Somewhere in the middle of most careers, a peer gets promoted ahead of you, and something shifts. You weren’t unhappy the day before. You liked the work, the team, and the problems in front of you. But now there is an itch in your head that wasn’t there yesterday: a title, a level, a compensation band, an org size. Within a few weeks, achieving all that has quietly become a goal. Within a year, it becomes the thing you organize your days around.
I’ve watched this happen to good leaders, and I’ve felt it happen to me. It rarely announces itself as envy. It arrives dressed as ambition, which is harder to question, because ambition is supposed to be good. Often it is. But there is a difference between wanting more scope because the problems call for it and wanting more scope because someone you measure yourself against just got it. The first want is yours. The second is borrowed.
The easy version of this is the old saying, “Comparison is the thief of joy.” That’s true enough, and also not very useful. Comparison is how we learn what’s possible and get pushed to grow, while borrowed wants are how we get stuck on the treadmill trying to keep up with the Joneses. The hard question is how to tell the two apart while it’s happening, when both feel exactly the same from the inside.
I learned the most about that question not at work, but on a quiet street in Virginia.
When my wife and I went looking for our first real family home, we were both working. We made one decision early that mattered more than any other: we would only buy a house that one of our salaries could support. Not because we expected to lose a job, but because we wanted slack. At the time, we had young children, a career in an industry still shaking off the dot-com bust, and a strong preference for sleeping well at night. We didn’t want to be spending at our limit.
Then we met the realtors. One after another, they showed us houses twenty to thirty percent above the number we had given them. Each came with a mortgage estimate that looked manageable at first, but left out the utilities, the upkeep, the furnace that dies in February, and the dozen other costs that come with owning a home. No one was dishonest, but they were doing what the system rewarded: raising our number, politely, one showing at a time.
It almost worked. I remember standing in gorgeous kitchens we couldn’t afford and feeling the pull. But we held, and eventually we found a house in our range, in a gorgeous suburban neighborhood overlooking a lake. We settled in to raise our young family.
We had lovely neighbors. I mean that. But I also remember walking the street and quietly wondering what everyone did for a living. Their houses were like ours, but their driveways were not. New cars, a boat on a trailer, motorbikes, a battery-powered car for the toddlers that seemed nicer than my first real one.
I’d be lying if I said it didn’t register. I assumed I would get to those things someday; that I was simply a little behind. In the meantime, we chose differently: trips with the kids, building savings, and preserving the feeling of not being stretched. I’m glad we did. But those choices had a cost: a persistent, whispering sense that we were the family on the street that hadn’t fully arrived.
Long before that house, while growing up in Ohio, I made myself one firm rule: I wouldn’t own a boat until I lived on a lake. I had watched too many boats sit in driveways all summer, used three times a year, a monument to a weekend that rarely came.
Our Virginia house overlooked a lake, which made the rule almost funny. But there was no dock, and no boats allowed. So the rule held, and our driveway stayed empty.
I didn’t think of it this way at the time, but the rule was a protection against borrowed wants. If you really want a boat, you use it. A borrowed want sits in the driveway.
Then came 2007. The housing market broke, and over the months that followed I watched foreclosure signs go up across our neighborhood, one yard and then another, sprouting like dandelions. Some families simply walked away from their homes. Some marriages didn’t survive the financial struggles.
I want to be careful here, because this is where essays like this one turn smug, and I don’t feel smug. Those were good people, and I never knew their full stories. They lived in a dream for a while, and I honestly can’t say which of them would trade those years back. Some made bets that were reasonable on the information they had.
What I learned was narrower, and it was what my parents had taught me from the very beginning: live within your means, and don’t compare yourself to everyone else, because you never know what’s really going on with someone who looks like they have more. The driveway tells you what someone has, not what it’s costing them.
I think about that street often when I watch careers and companies.
Careers borrow wants the same way households do. A peer’s promotion becomes your target just like your neighbor’s boat. Another VP’s headcount becomes your measure of importance, just like their new car. A title at a competitor becomes the reason you take a role you don’t actually want, with a scope twenty or thirty percent beyond what you would honestly say you can handle. The realtors in this version are recruiters, peers, and sometimes our own managers: well-meaning, all of them, and all showing us the bigger house we can’t really afford.
Companies do this too. During the hiring surge of 2021, many technology companies sized their teams less to their own problems than to their competitors’ org charts. Growth looked cheap, and everyone else was doing it. Then the market turned, and the layoffs that followed looked uncomfortably like that Virginia street: the signs going up, one team cut after another. The leaders who came through it best were the ones who had sized their organizations to their own work, and knew the difference between what others were doing and what they themselves needed to do.
I don’t want to pretend restraint is the moral of this story. It isn’t.
Comparison has stretched me in ways I’m grateful for. Some of my best career moves began when I saw someone doing work I hadn’t known was possible and I decided that I wanted it too. Some of those Virginia neighbors may have used leverage well and built something lasting that I never saw. And living within your means carries its own cost: the upside you didn’t take, the risk you didn’t run, the larger life you might have grown into. A person who never reaches past their current capacity will never discover what they are fully capable of.
So the question isn’t whether to want more. It’s whose equation you’re solving.
I don’t have a clean rule. The closest I’ve come is a question I try to ask before a want becomes a plan: would I still want this if no one could see it?
The trips with my children pass that test easily; nobody on our Virginia street ever saw them. The larger scope I took on later in my career, when the problems genuinely demanded it, mostly passes the test too. I can’t claim every ambition I’ve ever held would survive the question, and I suspect few of us could. But many of my biggest ambitions and investments would. I am proud of that.
Years later, I do own a boat: a pontoon tied up at our own dock, on the lake we live on. We have a JetSki and kayaks, too, because once you live on a lake, you should take advantage of it. All of them get used. I had wanted these things for a long time. But I waited for the want to be mine, for something I could use, rather than something for someone else to see.
Most of us have something big going on in our houses, driveways, or careers that requires a lot of upkeep, either in energy or money or both. The useful question isn’t whether to get rid of it. It’s to remember why we wanted it, and whether the reason was ever actually ours.
