I turned 73 this year. My closest friends are around the same age, and I’ve noticed that when we really get into it—when someone stops being polite about things—we tend to circle back to the same few regrets.
Not the dramatic ones. The quiet, structural ones. The ways we spent our energy for decades that, looking back, didn’t return what we put in. And the things we kept putting off that mattered more than we admitted at the time. I don’t know that you can learn any of this early. But I find myself wanting to say it anyway.
1. You spend years managing what people think of you, and it changes nothing
I spent a significant portion of my life—and I’m not proud of this—adjusting what I said, what I did, and how I presented myself based on what I imagined other people were thinking.
Not in obviously insecure ways. In the small, constant, almost invisible ways: choosing the safer opinion in a conversation, downplaying the thing I was actually proud of, editing out the part of myself that felt too odd or too much. I thought I was being socially intelligent. What I was actually doing was spending an enormous amount of energy on something that returned almost nothing.
The thing nobody tells you is that people are not thinking about you nearly as much as you think they are. They’re managing their own presentation, worrying about their own impressions, navigating their own internal weather. The careful image you’re constructing barely registers. And even when it does register—when someone does form an opinion of you—it’s based on a fraction of the information you’ve given them and filtered through everything happening in their own life.
You cannot control it. You never could. The energy spent trying to would have been better spent on almost anything else.
What I know now that I didn’t know then is how much of the performing was really just fear—fear of being seen clearly and found wanting. And the exhausting irony is that the people I’ve felt most connected to over my life are the ones who saw through the performance anyway. The relationships that actually fed me were built on the moments I stopped editing and said the true thing. Every year I spent before learning that cost me something.
There’s also the practical cost. When you’re busy managing an image, you’re not fully present in the room. You’re half-listening and half-monitoring—how is this landing, am I saying too much, do they think less of me now? I spent decades in conversations where part of me was always somewhere else, checking. You can’t get that attention back. But you can stop spending it the same way.
Research by Jocelyn A. Rutledge, Jadyn D. Williams, and Meaghan A. Barlow, published in Frontiers in Psychology, found across a systematic review of 31 studies that greater life regret is consistently associated with lower life satisfaction and poorer well-being—and that regrets stemming from inaction, from the unlived and the unexpressed, tend to be among the most persistent.
The years I spent performing for an audience that wasn’t watching were years I wasn’t fully living. That’s the trade I didn’t see clearly until it was already made.
2. The conversations you kept delaying were the ones that actually mattered
There was a friend I had for thirty years. We drifted in our sixties the way old friendships sometimes do—nothing dramatic, just less contact, less effort, the assumption that we’d reconnect properly when things settled down.
Things didn’t settle down. He died at 68. We never had the conversation I’d been meaning to have with him, the one where I told him clearly what his friendship had meant to me over the decades. I knew I wanted to say it. I kept waiting for the right moment. The right moment didn’t come.
I’ve talked to enough people my age to know this is not a unique story. It shows up in almost every variation: the parent you meant to ask about their childhood before they were gone, the apology you kept composing in your head, the estranged sibling you planned to call after the next holiday, the child you meant to sit down with and really talk to. The delay always feels reasonable at the time. There’s always a next time, always a better window, always a season that will be less hectic. And then there isn’t.
The particular cruelty of a delayed conversation is that it doesn’t feel like a decision. It feels like waiting. You’re not choosing not to have the conversation—you’re just choosing not to have it yet.
But “yet” is a door that can close, and it closes without warning, and then the conversation you were going to have becomes the one you carry around for the rest of your life wondering about. I’ve had a few of those. They’re heavier than the ones I actually had, even the difficult ones.
A meta-analysis by Neal J. Roese and Amy Summerville, published in the Personality and Social Psychology Bulletin, found that the biggest regrets people carry cluster around relationships, the self, and the things they didn’t do—and that regrets of inaction tend to persist longer and more intensely than regrets about actions taken. The conversation you didn’t have doesn’t fade the way an argument you had eventually does. It stays exactly where you left it, unresolved, available to revisit whenever the quiet gets loud enough.
What I do differently now is say it while I can. It doesn’t always land the way I hope. Sometimes the other person is surprised, sometimes a little uncomfortable, sometimes the moment is slightly awkward afterward. None of that is as bad as I used to think it would be. None of it is anywhere near as bad as the alternative.
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3. You don’t run out of things to want—you run out of time to stop waiting
There’s a version of this lesson that sounds like a cliché: life is short, seize the day, don’t wait until it’s too late. I’m not talking about that version. I’m talking about something more specific and, I think, more insidious.
The particular habit of treating your actual life as the thing that comes after the current situation resolves. After the kids are older. After the job settles down. After the money is more stable. After the hard season passes. There’s always a reason to wait, and the waiting feels responsible, even virtuous. What I didn’t understand for most of my life is that waiting isn’t a neutral act. It’s a choice, and it compounds.
I still want things. I still have projects I care about and relationships I’m invested in, and mornings I’m genuinely glad to have. The wanting didn’t stop. What stopped is the assumption that there’s a version of my life I’m building toward where all the conditions will finally be right. That version was never coming. The conditions were never all going to be right at the same time. The life I was
I see it in people around my age—the project they were going to start, the trip they were going to take, the version of themselves they were going to become once things calmed down.
Some of them got there. A lot of them didn’t, not because they ran out of desire but because they kept waiting for a signal that the time was right. The signal doesn’t come. Or it does come, and you’ve gotten so used to waiting that you don’t recognize it. I’ve watched people I love spend years in the anteroom of their own lives, managing the logistics of getting there, and the logistics were real—I don’t want to be glib about it—but the waiting outlasted the reasons for it.
What I’d tell anyone younger than me—and I mean this not as a comfort but as something I wish someone had said to me with enough force to land—is that the deferral feels like patience, but it functions like avoidance. The thing you’re waiting to start, the conversation you’re waiting to have, the version of yourself you’re waiting to become once the current circumstances finally sort themselves out: they don’t arrive on their own. You don’t run out of things to want. You run out of time to stop waiting for permission to want them. I can tell you that the permission was always yours. It was never coming from anywhere else.
Editor’s Note: This piece is part of our “As Told to Bolde” series where we share personal stories from individuals we have interviewed or surveyed. For more information on how we create content, please review our Editorial Policy.
