Hard On Purpose, Or Hard By Accident
Same level of difficulty. Completely different return. Here's how to tell them apart before you sink another month in.
Three years ago I took three months off from Apple. The first month I did nothing. I decompressed. I had been running engineering for a few hundred stores across twenty-plus countries, and I had nothing left.
About a month in, I had time on my hands, so I walked into a free real estate investing class. Then I signed up for a three-day workshop. The whole room kept repeating the same phrase. Find your value add. Find your value add.
I sat there and it hit me. None of these people knew anything about buildings. It was all I had done my entire life.
I drove home and told my wife, “I found something.” I had not been that happy in a long time.
Here’s the part I don’t usually say out loud. That break was hard. Walking away from a seven-figure stock package was hard. Moving from San Francisco to small-town Wisconsin was hard. Starting over at 42 was hard.
But it was a different kind of hard than the office.
The Reality: There are two kinds of hard, and most of us never stop to tell them apart.
There’s hard-on-purpose. You chose it. It moves you toward something you actually want. The cost is real, but it’s buying you something.
And there’s hard-by-accident. Nobody chose it. It just accumulated. The late nights, the politics, the scramble every time a big boss flew in. It was hard, but it wasn’t building anything. It was just grinding me down.
The office was hard-by-accident. The break was hard-on-purpose. Same level of difficulty. Completely different return.
Before I finally left, I sat in a weekly design meeting and watched everyone scramble because a big boss was flying in. I had done that scramble a hundred times. This time I saw it from the outside. I looked at them and realized I was looking at myself. That was the moment I knew. This is no life.
The trap is that they feel identical from the inside. Both leave you tired. Both make you feel like you’re working. And because they feel the same, we treat them the same. We grind through the avoidable stuff and call it discipline.
It isn’t discipline. It’s just friction you forgot to question.
There’s a line I keep coming back to. In order to achieve the same outcome, I needed to change the input or be open to different inputs. For years I kept feeding the same input into a system that was wearing me out, and I expected a different feeling to come out the other side. It never did.
So here’s how I tell the two apart now, before I commit another month to anything.
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I ask two questions. First: if this works, what does it get me? Not “will it feel good to finish.” What does it actually build. A skill, an asset, a relationship, a position I want to hold. If the honest answer is “nothing, I just don’t want to be the one who quit,” that’s hard-by-accident. Walk.
Second: am I the right person for this hard? The workshop room was full of people forcing themselves to learn something foreign. I had spent twenty years inside buildings. The work was hard either way, but for me it was hard-on-purpose, because I was building on something I already had. When the hard thing sits on top of your real edge, the difficulty is an investment. When it doesn’t, you’re just paying tuition for a seat that was never yours.
Two questions. Thirty seconds. It will save you months.
That same test runs through both halves of what I do now. Eyes Open is me teaching people to see what others miss inside a building, because reading a foundation crack is hard-on-purpose work that pays for itself. The lending side is the same instinct. I lend into deals other people avoid because they look hard. But hard isn’t the same as bad. Most of the time, hard-on-purpose is exactly where the return lives, as long as you can see the mechanics underneath it.
The reward part matters too, and I almost left it out. There’s another line I live by. You got to reward yourself, because if you don’t, that hard work is just for nothing. Picking the right hard is half of it. Marking it when you get through is the other half. Nobody hands you that. You take it.
The Bottom Line: hard isn’t the signal. Direction is. Hard-on-purpose builds something. Hard-by-accident just costs you and calls it character.
You’re not someone who avoids hard things. You’re someone who’s learning to spend your hard on purpose. That’s a different person than the one grinding through friction and hoping it counts.
That’s the whole shift this month. Choose your hard. Then make sure you reward yourself for clearing it.
—Jon
P.S. What’s a hard thing you’re grinding through right now that might be hard-by-accident? Reply and tell me. I read every one, whether it’s about a building or a deal.