My mother’s mother once told me, in a single breath, that my haircut was unfortunate, that I looked tired, and that I should eat more. Then she passed the rice. She was 84 at the time.
Nobody at that table blinked. That was simply how she operated. Say the awkward thing first, say it warmly, then get on with lunch. Six decades of this had made her the most feared and most adored person at any family gathering in Manila.
She died well into her nineties, and here is what I keep circling back to. She had almost nothing left to settle. No estranged children. No unsent letters. No confession queued up for a deathbed she barely used, because she was busy right until the end.
For years I filed that under luck. Some people are just born unbothered, I thought.
I don’t believe that anymore. I think she paid for it, in small uncomfortable instalments, nearly every day, for about seventy years.
She said the awkward thing first
My grandmother had a habit that I found mortifying as a teenager and now find close to heroic. She raised the thing nobody wanted raised.
She told her own sister, at some point in the 1970s, that she had been unfair to her over money, and then asked to be forgiven. She told a granddaughter she disapproved of the marriage, said it plainly, once, and then turned up to the wedding and danced badly for three hours. She rang relatives out of nowhere to ask whether they were being stupid about anything. Often they were.
None of this was comfortable for her. That is the part I misread for years. She wasn’t a woman without nerves. She was a woman who had decided that nerves don’t get a vote.
Bronnie Ware spent years in palliative care and later wrote down what her patients said when they looked back. The regret that came up most often was not having had the courage to live a life true to themselves, rather than the life other people expected. Close behind it sat the regret of never having said what they actually felt.
My grandmother front-loaded both of those. She spent the awkwardness early, while it was still cheap.
Skipped conversations follow you home
Here is the mechanism, and it’s the most useful thing I know about regret.
Psychologists Thomas Gilovich and Victoria Medvec asked people what they regretted and noticed something odd about the timing. Things you did wrong sting badly at first. But give it a few decades, and it’s the things you never did that hang around. In one of their studies, most people named an inaction as the single biggest regret of their life.
Which makes avoidance a spectacular deal, right up until it isn’t. Dodging the hard conversation costs nothing today. The invoice arrives in thirty years, with interest, and by then there’s no one left to pay it to.
I got a small taste of this when I sold my restaurants during the pandemic. That fortnight involved conversations I would happily have paid to skip, including telling people who had worked with me for years that it was over. Grim. I don’t regret a minute of it.
What I do regret is the eighteen months before, when I could read the numbers perfectly well and said nothing to anybody, including myself. The honest version was available the whole time. I just preferred the quiet.
Almost nobody regrets the phone call they made
Daniel Pink collected more than twenty thousand regrets from people all over the world, and the biggest single category surprised him. It wasn’t career or money. It was connection: if only I’d reached out.
And the striking thing is how undramatic these usually are. Not betrayals or blazing rows. Drifts. Two people who liked each other, a gap that got slightly too long, and then the awkwardness of breaking the silence became marginally heavier than the loss of the friendship. So nobody rang. For twenty years.
Bottling it up doesn’t come free either. People who habitually keep their feelings off their face end up with worse relationships and lower wellbeing than people who let it show, according to a well-known study by psychologists James Gross and Oliver John. Suppression doesn’t hide the feeling. It hides you.
My grandmother’s version of reaching out was crude and effective. A phone call, no preamble, no apology for the four years of silence. I was thinking of you. That was the whole technology.
Regret grows where the door is still open
Researchers Neal Roese and Amy Summerville combed through eleven separate studies on what people regret most, and a pattern fell out. The heaviest regrets cluster in the areas where people still see room to act: education, career, romance, parenting, the self. Regret grows where you sense the door hasn’t shut yet.
I find that oddly encouraging. If a particular avoidance nags at you, that itch is information. It means the door’s still open.
So the practical bit. Name the one conversation you’re currently swerving. You already know which one, because it arrived in your head before you finished reading that sentence. Then have it badly. Clumsy and this week beats eloquent and never, and the polished version you’re rehearsing is mostly a delay tactic wearing a nice shirt.
You are not choosing between comfort and discomfort. You’re choosing which decade absorbs it.
My grandmother wasn’t fearless and she wasn’t especially disciplined. She just kept a very short queue. Nothing sat in it long enough to calcify.
I’m nearly forty and my queue is longer than hers ever was. I’m working on it. Badly, and this week.