New Year, New Regrets

Embracing our regrets

Ximena Vengoechea
5 min readJan 3, 2023

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bunch of stones

Photo by Fernando Reyes on Unsplash

Happy New Year, and welcome back to Letters from Ximena. In this edition, we talk about how to make sense of our regrets. What better time to look back than the start of a New Year?

Maybe it’s getting older, or maybe it’s the malaise and existential dread the pandemic brought so many of us, but lately, I have found myself thinking about the past. Not in a wistful, “wasn’t it lovely” way, but in an uh-oh, “maybe I should have done things differently” kind of way.

I think back to the jobs I stayed in for too long, or the career decisions made from fear rather than passion or values. I’m reminded of the friendships I didn’t treat with nearly as much care as they deserved, and of the relationships that I botched in one way or another. Years later, I see so many missteps. I can’t help but feel embarrassed by these moments, disappointed in myself.

But I am also curious about them. As someone who tends to live in the future — often thinking about what comes next (and how to make it happen) — looking backwards is unusual for me. I don’t like to dwell. Why, now, are these memories coming back to haunt me? Is it possible these regrets are trying to tell me something?

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What is regret good for?

In an age of YOLO and “No regrets,” it can be easy to feel like you should have it all figured out by now, whatever life stage you’re in. But a life lived without regret isn’t really a life at all.

Having regrets means that you have lived enough to make mistakes. That you have been bold enough to err. That you have had the personal agency to choose, even if you ultimately made the wrong decision. It means that you have taken risks. You might choose differently today, but you tried something. You have earned your regrets by living.

Having regrets might also mean that you have played it safe. That you have prioritized stability over adventure. That you know how to compromise and make space for others’ needs, not just your own. That you have done what you could. You might do things differently next time, but your heart was in the right place.

Regrets are normal — and useful. If we listen, each regret tells us something about who we are. It exposes the gaps between our desires (who we wish to be) and our reality (who we are today). I’ve always thought of the past as just another means to propel me forward — to learn from my mistakes and do better next time. But more and more I realize it is also a call to be still. Sometimes, there is no immediate action to take; sometimes our regrets tell us to slow down. Examining our regrets helps us see where change or action or stillness and space are needed.

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Embrace regret

As we head into the New Year, now is a great time to reflect on your regrets. Let them teach you something about yourself — about who you are, how you’ve changed, and how you still want to grow. Perhaps you will decide that this year will be different in some way — that you will make changes (to live boldly, to live with more compromise, to slow down), that you will explore new opportunities (and yes, new regrets, too).

Accepting our regrets means accepting that we are human. That we are imperfect. That we are still learning, growing, and changing. When you think back to mistakes you’ve made or decisions you wish undone, remember to think back with self-compassion — not just self-critique. Be tender toward yourself — the self who was doing the best they could, given what they knew of themselves and their worlds at the time. The version of yourself who did not yet know how to listen to their intuition, or did not yet know that their intuition was not honed. The You who could not distinguish near-term payoff from long-term payoff. The You who trusted others instead of yourself. Know that this You — the You whose decisions you now lament — was learning (still is). Be kind to the part of you that makes mistakes.

Share your regrets

Today, I’m embarking on a new project to explore the nature of regret — how it works, what it’s good for, and when to leave it behind. As I explore this area, I’d love to hear your stories.

What regrets do you have? Which are fresh, and which plague you year after year? What lessons or insights do these regrets reveal to you, if you stop to listen?

Simply hit reply to reach me, or drop your regrets in the comments below.

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  • Listening Talks: Last year I had the pleasure of speaking at the TX and MA Women’s Conference, People Nerds Conference by Dscout, and a fireside chat at TroopHR about the power of listening in our careers, among others. I love these chats and hearing from readers about how listening fits into their worlds. If you’d like me to book me for a speaking event for your team or club, reach out.
  • LLYMI is now available in Chinese!
  • Worth reading: My forthcoming book on rest is now in production, meaning that the heavy lifting of writing and editing is now done (huzzah!), and we’ve moved on to color proofing and cover design!
  • xsvengoechea

With my newfound time, I’m reading a lot of fiction. Here are a few books I read and loved recently: Rumaan Alam’s Leave the World Behind, Blair Braverman’s recently published Small Game, and The Southern Book Club’s Guide to Slaying Vampires by Grady Hendrix. Genre-wise, these are far more otherworldly than what I usually read, and yet I loved them all. Each is propelled forward by intriguing plots and sharply drawn characters.

💌 As always, if you’re enjoying this newsletter, please share it with others who may enjoy it, too. Thanks for being here and for sharing the love. Happy New Year, friends. 💌

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Ximena Vengoechea

Writer, UX Researcher, Author of The Life Audit ('24), Rest Easy ('23), Listen Like You Mean It ('21). ximenavengoechea.com/books