What I Do When a Problem Won’t Move

I’m partly writing this for myself — for the next time a problem won’t move. Because it will happen again. It always does.

When I was running my company, I’d sometimes hit a problem that simply wouldn’t move. Getting a new product off the ground. Entering a new market. A hiring decision. A strategy question with no obvious path forward. I’d be at my desk, banging my head against the wall trying to figure it out, and nothing I did seemed to unlock it.

I assumed the problem needed more effort. More analysis. More grinding. It rarely did.

Over time — largely through experience — I realized something else: the difficulty wasn’t the problem itself, but the process I was using to think about it.

And once I noticed that, everything shifted.

The Structure of a Stalled Problem

No matter what the problem was (the content), the way I got stuck looked almost identical every time.
No one got stuck quite as thoroughly as I did — I became surprisingly good at it.

When I stripped away the business details about the problem itself, I realized I was usually looping in my head in one of two ways:

1. A Visual Loop

I’d be replaying imagined scenes or “what if” scenarios — like watching the same movie segment over and over.

2. An Auditory Loop

More often, I’d be running an internal dialogue with myself: Should I do this or that? What if I’m wrong? What if this backfires?

Different challenges, same underlying pattern — I’d end up looping in my mind, either visually or auditorily.

And what mattered wasn’t the specifics of the situation — it was the channel I was stuck in.

Once I understood that, the solution became simpler:

• If I was stuck in an auditory loop, I needed to do anything that pulled me out of my head and into movement or sensation.

• If I was stuck in a visual loop, I needed to do anything that interrupted the internal movie.

Everything that follows grew out of that realization.

1. Switching the Channel

Our office building had a gym on the basement level with a great steam room. I worked out there most days anyway, but every so often, when progress on a problem stalled, I’d go down at midday, bring my gym clothes, and sit in the steam room for fifteen minutes. This was quite an effective stress reliever when I was in the process of scaling up the company.

It was one of the simplest ways to get out of my head and into my body.

Heat, breath, and sensation interrupted whatever mental loop I was in. They replace inner noise with something immediate and physical. And once the loop breaks, clarity has a way of surfacing without any deliberate effort.

Running worked the same way. Rhythm, breath, movement — they dissolved mental knots in a way thinking never could.

Even a brisk walk around the block often did the job. Anything that shifted the channel was usually enough.

2. Surrounding Myself With Excellence

After a day of getting nowhere on a problem at the office, I’d sometimes find myself buying a last-minute ticket to something that evening.

One of the benefits of being in Toronto is that there’s always something happening. Koerner Hall. Roy Thomson Hall. The Four Seasons Centre for the Performing Arts. The Art Gallery of Ontario. Random pop-up events. You can decide at 6:45 p.m. that you want to hear a pianist at 8:00 p.m. and actually make it happen.

I wasn’t doing this to be cultured. I simply noticed that these performances pulled me out of whatever loop I was in.

There was always a moment — watching someone completely absorbed in what they were doing — when my internal dialogue would quiet. I’d become drawn into their mastery, their discipline, their years of repetition. And almost through osmosis, I felt influenced and inspired by their excellence.

It also reminded me that anyone who has achieved mastery has been worked through stalled problems many times before. No one escapes that part of the process. I noticed this when watching an excellent foreign film as well.

And once I was absorbed in what they were doing, I wasn’t in my head anymore. All of my attention was on the performer. I suspect my unconscious mind started working on the problem the moment I got myself out of the way.

3. Stepping Away Entirely

Another thing that worked for me was travel.

Sometimes it meant going to a new city altogether. Other times it was as simple as exploring a different part of Toronto. Either way, it snapped me out of autopilot.

In a new environment, my attention naturally shifted. I’d find myself figuring out the metro, scanning street signs, navigating unfamiliar streets, looking for a café I’d never been to, noticing small details I’d normally overlook.

It got my brain working differently.

I found that when I stayed in the same routines — same route, same cafés, same environments — I was also using the same mental apparatus to think about the problem. If that apparatus wasn’t producing answers, staying inside it rarely helped.

But when I went somewhere new, even briefly, my brain switched modes. It began using different pathways. And often, the solution to the problem lived in that different pathway.

Even short trips — Madrid to San Sebastián, for example — reset everything. Running through Retiro Park. A chocolate shop. A train north. Ocean air. Small rituals in unfamiliar places.

When my internal pattern changed, the problem rearranged itself.

The Meta-Pattern

Looking back, the three approaches — switching the channel, surrounding myself with excellence, and stepping away entirely — all did the same thing.

They broke the loop.

They changed the mode I was in.

They gave me enough distance for clarity to surface naturally.

And the moment I stopped trying to solve the problem from inside that pattern, the problem often solved itself.

When All Else Fails

When nothing else worked, I slept on it.

John Steinbeck once wrote:
“A problem difficult at night is resolved in the morning after the committee of sleep has worked on it.”

That matched my experience almost exactly. The solutions I couldn’t force during the day often arrived unannounced the next morning — as if some quieter part of me had kept working long after I had stopped.

Uh-oh — I think I’ve just come down with a case of writer’s block. I’m trying to find the best way to finish this article, and I’m stuck in my head.

Hang on a second. I hear Seong-Jin Cho is coming to town to play some Chopin. I think I need to follow my own advice and buy a ticket right now.

I’ve written about several other topics. Visit my writing page for a complete list.