There’s this pernicious stigma in Western culture that denigrates having regrets. “Live your life with no regrets” is the common refrain (although I prefer the Mystery Science Theater 3000 “I regret nothing!” version). But everyone has them, don’t they? I know I certainly do. It’s unavoidable. The thing is, I feel somewhat guilty about having those regrets.
My guilt stems not only from the stigma around my regrets but also because I’m doing fairly well in life—I have a family I love, a top-notch medical team and school to assist with my daughter’s disability, a house in a safe neighborhood, no debt beyond a mortgage, and the means to work less right now and explore new things like creative coaching. It’s the modern American dream, in a sense.
But if some of the things I regret hadn’t occurred, I would certainly not have the same life I have now. (This is the part where the guilt comes in).
How do I reconcile these two opposing things? On the one hand, wishing I had done some things differently in the past; on the other hand, being thankful for where I am now.
It’s a paradox.
So, what the hell do you regret?
Oh, hi there inner voice guy. It’s been a while.
Yeah, sure, hi. Anyway, stop avoiding the question.
Jeez, relax. The thing is, there are so many things I regret. I wouldn’t even know where to start.
I don’t know, man, why don’t you just brain-dump a bunch of them?
Yeah, okay, here goes.
The first regrets that come to mind have to do with my old band Pressure 4-5.
Our single was released to radio and our video hit MTV2 a couple of days before 9/11. We probably should’ve pushed back the album release date.
Uh, dude, that seems pretty unfair to regret.
No, no I don’t regret that. I’m just giving some context to all the new readers here. It was an unprecedented time so nobody really knew how to properly respond. Obviously, with the single and video released, there were a lot of promotional things already in the works. And it’s not like we were some established veterans in the industry that could’ve put our feet down and forced them to pull the plug and move everything back.
But before that, about ten months prior, right after we signed our record deal with DreamWorks, we had to fire our drummer because he had developed debilitating tendonitis in his right wrist, which is kind of an important body part for a right-handed drummer.
But, again, I don’t regret that decision either.
I regret not asking my brother, Owen, to play drums with us then. Instead, we hired a studio drummer with quite possibly the best drummer name ever, Brooks Wackerman. And while he was absolutely incredible and genuinely made our music better, he was a hired gun. When I finally asked Owen to join us, it was after our album was recorded. He would’ve been able to go on tour with us, and I’m sure he would’ve had a blast, but he would’ve been playing someone else’s drum arrangements the whole time. I kowtowed to the pressure from the record label and our management to get someone in quickly when my gut was telling me I wanted to ask Owen sooner.
I also have this—probably unrealistic—thought that if he joined us at that time then the album might’ve taken a bit longer and that would’ve meant the release date would’ve been pushed back and we would’ve avoided releasing our single to the world right as the world felt like it was crumbling down.
Yeah, that sucks. I get that.
I wish I stayed in the music industry longer too.
Later on, I joined Owen’s band Ambionic. We wrote some great music and we recorded it ourselves. It’s some of the music I’m most proud of writing and recording.
We loved the recording process and he and I were damn good at it, especially considering we were self-taught. We could’ve started producing other bands’ music and built a whole other career out of it. I’m still baffled as to how it never crossed our minds back then.
Okay, so what about non-music stuff?
I didn’t take the communication problems in my first marriage seriously enough. I took our relationship for granted, assuming we were both in it together for the long haul, and that we would eventually work things out as a couple. Y’know, the whole ‘til death do us part thing. But she was struggling with it more than I realized and was ready to move on with her life without me. And I was blindsided by it. I tried to work on repairing it with her through couples therapy. But it was a futile effort because she already had one foot out the door and our divorce was imminent.
Isn’t the key to regrets all about learning and growing from them so you do better the next time around, though?
Sure, I suppose.
That was definitely the case with my first marriage. I learned a lot from the experience. Things like seeking counsel early and often, which has helped me to be a better husband to my wife, Allison, now. We have worked as a team to be there for each other and to work on our communication regularly—seeing several different therapists over the years while navigating the inevitable issues that arise during the course of a marriage. I’m also lucky to be with someone who’s willing to continue to work on it with me.
But what if there isn’t a next time? Like with my old band. I’ve never had another shot at being in a major-label band. Instead, I’ll carry around the regrets and the what-ifs and the what-could-have-beens from that experience until I die.
That seems a bit dramatic.
Yeah, I know. It is.
It reminds me of a story a friend once told me about a family member of his who was a professional baseball player back in the day.
The story was that he was a pitcher and a star player throughout little league, high school, and college ball. He was drafted by the Boston Red Sox and spent a bunch of years in the minor leagues—way more years than he thought he would—before finally getting the call to head up to the big leagues.
After a few games sitting in the bullpen, he got his chance to pitch in a game at legendary Fenway Park in Boston. The Red Sox were up by something like six runs in the 7th or 8th inning. The game was essentially a done deal at that point. But the next thing he knew, he gave up six runs—including a homerun that sailed over the iconic Green Monster wall in leftfield—and he got pulled from the game.
A few days later, he was sent back down to the minors and he was never called up to the majors ever again in his career.
Could you imagine that?
All those years of practice, from when he started tee-ball as a kid until the moment he realized his dream and took the mound in a Major League game. And then all of it culminated in a nightmare debut on the biggest stage.
What if he threw this pitch or that pitch differently? What if he didn’t shake off a sign from his catcher? What if he never pursued a career as a pro ballplayer?
Dreams crushed. An unforgiving reality check. A recipe for regrets.
I know that I already knew that story, but damn, it still hurts to read it.
He has to take solace in the fact that he made it further than 99.9% of ballplayers. I mean, that’s basically what I’ve said countless times about my band experience. But in my case, I was able to play a bunch of shows, including taking the stage at Ozzfest and playing in front of tens of thousands of people.
At the end of the day, there’s only so much you can control in life. And when you’re trying to do something that only 0.01% of people succeed at, then you have to focus on the work you did to get there instead of the outcome. But man, that’s hard sometimes.
What good does it do to focus on it at all, though? Like, shouldn’t you be focusing on the present and where you’re going in the future?
Ugh, you’re gonna make me talk about those podcasts we listened to recently, aren’t you?
You know it.
Yeah, those have been on my mind. As you know. I guess I should fill in the rest of the people reading this.
One was the Huberman Lab podcast with Rick Rubin. First of all, I’ve been borderline obsessed with Rick Rubin for decades. I devoured his newly published book, The Creative Act, and loved it.
About 2/3rds of the way into the three-hour-long podcast episode, Huberman asked, “Are you somebody who is attached to the past?”
And Rubin replied, “I’m not attached at all. I’m not attached to anything in the past. I don’t look back at all.”
Huberman seemed a bit taken aback. There was a bit of back and forth and then he asked, “Nostalgia is not in Rick Rubin’s brain?”
“No,” Rubin said.
“Oh, lucky you, man,” Huberman said.
And man, I felt that response too.
A few days later, I was listening to
's latest Pathless Path podcast episode where he interviewed Derek Sivers. Right at the beginning of the episode, Sivers mentioned a line from a Bob Dylan song where he sings, “She’s an artist, she don’t look back.” He internalized that passage at a young age and interpreted it to mean that all artists don’t look backward, but instead always look forward.The two episodes got me thinking about my writing, and memoir-style writing, more generally. It’s inherently an art form that requires digging into your past. It feels at odds with the mindset both Rubin and Sivers talked about. But the more I thought about it, the more I realized it isn’t at odds at all.
Sharing a vulnerable story from your past is about going deep and exposing the truth about your experiences. But it’s not only about dumping those things out onto the page. It’s also about how they changed you. And that’s how the story goes from seeming like it’s dwelling on the past to feeling like it has energy and it’s pushing things forward.
I’ve shared multiple stories about my band days. And each time I did, it made the feeling of the rug being pulled out from underneath me sting a bit less. I used to feel depressed about it, even nearly twenty years after the fact. In those darker times, it was like I was that pitcher who had my shot at the big time and completely blew it—never mind the fact that my rational brain knew that was ridiculous.
Wait, does that make me the irrational brain then?
No comment. Anyway, we should probably wrap this up.
Wait, hold on a sec?!
Hey man, don’t dwell on the past. Let’s push things forward.
Nice, I remember that song!
I was encouraged by the outpouring of support after announcing my new Just Enough Coaching practice in my piece last week. I still have a couple of spots open too. If you’re a writer or creative who wants to up your game, let’s chat! There’s no upfront commitment and if you don’t feel like I provided value, you don’t have to pay.
If you enjoyed today’s piece, could you please let me know by giving the heart button below a tap?
Regrets are powerful things. And I suppose a lot of times they're just the shape that lessons learned take. Like, if I regret not doing something at one point (even if, like you said, I might never have a chance to attempt that exact thing again), I know that in the future I'll do things differently. If I did not feel bad about not taking that chance in the past, I might not be so driven to take the bull by the horns in the future. So...regrets are just lessons learned the hard way. I think that's powerful and something to be cherished.
I appreciate your insight: without the things you regret, you would have the life you have today. And yes, let's dance.