On Regret

And living a life you can be satisfied with

Photo courtesy of Jeswin Thomas

I spend most of my life preparing for my future. I do very few things that are outright “pleasurable” today. (Although, to be fair, I’m a relatively positive person and have learned to enjoy most things simply by choice.)

I eat tuna, rice, and protein oats. Because it saves a hell of a lot of money, and saving money is important to me. I drink water, not soda or seltzer. I spend time reading, and writing, and working on new projects. I go to the gym four days a week. I have very little “entertainment” in my life. I don’t travel (yet), I don’t spend money frivolously (yet), and I don’t have most of the things I want (yet).

And yet I’m utterly satisfied with where I am and where I’m going. Not satisfied materially, but satisfied that, if I live another twenty years, I will have more or less precisely the life I want. Because I will have spent decades building it. Making it almost mechanically impossible that I wouldn’t have it. Because what I understand is that having the life you want isn’t just about taking specific actions. It’s about becoming the kind of person who would have that life. It’s a process of foregoing what you want now in favor of what you want most.

If I died tomorrow, would people say I lived a life that was fun? Would they say I lived every day like it was my last? No, they definitely would not say that. My brothers and other people who know me probably see me as too stiff, as someone who takes himself too seriously. So they probably wouldn’t say that I have “fun,” much at all. What they might say is that I lived a life that was in preparation for a better life later. They would say I was working on something.

And I’m okay with that. I have to assume that my life is going to continue. I have to assume that I will be alive twenty years from now to enjoy the fruits of all of the sacrifices I’ve elected to make. If I’m wrong, I don’t think that means the assumption was wrong. It just means I got unlucky.

I think one of the biggest mistakes humans make is that we allow regret to retroactively color our memories. We allow regret to change how we feel about things without considering alternative paths that life might have taken. Life is a numbers game. Sure, 0 means you live and 1 means you die, but the fact that the numbers are particularly harsh doesn’t mean it’s not still a game of bets.¹

For instance, a father who is hard on his daughter may eventually be glad that she grew into someone strong. That she grew up tough and eventually became a warrior or a lawyer or a leader of some kind. But if that daughter dies when she’s 23, he’ll inevitably wish that he had allowed her to paint more. That he had been less focused on discipline and structure and toughness. Conversely, if that same father lets that same daughter grow up free-spirited and whimsical, she may eventually become a successful artist. And then he gets to be proud. And if she grows up to be a failure, he will inevitably wish he had been harder on her.

In other words, in any of these circumstances, the father will have a sudden moment of clarity where he thinks he knows what was “right” — what he “should” or “shouldn’t” have done. None of these moments of clarity is correct; they’re all merely a matter of rose or indigo-colored glasses. They’re all based on his allowing his emotions to dictate how he sees the entire trajectory of his daughter’s life, and the entire experiment of his fatherhood.

In some sense, they mistake luck for skill. They mistake what was possible for what was inevitable.

You also see this with drug addicts and alcoholics. No matter what happens to the patient, the family regrets their decision making. In all cases, always. That’s why it’s referred to as a family disease: it rips apart everyone involved not only emotionally but morally. “We should have been harder on him,” they’ll say after he winds up in a prison cell for theft. “We shouldn’t have enabled him,” they’ll say after he dies of an overdose. “We shouldn’t have been so hard on him,” they’ll say about his childhood after years of his addiction problems.

And all of these things are possibly correct, they are colored with correctness, but they’re not just plain correct. They’re right and wrong; they’re the inevitable things people say during the experiment of trying to keep a drug addict alive. They are trying to draw inevitable conclusions from an affliction that comes with an entree of luck. They are trying to moralize the unmoralizable.

If you’re hard on someone, you might create Michael Jackson the musical genius. Then again, you might also create Michael Jackson the person. All of life is an experiment in some sense. Sometimes the price to be paid for excellence is merely work. And sometimes it’s outright lunatic craziness. And sometimes you don’t know the price until you pay it. You don’t know the side effects until you get the disease.

Luckily, not everything in life must be left up to luck.

Something that always puzzles me is when people have this profound sense of guilt after a loved one dies. “I should have talked to him more,” they’ll say. Or “I should have spent more time with him.” This might sound harsh, but there is no shortage of reminders about our mortality. We all know we’re going to die, and that life is short, and that we ought to communicate more with our loved ones. The world is absolutely full of these reminders. There really isn’t any excuse not to heed them. If you love your mother, talk to her. If your older sister means something to you, tell her that. Give her good hugs. Tell her a couple of things you like about her. Tell her how much it means to your sense of well-being when she expresses affection for you.

My grandmother died a few years ago, and I felt exactly zero regret over how our relationship ended. She knew I loved her, I knew she loved me, and it didn’t require any grand gestures from either of us to make sure the other knew. We just... enjoyed each other’s company. Spoke to each other with warmth and dignity. Joked around with each other. I had precisely the relationship with her that I wanted to have — so what is there to regret?

That’s the key, I think: make sure, right now today, that you have the relationship with the people in your life that you want to have. And then put in the work to maintain that relationship, whatever it happens to look like. Live your life by deathbed wishes. If you do that, it becomes emotionally impossible to “regret” anything. You’ll still feel grief if something happens to them, but grief and regret are two different things.

Do you want to know something incredibly encouraging and yet incredibly sad? Sometimes, in fact I would say often, all it takes to have the relationship that you want to have with someone is to label the relationship out loud. To put into words what they mean to you, and share those words with them. That’s it. The simple act of your defining the relationship will forever change the texture of it, will forever emotionally bind that person to you in a way that you didn’t think possible.

I remember one time when my mother was talking to my stepfather about my younger brother. He was going through a tough time and my stepfather said he was worried about him. “You act like he’s your kid,” my mom said with a chuckle. “He is my kid,” he replied. I will never forget how nice it felt to hear him say that. Because I knew he was also saying it about me. He would do anything for us. And we get to bask in the unearned warmth of knowing it.

I’m not a very emotionally vulnerable person. I just don’t feel a need to share my emotions very often; I don’t find it useful. But I have tried my best to put into words how I feel about each person in my life, and to tell them at least one time. A single birthday card with a long handwritten message, or a single instance of stopping before I leave their house to say “hey, I appreciate you because of x reason. I just wanted you to know that.”

Now let’s be honest: it is very nice to hear loving, affectionate things from those you care about as often as possible. In an ongoing, recurring way. It’s reassuring, it makes you feel warm and good. (And I try to do that, too.) But what I can also say is that saying it out loud one time will last forever even if you unfortunately never say it again. Going from zero to one is life-changing; going from one to ten is merely nice.

So say it. You must not die without telling people what they mean to you. You don’t have to make it dripping wet with tears and sentiment; you don’t have to be a total sap about it. I’m not a sap, at all, and yet people feel my love profoundly. Because I had the nerve to tell them one time (or more).

If you never have the nerve to say it, you invite into your life the very regret that will eat you alive when something happens. You create, by your very act of leaving things unsaid, “the relationship you should have had.”

Don’t should have had a relationship. Just have it.

And understand that no matter how hard you try to be the perfect parent or son or daughter, sometimes life just takes from you anyway. That doesn’t mean you messed up. It just means life is horribly unfair and our job is to keep trying anyway.

“There are silences harder to take back than words.” - James Richardson

1. This is, in my opinion, one of the worst things about families having few (or fewer) children. If you lived a very traditional and/or religious life, you might have eight or nine kids. Then, if one of them died tragically, despite the horror and pain, you would be, frankly, less devastated than if you lost one of only two or three kids. There is a surplus of love and purpose in your life when you have more children. You can, fortunately/unfortunately, afford to lose one or two. Having kids, in some sense, can be a numbers game both genetically and emotionally. It’s not a pleasant thing to think about, but that doesn’t make it untrue.