Ask HN: How to overcome regret by missing out on opportunities to get rich? | Hacker News Reader

Ask HN: How to overcome regret by missing out on opportunities to get rich?

46 pointshighwayman4756 comments

I definitely had some character flaws that I didn't fully overcome until my late 20's. Basically, I was incredibly insecure and this led me to always try to do things on my own. This didn't really change until I started jiu-jistu.

Anyways, I was able to get my first job out of college at a top university. I met some amazing people there. But really held back from socializing much, because I wanted to do well at my very menial job.

A couple times colleagues tried to include me on projects, but I politely just focused on my work. Now many of them are leading very successful startups that I could've likely been an early employee at.

I ended up working at 2 failed startups (I got from cold applying), and have failed about 20 times building a side hustle of my own.

I feel like I needed to go through some struggle, but I can't help but regret my choices. I need a win badly. I have worked very hard and built nothing. I also lost a lot of money gambling but have since quit.

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Acknowledging that material wealth isn't worth much was liberating, and I'm so glad it happened in my early 20s, people who never get out of this mindset must live miserable lives. You really don't need much to live an happy life, especially in the west and especially with IT salaries, if I could I'd work one day a week and that would suffice to maintain my lifestyle. The needs are easy to meet but the wants are limitless, you'll always feel like you're missing something as long as you don't control your emotions.

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

> material wealth isn't worth much

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.

I'm not a wageslave. I still work. Money can't be the reason you do things.

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.”

> I'm not a wageslave.

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.

Isn’t wanting “enough money to not have to work” similar to wanting your body to not need oxygen or food or sleep? Sure, it would be amazing in many ways, but perhaps a tad unrealistic? I guess the problem is that we see some people who are in that position with respect to money and it makes us jealous? 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

> Isn’t wanting “enough money to not have to work” similar to wanting your body to not need oxygen or food or sleep?

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.

Can you tell us your age, I'm very interested

Money is worth it but if you are chasing only money (especially get rich quick like gambling) which OP seems like doing, you will mostly fail. Getting Rich is a great motivation but cannot be the ONLY motivation behind you to do things. It may work for some but you need more intrinsic motives and goals in life.

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.

> 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.

You have to strategically chase your dreams. If your dream is to paint all day, first start a business that can run itself so that it can provide you the freedom to do that.

Simple!

Step 1: start a business that can run itself

Step 2: profit

So easy! I wish I thought of it before.

> Money is a necessary means for chasing your dreams

That's a very personal definition of money

>you cannot just chase money. Chase your dreams of doing something that you want to do and money is always the side effect.

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.

My point is more about people not being able to draw the line somewhere, if your day to day life is miserable because you keep being eaten by remorse and fomo it's probably easier to change your mindset than your situation. One depends on you only while the other mostly depends on external factors.

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.

>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

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.

I missed some pretty big opportunities like co-founding a startup that went on to go public or joining a prestigious research lab at a FAANG. I was beating myself up about that pretty badly for a while, but then I realized I still have a shot at doing something great and by missing these opportunities, other great stuff happened in my life.

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.

As someone who grew up in an environment of rich people I can assure you that I have never met more bitter and unhappy people than those who chased being "just a little bit richer" their whole lives only to figure out in the end that nobody likes them, they spent their lives in shit jobs, talking to shit people, sharing the company of shit people, worrying about shit problems.

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.

How many % of local average incomes/wealth should be enough, roughly?

No one is getting rich in the next two years. I feel similar to you. I missed many opportunities. I also had some hits and spent a lot of my time working on the “wrong” things.

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.

Thanks for sharing, this is good advice. Best to just focus on changing my mentality. Why do you say 2 years though?

> Now I’m entirely focused on my personal skills and charisma

How do you work on these?

Rich people aren't necessarily happier, they just have different problems. I would try to be optimistic and think about all the problems you do not have.

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

My dude yes! Of course you missed it.

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

Recognize two truths: opportunities are all around you, as long as you are interacting with and learning from people. And "getting rich" is as much a matter of luck as anything.

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.

How to?

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.

There will be more opportunities. Holding onto this regret will only serve to hold you back. It sounds like you've learned a lot through this process and that in itself is incredibly valuable.

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...

Ironically this was shared with me after one of the startups I worked at failed.

Oh interesting. I'm curious about your perspective on it then. How does it change the way you think about regret, if at all?

Out of curiosity, I've got to ask: Why do you - and other people in similar situations - want more money? Is it because you want to buy some specific products such as a specific real estate you've set your mind to? Or is it for more general reasons?

In many cities, unless you have existing family money, you need to be outstandingly wealthy to afford a home.

I don't think I would let it bother me.

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.

With a lively spirit that you carry, Life is simply a playground. With actions and thoughts as your tools, you play, explore, and craft. No moment gets wasted, No actions goes in vain, everything that you do, feel or think, becomes an experience, that is to be cheered and appreciated.

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.

From social media analysis we know that exposure creates anxiety and depression. Comparing yourself to others is the culprit. Do not compare ! “It is difficult to find happiness within oneself, but it is impossible to find it anywhere else.” Arthur Schopenhauer

Problem is that "get rich" is a very good motivation but when that is your ONLY motivation, you aren't going to go too far usually. You gambled as well which tells me that you are too focussed on the "getting rich" part and not really thinking about what/why/how you did what you did. You just wanted to get rich. You tried 20 side hustles. You tried startups.

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.

Thanks - Most of my goals do require wealth. However, the last couple months I started doing what I can now with the resources I have and it has helped tremendously. But also made me more eager.

There are always more opportunities every day. You just have to catch em this time. Also, analyze why your side hustles are failing, or why the companies you worked at failed, and use that knowledge to fail less and eventually succeed.

If you have a free couch, get some couchsurfers in your home. You will realize that there are plenty of happy people, travelling the world, with very little money.

Might make you rethink this "regret".

There was a little boy, and on his 14th birthday he gets a horse.

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."

I have a similar background. I don't think you can regret it because it's the circumstances you found yourself in early in life I guess as a child. If you were severely bullied or mistreated to be insecure and lack confidence it's natural you will need to unlearn that and it will slow you down compared with those raised in a more positive environment. Just bad luck. Look at the positives instead, you have a decent brain, you're not severely handicapped etc. Just try your best man.

Have you considered your alternate wealth? Say, good physical health. Many folks have money/richness but not good physical or mental health. Of course, I am not saying you shouldn't get rich or anything but count your blessing, which could worsen. Don't overthink the future or past and missing out stuff; it is an unnecessary burden. Live in the current time and enjoy each day. The anxiety will reduce slowly, and wealth+happiness will follow gradually. At least, that is how I see it. YMMV.

I feel similar in a lot of ways: stayed too long at dead-end jobs early in career, avoided going to startups (risk) or faang (scared?) for too long, failed to have a side-project of my own 'take-off' into something really substantial.

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.

Sounds like you could go work for your former colleagues.. plenty of opportunity there. What is stopping you?

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.

Thanks - I have a good relationship with the co-founder. I spoke to him after his last round and we discussed potential opportunities, but nothing was open that was a fit for me. But I know he could've squeezed me in somewhere if he wanted too, so I assume he wasn't interested. We still talk, but I don't try to work there.

In one alternate timeline you joined your friends, and the companies failed. No one has perfect information to make perfect choices.

Your options are to learn from it and do something else now or spend time regretting what you didn't do, probably regretting this time at some point in the future.

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

If you have a 1:10 hit rate for side hustles (which from random online anecdata seems in the ballpark), that still leaves about a 12% chance that even after 20 attempts you hit none out of just bad luck.

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

I think you need to stop this and find a job you like, are good at and start doing hobbies and life instead.

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

"Regret is an inevitable consequence of life"

Do you have a home? A family? Do you need to worry about keeping those?

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.

I would like a home, family and more flexibility in my schedule.

Meh. I could be sitting pretty for I am the guy behind every credit card reader at every gas pumps since 1979.

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.

What are you doing now that you (likely) dislike, if you don't mind me asking?

Working a very menial job in biotech, however I do have 3 interviews lined up this month for jobs I think would be more tolerable and interesting.

By global standards you are already rich. Be less greedy and try to enjoy the life you got as it’s one of the better ones.

Why don't you just start saving? Or am I missing something?

> I also lost a lot of money gambling but have since quit.

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.

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