Things for when you think it’s too late

How to free yourself from “unlived life” regret and begin anew

There are moments—admittedly, not my finest and full of appreciation—where I regret the life I’ve lived and long for other lives I could have had.

In my unlived life, instead of interviewing novelists, I wrote a novel. Instead of reading poetry, I wrote poetry. Instead of watching plays, I directed and starred in them. Instead of focusing on how other people were creative, this version of me was creative. I can’t help but wonder what it would be like to be that Madeleine instead. Did this unlived version of me get life right, while I’ve got it wrong? And can I still become her, or have I missed my chance?

I find comfort in F. Scott Fitzgerald’s words, “For what it’s worth: it’s never too late or, in my case, too early to be whoever you want to be.” 

I know intellectually that it’s never too late to begin that life, but if I keep going along this downward spiral of comparison to myself, another decade will go by where I’ll say I wasted my 30s thinking about how I wasted my 20s. From here on it will only ever be later. The next month comes around, the next year, the next decade, and I’ll have wished I began today rather than worrying about how it’s too late. 

Artist Lisa Congdon’s trajectory is an inspiring reminder that it’s never too late. She has written an entire book dedicated to late bloomers, A Glorious Freedom, in which she shares her pathway from teacher to artist. On Instagram, Lisa shared how a philosophy of “it’s not too late” is not only reserved for career changes but also the things we enjoy. At the age of 30 she fell in love with cycling after signing up for a long-distance event. She enjoyed it, thought she could be good at it, contemplated getting a coach but then thought “I’m too old” and stopped riding a bike altogether for another 14 years. Now, at 55, she’s finally training with a coach and racing bikes simply because she loves doing it.

Instagram post from Lisa Congdon

Yet even with these wholehearted assurances that it’s not too late, it can be hard to commit to a new direction.

I know for myself, my hesitancy is tied to the idea of needing to be the best at something. If I’m to begin anew, then it needs to be a new career path, a profession, a prized skill. I leap ahead to the part where I’ve made it, only to fall into the expansive gap in between.

I forget that it’s about the joy of doing something.

We expect ourselves to know how to do everything before we do it, to get it right, to be the fastest, the most successful, the best. But we can put these stifling markers aside, embrace being mediocre, and simply pursue something because we enjoy doing it.

Maybe that’s the task—to learn how to enjoy the things we do. 

Here are some reminders for when you’re caught up in regret over your unlived lives.

Define success for yourself

“For me, success is not a public thing. It’s a private thing. It’s when you have fewer and fewer regrets.” — Toni Morrison

We need to dismantle the part of us that wants external validation and arrive at an internal measure.

Perhaps success, as Morrison said, is arriving at a life where we have fewer regrets because we’re doing what is important to us, irrespective of whether we feel “worthy”.

Perhaps having fewer regrets begins by saying who cares? Sometimes I have to take that far out to remind myself we are here, a speck on a speck on a speck, and it’s amazing that we do things, the piles of dust floating in space that we are.

Become it

“If you inherently long for something, become it first.” — Victoria Erickson

Sometimes it’s not regret so much as a longing for a different kind of life that I’m experiencing. This is comforting, as longing has a direction—I can move towards something that I long for.

Ask, what is it that you want? Remember, we can want things outside the parameters of success—we can want traits and values.

As Victoria Erickson continues, “If you want gardens, become the gardener. If you want love, embody love. If you want mental stimulation, change the conversation. If you want peace, exude calmness. If you want to fill your world with artists, begin to paint. If you want to be valued, respect your own time. If you want to live ecstatically, find the ecstasy within yourself. This is how to draw it in, day by day, inch by inch.”

We don’t know if we’ve got it right or wrong, so do it anyway

“I enjoy life when things are happening. I don't care if it's good things or bad things. That means you're alive.” — Joan Rivers

Everyday life unfolds without us ever knowing how the story ends. Something we deem bad could turn out to be good, and so on.

Milan Kundera writes “There is no means of testing which decision is better, because there is no basis for comparison. We live everything as it comes, without warning, like an actor going on cold.”

What makes the act of living both painful and glorious is how things can change in an instant. We can only ever say “we’ll see.”

No time is lost

“You are dismayed at having lost a year, maybe, because the school fell apart. Well—I feel as though I’ve lost the years since Slaughterhouse-Five was published, but that’s malarky. Those years weren’t lost. They simply weren’t the way I’d planned them. Neither was the year in which Jim had to stay motionless in bed while he got over TB. Neither was the year in which Mark went crazy, then put himself together again. Those years were adventures. Planned years are not.” — Kurt Vonnegut, letter to his daughter

It hasn’t been a waste—this life that we have lived so far.

There is something in everything if we know how to look. We are always learning—even if it’s learning how to enjoy our own lived lives, learning how to be who it is we want to be, learning that there is such a thing as “yet” and therefore no time can be lost.

Maybe the life you are living today is the dream

“Whatever happens. Whatever what is is is what. I want. Only that. But that.” — Galway Kinnell

While I run, I sometimes listen to Alan Watts lectures, and there is one remix by Jacoo Watching You Breathe that begins:

“Let's suppose that you were able every night to dream any dream that you wanted to dream. And that you could, for example, have the power within one night to dream 75 years of time. Or any length of time you wanted to have.”

You would begin, Watts says, by pursuing every kind of pleasure. Fulfilling all your wishes. And then you’d get a little tired of that and wish for a surprise. A dream that isn’t under your control. You would become more adventurous. And finally, “you would dream the dream of living the life that you are actually living today.”

I decide to look around my own life as if it is the dream I wanted to dream. 

It all got me here. The supposed wrong turns. The surprises. The lost years.

I am in an apartment I’ve subleased in London. I have made friends with the neighbours upstairs. I can hear a bird. I can see the sun. I am writing. Later I will apply for that poetry course. There is coffee.

How could I want anything other than this?

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Some extra things:

I’ve curated a collection of poems, quotes and longer reads for paid subscribers who want to further contemplate their unlived lives—and find comfort in moments of regret. 

Some things to help you contemplate your unlived life