Living in the In-Between: The Art of Staying Playful
I used to believe the ultimate challenge was simply finding the right path—the right job, the right business, the right routine, the perfect equilibrium. I lived as though somewhere out there existed a version of life that finally stopped asking us to adapt. But the older I get, the more I realise life isn't asking us to find a flawless trajectory. It's asking us to keep adjusting our stride while we walk it. Every season offers us something, and every season asks for something in return.
For years, I worked as a Marketing Manager for a multinational company while quietly building The Happiness Compass on the side. My lunch breaks became writing sessions, and the train ride home became keynote rehearsal. I'd mouth sentences quietly into the train window while commuters scrolled on their phones around me, hoping that one day someone might actually invite me to give the talk I was practising. Late at night, I'd stand in front of the bathroom mirror rehearsing again. Looking back, I possessed something incredibly valuable during that era: financial certainty, a regular paycheck, talented colleagues, and structure. But every one of those gifts carried a cost. My evenings belonged to my ideas, and my weekends belonged to my projects. There wasn't much space left to breathe.
Later, I started my own copywriting agency. From the outside, it looked like the perfect transition—more freedom, more flexibility, more control. Yet I slowly discovered a friction I hadn't anticipated. Writing for clients all day made it surprisingly difficult to write for myself at night. I wasn't running out of time; I was running out of creative freshness. The work looked similar, but the energy it demanded was identical. The season had changed, and so had the negotiation.
Today, building SwiftReporter has brought a completely different lesson. For the first time in years, I have the opportunity to build something that feels deeply aligned with my own values. There is enormous creative freedom in that, but there is a new reality too. I'm no longer twenty-five. I'm a husband and a dad. Our little family doesn't use daycare or nannies; my wife and I deliberately work around each other so that one of us is always present. Consequently, my day isn't divided neatly between "work" and "life." It flows constantly between the two.
I might spend an hour deep in product strategy, then suddenly find myself outside looking at a caterpillar, making lunch, or answering a hundred questions only a three-year-old could invent before returning to solve the exact same problem with fresh eyes. A decade ago, I would have viewed those moments as interruptions. Now I often realise they are the exact reason the next piece of work is better. Not because less work gets done, but because better work gets done. That has become one of the unexpected gifts of this season. For years I managed my calendar. Now I find myself managing my attention instead. They're completely different skills.
Learning to shift between worlds reminds me of one of my favourite memories from living in San Francisco. While waiting for my work authorisation, I spent a few days helping a friend on his removal truck. Most of the guys I worked alongside had come from different corners of the world. Some were waiting for visas, while others barely spoke English. We spent the day carrying heavy furniture, sharing stories, and laughing over lunch while sitting on the tailgate of the truck. Nobody cared what I'd done before. Nobody cared whether I'd written books or spoken on stages. And I loved that.
A few weeks later, I was standing on a stage in Copenhagen speaking to an audience of thousands. One day I was carrying couches; the next I was giving a keynote. I was exactly the same person, navigating a different room, different clothes, and a different conversation. Neither experience felt more valuable than the other. Both expanded my worldview, both taught me something different, and both became essential parts of the same life.
Experiences like that make me wonder if we've become a little too obsessed with certainty. We want to know the business will succeed before we begin. We want to know the book will sell before we write it. We want guarantees that simply don't exist. Every meaningful thing I've ever built has taken longer than I expected, because life has never worked on our timeline. Jobs disappear. Businesses take longer than expected. Children grow, parents age, bodies change, and the people we love get sick. Everything keeps moving. Perhaps the central question isn't how to eliminate uncertainty. Perhaps it's how to move gracefully with it.
One of my oldest friends, Lou, is approaching ninety. During COVID, the local tennis courts closed. While most people complained, Lou quietly invented something new. He called it "Ten-Chi"—part tennis, part Tai Chi. He never mourned the game he'd temporarily lost; he became curious about the one he could invent instead. I've never forgotten that. Children do this instinctively. When one game ends, they immediately invent another. Adults often stop playing altogether. We become rigid, and we mistake certainty for wisdom.
Lately, I've been thinking that playfulness isn't about being silly. It's about remaining adaptable. It's trusting that if one chapter closes, another can still be written.
We built SwiftReporter because we believe your work should support your life—not consume it. That wasn't just a marketing slogan; it emerged from trying to build a company without losing ourselves in the process. The more I reflect on it, the more I realise that idea extends far beyond software. It applies to businesses, relationships, health, creativity, and ambition. None of these should require us to postpone living until we reach some imagined finish line, because the truth is, none of us knows when that finish line arrives.
Perhaps that is why the good life requires more than discipline. It requires range. It takes enough curiosity to keep learning, enough courage to change direction, enough perspective to know this season won't last forever, and enough playfulness to enjoy the strange, unpredictable negotiation that life has always been.
Perhaps resilience isn't about holding everything together perfectly. Maybe it's about staying flexible enough to keep moving when life changes the rules. Because life was never a problem to solve. It has always been a negotiation.
I'm still learning that. And strangely... I'm starting to enjoy the negotiation more than the certainty I used to chase.
— Evan
Continue Exploring This Field Note is part of an ongoing exploration into what makes a good life. Explore The Human Baseline, download The 42, or join The Aliveness Dispatch at evansutter.com.