Mr. Olmsted Regrets

Mark Olmsted
11 min readSep 11, 2023

The older I get, the more I realize what a completely zigzaggy and very melodramatic life I’ve led next to so many of my peers. I don’t say that in a way to suggest I’ve had more adventurous fun than they had, not remotely, it’s just a clear-eyed recognition that I’ve followed a wholly unpredictable and frankly strange trajectory, and I think I spend more time trying to make sense of it than almost anyone I know does of theirs.

I have learned how to look back without swimming too much in the seas of regret, though. What I do rather is occasionally fugue into imagined alternate histories of my life, had I chosen to do this instead of that, gone to this place instead instead of that place, managed to avoid that man entirely.

After keeping most of these scenarios in my head for years, I finally wrote down a top ten list of things I might do differently if I could do things all over again. This makes it sound like I could have done them all, but they are pretty much mutually exclusive, as each one would have created its own timeline, with different friends met, other love stories, alternate career paths. The only thing they all might have in common would probably be that in all these futures, I would now be penning this same Substack entry on this same date, just with an entirely different list of regrets/should’ves/what-I-would-haves laying on the desk next to me.

And I think all of the my alternate selves might have come up with the following story.

Mr. Olmsted’s Regrets

“Next” intoned the clerk.
I was ushered into a spare white room and motioned to sit. St. Peter (I knew because of the nameplate on his desk) peered over his bifocals at a file. I wondered aloud why he needed bifocals in a place like this.
“Oh, of course I don’t need them. I wear them because the afterlife takes on whatever appearance each new arrival thinks it will.”
The ‘afterlife.’ I guess that sounded nicer than ‘Judgment Day.’
He smiled, able to read my thoughts, no doubt.
“Let’s begin, shall we?”
I squirmed. Surely, I was in for it. I was going to find out that all the redemption I’d experienced in the last part of my life didn’t even begin to compensate for the wreckage I created in the first part of it.
He lifted a paper from the folder. “Your ‘Ideas’ list.”
“Your list of ideas. For writing projects.”
I was all too familiar with it. I’d been adding to it several times a year, year after year, right up until the untimely encounter with a speeding cab that brought me here on the eve of my 57th birthday. Nothing in my life had haunted me more than that list of possible novels, scripts and creative non-fiction — my Library of Undoneness.
“Let’s review, shall we…? Kill Baby Hitler!” he began.
I jumped to the conclusion that I had to explain the story. Who knew the afterlife would start with a pitch session?
“Well, this scientist from the future goes back in time to kill Hitler as a baby. And he does, smothers him in his crib. But when he comes back to the present, everyone is speaking German, and he finds out there was a worse guy than Hitler who came to power but who won the war. So he goes back in time to kill himself — his other self — before he can kill Hitler. And he’s too late! His other self has killed baby Hitler, and disappeared, but they arrest him for it! And then”–-
“Yes, we know how it ends.”
“Oh, but let me finish… it’s the best part.”
“If you wish.”
“So our hero gets put on trial for killing Aryan babies. And he’s Jewish, and he’s found guilty — because nobody believes his cockamamie story, of course — and there ends up being huge pogroms and all the Jews are basically hounded out of Germany and Central Europe and forced to immigrate to America. Which is still possible, cause it’s the 1890s. So, final twist, our hero goes to the gallows, but he’s accidentally accomplished his mission. With no Jews to provide the anti-semitic glue of Nazism, it really never takes hold. There’s no World War II — in Europe, at least — and no Holocaust. And Israel never really happens either, so the Mideast doesn’t blow up later.”
“Well, we thought it very inventive. Too bad Amazon never saw it. Instead they went with The Man in the High Castle.”
It was worse than that. No studio saw the script because I never wrote it. He was reading off a synopsis — that’s as far as I’d gone with it.
“Let’s move on. ‘Prequel to Gone With the Wind.’”
“It’s the love story of Rhett Butler and Belle Watling, in the years leading up to the Civil War. Since they had a son and everything. And then after the war, this son, as a young man, falls in love with Scarlett.”
“That was a great love triangle,” observed Peter.
“But I couldn’t get the rights, of course. Hell, the Margaret Mitchell estate couldn’t even come to an agreement with Pat Conroy.”
Peter peered at me skeptically over his half-moons. “You never even tried to get the rights. You gave up after Chapter III, years before any of that. Another good beginning of a work you never finished.”
Oh, so that’s what this was about.
“Well…” I thought of blaming the 25 years I drank and used, but they had weirdly been some of my most productive. It was the years since prison that had been the problem. All I ever managed to write were blog posts. I didn’t say that out loud, but he heard me think it.
“Yes, we actually liked your substacks very much. But they only took a few hours a week to write, if that.”
“Well, I had to read other writers, too. You can’t expect people to follow you if you don’t follow them.”
”That’s not what we’re talking about, either.”
The use of “we” was really getting on my nerves.
“Are you saying I’m going to hell because of my lack of follow-through?”
He frowned. “Hell? Don’t be melodramatic.”
He waved his hand. A huge screen materialized, and a video began. It was a fast-motion montage of me in front of one of the screens that were my signicant others — laptop, TV, iPhone. With dizzying speed, every show I’d ever watched flashed by. The networks and streamers, HBO and TCM and MSNBC. There was Project Runway and So You Think You Can Dance and The Vikings; Downtown Abbey and Poldark and Breaking Bad; Ozark and The Bear. So many shows. So many channels. And Facebook — oh, Lord, there was a lot of Facebook. And Twitter. And Instagram. Hundreds of hours sped by in minutes, all showing the damning and incontrovertible evidence of how much time I spent consuming media when I could have been writing.
Like a judge reading out a verdict, he recounted the rest of the undone, unsung projects listed in my “Ideas” file.
“Black High Society.” ‘ Uncles and Nephews,’ ‘War Occupation-Fay/Mom Story.’ ‘Children’s Color Story,’ ‘What if I’d Grown Up in France Story,’ ‘Nico/Chile Coming of Age YA novel,’ ‘Grandfather’s Suicide Play’–
“Hey, I wrote that one. Called Brookside. In a playwriting class. It was good too.”
“Yes it was, and did you do anything with it? Did you try to get it produced?”
“Funny thing, that’s even harder in L.A. than a getting a movie made.”
That was a lie, and we both knew it. I hadn’t really tried to get it produced. Oh, a few feelers here and there, but no follow-up. Always the same with me. All get-up and no go.
“Please, stop,” I pleaded. “I get the idea.”
He snapped his fingers, freezing the video on a frame of Ryan Lochte doing the mambo on Dancing With the Stars.
“So why are you showing me this, exactly?” I asked.
“It is Judgment Day, Mark, but not God’s Judgment — your own. For all the ways you know you could have better spent your time.”
“Well, I’m guilty as charged, then.” I mimed bringing down the gavel. “Off to the dungeons with me.”
“Not quite. You’ve been chosen for a pilot program. An experiment, really.”
“God does experiments?”
St. Peter nodded. “She gets bored.”
(“She?” Well that was interesting.)
“You’ve been selected for do-over, if you’d like.”
“A do-over?”
“Yes. We’ll put you right back into your past — starting at 9th grade or so — and you can live your life from there over again.” I guessed 9th grade because that’s when the mistake-making started. I had a pretty regret-free childhood.
”And I will know everything I did wrong in this life?”
“More or less. We’re still trying to figure how much awareness you’ll have exactly. It’ll probably be more of a keen presentiment of what choices will make you happier.”
I looked at him skeptically. “The rules seem pretty loosey-goosey.”
“What can I say?” he shrugged. “It’s in beta.”
“So the only thing I can be sure of is that I’ll know not to waste half my life watching TV?”
“Well, that wasn’t all a waste. It really has been a golden age for scripted drama.”
“And comedy. The Other Two is hysterical.”
He nodded in agreement. “But really, Vanderpump Rules? C’mon.”
Another possibility occurred to me. “Please let me be aware of Trump, so I can do something about him in the 80s.”
St. Peter smiled, but shook his head.
“An admirable sentiment. But if you end up in prison again, you’ll ruin your timeline, and you’ll screw up the program for everyone else. Trust me, you’ll know enough to change your own life for the better. It’s about you, not altering world history.”
“All right.” I guess I didn’t want to spend my do-over life on death row, especially considering I’d be the only one in the world who knew what I’d spared the country.
Peter looked left and right, then whispered. “I totally did not tell you this, but remember to buy Apple and Microsoft early on. Hold onto it, and then when something tells you to sell in 2008, do it. That’ll be me.”

And with a snap, I woke up in 9th grade, wondering if I’d just had the most awesome dream ever. But something was definitely different, a sense of déjà vu infusing every moment. I suddenly appreciated my family so much more — gone was the snark when I spoke to my siblings or parents. I didn’t avoid homework or chores — it just felt like a privilege, somehow, to do them. My family openly wondered if aliens had abducted the real me.

When I was torn between joining the swim team or the drama society, a third option came into my mind, and I tried out for gymnastics instead. You have no idea the difference that made later on. I was way more confident in college because I had a much hotter body, which meant I didn’t seek near as much validation with so many men. So many of the wrong men.

I intinctively knew to have safe sex before anyone knew what that meant, so avoided getting HIV — another wrench not thrown into my life. I went to Yale instead of NYU Film School. Two years at the Sorbonne, and then Columbia for a Phd in French Language and Literature. I pursued a serious career in academia, instead of the life of a struggling screenwriter. I landed a tenure track position at a leafy northeastern college, leading a much more civilized existence. I avoided drugs, traveled a lot more, invested well. (Thanks, St. Peter.) I became very wealthy, the rich and generous uncle instead of the perpetually broke one. I had two houses, three if you count the one in Italy that I eventually lost in the divorce.

I made plenty of mistakes, whoppers, even, like sleeping with a grad student who was actually an undergrad — that little settlement cost me half of my Berkshire Hathaway stock. And though I did avoid drugs, I conveniently forgot I shouldn’t drink. It led to jealous fights with boyfriends and a DUI, but court-ordered rehab was a lot better than prison, and it did scare me sober.

And there was Allessandro, beautiful, fucked up Allessandro. I hope he’s happy in our house in Tuscany.

So yes, I avoided the old mistakes, but made just as many new ones. Bad ones. Sad ones. Guilt and cringe-inducing ones. And yet, with the strange awareness of my previous life that had been granted me, they didn’t feel like my mistakes. They had given me scars in different places on my do-over body and soul, and I kept reaching for the old ones to obsess over, and at times to longingly caress.

It slowly become clear that I missed my old regrets. Even worse, that I didn’t know who I was without them.

By the time I realized this, I had made so many different choices that I couldn’t have started making the same mistakes over again even if I wanted to. Or could I?

In this life, I’d read a lot instead of watched TV, had written reams, even edited an anthology about Emile Zola that garnered favorable reviews in the academic press. My C.V. was bursting with articles in this journal and that; exquisitely researched, perfectly argued, and read by practically nobody. I had tenure. What stopped me from curling up with the remote now, instead of a good book?

And who said I had to be such a globe-trotter? In the past year alone, I’d been to Buenos Aires, Chamonix, and Capetown. It was exhausting, frankly. So I sold my skis and scuba gear and donated my frequent flyer miles to Doctors Without Borders. I got an obnoxiously large flat-screen TV and the highest-tier cable subscription, and revived my moribund Facebook account. I made another long list of ideas for screenplays, and three different novels, never getting past an outline — but not really trying to. I didn’t need to write them. Only regret not writing them.

I started to feel better, more in my old skin. My ROKU became my new best friend. Instead of tossing and turning at night, kicking myself for caring so much who won the Snatch game on RuPaul’s All Stars Season 7, I floated into a contented sleep, knowing I could post about Jimbo’s hilarious turn as Joan Rivers on Facebook the next day. It was a paradox really, to recreate my old regrets, while not really regretting them, like wearing an old sweater because it was warm and familiar, and not because I couldn’t afford to buy a new one.

By the time 57 rolled around again, I realized I hadn’t been depressed for months. Unfortunately, I didn’t realize I was crossing the very same street on the very same day that speeding cab had found me the first time around. What can I say? I was lost in The Gilded Age podcast.

So here I am again in heaven’s waiting room, about to be debriefed by St. Peter about my failure or success in the grand experiment. I doubt it will be the latter, as I suspect I totally screwed with their algorithms. Who intentionally repeats their mistakes, just because he finds their familiarity comforting?
“Next,” calls out the handsome clerk.
As I pass him, our eyes meet for a delightfully lengthy second. I notice how much he looks like Allessandro. He smiles at me, and I smile back.
It’s heaven to be yourself.

MCO 2023



Mark Olmsted

Author, "Ink from the Pen: A Prison Memoir" about my time behind bars. See GQ dot com “Curious Cons of the Man Who Wouldn’t Die” for story of how I got there.