Nine years in at Apple, running engineering for their global retail store portfolio, I took three months off for my mental health.
Then I came back. I was sitting in the weekly design meeting when the room started scrambling because a senior executive was coming through. Everybody straightening up. Nobody building anything.
I watched them do it and I saw myself. I just realized what I looked like. This is no life.
A month after that meeting I was sitting in a free real estate investing class.
Not because I had a plan. Because I had a Tuesday and nothing on it.
Then I signed up for a three-day workshop. Everyone in that room kept saying the same thing. Find your value add. Find your value add.
I sat there, and it landed on me all at once. None of these people know anything about buildings. It is all I have done my entire life.
I went home and told my wife I found something. I had not been that happy or that excited in a very long time.
The Reality: I had spent nine years reading the discomfort wrong.
I thought it was the price of doing something hard. Hard things are supposed to hurt, so I paid it every year and called it growth.
Here is what nobody tells you. Growth and rot feel identical from the inside. Same tightness, same Sunday night, same tired.
You cannot tell them apart by how bad it feels. That is exactly why people stay nine years.
You can tell them apart with two questions, and both are answerable this week with a pen.
First question. Is the hard part the work, or the room?
Do not answer that from memory, because memory grades on mood. Take last week. Not a good week, not a bad week, last week. Write down where the hours actually went.
Then mark each block one of two ways. That was the work, or that was the performance around the work.
Meetings held to prepare for meetings. A deck that exists so somebody senior feels informed. Rehearsals. Status. Scrambling because a big boss is coming through.
Now count. Here is where I would draw the line. If more than half those hours are the second kind, and you would still do the first kind for free on a Saturday, that is not a hard job. That is a fit problem, and a title does not fix a fit problem.
The version for a deal is the same exercise. Where did your hours go last month? Into the asset, or into managing a person? If the answer is the person, the asset is not your problem, and fixing the asset will not help you.
Second question. What did the discomfort teach you in the last twelve months?
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Be specific here, because this is where people flatter themselves. Name three things you can do now that you could not do a year ago. Not three things you know. Three things you can do.
If you cannot get to three, you are not growing. You are enduring. Those are different activities that produce the same amount of tired.
On a deal, name three things it taught you about the asset class. If all three are about the counterparty, you did not buy a building. You bought a relationship problem with a building attached to it.
There is one more tell and it is the cleanest one. Growth problems are new every time. Rot problems arrive on a schedule. If you can already predict the shape of next month’s problem, you know which one you have.
Put the two answers together and you get four outcomes.
The work is hard and you are learning. You are climbing. Stay, and stop reading things like this.
The work is hard and you are not learning. You have outgrown the seat, or you are in the wrong discipline entirely.
In order to achieve the same outcome, I needed to change the input. That is a solvable problem and it usually takes months, not years.
The room is hard and you are still learning. This is the dangerous box, because the learning pays for the room and buys it another year. That is where nine years go. If you land here, put a date on the calendar. Not a decision. A date.
The room is hard and you are not learning. That is rot. It does not turn back into growth on its own, and waiting costs you the only thing you cannot buy back.
I was chasing success. I was really chasing my tail.
Here is what the answer cost me when I finally had it. I did not get severance. They dragged their feet on the exit agreement until I got tired of waiting and left. Well over a million dollars in stock options stayed on the table.
People ask if I regret that. Not at all. I was confident I would earn it back.
What I was actually afraid of was never the money. I am not afraid of getting something wrong. I am afraid of not meeting my own expectations. Nine years in a room that had stopped fitting is a slow way to fail that test.
The three months bought me the answer. You do not need three months. You need last week’s calendar and one honest hour.
Waiting for something bad to give you permission is how nine years go by. Reading the fit before anything breaks is a different skill, and you can have it by Friday.
—Jon
P.S. The same two questions work on a building. The scored version, every system ranked by what it costs you when it fails, is The $100K Blind Spot. Reply ‘blindspot’ if you are in diligence now.