BY Table of Contents
Here’s the scene: It’s Christmastime 2017, and I’m staying with my friend Andrew Hansen and his family in Australia.
Andrew and I know each other through Frontier Club, a “brotherhood of entrepreneurs” (whose pre-PC name was The Brotherhood) which I’ve been part of for over a decade.
We were having one of those unhurried holiday conversations – the kind you only get when you’re in someone’s home with nowhere to be – and he said something that landed spot-on with me:
“The difference between a problem which is solvable and one which is manageable.”
I wrote it down that night and then wrote underneath it:
“My quest/obsession to solve every problem is keeping me from simply managing.”
That note sat in my notebook for years before I actually grokked what it meant. Forgetting that distinction, mistaking something as solvable when really it only needed to be managed, was a bad habit of mine. (And still crops up more than I’d like.)
That’s what this essay is about.
The Two Categories
Solvable things have a finish line. Launching a product. Fixing a bug. Setting up a bank account in a foreign country. Hard, maybe. But finite. There’s a before and an after.
Manageable things don’t. Marriage. Health. Parenting. Your relationship with money, with alcohol, with your own ego. They never resolve. They just shift.
The mistake I kept making — and that I see other founders make constantly — is mistaking something which is manageable as something that is solvable. Expecting a finish line that doesn’t exist.
The Stoics had a version of this two thousand years ago. Epictetus split the world into what’s “up to us” and what’s “not up to us.” That’s close, but it’s not quite the same thing. The solvable/manageable split isn’t about control — it’s about whether the thing has an endpoint. You can control your effort on a manageable thing and still never be done with it. That’s the part that wrecks people.
The Gap
I picked up a framework from Dan Sullivan’s Strategic Coach workshops in 2013 that I didn’t fully understand until years later. He called it The Gap.
Picture yourself standing on a beach, looking out at the horizon. You know — physically, intuitively — that you can never reach it. No matter how far you walk, it moves with you. That’s fine on a beach. Nobody expects to reach the horizon.
But with goals, we do exactly that. Set the goal on day one. Start moving toward it. Reach it on day five or day ten. And immediately set another one. The internal “goal horizon” keeps moving because you keep moving it. You never arrive. You can’t. The whole thing is structured so that arrival is impossible.
Sullivan’s point — which he’s since turned into a book called The Gap and the Gain — is that high achievers live in the gap between where they are and where they want to be. They measure backward from the ideal instead of forward from where they started. The gap never closes because the ideal keeps moving – and their means of measuring their progress makes them miserable.
That’s the solvable/manageable thing in disguise. The achiever treats their entire trajectory as a problem to solve — get to the goal, cross the line, be done. But the trajectory is a condition. It doesn’t resolve. The horizon doesn’t get closer.
The founders I know who burn out aren’t the ones who work too hard. They’re the ones who keep expecting to arrive at a point where the hard things are solved. They’re waiting for a finish line that doesn’t exist. And the gap between that expectation and reality is where burnout lives.
The antidote, for me, has been the boring stuff. Quarterly offsites where I actually take stock of what’s been achieved. A daily journal. Not goal-setting tools — management tools. They let me see that I’ve moved, even though the horizon hasn’t. That’s the gain. And it’s the only thing that keeps the momentum from curdling into frustration.
Marriage and Fatherhood
Marriage and fatherhood have been my most humbling education in this.
My default mode as a husband is problem-solver. Anne’s frustrated? Identify the issue, fix it. She’s carrying too much of the household load? Restructure, hire help, show her the new system. We’re not connecting? Schedule a date night, book a trip, create a solution.
Each of those interventions might be correct. But the frame is wrong. I’m treating a living relationship like a sequence of bugs to fix. And I like it — I like playing the hero. Swoop in, diagnose, fix, save the day. A coach named Dennis Holtz spent two years excavating this with me: the need to feel safe by being indispensable. The hero needs a crisis. The hero is useless on a quiet Tuesday when nothing is broken and nobody needs saving.
The real work of marriage isn’t solving crises. It’s showing up on Tuesday when nothing’s wrong and the only thing required is presence. The hero gets no applause for presence. But presence is the whole job.
We have two small kids. We live abroad. We’re building a life across multiple countries and cultures. The logistics are solvable. The marriage is not. The marriage is tended or it isn’t. And the moment I start treating it like a task list — optimize the childcare, solve the relocation logistics, fix the schedule — I find that Anne and I grow apart.
Same with the kids. The solver’s instinct is to fix every problem in front of them. She’s upset? Fix it. He’s struggling? Remove the obstacle. But that robs them of agency. The best parenting I’ve done is when I’ve held back. Let them struggle. Let the consequence land. Let them feel the friction and figure it out.
The Business Version
Running a portfolio of digital companies has been the most thorough education in this I could have designed.
When I had one company, I could treat problems as solvable. Fix the rankings. Hire the person. Ship the content. One company generates problems in a sequence you can address linearly.
Multiple companies generate problems in parallel. And the problems aren’t just more numerous – they’re different in kind. Because the job isn’t to solve each company’s problems. The job is to manage a portfolio. To allocate capital, attention, and people across properties that are all pulling in different directions at the same time.
That’s not solvable. There’s no state where they’re all optimized simultaneously. The best you get is a dynamic equilibrium – some growing, some stable, some being divested – and your job is to manage the equilibrium, not to “solve” the portfolio.
I spent two years trying to solve it. Get every property to a certain revenue threshold. Fix every team issue. Optimize every site’s content and rankings. It was exhausting and it didn’t work. Not because the individual fixes were wrong, but because the frame was wrong. I was treating a condition like a task list.
The shift happened when I started thinking of myself less as a problem-solver and more as a gardener. A Brahman priest in Bali once told me my protecting god was Dewa Brahma – the fire god, the creator. “Scientist energy,” he said. Creative and innovative. That tracks. But a scientist solves. A gardener tends. And the portfolio needs tending, not solving. Water, sunlight, soil, weeds, pests, seasons. Some plants thrive. Some need to be pulled. The garden is never done. It’s never optimized. It’s just tended.
That mental model changed how I operate. I stopped trying to get every property to peak performance and started asking different questions. Which ones are worth more attention this quarter? Which ones can run on autopilot? Which ones should I sell? The portfolio is a garden, not a checklist.
The Deeper Layer
I spent years trying to “solve” my core stories. The ones that say I’m not enough, I’m not safe, I need to prove myself. (I built an office with a treadmill desk in it. The metaphor was lost on me at the time.)
They don’t go away. They’re not solvable. They’re manageable.
I spent six years in intensive coaching with four different coaches. Dennis Holtz, Rob Scott, Jesse Elder, Jordan Gray. They all identified the same core wound from different angles: “I’m not good enough.” Every one of them, working independently, arrived at the same place. Rob named it directly: “Really poor at loving myself. Incredibly poor at loving myself.” Jesse saw it in how I showed up. Jordan saw it in my relationships.
For years I kept hoping one of them would help me fix it. That’s the solver talking.
Rob said something to me in 2014:
“The goal isn’t to get rid of the story. The goal is to catch it faster.”
That’s the most useful thing anyone’s ever told me. You don’t solve the story. You get faster at catching it before it runs the show. From days to hours to minutes.
The Filter
When something is frustrating me now, I ask one question: is this solvable or manageable?
If it’s solvable, I solve it. Full force. Set a deadline, execute, cross the line, move on.
If it’s manageable, I stop looking for the line. Show up on Tuesday. Do the boring work. And resist the urge to play hero, because the hero needs a crisis — and the whole point of managing well is that there isn’t one.
Andrew said it at Christmas in Australia nine years ago. I didn’t understand it then. I’m not sure he did either. But it’s the most useful filter I’ve found for knowing when to push and when to just show up.