Better Problems · Issue 05

You're solving the wrong hard thing

August 18, 2026 · 4 min read

If something in your life looks like it's going badly right now, check it before you start fixing it.

Some problems only exist because things went well. They're still real problems, which is what makes them tricky. You can be genuinely stuck and genuinely fortunate at the same time, and the stuck part doesn't get any softer for it.

What usually happens next is you go to work on the wrong part.

Here's how I nearly did that this month.

The mess I made

Next Monday I fly to San Francisco for a creator event at Adobe. I'd also booked a virtual kickoff for a business school that same afternoon, which I noticed six days after it had been sitting on my calendar.

I come home on a red-eye and start a full day of recording the next morning.

The week after that, I'm on campus in Buffalo, speaking Tuesday and Thursday, with an open Wednesday in between.

You're going to read that as a humblebrag. Fair. Stay with me two more paragraphs, because the part that matters isn't the schedule.

Three rooms I walked out of, and I'm walking back into all of them

I worked at Adobe from 2009 to 2012. Best team I've ever been on. Two years after I left, people I worked with there came to my wedding. Next week I walk back in, fourteen years later, as a creator instead of an employee.

I started at Buffalo as a freshman in August 1996. Seventeen years old, on a campus of thirty thousand people, no cell phone. If you got lost, you stayed lost. If you missed somebody at the dining hall, you missed them. Nobody was coming to find you.

In two weeks I'm back on that campus, thirty years later, talking to first-year students in their first week.

And on September 26 I've got my thirty year high school reunion. I grew up in Webster, New York, which is nothing like Brooklyn. The lessons still travel.

What that calendar looked like in 2015

Eleven years ago, Facebook fired me for drinking.

My wife had found out she was pregnant with our first near the end of my time there. I remember telling the HR person that, in the room, while it was happening.

By May I was in rehab in New Jersey.

My calendar that year was empty. Not clear. Empty.

You cannot have a scheduling conflict without two invitations, and I had none.

That's the version of my life where none of this month's problems are available to me. You have one of those too, and it's probably closer than you'd like.

Hard, or wrong?

So run the test.

Is this month hard? Yes. Three cities, an open day with no plan, a red-eye into a full recording day.

Is any of it wrong? No. It's the road, and I built it.

Complaining about this would make me an idiot. Ignoring it leaves me on a red-eye with no plan.

That's usually where I stop. And stopping there is exactly how you end up solving the wrong thing.

Hard how?

You know that feeling where everything on your calendar is something you asked for, and you still feel heavy about all of it? That gap is the tell. It means you've named the situation and not the problem.

Because hard isn't one thing, and I almost didn't check which kind I had.

The travel is fine. I've done more than this. The work is work I want. Neither of those is what's actually sitting on me.

It's being away from my kids across both of those trips. That's the whole thing.

And the second I said that out loud, the move changed completely. I'd been trying to optimize a schedule. The schedule was never the problem.

So now I'm looking at bringing one or two of my kids to Buffalo with me. And that open Wednesday, instead of hunting for something to fill it with, we drive to Rochester and see their grandmother.

Same trip. Same days. Completely different week.

Somebody else's version of this

You're probably thinking this only works if you like your problems. It doesn't. Here's an organization that solved its problem completely and nearly died from it.

The March of Dimes was built to beat polio, and in 1955 it did. Then the money stopped, because nobody donates to a solved problem. Their first move was to get broader and take on more causes, and it made things worse.

What worked was picking one new problem and saying it out loud. They chose birth defects and announced it in 1958. It took until 1965 for contributions to rise for the first time in a decade. Seven years of being right before it paid.

They didn't have a polio problem anymore. They had a what-now problem, which is the better one, and it still almost took them out.

Better does not mean easier. It means the thing you're up against changed shape because you got somewhere.

One thing this week

Take whatever you've been complaining about and ask what had to go right for it to exist at all.

Then ask the harder one. Hard how? Not the whole situation. The specific part that's actually sitting on you.

Most people answer the first question, skip the second, and spend a month fixing something that was never the problem.

I wouldn't trade any of this. I also would have spent both trips missing my kids and called it a scheduling problem.

Run the test on your own decision.

Run the test

Originally published in Better Problems on LinkedIn.

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The three questions and the card are free. The keynote and the call are how I make a living.