On Things

On Things

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On Things
On Things
On the things we regret

On the things we regret

A miscellany(formerly Weekly Things)

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Madeleine Dore
Feb 24, 2025
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On Things
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On the things we regret
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“What do you do with regret?”

I ask the three incredible women around the table. We’re gathering for a sequel to a funeral-themed dinner we hosted a few years ago. As sentimental types who love to dress up, we wanted to create a space to mourn our missteps, let go of what’s no longer serving us, and eat devilled eggs.

“I grieve my regrets,” says V.

This felt like an answer to something I’ve long grappled with. So much of the rhetoric around regrets is to just not have them. But to grieve them is to acknowledge their striking inevitability. Regrets can be a form of grief—something to hold, something to grow bigger around in time.

“Regret cannot be avoided,” says S. “It’s a part of the human experience. Life is full of different shades of grief.”

Earlier in the week, I’d made a list of my regrets. It was partly in preparation for the dinner, and partly an attempt at riddance.

As we nibbled on what remained of the wake-inspired spread—aforementioned devilled eggs, a fruit platter, a morbidly delicious ‘death dip’ I’d made from black beans and nduja, all set amongst roses and black candelabras—the desire to cull my regrets dissipated. In its place, I could see the antidote so clearly.

For every regret on my list, there’s also something to appreciate.

Obvious, maybe, but nevertheless something I overlooked—I’d been keeping a ledger as if only one team was playing.

It’s comforting to know these women I admire have regrets, too. It’s rare to be privy to these things (it’s not every day we have a funeral-inspired dinner to mourn regrets, after all.)

Not only do we tend to keep our regrets close, but our regrets shift in their acuteness in different seasons.

“For me, regret can be more heightened during those periods when I’m adopting new values,” says S.

You did things differently back then because you were different. You didn’t want to, or think to, or have the space to. You had different experiences that informed different choices.

Another motivation for writing the list of regrets is that I wanted to learn from my so-called missteps and make better decisions.

While there are always things to learn, now with my different past-self in mind, I can come to accept rather than admonish the part of me that made a particular decision.

Trying to shape our lives in such a way that we avoid regrets is futile. Even if you did everything perfectly, there will always be foreclosures and failings we have to live with.

And that doesn’t have to be morose—it can be motivating. Sometimes our very commitment to one path over another can minimise future-regret. As Pete Davis said in this CreativeMornings talk, our commitments change who we are: “By making a commitment, it rewires the constellation of meaning in your life. It becomes hard to regret the choice you made because you are converted into the person who made that commitment.”

We reframe regrets by recognising the fruits of commitment.

We can find an appreciation to balance every regret.

When refutations fail, we can hold a vigil for the things wish we did differently, what we did or didn’t do, and the person we can no longer be.

And remember, to avoid regret, would be to avoid life.

If you aren’t already a paid subscriber, you can upgrade here to access more things below, including: notes on reframing regret, a playlist for a funeral-inspired dinner party, a handpicked poem, and my latest daily observations

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