Photo by Eric Ward on Unsplash

How To Avoid A Life Of Regret


I’m sitting alone in my apartment. It’s Sunday night. Too late to be productive, too early to sleep, and I’m too hungry to do either. A flash of insight reveals my immediate fate: dumplings.

I don’t know where the gods of culinary inspiration sent it from, but the thought instantly grows roots. As they wrap around my stomach, squeezing it ever tighter, I message some friends to see if anyone wants to go.

One said he was out of town. Another on a date. Some didn’t reply and one already ate. With “no”s piling up faster than even the speediest cook could fold and fry the delicious dough bags, I began to think.

“Maybe, I should just stay in.”

“I still have food at home.”

“It’s cold out anyway.”

But then, another observation — not sent by a god but my gut — hit me. It took some mental debating, but, eventually, I snapped out of it.

“Screw it. I’m getting dumplings.”

I got dressed, walked to the restaurant, went inside, sat down, ordered, and, within a few minutes, I was munching on a dozen of a Chinese delicacy called wonton. The owner even gave me a free mango pudding for dessert. Score!

I won this round, but the conversation that had to happen earlier in my head for me to do so was just one of the many encounters we all have with a dire, devastating force called ‘potential regret.’ What was really going on was this:

I was afraid of doing what I wanted because I was alone.

A Feature We Can’t Turn Off

Being alone is a weird state for a social animal. First, there’s the physical discomfort, from the silence to the goosebumps to the sensory triggers our brains begin to manufacture. Then, there’s the psychological toll.

If you’ve ever sat with emptiness for a while, you’ll have noticed that, at first, your mind continues to tell the story it always tells. Maybe, it’s the one about work or the one about the friend you just dropped off or the one about what you should eat. Maybe, you’ll even flick through a couple of those. But soon you’ll realize — and this rarely happens in everyday life — that you are telling yourself a story. That most of what you do is just fighting your inner silence.

We’re having this big, public discussion about our technology fostering a culture of escapism, but if we’re honest, that’s nothing we needed devices for. It’s built into the human experience. A feature we can’t turn off. We say we ‘think,’ but mostly we’re just letting whatever thoughts come wash over us.

To some extent, this is normal. Permanently squeezing your gray matter with pressing questions — “Who am I? Why am I? What is life’s purpose? What’s mine? Who am I meant to be? And why am I not there yet?” — only drives you insane. But if we shut them down every time they creep up, we stand to lose our minds just the same.

The way we architect this second, equally inevitable collapse, however, is a lot more fascinating.

Agency Over Accomplishment

When she asked 90-somethings what they regretted most, Lydia Sohn made a fascinating discovery: old people don’t get nearly as much satisfaction out of their past careers than young people expect out of their future ones.

“Their joys and regrets have nothing to do with their careers, but with their parents, children, spouses, and friends.”

As it turns out, it’s not their work, but their relationships that contributed most to their happiness. They didn’t crave a longer list of accomplishments, but more quality moments with their loved ones. This finding contradicts the popular idea that our life’s happiness curve shapes like a U-bend, with spikes early and late and a big trough in the middle. People felt their best while being hard-working fathers and busy housewife mothers (and vice versa).

Bronnie Ware, a palliative nurse, regret researcher, and author of a popular book on the topic, identified a different, but equally powerful source of remorse: living a shadow-life.

“Of all of the regrets and lessons shared with me as I sat beside their beds, the regret of not having lived a life true to themselves was the most common one of all. It was also the one that caused the most frustration, as the client’s realization came too late. ‘It’s not like I wanted to live a grand life,’ Grace explained in one of many conversations from her bed. ‘But I wanted to do things for me too and I just didn’t have the courage.’”

Everyone is different and no one person’s experience can dictate your own best path of action, but when it comes to aging, the advice of those who’ve done it already is sure worth considering. These two insights are interesting all on their own, but if we piece them together, we can learn even more:

  1. We may be our best self when we’re not focused on it all that much.
  2. In order to feel like we are, we need to decide some things on our own.

Whether they were happily married or not, these people’s relationships with their partners took a back seat as their family grew. But for those where either ended up suppressing their own desires altogether, a busy life turned into an estranged one — and that’s not something we’re fond of looking back to.

Now I’m really glad I decided to go eat those dumplings.

Miserable Always Does The Job

A friend of mine is currently trying to settle on a topic for her thesis. But, as she says of herself, she’s not very decisive. After researching multiple angles and approaching several faculty members, it came down to two options. When she got accepted for only one, I congratulated her. I was wrong.

Having had no clear preference for either topic before, she was now sad about one road being blocked — and back to brainstorming more options. This may sound silly, but it’s not uncommon. A very real struggle for a very real group of people, particularly those around my age. We know we have a wealth of options, so we try to look at them all, and, without ever deciding, feel bad about the ones we miss, the ones we might have missed, and the perfect ones we think should exist somewhere, even though they never do.

We know abundance does this to us from science. Barry Schwartz wrote The Paradox of Choice about this. The more choice, the harder it is to choose and the easier to make mistakes. And even though finding ‘perfect’ is as impossible as it ever was and we know it, we’re still disappointed if we don’t.

What my friend is doing — what most of us are doing — is not distracting ourselves with meaningless entertainment or existential problems.

We do it with an abundance of good options that don’t reflect who we actually are.

For a lot of us, life is too easy. We know we’ll get dinner. A date is just a swipe away. Our work may be boring, but it pays. At worst, we’ll cancel Spotify. But instead of using all this amenity and time to figure ourselves out, instead of saying “this one feels like me” and running with it, we choose whatever outcome we get to be the one that makes us feel miserable.

But, as we learned from those senior to us, being happy is not about choosing the best, but about loving what you have chosen. How much you dictate the outcome won’t matter nearly as much as having had a say. Whatever agency you have, as long as you don’t second-guess yourself, you’ll likely be content.

And sometimes, that is as simple as eating the first food that comes to mind.

Everything Starts Small

Maybe, you really want to try a new style of pasta. Or to go see that movie. Or just get ice cream. But then you ask around and find out no one wants to go. They might be busy. Maybe, they’re not around. Not hungry. Or they don’t want to hang out today. That’s okay.

What’s not okay is what we usually do next: we stay at home.

We choose to feel sorry for ourselves instead of doing what we want, even if no one’s stopping us.

We do it because moving in a state that’s already uncomfortable when you’re still is extra disconcerting. We do it because we pressure ourselves to optimize among a sea of options despite secretly knowing most of them are irrelevant to us. And we do it because of what people would think; what they would say if they caught us being happy on our own.

I love sharing. I love doing things together. But when your support goes down the tube, you can’t just throw your life right after. Don’t stop living when no one’s watching. Have pride. Get dressed. Show up. Not for others. For yourself.

The person who should be most excited about everything you do in life is you.

But if you can’t live true to yourself when no one’s around, how do you expect to do it in the face of a growing set of responsibilities? How do you expect to do it with more and more agents thrown into the picture? A partner, two kids, an elderly parent. A team you’re leading, a host of fans, or a stubborn boss?

What we want is rarely impractical. Eating alone doesn’t make the food taste worse. But sometimes, it is uncomfortable to be authentic. To act on what you know you want. And yet, we can’t let that prevent us from going after it.

Because it starts with dinner or a movie, but that’s not where it stops.

One day we resort to frozen pizza, the next it’s going back to our shitty job. All because we were too scared to be the lone fighter for the right cause. Yes, your friend should not have chickened out on that startup idea. Yes, finding a great job takes time. But you were never meant to face those struggles unprepared.

Because staying true to yourself, like everything, starts small. It’s not about nailing your Ph.D. or choosing the perfect partner. It’s about listening to your gut when you want to eat dumplings.

Even if it means that, sometimes, you’ll have dinner by yourself.