Regret is Stupid

“If you marry, you will regret it; if you do not marry, you will also regret it; if you marry or do not marry, you will regret both; Laugh at the world’s follies, you will regret it, weep over them, you will also regret that; laugh at the world’s follies or weep over them, you will regret both; whether you laugh at the world’s follies or weep over them, you will regret both. Believe a woman, you will regret it, believe her not, you will also regret that; believe a woman or believe her not, you will regret both; whether you believe a woman or believe her not, you will regret both. Hang yourself, you will regret it; do not hang yourself, and you will also regret that; hang yourself or do not hang yourself, you will regret both; whether you hang yourself or do not hang yourself, you will regret both. This, gentlemen, is the sum and substance of all philosophy.”

Søren Kierkegaard

That Kierkegaard quote might very well be a big spoiler. All the same, I think that regret is worth talking about, because it can be a tricky and slippery thing.

Regret has a few sources. Obviously, it can come from the consequences of poor decisions. After getting a speeding ticket, one might regret driving so fast on the highway.

But regret can come from some other surprising sources.

Today, I’ll be writing about a few different kinds of regret that I have experienced. These experiences inspired my setting boundaries on time travel, and you’ll see why.

I will be covering three difference experiences [as well as other points] that I’ve had with regret. They are what I call “Old Man Regret,” “Buyer’s Remorse,” and “The Alternative.”

This involves a conversation I’d had with my grandfather in 1985 that I have given mention at least a few times.

It was late 1985 and I was going to pursue my dream of moving to LA to be a musician. My grandfather was particularly rough on me about the pursuit of my dreams.

When I had heard enough, I yelled back and told him that he probably didn’t have any dreams. That assessment made sense to me at the time, because he clearly couldn’t relate.

Circa 1986-87: Me, in my best Miami Vice garb, with grandpa and my sister. I miss them both.

Then he told me about his dream, as a young man, of being a race car driver. But then he met my grandmother, they’d had my mother, and other kids were on the way, so he gave up his dream to work in a factory for 38 years.

He cried as he told me this.

It confirmed to me that I did not want to have “Old Man Regret” in my future. What if I didn’t go? Then I’d never know what might have been.

Now, if you’d asked me maybe 10 or 15 years ago, I’d probably say that I had successfully avoided old man regret. That sentiment changed, at least for a while. More about that in the third segment.

But in this case, grandpa’s regret came when he wondered “what if.”

This one is easy. One day I went to Best Buy to get the latest Palm device. I was really into Palm Pilots at the time, and the device was the i705. I think the device was somewhere around $400 at the time.

Best Buy was offering a special promotion. Get $250 off any purchase when you sign up for two years with the Microsoft Internet Service Provider [ISP].

I was thrilled to death. Knowing there was no way I’d NOT want to have internet access, I went for it.

My motives were a bit complicated. At the time, smart phones did not exist, and being online in a mobile way hadn’t really caught on. By this point, I’d been getting online with mobile devices for almost a decade, so I knew what I was doing.

I took my Palm device home and logged into my Microsoft ISP. I could send and receive emails from my Palm device! Cool! I was very happy.

But after one month, something changed. Microsoft changed the security configuration for the emails that are sent. I won’t get too deep into that technical issue. Bottom line was that the Palm device and software did not support this added security.

What this meant was that I would NOT be able to use my Palm device as I had planned. Of course, I was upset, so I called Microsoft to complain about it. I was even willing to return the device if they would cancel the TWO YEAR contract.

They said “no,” and told me that the contract I signed CLEARLY STATED that there is “no guarantee of service.” What this means is you could sign up, then move, NOT have access, and there would be no recourse for you at all.

So I set a reminder on my digital calendar, TWO YEARS TO THE DAY, so that I could call and cancel.

Two years later, I call, and finally get into the call queue at around 7:30pm. They don’t help me until 9:05pm.

My account got cancelled, but I got charged for an extra month! So I called back, and they told me that the customer service hub I had called was located on the east coast, three hours ahead. They said my account was NOT cancelled in time, and since I technically had service into the next month’s billing period, I would be charged for another month.

It was insult to injury.

These days, I do as little business with Microsoft as humanly possible.

In this case, the regret was due to my signing of an abusive and criminal contract. The best course of action is to not sign a contract with this company, ever again, to read contracts better in the future, and to not ignore contract issues just because I really, really want that product or service.

This is actually a follow-up to Old Man Regret.

When we last left our hero [me], he believed that he was going to escape old man regret by pursuing his dreams. For even if they didn’t work out as he wanted, he would still not be wondering “what if.”

Enough of that third-person talk. I hate doing that!

Yes, I pursued my dream and I dedicated 33 years of my life in that active pursuit. Unfortunately, I was unable to get into the music business or earn any significant sums of money with this type of work. All the same, I don’t have the question of “WHAT IF?” hanging over my head.

But if I really wanted to generate some regret, then I can look at alternative life paths where I did not pursue my dream.

On the positive side of my dream pursuit, I got to play all of the famous venues on The Sunset Strip. I got to record in a few big studios. I got to meet musicians I admire, and some of them even became friends. I got to play some really fun shows and had some wild interactions with those who came to the shows.

Drumming at The Dragonfly in Los Angeles.


My biggest audience, with regard to my Pop Rock pursuits, was 5,000 people in November 1985, just one month before I moved to California. Yea, my biggest audience was in Indiana.

Also, the most money I had ever made with music was in the Spring of 1985 with my college band. I could make enough money off one gig to last me 3-4 months.

WHAT IF I had stayed in Indiana? What if I had kept on with The Switch?

Fall 1985: Me [far left] rehearsing with The Switch, playing my first homemade electric guitar.
We played to a crowd of 5,000 at Warner Auditorium. It was my biggest audience as a Pop Rock musician.

Maybe I would have had more success with music if I had stayed. But the paradox of it all would be that I’d have ended up with the Old Man Regret, wondering what would have been, had I moved to LA.

Accommodating 7,200 seats or 7,500 people standing, Warner Auditorium at Anderson University had the largest thin-shell concrete dome in the world.

While I don’t notice and won’t feel it, hundreds of people will hear me on the radio today, performing on Noodle Muffin tracks. They’ll be listening to college radio, or Dr. Demento.

Had I stayed, I’d probably not be on the radio at all. But radio today barely matters. There’s no predicting some things.

Of course I have to present the Autistic angle in all of this. One big issue that I’ve had as a result of my Autism is a thing called “Rumination.” It’s the kind of intrusive rumination that gets in the way of the present and future. It’s the past never letting go, and I know this has been visible in some of my previous writings.

When a person engages in excessive rumination [in my case, it was against my will], they can generate more regret than a person can naturally find with lower and more reasonable levels of rumination.

Medications, such as Wellbutrin, can help eliminate this type of destructive rumination. I couldn’t ruminate right now if I wanted to do it.

Many forms of regret can be written off as such. The Kierkegaard quote at the beginning best illustrates this idea.

Write this blog entry and regret it. Do NOT write this blog entry, and regret it. This is an inescapable paradox that can keep a person trapped.

The solution for this, of course, is to appreciate the actual grass that is beneath your feet right now, instead of wanting the hypothetical grass that could be.


But probably not.

In late 2019, an opportunity presented itself to me, when I had made contact with an old girlfriend from 1982 [We’ll call her “Jane Doe”]. We dated for the summer. This all came to an end when he father found out the hard way that his 16-year-old daughter had a 17-year-old boyfriend.

He tried to kill me with a big crescent wrench. Cross-country running was the ONLY skill I learned and refined in high school that has served me well. But I digress.

I was in a relationship of 20 years with a woman, and it wasn’t really working [We’ll call her “20”]. She was on her fifth marriage, and that wasn’t working out for her.

Fate was presenting us with a chance! So Jane Doe left her husband of 16 years, filed for divorce, bought a one-way ticket, and flew out to stay with me. She was supposed to visit for a few weeks, so I should note that the one-way ticket was not my idea.

I wasn’t really ready for things to go to that level, but I went with it. After all, this was a chance to right a wrong, so far as we were concerned.

A “what if” was getting rectified. That’s what I believed, anyway.

She moved in while the girlfriend of 20 years was still here. And she stayed for FOUR months before moving out to Rhode Island during the pandemic. But she moved back in August because she decided that she wanted to live in Oregon.

Jane Doe, me, and 20, drinking White Russians while waiting for the pandemic to blow over. Looking outside the window, it appears there was some kind of nuclear blast that occured while we weren’t looking. Sure felt like one.

We all made the best of it, even though it was kind of strange.

One day, in early October 2020, Jane Doe walked out the front door in the morning and never came back. I struggled to get in touch with her for over two weeks, as she had received a $60,000 check from her divorce, and quite frankly I didn’t want to be responsible for holding onto something like that.

This did an interesting thing to my regret. Previously, my regret was that her father interrupted our courtship and we never knew what could have been.

20, me, and Jane Doe, out for coffee and a walk along the Oregon coast.

Now, I simply regret ever having talked to her in the first place. Getting with her in 2019 destroyed some wonderful 1982 memories. The whole situation is heartbreaking.

Remember your boundaries on time travel!

All the same, maybe things would have worked out if we had been allowed to stay together in 1982. Or maybe it would have destroyed my life. Maybe I’d not be alive to write this. It’s anybody’s guess.

On the positive side, Jane Doe has stayed away and I’ve not had any contact with her since the last time I saw her, when she picked up her stuff.

As for 20 and I, we still live together, although we are currently living with boundaries typically set by roommates. We are still best friends and care about each other. We just don’t have a romantic relationship. To be fair, we never did.

As I write this, we’re working with our individual therapists to see if we should stick things out and try, or go our separate ways. Considering how sick and horrible life is right now, we realize that sticking together and working through life is more important.

Capitalism often forces people to do things they’d not normally do. But I digress.

Regret, so far as I am concerned, is nothing more than psychological bullshit where our minds play games with themselves.

I could have been this or that.

I could have gone here or there.

I could have taken THIS path or THAT path.

I could have died in my sleep as an infant.

I could have never existed at all.

Indeed, the grass always appears to be greener on the other side.

We humans have these constructs of “good and bad” or “right and wrong.” It is a scaffolding upon which we build our boundaries. We can attach memories to it as well. When something happens that we like or do not like, we can attach “good” or “bad” labels to them and then go about our way.

The next time we encounter these things, we don’t have to take a risk or even think about it, for we are already informed. We may find exceptions along the way, or new experiences might re-shape previous avatars of good or bad.

These concepts fill up our heads and feed our cognitive biases. To me, being a musician was the right thing for me to do. Meanwhile, the opinions of others was that my being a musician was a wrong thing to do.

On top of cognitive biases, we also have personal desires flying around to clutter up the scene. I’m a Type 2 Diabetic, and I still want to eat some milk chocolate on occasion. That’s a personal and biological desire that works to make my illness worse.

In the big picture, it is best to do away with regret. It only causes trouble.

Removing regret will leave a major gap in the works, so you can fill that gap. Consider your life where it is right now. Think about all of the things you went through, both labeled good and bad, to get where you are right now.

Then tell yourself that you would live your life, precisely has it happened, all over again to get where you are now.

Yes, you could have been in a variety of other places. You are not. Where you are is nothing more than where you are.

Life is an illusion caused by death.

Every path is the right path.

If you like what I write, then please consider sending a one-time donation to me via PayPal. Please use the following link and click SEND to donate, and thank you for reading!

Published by DrumWild

Writing about drums, music, and philosophy.

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