I used to lump all my regrets together in the same bucket. And then I'd drag that bucket around with me, day in and day out, with all my regrets glooping around in there like stinky fish heads.

But I've come to realize lately that maybe my bucket doesn't need to be so full. Maybe if I downsized a bit in the regret department, I could exchange my stanky bucket of regrets for a sleek satchel of regrets. Nothing fancy, you know, but nicely tailored. With enough space for just my most essential regrets.

Well, reducing my regrets was easier than I expected. Because it turns out more than half of them were misfiled in the first place. A simple clerical error.

I discovered the mistake while reviewing a massive sample size of regrets (mine! all mine!). Each, of course, has its own unfortunate spin. Some include people I love, some include paths I was too fearful to follow, some include a hill, a Schwinn, a plywood ramp, and four garbage cans. You could argue that each of these regrets has entirely unique specifications and, as such, should be filed independently – always ready to be called up for granular analysis. You could also argue "eff that" and throw them all into a big bucket... fish heads glooping... etc. 


You could argue (and I am) that there aren't a million kinds of regret. And there isn't just one. In fact, there are two kinds of regret:

  1. I regret I tried that.

  2. I regret I didn't try that.

It's been helpful for me to think of them in those terms.

I regret I tried that. 

This kind of regret usually hits quick. And it hurts – leaving you feeling stupid, angry, resentful, embarrassed, cynical, sad, or whatever else depending on exactly what stupid shit you got yourself into. It's a highly targeted, looping kind of pain:  "shouldna dun that...shouldna dun that...shouldna dun that..."

But on the bright side, while it's a sharp hurt, it's often a short one too. A mental bruise that might last a week or a month or a year, but eventually subsides. Unfortunately, it'll turn all shades of greenish-purple along the way... a blotchy reminder of botched decisions past. And a reminder, too, that maybe trying new things isn't always in our best interest. That's where it gets dicey.

So. I think now would be a good time for some sentence parsing! Because all these "I regret I tried that" regrets? I don't think they're regrets at all.

To wit: 

I regret I tried that.

After parsing like a mofo, we arrive at:

I regret  /  I tried that. 

The two operative phrases here are "I tried that" and "I regret."

Basically, "I tried that" is the crime in question. And "I regret," is my (self-imposed) punishment.

Once more, the crime in question? "I tried that." 

Well, long story short, I've come to the obvious conclusion that trying things shouldn't be a punishable offense. Trying things, even dumb things, especially dumb things, is how we learn/grow/thrive. As such, I've decided that all my past transgressions are pardoned. I'm free to go. Whether the things I tried worked or not, whether they're examples of towering genius or cratering dumbassery, I gave them a try. Dammit I gave them a try. 

Bruises are badges if you look at them right. 

Sure, this is overly simplified. And I realize all I did here is take "Well, at least you know not to do that again," and stretch it into several hundred words worth of ramble and strained metaphors (which I then mixed for good measure).

But it's helped me, this way of thinking. It really has. Because trying things helps me avoid not trying things. And not trying things is a far more serious offense.

I regret I didn't try that. 

To me, this is a different kind of regret entirely – a deeper sludge of a thing that's harder to overcome because the opportunity to address it is usually past. We missed our chance. Now, I'm not talking about "I regret that I didn't try the fondue." We can all rest easy, there will be more fondue.

Instead, I'm talking about the larger scale "didn't tries." All those things, potentially life-altering things, that we were too self-conscious, too lazy, too distracted, or too scared to try. Of course, the ensuing regret can be the same as those behind door number one above: embarrassment, anger, sadness, etc. But it can run deeper too. Wider. Heavier. Regret for the things we didn't try can lead to a more pervasive sense of dissatisfaction, a sense of possibilities being left on the table, a sense of life not fully lived. 

I'll be honest. I don't know of any parsing tricks or existential pardons to undo the regret we have for things untried. It's especially unfortunate because all my biggest regrets, my only true regrets really, are for what I didn't try. 

But I do know this:

It's easy to avoid these kinds of regrets going forward. To make sure our list stays capped at its current length. 

All we need to do is try things.

All we need to do is be ambitious and allow ourselves the opportunity to fail proudly, majestically, gloriously.

All we need to do is be brave and curious and resilient.

All we need to do is embrace Yes. 

And Maybe. 

And Hold My Beer, I'm Going To Try Something.

That's all we need to do. Try things.

I believe it was the mythical spirit Tim Riggins, speaking in the form of a Panther, who decreed: "No Regrets." Now obviously, having no regrets isn't as easy as just saying "No Regrets." (Poor dumb yet broodingly sexy Tim Riggins.)

But LESS regrets? Less regrets is entirely doable.

To conclude, I'll tap into the magic and power of a few tools known as:

  • Sharpie pen
  • Camera telephone
  • Thumb

Less Regrets. Go get 'em.