September 4, 2026

It’s Not the Work. It’s the Job.

What an old iPhone, and a message I hadn’t thought about in years, are teaching me about the leadership mistake I made for years without realizing it.

I found an old iPhone in a drawer a few years ago, and it took me straight back to a version of myself I’d half forgotten (or at least hoped I would).

I charged it up and started scrolling through old photos and text messages, mostly out of curiosity. There were some really cute photos of my daughter from before we had our son. A few of my mom and dad coming to visit before we lost them both. Some sweet messages from my wife. The kind of stuff that makes you realize an old phone is basically a little time capsule you forgot you owned.

And then, buried in one thread with a former business partner, was a message I hadn’t thought about in years. I told him I didn’t particularly like the company we had created. I also didn’t particularly like my own job anymore. What bothered me even more was that I wasn’t sure I liked the jobs we had created for everyone else either.

He wrote back something like, I know you don’t, and not to worry, we’ll work on making it better. We never really did.

Reading that message years later hit me harder than I expected. I sat there in my kitchen holding a phone that hadn’t worked in years, rereading four sentences I’d written to a man I no longer worked with, and felt my stomach actually drop. All of it was mine to answer for. The reporting structures. The responsibilities. The meetings. The goals. The expectations. The processes. The way decisions got made. The little frustrations people had to work around every day just to get something done.

I had helped design my own job. And I had helped design theirs. And yet, there I was, complaining about how much my own job sucked.

Which left me with a pretty uncomfortable question. If I couldn’t get excited about working at my own company, how could I expect anyone else to?

I’ve thought about that a lot since. For years, when someone wasn’t performing well or seemed disengaged, my first instinct was usually to look at the person. Were they good enough? Did they care enough? Were they working hard enough? Had we hired the wrong person?

Sometimes the answer was yes. We absolutely hired people who weren’t right for the job. Some people underperformed. Some didn’t want the responsibility that came with the role. Some simply weren’t a fit. But I think I was too quick to stop there. Because sometimes the person wasn’t the whole problem. Sometimes the job itself wasn’t very good.

I’m starting to think most people don’t hate work nearly as much as they hate bad work, and bad work has almost nothing to do with how hard the work is. Some of the most satisfying work I’ve ever done has been difficult. Long hours. High stakes. Big expectations. Problems I didn’t immediately know how to solve. That kind of work can be energizing. What wears people down is something else.

It’s responsibility without authority. Goals without clarity. Urgency without priorities. Accountability without the tools to succeed. It’s meetings that don’t lead anywhere, decisions that get made and then unmade, work that has to pass through five people before anyone can act on it. It’s being asked to own an outcome while having very little control over what produces it. It’s fighting the company itself just to do your job.

That’s the real difference. Hard work asks a lot of you. Bad work asks a lot of you and then takes away your ability to actually deliver on it. Looking back, it was never really about the work itself. It was about the job built around it.

I know because I helped create some of that. Not intentionally. I don’t think most leaders wake up in the morning wondering how they can make work more frustrating for everyone. Usually the opposite. We’re trying to grow. Trying to serve customers. Trying to hire good people. Trying to fix whatever problem is screaming the loudest that day. And somewhere in the middle of all that, jobs get built almost accidentally.

A responsibility gets added here. A meeting gets added there. A new approval gets inserted because something went wrong once. A process gets created to solve one problem and then lives forever. Someone leaves, so their responsibilities get divided among three other people. The company changes, but the job doesn’t. Then one day you look around and wonder why everybody seems worn out. Or worse, gone.

I don’t think I have the perfect formula for a good job now. I’m not sure anyone does. But I know I’d ask different questions than I did back then. Questions about whether the job actually sets up whoever’s in it to succeed, not just whether they were the right hire.

• Is the job clear?
• Is the job realistic, or does it quietly demand more than one person could ever actually deliver?
• Is a good outcome, for the customer and the company, actually defined anywhere in the job itself?
• Does real measurement come built into the job, so they know if they’re winning or losing?
• Does the job hand them enough authority to actually own the outcome they’re being held responsible for?
• Are the tools and information they need actually part of the job, or something they have to go find on their own?
• Do decisions made inside this job actually stay made, or does the same work get redone every time someone changes their mind?
• Is this a job that puts them around people who care about doing good work too?
• Does the job make visible how what they do actually matters?
• Is the job hard because the work is meaningful and demanding, or hard because we’ve made it unnecessarily difficult?

That last question is probably the one I think about most. There’s a kind of difficulty that makes people better. And there’s another kind that just makes them tired.

I used to spend a lot more time thinking about whether we had the right people. That still matters. It just was never the only thing that mattered, even though I spent years acting like it was. Leadership also requires asking whether we’ve built the right jobs for those people to succeed in. That’s the part I didn’t understand nearly well enough when I was running that company.

That’s what Labor Day has me thinking about this year. We spend a day recognizing workers. Maybe those of us who lead them should spend a little time actually thinking about the job we’ve created for them. Not whether we’ve made it easy. Not whether everyone is happy all the time. Just whether we’ve made it good.

I never went back and fixed it at that company, the way we said we would. That message is still sitting there on an old phone, a promise I made and never kept. I can’t go back and keep it now. What I can do is ask the questions I didn’t know to ask then, whether that’s with a client trying to build something better than I did, or in whatever I end up building next myself.

Because most people don’t hate work.

They hate bad jobs.