Dolphins IT Solutions Inc.