It’s the not-knowing that is the most haunting.

I know I’ll never be able to take martial arts; I have made peace with that.

I know I will never be an amazing athlete; I have made peace with that as well.

Same with my body composition: I will never be rail-thin, I will never “fit” into most “fun” cars even when I finish my weight loss journey, I will never be the kind of guy who can fit into a Medium of anything clothing-wise. I have made peace with all of this.

But what of my dreams of homeownership? If this apartment is the best I will have, then knowing that at least lets me cherish it properly and redirect those savings toward a more immediate improvement in life.

What of my dreams to find a partner? If I’m going to spend my life single and unwed, then I’d at least like to know so I can make peace with that reality and focus my energy on friendships rather than dating.

Yet if I knew whether something was guaranteed, I would not take the risks to achieve it. I wouldn’t meet new people and learn more about my own flaws or strengths in pursuit of a relationship. I wouldn’t have evolved my tastes in food or drink, diversifying away from sugar-laden American foods in huge portions towards curries, and cocktails, and rice, and stir fry, and gyros, and even - dare I confess - salads.

Perhaps I need to make peace with the fact that some dreams are worth fighting for until the bitter end, never knowing if they’re achievable or not.

I really appreciate the article and responses here. This is a topic that resonates with me, and is something I often struggle with... my early dreams were to be an ecologist, wildlife biologist, or conservation scientist, along the lines of Jane Goodall, George Schaller, or E.O. Wilson. Life circumstances and choices I made early on diverted me from that, and I ended up in a relatively comfortable, tech-focused career. I have a loving family, live in a beautiful area, have great friends and my income is good...

And yet I still wrestle with "could-of" or "should-of" thoughts about my life. It's tiring, and often detracts from my well-being and happiness.

I turned 40 the other day.

There has been unrelenting reflection on where I am and how I got here. A lot of lament for a small handful of decisions and a life marked by avoiding uncomfortable decisions. I don't know where the last 20 years have gone. Last I remember, I was playing Wii in my friend's basement. I remember the seemingly endless opportunities nights laid out before us. DVDs and pizza and furious laughter. I remember waking up in strange places. I don't know when that all ended. It ended.

I had a friend describe middle age as suddenly being able to see the outline of the cage. It's apt.

I'd have liked to have gone to a real college, had the college experience. I'd have liked to have mended friendships.

40 has such a strange loneliness to it, I take solace in my children. My friends had children years before me and it made friendships tiring. The age gap in our children now that I have my own has not helped.

I spent much of the last decade collecting retro video games. I have a room full of them. It came to me recently, I don't think I actually enjoy games. I enjoyed playing them with friends, but by myself they're hollow. I don't play games with friends anymore. When my kids get a little older we'll have fun.

I've had Damien Rice's "Older Chests" playing in my head on repeat despite my best efforts to drown it out.

I am in therapy, but I think I have just too strong of a mask for anyone else to truly pierce.

I'll get out of this funk eventually, I should take this as a wake up call.

I read the article and fight with this from a different angle.

My son was diagnosed with cancer at 3, then during chemo it became abundantly clear that he had far more severe autism than we originally thought. Could have been made worse by the chemo and trauma; no real way to know.

Now my wife and I have had to give up all the dreams we had for when I retired from the military. A few good moves means that I actually retired at 40, though more modestly than I planned. But we will forever be taking care of him.

So we struggle with the unlived dreams often.

I have an understanding/interpretation of the philosopher Kierkegaard's metaphor of the Knight of Infinite Resignation from his work Fear and Trembling [1] that relates to this.

He tells the story of a Knight that falls in love with a princess. In the olden days princesses were married off by their parents for political reasons. There is no way his love, even if it is returned, can ever be fulfilled.

So the Knight resigns himself and marries the butchers widow. After all, she is pretty enough, she has inherited a profitable business from her late husband. And she will be elevated socially by a marriage to a Knight, so she is very keen.

But the Knight has to resign himself constantly, like in the dead of night while lying in bed and dreaming about what might have been. He must avoid falling into resentment and maintain the strength of his will.

This is a central concept to Kierkegaard, started in Either/Or and continued in Fear and Trembling.

1. https://en.wikipedia.org/wiki/Fear_and_Trembling

We have to distinguish "our" dreams from, let's say, cultural ones. A lot of what we want, what we perceive as living a full life, having fun and so on comes from culture (and increasingly in the last decades/centuries, with mass media).

Besides that, we can't achieve everything, we could not be everywhere when something interesting happens there, at the very least because a lot of those things happened in the past, or do everything because physical condition, economics, or extra conditions (i.e. being an astronaut).

So you draw lines. This is what I can do, I can go, I can be. You may push boundaries, but in the end it will always be more things outside than inside. And try to be the best on what matters on those boundaries.

Reading many comments here, I feel like there is a dimension to dreams that hasn't been emphasised enough: community/social dreams.

Post-COVID, I made an conscious effort to be more social, and take on more community activities, like doing Improv, making games for friends, and attending conferences just for fun.

By doing that, my dreams have become more of a broad North star: "I wish to keep investing in my community (family and friends, old and new), understand those around me, and thus myself".

Like others said, it's a qualitative difference when dreams are more of a path, rather than a destination.

When I was young, I wanted to become a physicist. The physicists I admired were people like Faraday and George Green. I was moved by the lives of people who, despite difficult circumstances, reached toward nature through their own curiosity and discipline.

But when I actually entered graduate school, I realized that I had not learned English well enough. I could understand books written in Korean, but reading papers in English was too difficult for me. During my two years in graduate school, I could not keep up. I eventually dropped out, carrying a large amount of debt, and began living in Seoul.

After that, I was scammed and began my career as a programmer under bad conditions. I was cheated over rent, and then my first development job started at a Korean dispatch-development company where my experience was inflated and I was registered not as an employee, but as a subcontracted development business owner. Because of that, I could not receive severance pay.

I have paid off all my debts now. Still, what I became was not what I wanted to become: a single man in his mid-thirties, with no house of my own, no rented room of my own, and freelance work that has been cut off since May after the Iran war disrupted the market. I did not want my life to turn out this way. Even so, in my own way, I live with a certain contentment.

In that sense, I am always grateful to programming. Whether the code was written with AI or by my own hands, the computer has never betrayed my expectations.

These kind of articles remind me of an article in Polish I read few years ago: "Millennials are a generation that has fallen into the trap of constant self-development" It helped me to deal with my own unrealistic and unrealized dreams/aspirations/etc. Here's a version in English done by Google Translate https://archive.org/details/millennials-are-a-generation-tha... The original article in Polish: https://weekend.gazeta.pl/weekend/7,177344,30226401,milenial...

my son recently got into skateboarding which warmed my heart because i use to dream of being a pro-skater at his age. I dug out my old board and have gone to a few skateparks with him. Seeing a vert ramp was like seeing an old friend, i'm doing a lot of core and lower body workouts to see if I can get in a few more runs. There's one trick i've never been able to do and this is my last shot (I'm 50). After this summer, the cards will be on the table and, hopefully, I'll stop thinking about it hah.

> And yet, somehow, the more years go by, the more rarely I watch snowboarding videos.

I'd argue that snowboarding wasn't author's "dream" to begin with. I think it's reductive and unfair to compare your "oh it would be cool to do that" with someone else's actual dream: as in, a passion they pour their life and soul into. Being great at anything takes much more than a passing "it would be neat to be able to do X."

And achieving a dream (say, competing at the Olympics) is a lot less glamorous than a casual tourist might imagine.

I think I will always get more fulfillment from the rush of leaving work a bit early on a Friday afternoon, knowing I have a couple of plans for the weekend but not being too busy, picking up a treat for my wife and I on the way home, when the weather is good (cool and crisp or partly sunny and dry), and the city is alive; I will get more satisfaction from that feeling than any "dream" I could imagine.

I took this article to be more along the lines of the author perhaps loving the idea of being a snowboarder, rather than actually becoming one.

I know it sounds a bit cynical but I think that's the case for me in a lot of ways: I love the idea of being able to play the piano. However, I've given it up many times (I'm 51 now).

I think I just prefer the idea of being a piano player but when it comes down to it, I don't have the willpower/dedication/motivation (delete as appropriate) to follow it through.

My 15 yo son, on the other hand, is hell-bent on becoming a pro hockey player (not necessarily the NHL but that's the goal, of course!) and he's working his ass off 6 days a week at various aspects, and missing out on stuff like playing football down the park with his pals after school on a Friday coz he has training).

So, I think for some of us there is a disconnect between the desire to work hard anc become something, and liking purely the idea of being something... I think they're quite different (for me they are!)

Having kids really helps with making peace with unlived dreams. You simply are too tired to even think about those dreams. You are lucky if you can get one night of good sleep —- and trust me a good sleep when you have kids is different from a good sleep before that.

One thing I’ve learned over the years is that dreams are often just that, dreams. Once they are realized, many will not live up to the expectations.

Managing your expectations plays a big part.

So at least for me, that knowledge has helped. Another discovery I made, was that some of my best experiences and decisions have been by pure chance. Things I never planned to do, or had any desire to do, but turned out to be more than I could ever imagine.

It’s ironic how some things you plan for your whole life, but never get to do, while some things you never planned for, ended up overshadowing those initial dreams.

And lastly, many things in life is like a bus stop - there’ll come another bus if you just wait.

In my professional life I chases “prestige” for the sake of prestige, and ended up hating those things.

Of course, there are things I really wanted to do, but never got the chance to, and I’m too old to do now, but that’s just something I’ll live with.

My FOMO and regrets plummeted as I started approaching 40.

A life well-lived is really what we should all hope for. What that actually means varies by person.

Sitting and thinking for 10 minutes about snowboarding when your knees are blown out is 10 minutes you could have used differently.

Everyone has regrets but my attitude is: I can’t change the past, but I can change the future.

The trick is to widen the scope of what you means.

If it means, us and we, then we are pulling 1080s. The dreams become what we can achieve. When anyone broke the 2hr marathon, we were happy for us. We did it, we landed on the moon. We ran a 4 minute mile or summited Everest w/o oxygen. Dreams are a dance and we have to figure out how to include ourselves and others dynamically.

One of the best lessons I've learned was that the happiest I've been (so far) was a time when I was dirt poor, while chasing my dream that everyone assured me ends in poverty.

Things have changed, but it takes some of the financial anxiety away when I remember that I would still give up everything to go back to that time.

Dreams can come to a sudden halt, and as Walt Lawrence, John Callhan and Mark Zupan have demonstrated, it strengthens the reinvention and creative problem solving muscles.

It's common to hear folks in these situation saying that the "tragedy was the best thing that happened to me"; when I was young, I didn't really believe it, (watching the documentary of Walt Lawrence or reading John Callahan's book 'don't worry, he won't get far on foot'), but now that i am older, i can confirm it is definitely believable :)

As someone that has done snowboarding and skying in Central Europe, the paradise of snowboarders and have been friend of profesionals, you probably don't want to be one of them.

It is one thing to go carving whenever you want, where you want because you have a good job outside it. Another totally different thing is spending all your time training. Most people will hate that.

Everybody wants to be a tennis player when they see one player raising the cup and earning millions. But a professional player spends most of her life doing extremely boring things. And only a very minority get enough money to live from the sport.

Fascinating comments on this post. I recommend everyone here to read a lesser known philosopher: Baruch Spinoza. It is one of the greatest thinker of our time, but it is unfortunately not the easiest read you will find in the library. Reminds me in some ways of Penrose’s Road to Reality, which is a life project in and of itself.

> Sometimes, dreams can just be dreams.

If (for any reason) we know that dreams cannot be achieved, there is a clear cut. And while it might take time to accept the situation, this realization is Stoic/Zen.

It is way harder if there is a chance, we try, yet fail. When do we keep trying, and how do we do so without losing hope piece by piece? It might be even harder when the dream is not something like "win a gold medal in snowboarding", "build a unicorn startup" or "publish a bestseller". But it is in the line of having kids, or being healthy, or other things that a lot of people take for granted.

I don't dream or care about things I definitely can't do.

But there are still so many I can actually do that the opportunity cost of choosing any single one of them is infinite, and that leads to paralysis at worst and diluting your self while half-assing dozens of things at best.

Maybe one of them pays the bills, and even a nice house and a decent car. But it's just that, it is not what you really wanted to do, so you keep searching.

The "gift" of being a fast learner becomes a curse. In a few weeks you are an advanced beginner at almost anything. People marvel at how well you are doing, but you know you have just started and can now see how far you are from being any good. But to become good, you'd have to leave behind all the other things, and you can't pick. So you just start a new one for the quick dopamine hits and easy praise...

And then you are 50 and still don't know what you will do when you grow up.

There is irony in "wanting" something:

achieving it depends on different qualities than what starts to ramp up once you are strategically trying to get what you "want".

Suddenly your perception does not come from exploration, genuine interest or the human part. It starts to come from paying attention, sensitivity to setback, monitoring yourself in what you believe will make you achieve what you want, strategic behavior that isn't "natural" and attachment to a very specific outcome.

It was very hard to see this, sometimes you have to feel and be less analytic about stuff, then your perception will open doors as you walk through life, because deep down you were never attached to a specific outcome and therefore don't limit or sabotage yourself with what your beliefs about the world are at that time.

"Becoming a great snowboarder" is operating on a very different layer compared to "I really like snowboarding and then I somehow showed up over here and everyone here tells me I am a great snowboarder". Even being in this situation introduces perception that you may not be "a great snowboarder" at some point, which makes you become analytical about it.

I had the same mindset about wanting to be good at a lot of things, working on myself, not "wasting time", but now in my mid thirties I figured that if I really wanted to do something, I'd be actually doing it, and a lot of these goals boil down to "it would be cool if I was good at X", and aren't actually things I care about.

Japanese here. Took me years to stop looking up and wishing for what I'll never have, and just accept this is the body I've got and live with it fully.

I don't even follow baseball anymore, but every now and then Ohtani (the Dodgers guy) is in the news and the kid who dreamed of it is right back there for a minute. Not painful, just bittersweet.

I would love to be a star ship captain in a universe with faster than light travel. Or a surgeon. But you know actual life is good and I do enjoy watching DS9 with my young adult son, Benjamin. And reading about all the other cool things. It is better to live an imperfect experience than just wish for an ideal imagined experience. And better to act wrongly than to be right but do nothing.

To me, putting up a fight against the obstacles is the key to satisfying life. Yes, I'm not always winning (duh!), but it is the act of defiance that does it for me.

So yes, make peace, but do continue to say "I can do it" before you do.

I just finished reading Four Thousand Weeks and this post resonates with me a lot. I recommend it. Despite its subtitle, it's decidedly not a conventional "time management" book, just a reminder that life is too short to do all the things you are wishing for today, that the day where you'll finally find the time to tackle that project will never arrive, and freedom is found when you just drop all that hope and need to control your life.

Actually I think poorly imagined dreams is a big problem.

People who have poorly imagined dreams are likely to screw up their working life and their retirement too.

There is more that you can pull off during your working years. As a matter of fact, you SHOULD. instead of sitting in front of the tv this weekend, go somewhere.

And in retirement, there is probably less you can pull off unless you focus and make it your job. You should do vigorous cardio, do strength training, connect with people more, not less. and make a good healthy retirement your job.

As I always say - do what you will regret NOT doing once you are old.

I wanted to join the army as a kid, was infatuated by the forces. I had memorised spec-sheets, obsessed over the operations and used to be awestruck everytime I saw someone in olive green. Tried out a couple of times in college and was deemed medically unfit. I tried again last year but didn't make the cut either. Now I have crossed the age limit and will remain a code monkey for the rest of my life.

Nothing too bad. The life I live now is so much contrasting than the life I promised myself as a kid. I still have other hobbies and I still read a lot about the forces.

There is a strange grief in realizing that even a good life necessarily excludes almost all other possible lives

Appropos of nothing, snowboarding is so unbelievably fun once you’re past the immediate beginner phase of painfully flip-flopping down a slope, that it’s very reasonable to be a tad angry at not being able to live that dream.

This article reminded me of this game called "Before your eyes" that is sort of tackling this same theme of unlived dreams. That game helped me realized that I will definitely not achieve all of my dreams but it also gave me the power to pursue them anyway.

I love that game. It's a 1-2h hour long game that I recommend everyone to play (and it's kinda a unique game that use your blinking as a game mechanic)

“I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked. One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn't quite make out. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn't make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.”

One of my favorite quotes by Sylvia Plath from the Bell Jar.

No way, dreams don't have to be realistic, that is what makes them dreams not goal or checklist. And I miss the time I still had any.

> You know what else I’d like to do besides becoming a great snowboarder? I want to learn kung fu. I’d also love to be a lot better at video games, get my Yu-Gi-Oh! hobby back on, and become at least fluent enough for everyday conversation in oh, I don’t know, eight more languages.

I think this sort of underplays the feeling of "lives unlived, paths not taken" that everyone gets hit with. Just flattens the whole thing that had been building up to that point, instead of allowing it to open up further.

Dreams are a attack vector on the young, used by exploitive industries. Life-experiences hardens you against all things. Adds, Rockstars and Models..

Having dreams tethered to physicality if you are not physically gifted(Snowboard champion) and/or dependent on gate kept power structures allowing you in ("famous" film director) are dreams built for disappointment if you don't meet the required pre-requisites-

This is why the realms of art and creativity are great substrates in which to plant the seeds of your dreams in-

IF your dreams are to make/create things nothing can stop you these days except yourself with all the tools and knowledge available now- you can't control the outcome after you've made the thing- but the happiness and joy comes from the excitement of the happy accidents on the journey and the pride of completion of course-

I'm an artist/filmmaker/animator/dev/musician and the best moments of my life are still from creating things that almost no one sees- they get no acclaim- they win no awards- almost no one cares- but that doesn't matter as the joy comes from the creation- I'm happy with the works I create-

If your dream is to write a book, write a song, make a film, make a game, create a piece of software/useful tool, make a painting etc- the skill and budget required for these things is lower than ever-

That is not to say it has been cheapened- especially with "AI" tools-

Idea is always king- always use your original ideas- never "AI" suggestions and the things you make are yours, forever.

Absolutely ZERO of my dreams will be unlived, except the project I won't finish because I will die while it is progress- so I'll die happy anyway doing the work I love (shrug)

TLDR: make realistic dreams that depend on your willpower and creativity not your physical attributes and you will live all your dreams except one.

I took running fairly seriously for six or seven years. I never really enjoyed it, but I ran religiously every week. I went from barely being able to run 1/6 of a mile without walking, to being able to finish a 5k. I ran a couple of local fun runs. I was never particularly good at it, but it was a real part of my life.

Two years ago, I slipped in a puddle on my bike and wrecked my ankle. There were many complications. Four surgeries later and I now have two pieces of titantium and a little slip of ultra-high molecular weight polyethelene (very strong plastic) where my ankle joint used to be.

I can never run again. Technically, at some point when I'm recovered enough from my last surgery, it should be possible. My surgeon said, "if you need to catch a flight or dodge traffic, sure". But I can't ever go out and run miles. It will just wear out the implant too quickly. The plastic can literally crack.

When I was recovering from surgery #3, my physical therapist told me to start walking regularly and keep track of distance. The first time I did, I opened Strava. All of my old runs popped up. I realized with a shock that I could scroll down and see not just the longest run I ever did, but the longest I ever will do.

I have dreams sometimes where I'm running, gliding across the ground effortlessly and painlessly. Usually, at some point I remember, "wait, you're not able to run anymore, you must be dreaming", and that tends to wake me up.

When I drive around the city, sometimes I pass places that used to be on my regular running routes. I remember what it felt like in my body to pound my way down that sidewalk, over that bridge. At first, these moments felt like a stab in my heart. Like a little part of my soul was being ripped out. Over time, that sharp stab faded to an ache, and then something more bittersweet. I lament that running is no longer part of my future, but I am at least grateful that I did run for a while. That chapter of my life is in the past, but at least I wrote the chapter.

For a long while, I was afraid I had lost much more than just running. But it seems like maybe the chronic pain is better and I will at least be able to walk and hike and dance without debilitating pain. But the running is over.

Losing a capability like this feels sort of like a fraction of death. Like a slice of my personhood has been amputated. It's made me realize that for most of us, the final chapters of our story aren't going full bore until the last page. Instead, aging means incrementally giving up more and more ability to do things, and accepting that more and more of our story is written and less and less is left to write.

It's still a struggle to accept that with any level of grace. I get where the author is coming from.

There is an analogy to be made between the space of human possibility and the space of possible Turing machines: in an unconstrained machine everything is possible and nothing is probable. If you accept constraints (e.g. the shape of a language) then most things become impossible but some things become probable. That is you gain access to some space and lose access to other space. It's a very fundamental trade-off and it's foolish to worry about it too much, especially considering that there is always some level of zoom where every hero, every winner of every game, is irrelevant.

Indeed the underlying insight that our lives are arbitrarily small and irrelevant, (yes, even the greatest titans of politics, tech, science and art), that drives the tech-elite long-now accelerationist ideal. Every life is characterized by [trade-offs + luck] and none of them have any meaning unless we get through the Great Filter. (Sure, this belief is mostly a post hoc rationalization to just do what you wanted in the first place, but I appreciate the attempt to paper over the naked self-interest.)

> given my orthopedist told me to stay away from anything that’s heavy on the knees, “like tennis, skiing, or, say, snowboarding,”

Obviously not knowing the background of this person, maybe they really have bad knees, but without more info, they could simply have an orthopedist that says this to all his clients, to help all of them not have problems in the future - no matter the current state.

I have decided long ago to not let anyone, especially experts, dictate what I can and can't do.

Ime with sports and injuries. Doctors say alot of things, unless they are sports doctors that work with you to get back to sports or athletic them selves, they just give useless generic advice.

I lost a year becasue of doctors just telling me to rest for a constant pain I had.

Author should just go learn to snowboard. There's athletes out there competing with torn acls.

Have you thought about absolutely monster knee braces? And then daily squats. They worked for me. Unfortunately now it’s my neck that’s trying to paralyze me, which would be such a not fun outcome.

Making peace with the lived ones might be harder. Chasing the startup dream ended in bitterness, disappointment and debt. It forever damaged my marriage and my mental health. Be careful what you wish for.

Never let your memes be dreams nor your dreams be memes.

Desires are severely overrated. The more you get the more you desire. The more you know the more you desire.

You can only get some of it. But you also only need some of it.

The key isn’t to get more. The key is to practice quietism about all the “unrealized” and eventually equanimity.

And there is still room for discontent and rebellion. But with more quietism there is more space to focus on those few things you can indeed change.

For the record, snowboarding is not hard on your knees, not like skiing.

You guys have dreams?

As someone with less than stellar knees who skis a lot, ski/ride powder. It's way easier on the body and more fun too. And maybe skip the big jumps. You can definitely still ride big/steep enough mountains for a big adrenaline rush.

I struggled quite a lot with this. I want to do everything, learn everything thus I ended up mastering nothing.

I've learned to play few instruments in last four years so I can jam with people but I still feel it's not enough.

As I got older I started to value relationships much more and overall became a happier person.

But still the knowledge that I never be a skilled doctor, physicist, exceptional chef, biologist, blacksmith, economist, successful entrepreneur and many more will still somehow hunt me.

Just wait till you forget to have (more) kids then you’ll really know regret.