If I could do it all over again, I would say screw the startup, the money, the IPO and all that crap. I'd run away to an island and spend maximum time with my first partner - who I lost far too soon in life. No money will ever bring them back. The time lost was not worth it. It's the biggest regret in my life that can still bring me to tears as a write this. I would give up everything to go back and tell my younger self to change that one fateful decision.
Family and children eliminated thoughts of my “unlived” lives.
Life is hard. Focusing on gratitude helps me be thankful for what I have instead of thinking about what may have been.
I think the fantasy of going back hides the reality that new possibilities are always stretched out ahead. I have lived many lives. New careers, new cities, new countries, new friends, new families. By my count I’ve lived 14 iterations of life and counting. New lives are always beckoning. After awhile you get good a recognizing the ones worth stepping into.
My life turned out alright. Full of problems, pains and questions like everyone's else's but, in the grand scheme of things, I'm incredibly fortunate given the amount of poverty and misery in this world.
I always liked the thought experiment of living my life again. However, I'm much more interested in the thought of living in the future. If I could do it again, I'd take the risk of living 1000 years from now. I know this could be a mistake, but I'm an optimist.
Once upon a time a certain someone wanted to come over,in reality I had to decline, but in an alternate timeline she does. We have fun, she decides to keep it, but signs over custody to me. Our daughter is a musical prodigy. With her sights on Juilliard.
I can play out a similar scenario with quite a few slight variations. But this what if stuff is almost always positive.
It's never what if I never downloaded Unity and taught myself to program.
It's never, what if that eviction was a bit faster.
For most of us reading this our lives are modern miracles. I came from nothing and I've made a comfortable 6 figure salary for a decade.
Be content with where you're at, you will never have everything you want.
I believe that our "success trajectory" is something like 10-20% our own choices and 80-90% pedigree / where we start from. And probably some percentage of "other luck." So I don't really think too hard about doing it over because I don't feel like I've made many really bad decisions. I've gotten about as far as I could have reasonably expected, given being born to a family of school teachers living in a rural middle of nowhere, where success meant getting a decent job at the local mill. No do-over would make my father a rich, well-connected businessman. No do-over would get me into Phillips Exeter Academy as a high schooler and then Harvard or Yale. No do-over would land me in Goldman Sachs post-graduation. So I really don't dwell on what might have been.
If I could go way farther back in time and bend my entire family tree's trajectory such that I started out on 3rd base, that would be a different story.
If you had perfect future knowledge (which is what this article is really about) you wouldn't want to invent Slack (or Google), which lets face it would have been a ton of work with a very uncertain outcome. You'd want to invest in Slack / Google at some early stage, do no work whatsoever, and enjoy the proceeds.
There's a great book called Replay that tackles the ground hog day problem but at a life scale. I read it every few years and it always gives me some perspective about what is truly important in life.
https://www.amazon.com/Replay-Ken-Grimwood-ebook/dp/B0F9MY5M...
I "died" in 2018 and it felt like waking up from a dream. This world just melted away like an amusing afterthought. That helped informed my attitude to life: enjoy it, make life enjoyable for others, spread love.
>For some people, imagining unlived lives is torture, even a gateway to crisis.
I was either born without the gene or raised to not do this for myself but I do, quite often, dwell on the unlived lives of people I knew who were never given the chance to live their lives.
My best friend was murdered at school when he was 16. In the Army there are several guys I considered to be "old men" at the time who I am now decades older than.
Now I'm the old man.
Others have taken their own lives or had it stolen from them by drunk drivers or disease.
But me? I just happily (for the most part) stumble through my own life, knowing the past is immutable.
The utility of "what ifs?" seems very low when looking at the past.
The present is a different story, but the convoluted fantasies people seem to build in their minds about going back and marrying that person or taking that risk seem futile because anything you create in your mind is as real and likely to happen as a myriad other options and knowing how that path would have unfolded is impossible.
"I would have been happier/better off/more X if only I.." No. That is unknowable.
Yeah. Go back in time and invest in a sure bet. You got fabulously wealthy and Very Important but ended up dying in your comfy first class seat sitting next to the cofounder of Akamai on 9/11.
"No with my time machine only good things happen"
I have always found this question haunting. I would imagine if I had the ability to forever banish a single though from my head, this would be it.
One thing I wonder is that - assuming no extreme personal calamity - I would be just as happy/sad/depressed no matter what life I had led. How much of our inner sense of well being is determined by outward life circumstances. Living in the first world and working in the tech industry, I live better than 99% of the people that ever lived, including all my ancestors. What’s really crazy is that I’m not insanely happy all the time with my incredible good fortune. It seems that no matter what I got from life - I’d calibrate back to where I am now.
I stand for every decision I made even if they were not perfect from current perspective. I can compare starting conditions of other kids from same school and I must admit, I am doing amazingly well. I am pretty sure I don’t want it to do all over. The future is more exciting. It became clear, I can’t pull all alone patient monitoring startup and I need to do something simpler during the time I have. I rolled the dice and let’s see decade later if it worked out. It’s so exciting!
Reading the article and the comments I free-associated to Treebeard from Lord of the Rings:
"Still, I should have liked to see the songs come true about the Entwives. I should have dearly liked to see Fimbrethil again. But there, my friends, songs like trees bear fruit only in their own time their own way: and sometimes they are withered untimely."
The real question is how much of my current knowledge would I take with me? If I don't get anything, all I'd do is repeat everything again.
The next is what the restart age would be... Too young and I might get myself killed by a vengeful father.
If I could go back to somewhere around my 20th birthday, with all I know now. Technology wise, I'd do everything I could to make sure Email was autheticated, zero terminated strings were abolished and get a BitGrid chip made.
Oh... And HTML would definitely be a language for the separate addition layering of hypertext markup, instead of the crap we have now.
I question whether the author's story about their mother's farm stand is really about unled lives in the past sense. They seem to be telling a cautionary tale about it but his mother was trying to change her future life in the present. I don't think that warning about dwelling on possible past lives and suggesting you shouldn't make changes in your current life are the same thing.
Probably relatedly though, I never really think about how things could have been and yet I am haunted by disatissfaction (despite having a great life) and always looking for how I'll change myself or my situation (work mostly) going forward. Maybe these are two views on the same neurosis.
Hope I’m not too off-base here, but reading this really hit home as i recently decided to make some drastic changes.
I get it, life throws different stuff at all of us. I’ve had more lemons than I ever asked for. But for me, it’s not about living in the what-ifs. It’s more about asking how can I?
Sure, we all think about starting over or going back in time. But for me, those thoughts usually fade when I ask myself: Why not now? Is it really too late?
What helped was letting go of regret.
Just my two cents: drop the what-ifs mindset. If something needs to change, don’t dwell on what could’ve been. Ask yourself: How can I make it happen now?
Once, in another life, I was a tech founder. It was the late nineties, when the Web was young, and everyone was trying to cash in on the dot-com boom. In college, two of my dorm mates and I discovered that we’d each started an Internet company in high school, and we merged them to form a single, teen-age megacorp. For around six hundred dollars a month, we rented office space in the basement of a building in town. We made Web sites and software for an early dating service, an insurance-claims-processing firm, and an online store where customers could “bargain” with a cartoon avatar for overstock goods. I lived large, spending the money I made on tuition, food, and a stereo.
In 1999—our sophomore year—we hit it big. A company that wired mid-tier office buildings with high-speed Internet hired us to build a collaborative work environment for its customers: Slack, avant la lettre. It was a huge project, entrusted to a few college students through some combination of recklessness and charity. We were terrified that we’d taken on work we couldn’t handle but also felt that we were on track to create something innovative. We blew through deadlines and budgets until the C-suite demanded a demo, which we built. Newly confident, we hired our friends, and used our corporate AmEx to expense a “business dinner” at Nobu. Unlike other kids, who were what—socializing?—I had a business card that said “Creative Director.” After midnight, in our darkened office, I nestled my Aeron chair into my IKEA desk, queued up Nine Inch Nails in Winamp, scrolled code, peeped pixels, and entered the matrix. After my client work was done, I’d write short stories for my creative-writing workshops. Often, I slept on the office futon, waking to plunder the vending machine next to the loading dock, where a homeless man lived with his cart.
I liked this entrepreneurial existence—its ambition, its scrappy, near-future velocity. I thought I might move to San Francisco and work in tech. I saw a path, an opening into life. But, as the dot-com bubble burst, our client’s business was acquired by a firm that was acquired by another firm that didn’t want what we’d made. Our invoices went unpaid. It was senior year—a fork in the road. We closed our business and moved out of the office. A few days before graduation, when I went to pay my tuition bill, a girl on the elevator struck up a conversation, then got off at her floor; on my ride down, she stepped on for a second time, and our conversation continued. We started dating, then went to graduate school in English together. We got married, I became a journalist, and we had a son. I now have a life, a world, a story. I’m me, not him—whoever he might have turned out to be.
Damn, that was a good opener.
I would live life exactly as I've lived it so far. The thought of my kids not existing in an alternate universe is too painful to endure.
I wouldn't want to but if I could I would move away from the city much younger. At birth if I could arrange.
No, thank you. One ride on this carnival crazy-house-of-mirrors and illusions is good enough for me.
What’s that rule about question titles?
No. unless you also change my starting conditions.
I'd not invite partner #1 to move in. I'd quit job #1 sooner. I'd try to keep job #2 going longer. I'd not take job #4 at all.
I wouldn't date partner #5. That probably says something huge.
My mid life has been by design and its going great. My father had a lucrative career at the significant cost of family time. I'm around and engaged in being a dad and husband. I got into software because it offered great work life balance and its relatively easy and fun. That said, I'm the type of person who has a hard time not working into the early hours if I get caught in a problem. Sometimes I wonder if that's truly nature or nurture from watching my father. I take issue with companies that force that lifestyle on me though.
The other day we went for ice cream after dinner out and movie. I can't tell you fine people enough how much of an accomplishment that felt to me. It's something so simple it must seem ridiculous. I never wanted big money. The cost is simply too high.
Honestly I wouldn't change much. I think I'd have kept some relationships going that I let fizzle away. I would have done more academically earlier in my life. But otherwise, I think I've made good decisions, served my family and community, and done work that I'm proud of that I feel is morally and ethically defensible. Had I done things differently, I would hope I could have done more to give back than I have done in this current life, but at the end of the day I'm pretty happy with where I'm at.
I felt a strong resonance with the line: “If I had made a different choice back then, how would things be now?” It’s a question everyone has asked themselves in some quiet moment. I remember when I was going through a tough time in my entrepreneurial journey — I felt like I couldn’t go on, crushed by the weight of it all. In those moments, I always thought: if only I had chosen differently, maybe I wouldn’t be suffering so much now. But when I got through the crisis and found some success later on, I would look back and think: I’m actually glad I made those choices. No matter how our other parallel selves might be living, there will always be some regrets. Regret is simply a part of life.
I would be less of an a*** and a bit braver, but otherwise mostly the same.
https://archive.is/pbWhS