You'll never satisfy a need of something that has no limit, being around rich people will show you that. Two houses, three cars, the best schools for their kids, vacations in the best places, they're still miserable and most of them still work as much if not more than employees, if anything they're even more miserable than the average person because they live in fear of losing it all. Once you unlock the next level you discover it's just as empty as the one you came from, some people are too proud to acknowledge that and keep on climbing, they'll be miserable all the way to the grave because you don't cure that by accumulating goods

Take a break, breath in, and ponder on the reasons of your fears/desires. You might very well be sabotaging your well being in a futile quest for wealth, you can't lose the game if you're not playing it.

On top of that I'd say if wealth is your goal the best way to never get to it is to chase it directly. You can go through 20 startups creation, if your sole goal is personal wealth you'll most likely miss the point 20 times

> Life is well enough furnished, but we are too greedy with regard to its furnishings; something always seems to us lacking, and will always seem lacking. Seneca

It's not about cars, houses, best schools and vacations - it's more about having the freedom not to work, but spend time doing what you actually want, or doing nothing at all.

This whole "money isn't worth it" story seems like a coping mechanism for people who've somehow made peace with being wageslaves for the rest of their lives. I'll never make peace with it, either I'll stop being a wageslave one day or I'll die trying.

It eventually comes too easily to be worth the pain.

Meaning has to come from somewhere else.

Jim Carry said it well with “I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it's not the answer.”

How long can you go without working before being completely broke? If the answer is indefinitely, then congratulations, you're rich. Otherwise, you're a wageslave, since you have no choice but to keep working.

I know, I know, you can be forced to work and still enjoy it. But you can also enjoy rape, that doesn't make it universally good.

> Money can't be the reason you do things.

Money is not the end, money is the means to an end. My end is to live a life ungoverned by the system in which I have to spend the third of my life doing whatever someone else tells me to. For that, I need enough money not to need a job.

It is, by proxy. However, breathing, eating and sleeping are activities that don't require much effort, and some of them are in fact pleasurable due to our biological imperative.

Work, on the other hand, is rarely pleasant - you have to be lucky to have a job you actually enjoy, the real world work is full of pointless bureaucracy, goals that don't align with your beliefs, repetitive boring tasks, synthetic deadlines, and so on.

> Sure, it would be amazing in many ways, but perhaps a tad unrealistic?

There are people out there that have enough money not to work, so it's not that unrealistic.

> But we can choose whether to feel gratitude for what we have or feel jealousy for what we don’t have, and it’s probably obvious which course is healthier IMO

Feelings, by their definition, are not voluntary. I don't believe I can simply "choose" how to feel.

Feel free to grind for that sweet $1m but until then you're an equal slave to all of us, if not more. I have enough money and time to sustain my hobbies, actually too much of both. The only way I'd give up work is to go build a house somewhere rural and become self reliant, which arguably I could do very soon, but it would probably be more work than my job's work

I also thought not working and doing whatever would be the dream life, I've done it for a year, it gets boring real quick, quicker than I expected.

Source: I am not a wageslaver and I am in top 10% of Income earners in America and I am telling that you cannot just chase money. Chase your dreams of doing something that you want to do and money is always the side effect. OP seems to be focussed on the wrong thing.

You also cannot just chase your dreams. Many people have tried and failed miserably. You need money in order to be able to chase your dreams.

I see your point, but both sides are kind of extreme - both the "money is meaningless" and "money is everything" - neither are true. Money is a necessary means for chasing your dreams, but an insufficient end in itself.

Step 1: start a business that can run itself

Step 2: profit

So easy! I wish I thought of it before.

That's a very personal definition of money

I enjoy waking up late, quiet enjoyment of nature, listening to music, and unstructured enjoyment of various hobbies.

Unfortunately, none of those are particularly lucrative activities.

So I'm forced to chase money by doing things I don't enjoy.

How exactly does this work? Is there some divine comedic rule that prevents you from attaining money if you specifically desire it? Is it somehow a sin that you will be punished for by not having it, like some sort of modern man's version of Tantalus?

Many people who just want to get rich do indeed get rich by specifically having that as a motivation, and they might even lead decently happy lives as a result. Not being guided by some "higher purpose" as a motivator in life doesn't make you a less worthy person, or one especially less likely to succeed because wealth (and the freedom to do other things it usually brings) was your main milestone.

The grass is always greener on the other side, so one often romanticizes forgone opportunities because they represent an ideal world where you see only the upsides but not the downsides. So my advice is to keep looking for your upsides and don't over-idolize what could have been. And try to seek happiness and balance in what you do, in my experience these negative thoughts often came when I felt downtrodden and unbalanced, never when I had a good routine going and was feeling productive. Another thing: If you feel stressed out by seeing other people succeed and thinking "why not me?" just stay away from social media (including HN) for a while, being constantly bombarded by awesome success stories can have a really detrimental effect if you're struggling with your life already.

Unless you are really struggling just relax. Getting rich won't get you happy ever. If money is a constant problem that is a difference. But I have seen stupid rich people argue over peanuts as if they were on the brink of bankrupcy — that existential angst will not go away with more money, if anything it will grow bigger as you have more to lose.

What counts is doing what you enjoy, making decent money that lifts your worries, spending time with good people both in work and in private, living in a place you like. Nobody will give you back your life once you are rich, and once you are rich that dream might become the thing you will spend your life worrying about.

Sure, speaking from a nation with universal healthcare and social security this is all a little easy to say, but if your goal is a good life there is such a thing as enough money. Too much money is poison.

If you feel really bad just remember it’s everyone. No one is hitting grand slam home runs right now. It may be years until we see that market again.

I thought with each move I would be in an ideal position to succeed and every time, something changed.

My experience is that the “carrot” always moved or doesn’t turn out the way I thought.

That product I thought would be a career game changer? Cancelled and everyone laid off.

I joined one company thinking it would IPO and then five years later and a lot of lying it still hasn’t.

I joined a AAA faang and made a ton of money for a little while then realized I wasn’t learning anything and boxed in, surrounded by lifers who were stagnant in their careers with no chance of upward movement.

However, you have to change your mindset for this market. The boom time is faded. If you missed it, you missed it.

This is the time to position yourself to maximize your skills and learning. You have two years to get in the right place.

Money happens very fast and randomly is my experience. If you join an ultra elite team the chances are way higher imo.

Now I’m entirely focused on my personal skills and charisma. I’m working entirely on my inner game now. I am going to maximize my learning the next two years.

And I am working on practicing becoming positive and energetic and getting in shape.

I don’t think I’ll ever afford to retire. Which maybe is completely wrong.

Now I’m starting to look at my life as a work of art like Rick Rubin. Rick never had a career in mind he just loved working on music and with artists. He tried every genre and made hit records across the board.

Maybe it’s a better mindset of just seeing your work as a series of records you are putting out. Some will be good and some bad.

How do you work on these?

Related: https://en.wikipedia.org/wiki/The_Pearl_(novella)

Related to regret: https://existentialcomics.com/comic/204

Just like sleeping with the prom queen, becomming a wonderchild, being a kid on star trek and maaaany more things that where on the way.

But that is okay and there are still plenty of experiences left for you and even though you might not have done so actively, you choose your activities.

Ignore the other doomers though, life is still far from done and who knows, maybe your actual calling is having an emu farm in the middle of Kansas.

Just trust in yourself that you have skills to put bread on the table and realize that EVERYBODY is just cooking with water and you can cry just the same in a Mercedes that you can in a tata nano

What this means is that you haven't missed the boat in any permanent sense. You've missed a couple of specific boats, is all. Others are always coming down the river.

It also means that you haven't failed. Every successful person I've ever met can talk all night long about the many times they've failed. But all others see is the few times they succeeded. Recognize that you're rolling dice and the more times you roll, the better the odds that one will hit. You've only failed when you give up entirely.

But it can be despiriting sometimes. What I do then is to get a nice, normal job for a while. That gives psychic relief, a chance to meet more people (opening the door to unexpected future opportunities), and stash money away into what I call my "bankroll" -- seed money for next venture once I've decided what that will be.

Read philosophy. Introspect. Do stuff you love.

You cannot compare yourself to anyone but a previous version of you. Even then, it's not helpful. You don't need a win. You need to find meaning/purpose. That's how you win constantly. If your only purpose is to make money or be "successful" by a material definition, I'm afraid you'll be stuck in the rat race.

Have you heard the fable of the Chinese farmer? You might find it insightful for your situation: https://www.craftdeology.com/the-story-of-the-chinese-farmer...

You know, there's something that (almost) all of us have to face.

If you're like me and failed to buy bitcoins when they were only a dollar each, how may other opportunities like that are you going to be able to miss in one lifetime anyway?

All these other missed opportunities are small change by comparison.

With that hanging over our heads you can get over anything, you certainly don't want it to be bugging you if you never get a chance for such outsized winnings again.

You can never control the outcome of your actions. Most of the times, "Failure" and "Success" happen by chance. All you can possibly do is to find joy in your journey.

You need to start asking yourself on what your Goals are in life ? Getting rich should not be the ONLY goal even though nothing wrong with it. Until you can find the answer to goals in life, you will struggle.

Hope this helps. Wanted to give it you straight.

Might make you rethink this "regret".

And everybody in the village says, "How wonderful! The boy got a horse."

And the Zen master says, "We'll see."

Two years later, the boy falls off the horse, breaks his leg.

And everybody in the village says, "How terrible!"

And the Zen master says, "We'll see."

Then a war breaks out, and all the young men have to go off and fight, except the boy can't because his leg's all messed up.

And everybody in the village says, "How wonderful!"

And the Zen master says, "We'll see."

So I clearly have no silver-bullet advice, but I say 20 failures sounds like a good start :).

There are very likely nuggets you've learned within these roles and projects that you may not even realize, but will naturally come forth and be applied in a future project. Just keep moving.

With respect to your self esteem etc... Journaling might help you figure things out. I would also look into therapy as well especially for the gambling if you think it might be an addiction. Whatever you learn there will help you in all areas of your life and startups.

Personally I take the lessons and write off the time, if I ever come across a time machine I'll fix it but until then it seems silly to pump more time into regret

What kind of side hustles were they? Wondering if there was anything in common that could make success less likely than usual.

Get rich is a shitty bet most people don't win.

If you are a software engineer your best bet is to go to Google, Microsoft, azure, LinkedIn or similar companies and just make really good Money

I'm not saying money doesn't matter cause it definitely does, but maybe you need to redefine your notion of success, without factoring in what those around you have done.

Getting away from gambling was also a good move. My wife is awesome, and she left her previous dude cause he couldn't stop gambling.

It is important to stay focus and keep looking forward.

And eventually, I managed again on something else some 20 years later.

I've chosen to be modest because it is a world-wide impactful outcome but not am not an attention seeker.

Stay focus and look forward.

Also, I'm trying again.

From your title I was going to guess you had a gambling problem, it's interesting you mentioned it. The two are related and you know.

Can't help with how to fix it, but perhaps identifying the relationship helps.

> Now many of them are leading very successful startups that I could've likely been an early employee at.

I'd guess you are only looking at the wins you missed, not the losses you also have missed. And by win, even in the right company you might have left early. When do you pull out of bitcoin, when it doubles to $4? This is all related to how you view the world. This won't help you, but perhaps it's something you can work with someone on.

Go check out Gamblers Anonymous. Not sure how you overcame your gambling but if you haven't been it might help. And at minimum it'll be interesting.