There was a regular at one of my restaurants who ordered the same thing every Thursday for four years. Sea bass, no starter, one glass of white. Lovely man. Successful by any measure you could fit in a spreadsheet, and he asked after the kitchen staff by name.
The last time I saw him he mentioned, apropos of nothing, that he had wanted to be a marine biologist. He had got as far as filling in the application. Then he paid, tipped well and went home.
I never once saw that man look unhappy. That is the part that stayed with me. He was fine. And fine, it turns out, is the best hiding place ever invented.
The despair that doesn’t feel like despair
When most of us say despair, we mean the loud kind. Grief. A redundancy. A marriage coming apart. You know when you are in it, because it hurts.
Søren Kierkegaard used the word very differently. In his 1849 book The Sickness Unto Death, published under a pseudonym because even he thought it was a lot, he treats despair as a permanent, structural condition of the self, present whether or not you happen to feel anything in particular. The Stanford Encyclopedia of Philosophy describes his self as a relation that has to keep relating to itself, which is philosopher for a job with no finishing line.
Then he lands the horrible bit. One of the forms despair can take is having no idea you’re in it. He compares that person to a tuberculosis patient who seems perfectly healthy to everyone around him, precisely when the illness has become most dangerous.
So the worst version of this thing never announces itself. It sits in the space where a life was supposed to go.
Why the road not taken keeps its grip
I assumed this was poetic nonsense until I read the research. In 2018, psychologists Shai Davidai and Thomas Gilovich published six studies in the journal Emotion under the title The Ideal Road Not Taken.
They sorted the gaps in a person’s self-concept into two types. Ought gaps are the duties: the calls you never returned, the gym membership, the friend you let down. Ideal gaps are the hopes: the business, the move abroad, the person you assumed you were on your way to becoming.
Per Cornell’s write-up of the findings, participants named ideal-self regrets over ought-self regrets by 72 per cent to 28 per cent. Asked for the single biggest regret of their lives, 76 per cent picked one tied to the ideal self. Gilovich puts it well. The ought regrets are potholes you have already driven over. The ideal ones sit in the windscreen.
Shoulds are easy to tick off, which is the trap
The researchers also worked out why the ideal ones linger, and it is almost funny. Ought regrets come with instructions: apologise, pay it back, turn up next time and do better. The thing gets filed as handled.
Ideal regrets come with nothing. Be a good father. Do something with the writing. There is no deadline, no moment where you visibly fail. So you never resolve it. You carry it at a low simmer for thirty years.
Which explains my Thursday man completely. Every box on his ought list was ticked. The single item that never made his list was the one that never happened.
From the outside it looks like a good life
Bronnie Ware spent years in palliative care in Australia and wrote down what her patients said in their final weeks. Her list of the top five regrets of the dying opens with the wish to have had the courage to live a life true to themselves, rather than the life others expected. That is an observation rather than a controlled study, but it lines up uncomfortably well with the lab work.
What strikes you is that these were not tragic people. Well behaved. Reliable. They had done what was asked of them for sixty years, and the bill landed at the very end, with no time left to pay it.
How to actually check on yourself
This is not a call to blow up your life. Most dramatic reinventions I’ve watched up close were just ought lists with better lighting.
Start by sorting whatever passes for your goals into wants and shoulds. Anything phrased as “I should” is usually duty wearing a costume. Then look for the item you have never said out loud to anyone. That one is the tell.
Do the smallest possible version of it this month. Gilovich’s own advice from the research is blunt: stop waiting to feel inspired, because inspiration mostly arrives after you start moving.
And give it a date. Not “get back into music” but “book the studio for the 14th.”
The bill nobody sends you
I sold my restaurants during the pandemic, mostly through a string of phone calls I couldn’t win. For about a year I felt like a man who had been fired from his own biography.
What surprised me afterwards was the inventory, more than the grief. Once the ought list went up in smoke, I could see what had been sitting underneath it the whole time, untouched. Writing was on there. So were about nine other things I had never mentioned to anyone, including myself.
I got lucky. Something forced the audit. Most people never get one, which is exactly why this failure is so easy to miss.
Nobody sends you a bill for the life you did not live. It simply goes unpaid, quietly, on time, every year.
