The Million Dollar Question

This is a fantastic post, very thought-provoking. But also very sad to me. I disagree with the underlying premise that success and happiness are somehow negatively correlated. There's this idea in the post that if you want to be uber-successful, you can't have a "normal" life.

I know very successful people who are miserable, stressed-out workaholics. And I know very successful people who could have been one of the people strolling around Sebastian when he was writing this post. I know people who run startups from their home office and take their kids to school in the morning. Hell, look at Sebastian's own situation: he apparently has enough time to sit and pontificate for a couple hours on a train platform in Japan, in the middle of the day. He can't be working THAT hard :) Maybe what he's trying to say is that you can't have the idyllic suburban family life if you want to float around the world living off of random consulting gigs? But there are probably quite a few very successful people here on HN that live relatively idyllic family lives in cities and suburbs all over the world.

I think the idea of feeling isolated for being very ambitious is true, but I would caution Sebastian and others against the idea that you have to sacrifice your connection to a community, your face-to-face relationships, your health, and your overall happiness on the alter of amassing $40m for an amorphous purpose like being able to build a shrine with 5% of your wealth or less. You certainly can sacrifice all those things, but most people will never amass $40m no matter what they sacrifice. Better to find something (and someone) that you love, work hard at it, and enjoy life. Yes, you should take chances, yes you should push yourself and be ambitious. But this is the only life you get; don't squander it living a life you don't enjoy because you're hoping for the big payoff down the road. It probably won't come.

Almost every millionaire I know is married with kids and living in the suburbs. Unless you win the lottery or are a professional skateboarder, becoming rich is more like boring suburban reality than being an international flaneur. (Interestingly, the rich pro skaters I know all live in the suburbs with their kids, too)

As someone who has also floated around a lot, even through Japan, it's an interesting lifestyle but sort of the opposite of how to get rich.

I'm not sure I buy it. I've met plenty of wealthy people who were happy to come home to a pretty normal family because their jobs are a constant source of novelty, stress and challenges. If one feels the need to stick out as part of one's identity, great, but it's just one way of living. I kind of like sticking out as a foreigner over here in Italy sometimes; it has its positive aspects. I certainly chose a road less traveled, but whatever, to each his own. For other things I'm happy to be pretty ordinary: I have a wife and two fantastic children and live in what passes for burbs over here.

Also, being a bit of a skeptic and contrarian, perhaps some of these people had other good reasons to say no to his plans. Without knowing their point of view, more about his proposals, and other particulars, maybe their inaction was sensible.

There are lots of bugs in peoples' brains that prevent them from doing things that seem like good ideas, and I don't think the fear of becoming illegible (http://www.ribbonfarm.com/2011/07/31/on-being-an-illegible-p...) is anywhere near the most important one.

My vote for the most important bug is as follows.

It looks as though human brains were architected to think in two modes: "near" mode and "far" mode. The reason for this is that early human tribes had important rules that directly impacted survival and reproduction (for example, "don't take more than your share of the food", "don't sleep with another man's wife"). It was critical for us to tell others that we were going to uphold these rules or we would get kicked out of the tribe. At the same, time our genetic fitness would increase massively if we could find a way to covertly break those rules while still upholding them verbally (more food and more descendents for successful rule breakers).

The upshot of this is that even if something looks good when processed using far mode it's not necessarily easy to translate it into near mode where it actually gets done.

In my view, this is an explanatory factor for procrastination as well. For example, the popular Google Chrome extension Chrome Nanny (https://chrome.google.com/webstore/detail/gpdgmmdbbbchchonpf...) requires the user to enter 64 random alphanumeric characters before visiting a distracting site--which moves the idea of visiting this site from near mode (where it might actually happen) to far mode (where it won't).

For more on near and far modes you can read http://www.overcomingbias.com/2010/06/near-far-summary.html. Note that novel tasks and desirable risky acts are both associated with far mode.

"Why won't you?" Indeed. I created this HN user almost two years ago, before I applied to YC. In these two years I did pretty much nothing towards my goal, except reading HN, nodding in agreement over good posts, and bookmarking stuff on Delicious, adding to the hundreds I already have. What stops me? Fear? No, I just know I can be successful with my idea. Laziness? Maybe, but I've worked 18 hr days on projects I liked. So what? I don't know.

Meanwhile I will upvote this article and bookmark it.

Very powerful - thanks for sharing.

But the more you do, the further away you get from being understood, from the joys of normal life, from being understood by your neighbors and backing each other up and living together harmoniously.

I cried for the first time in three years when I realized it.

The million dollar question… why don’t people take the large opportunities in front of them? Why don’t they allow their dreams to become realities?

Become it means you won’t be understood. And we need to be understood, fundamentally, it’s so important to us.

Wow.

I really enjoyed this article. I'm not actually convinced that the answer is a fear of not being understood by others, but it's very close or the writing wouldn't resonate the way it does. The problem is that I know lots of people who couldn't give the slightest damn about fitting in, or who are already occupied in a field far enough from societal norms that their job description takes a whiteboard and a venn diagram on a good day.

I wish I could remember who said this; I think it was M. Scott Peck, but I can't find the reference: we are attached to our own mental model of ourselves. So attached that we will fight to maintain that model even if it's useless or actively harmful.

An example: have you ever noticed that if someone's depressed, complimenting them doesn't work? Have you noticed that you yourself feel awkward when others compliment you? That might seem obvious, but only because you've absorbed it through repeated exposure. Think about it: why in the world would someone saying good things about you feel uncomfortable? Shouldn't it be basically the best thing you can get?

The answer is that when you're thinking "I'm average looking at best" and someone says "you're beautiful!" it's like someone just tried to rip your left brain from your right. How can you possibly reconcile these two things? You have to either destroy your own sense of self or reject the person's compliment.

I suspect that in this case what looks like fear that the world will misunderstand you is actually fear that you misunderstand yourself. Jumping head-first into a crazy idea isn't just changing what you do; it's changing who you are, and that's goddamn terrifying.

Sebastian identifies a key problem that underlies a lot of how society works: lots of people effectively have motives to avoid things they want. But I'm not sure he's right about his reading of why the problem exists. As nice as it is to think of this as some kind of trade-off, I'm not sure that most people gain any normalcy or understanding, at least not in any positive way.

Think about his friend, the one who's big goal is financial independence. It's his primary first-order objective, and he's being shown a plan to pursue it. He's not afraid to pursue it because he thinks it's going to cause him to be less understood (at least one of his friends, Sebastian, will probably relate to him more). He just flinches at the thought of really going after what he wants.

The million dollar question is the right one: why do people get anxious and self-sabotage when a path to success is put in front of them?

Unfortunately I think the answer is that most people have a lot of psychological conflicts around being happy/getting what they want. Why this happens is probably some complicated mixture of neurology of and pain acquired in childhood, and how to fix the problem is one of the central aims of psychology and psychiatry. The behavior Sebastian describes in his friend is a great example of one's ability to function being impaired by his psychology.

Hopefully we'll get even better at fixing these sort of problems, but in the mean time, hopefully more people will understand that these problems aren't inherent to living life, that there's no sad tradeoff to going after the life you want, and thus be comfortable seeking treatment. You don't have to be crazy to pursue psychological help, you just have to notice that your feelings sometimes get in the way of you functioning the way you want to.

Man, what a memorable post.

I like to think about his main point of "people won't understand you" a little differently. Humans were originally pack animals, and it shows. You are nothing without your pack, but together the pack is strong. Modern life isn't nearly so simplistic, but we still have our packs, albeit a little more nuanced. The place we work. The neighborhood we live in. Our family. Our friends (who are probably drawn from work, neighborhood, and family).

Doing what Sebastian does seems to be a lonely path. You get to be the alpha, but only of a pack of one. I get this feeling when seeing a lot of executives interviewed - men and women who are supposedly at the helm of enormous packs, but in practice seem a lot more alone than one might imagine.

Thanks, I enjoyed this post. I don't resonate with everything he says, but it was worth reading. The more philosophical points of his post were an interesting contrast to this piece I read yesterday: http://youarenotsosmart.com/2011/08/21/the-illusion-of-asymm...

Reading the OP I was actually a bit put off by what seems like vague braggadocio, but then I turned it around on myself - maybe that's me suffering from the same illusion as a mask for my own jealousy?

When I decided to embark on a new project this summer, I was at first held back by fear of failure. When I looked closer at the fear I realized that I could hack it by redefining my terms of success. Instead of defining success as making it big, I defined it as climbing up a steep learning curve. To do something new and learn from it, that's my definition of success.

And like that, the fear was gone. I'm now one month into my project, and I'm crushing it. Never been happier.

I really liked this post. Sebastian continues to develop his conversational style. Very nice.

Asshole consultant inside of me kept nodding early on: "You just don't get it, Sebastian! Charge more!"

You see, there's a very sad truth consultants learn early on: it doesn't matter how much you know that can help somebody. All that matters is how much influence you can have.

The reason some consultants charge ten times what others do for the same information? It's not that they are ten times as smart; it's that they don't want to waste their life giving great advice to people who aren't going to value it. If you walk in the door at 10K per day, bet your bottom dollar people are going to listen to you. And that means you can help. Walk in the same door for free, just to help out a friend? Your advice, by definition, is worthless. You'd be lucky getting them to accept just a tiny piece of advice.

But then I got to the key of the piece: when you do finally "get it", it changes your relationship with "normal" folks.

I think Sebastian's being a bit over-dramatic here, but I firmly agree. There is something very crazy about making money from thin air. Especially how it's done today, with some keystrokes and a bunch of virtual magic. At least in the old days if you met a millionaire he could take you down to his factory or something. Maybe told you about all the hard work he's done.

Nowadays the same type of guy made much more money that than that and there's not even an office. For most people, it just doesn't compute. In fact, I'd go so far as to say that to most people, there's something just wrong about making money the way it's made today on the net. Something shady. If you're lucky you get the "odd weirdo" label. If you're unlucky you attract attention from people you would rather not.

Because of that, I think I'm giving up on the $40Mil dream. I'm happy just to make enough to free up my time to work on things I love doing. I'll let the other guys be the really extreme weirdos. :)

Short side story: I sold a piece of land a year or so ago. It wasn't much, but it was in the tens of thousands of dollars. The guy who bought it paid cash. He was a contractor. Over the past decade he had been saving here and there, scrimping up enough in cash to make his dream come true. He kept it all in hundred-dollar bills in a large ziplock bag. It wouldn't have been my choice but it worked for him.

As he paid me, he told me he had gotten stopped for a bad taillight by the police a few months back. Once they saw his money that he had been saving, he had a hell of a time convincing them he wasn't a drug dealer. While I understand that carrying large amounts of cash is suspicious, to hear him tell it the police went far beyond suspicious and started thinking there was definitely something wrong going on. You see, to those small-town cops, you just don't carry that amount of money around. Somebody who looked like that should not have the amount of money like this. Just having the money was an indication of something really bad, even if it could all be explained.

He almost lost all of it.

You can only stand out so much -- the forces of society will gently (or not so gently) pull you back into line. You either have to conform or move to some place where the definition of "normal" is different.

Fantastic insight that people tend to say "no" when offered a chance to pursue their dreams. But I disagree about the reason. I don't think it's that they don't want to be different; having an interesting dream is already being a bit different. I think it's that once you can have something, it's no longer a dream.

This is awesome, and I totally agree-

"It’s like everyone fantasizes about… whatever… but once their fantasies start to become reality, they piss their pants and self-sabotage."

Very inspirational. If you're a startup founder/entrepreneur, worth your time to read fully.

Reading from beginning to end, I found the last paragraph powerfully moving. (Skipping to the end won't work - that last short para builds on everything before.)

Change in financial situations creates lot of stress. When your stress level is high, the typical path you are going to take is the one that alleviates your stress and not increase it.

Sebastian is suggesting x10 higher wages for his clients. This is a financial breakthrough in the life of the client. It creates enormous amount of stress. The stress pushes you back, for a less stressful zone.

I say this because I was there, and I'm sure I'll be there again. I see this differently than the OP. I don't think that people don't understand you, especially when they are smart. The simple fact of thinking of it generate stress and they hide from hard/stressful situation.

It proves, once again, that extrinsic motivation does not work.

If you help someone achieve a goal, they will owe you some of their success, lessening their own merit.

On the opposite, as this story shows, the intrinsic motivation can make you do stuff that you thought impossible: http://www.maximise.dk/blog/2009/04/moving-boat.html

So maybe to help people achieve their dream, you have to tell them that it can't be done, that it's impossible.

This would be a truly altruistic way to help people, since you can't claim any part of their success in that case. All they will tell you will be "I told you it can be done!".

This is a great post, but what I really want to know is how to make a million bucks without Sebastian Marshall mentoring you and no real connections. Actually, maybe I start by trying harder to make connections.

Holy shit, yes. But you don't even have to talk about the kind of skywalking he's engaged in. Anyone from a blue-collar or lower-class background who does non-manual labor is automatically alienated from everyone and everything they knew. See Limbo: Blue-Collar Roots, White-Collar Dreams by Alfred Lubrano. http://www.wiley.com/WileyCDA/WileyTitle/productCd-047126376...

Amazing post. I read every word of it (as opposed to just scanning it).

What type of work does he do* and where can I meet/read more people like him?

He strikes me as a kind of mentor...something which I find is lacking in the IT industry. Mentors don't always need to be the smartest person in the room, they just need to have experience and patience to see the things that you are blind to.

* He says he's a strategist, but that's awfully vague.

Great writing, but here is a quibble regarding the "...pretty girl, maybe 23 years old. She’s not beautiful... she’ll... be a very good wife for someone."

Ouch. I know he's just day-dreaming there, and his point is that she is a "normal" person. But why define her success in terms of being a "wife for someone"? She could -already- be an incredibly successful, independent person living life on her own terms, making her own rules.

And for all we know, she may be just as alienated from normalcy as the author. Sorry to nitpick but this hit home for me.

I'll be fair with him: I would also decline because I would not like to be like him. For me it has nothing to do with being understood. I read his 'who am I' and all I thought was "man, his life is so empty". But I can't say why.

Sometimes people just want a simple life. Making a lot of money or working less hours does not mean your life will be better or more enjoyable.

The call to action on this post seems to be stop worrying about the fact that you will not be understood and go ahead with your plans.

I am curious. Does the fear of not fitting in outweigh the benefits of financial freedom?

I dont know the answer to this question since I have never been in that situation, so I thought I would ask.

I just want to say.. this is 1 of the most insightful, and meaningful posts I've read in my entire life. Thank you so much for sharing this. I resonated with every single bit. Thanks for not making feel alone in my thoughts.

Way too wordy, not nearly as insightful as he thinks it is.

This guy is clearly so full of it on so many levels. All hat, no cattle.

What.

A prolix.

Douchebag.

When the headline is meaningless it doesn't make me want to click off.