Dear Tristan: Have Regrets

Dear Tristan,

Early on in the evolution of this list of Christmas letters I planned to write to you, I was going to write a letter about responsibility. As I began writing, though, I realized that responsibility, rather than a topic for a single letter, is kind of the theme of the whole list. Responsibility for yourself, for your actions, your thoughts, your preferences, your beliefs, is what lies behind most of these letters.

Yesterday I wrote about expectations and how they play into the paradigm of internal vs. external motivations that I’ve mentioned in other letters.

If, however, you live a life of internal motivation as I hope you choose to, you will discover something. You will discover regret.

As I mentioned in one of my early letters, none of us is perfect. I will make mistakes as a father, and you will make your own share of mistakes too. But when other people are making your decisions for you, you don’t have to have regrets, because your actions aren’t “your fault.” When you’re motivated by external factors such as the desire for reward, fear of punishment, or approval of another person, the only thing to regret is not having received the reward, or avoided the punishment.

That’s not true when you’re internally motivated, though. When you’re the one making your own choices, the probability of regretting some of those choices is somewhere right around 100%. But I think this kind of regret hurts more, because the failures carry so much more meaning with them. Instead of failing to achieve a reward or avoid a punishment established by someone else, you’re failing to live up to an internal goal you’ve set for yourself – and it can feel like you’re betraying a piece of yourself in doing so. Trust me, I’ve done it enough to know.

But the very first thing to realize about regrets is that they don’t have to feel like that. In her very first letter, your mom wrote about failing to live up to ideals. One of the things she wrote in that letter was,

“I hope this is something I will be able to model for you – to never, ever give up. Even if you’ve failed at something, to pick it up and try again. To not just go for the easy things in life. The truth is, the things most worth doing ar hard. The things most worth doing are things you might fail at many times before you finally succeed.”

The simple fact is that you will make choices you will later regret. And it will hurt. But that doesn’t have to be the end of the story. Like your mom wrote, a great success can be preceded by many failures, and the great epic narrative of humanity is, after all, a story replete with failure and redemption.

But there’s another reason it doesn’t have to feel like you’re betraying yourself every time you don’t succeed in living up to your own ideals. Too often we approach regret from a place of judgment – we subtly buy into the paradigm I’ve been trying to refute throughout these letters, that we are defined by what we do. We agree with that insidious notion and we condemn ourselves for our actions or lack thereof. And so, when we judge ourselves (and we humans are especially talented at being our own harshest critics), we don’t judge only the action, but the part of the person . . . the part of our self . . . to which each action is tied.

But those deeds do not have to be a reflection on who we are. You are so much more than the sum total of everything you’ve done, or not done . . . we all are! Earlier in these letters, I urged you to reject being defined by others as a product of your actions. Now I urge you to resist defining yourself that way as well. Just as I urged you to have empathy for others even when you are upset or frustrated as a result of their words or actions, I urge you to have the same empathy for yourself!

Once you do that, regret becomes a powerful ally, rather than an enemy.

Let me give you an example. When your mom and I got married, very early in the process of planning our wedding we decided that one of the areas we were NOT going to skimp on was photography. It was important to both of us to capture not just what the day looked like, but what it felt like . . . something a good photographer can do, where a less-skilled one would have difficulty.

We researched many photographers, and interviewed a few whose work seemed to be what we were looking for. We ended up choosing a photographer who was very experienced and highly recommended. And our pictures turned out . . . ok. Not bad, not great, just ok.

It turns out neither of us really knew the specifics of what we wanted. We didn’t really know what to look for in a photographer. We had a vague idea of the sort of photos we liked, but nothing behind the mechanics of how to get those photos, or which photographers typically preferred those mechanics as opposed to different sets of preferences that yield different results.

We both regret that decision, and it’s not because we didn’t get what we wanted at the time (a skilled, experienced photographer). We did get exactly that. No, the regret is in ourselves . . . that we didn’t learn more about the way photography works, and refine in our own minds what it was that we wanted.

But rather than being a source of self-judgment and discouragement, this regret has spurred us both to not only become more knowledgeable about photography, but to work toward becoming exactly the type of photographers we wish we’d had at our wedding. That’s why you always see us – especially your mom – peeking out from behind the big funny-looking black box that is so often pointed in your direction. Your mom is now running a budding photography business, and I’m coming along behind her learning more slowly, but learning none the less, how to capture moments in camera the way I wish that some of my favorite moments had been captured on the day your mom and I got married.

Regret can be an unhealthy thing if you use it as a weapon against yourself, judging yourself for your failures and allowing those failures to define you. But if you take responsibility for the decisions you make, if you act from a place of internal motivation, doing what you choose to do, owning that choice and, after the fact, providing empathy for the self that made that choice even when it turns out to be the wrong one, regret can be a powerful way to learn more about yourself, grow more fully into the self you want to be, and ultimately, share that self fully in relationship with others.

And really, that’s what it all comes down to . . . why regret is such an important thing to let yourself feel. Because we’re all human, and therefore capable of failure, each time we squelch the regret when it wells up in our hearts and tells us something is wrong, we kill off a piece of ourselves. When we live life out of a commitment to never regret, then when something occurs that is worthy of regret, we deny the piece of our soul that tells us that, and try to go on blissfully with our lives.

I say “try to,” because when that happens . . . when we smother the regret as soon as it first shows signs of life . . . we’re not really killing it. We’re just burying it, and it will rear its head in the future whenever something else occurs to trigger a reminder of that moment. Enough buried moments of regret can, when triggered, turn to heartache. Worse, they can affect your relationships, both with your own heart and soul, and with those you care about.

So I urge you not to try to live your life by the mantra of “no regrets.” I can tell you from personal experience that if you try, you will almost certainly fail. Instead, regret the moments that are worth regretting. Let them teach you who you are, and who you want to be. Then share that person with me, because I’m so excited to get to know him.


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