This is getting old.

DHH routinely posts "humble brag" type photos on Instagram of his exotic cars and his ocean side view. Meanwhile he's telling the rest of us not to bother trying to "make it to the top"?

If he feels so guilty about his luck, he should give it away or pay if forward in a constructive way.

So I didn’t know who he is (still don’t) and this article doesn’t actually come across as humble bragging when I read it without your context. He doesn’t even mention how successful he is, and just says change the things you can control and don’t worry about the things you can’t.

read his post just before this one. its him apologizing about the sick lifestyle of humblebragging he let himself get into.

Written in the most pompous style I've read in a long time. He still has ways to go.

There's a paragraph from a long-disappeared blogger about how to set life-long goals that's the exact opposite of what DHH says.

> One of the great insights of psychoanalysis is that you never really want an object, you only want the wanting, which means the solution is to set your sights on an impossible ideal and work hard to reach it. You won't. That's not just okay, that's the point. It's ok if you fantasize about knowing kung fu if you then try to actually learn kung fu, eventually you will understand you can never really know kung fu, and then you will die. And it will have been worth it.

It's virtually impossible to be the best, and it's actually impossible to stay the best, which is why it's such a good goal to chase. Trying to be the best programmer will fly you around the world, push you to talk to strangers, get you up in the morning before a conference or before work, fill your github with interesting experiments, top up your bank account, and mould your personality.

I know that DHH is saying something superficially similar about the journey being more important than the destination, but I wonder whether it's possible to walk the road without picking an impossibly distant destination to aim for.

DHH has been cursed by success and he doesn't even realize it. This is a rather tone-deaf and unfortunate article.

From what I get from the article is: You can't be like me, but the best you can do is to better yourself. It's a completely demotivating and dangerous message.

It completely ignores the role that luck played, ignored the factor of social connections, and the struggle it takes to get to where he got to. He waxes on a lot in the article and completely ignores the economics of why he succeed and others didn't.

I think you may need to forget who the author is for a second and reread this.

He admits luck plays a huge role in success [0] (especially if you're using the success of others to measure your own success).

He's saying competing with yourself is the best way to measure success and achieve fulfillment. This probably stems from a lot of people using him as a barometer of success in tech. Comparing yourself to others is a great way to be miserable forever.

[0] "Besides, you only have limited influence on whether you’re going to succeed at whatever you put your mind to. It’s by no means within your exclusive sphere of control. There are so many things that have to come together at the same time. Only a couple of which you own."

There's many better ways to explain the role of luck in success, but I felt the way he mentions that was an add-on to his whole message of "don't bother." Competing with yourself improves you, not your positioning in the real world. When you improve yourself and the real world is more bountiful, that's a minor side effect purely based on your context and environment.

In the whole article, he doesn't bring up examples of others to make his point. His only source in this is himself from his point of view.

> From what I get from the article is: You can't be like me, but the best you can do is to better yourself.

That's not what he's saying. His message is - it's not impossible that you'll be successful, but it's just not very likely, so don't hung up on that too much. Jordan Peterson has made a similar point, where he said that only a small minority of people entering a workforce will have careers (which imply substancial degree of self-direction and fullfillment), and the rest will just have jobs. So don't invest too much into trying to have a career, as you're likely regret it 10 or 20 years down the road.

I'm not aiming for the top. I'm aiming for a good position on an alternate path. My 6-year goal is to have my own company that I work for full time, and my 10-year goal is to have a few employees. I don't want to build a tech company that will be acquired, I want to build a tech company that sells a product and provides me with a decent income, a solid upper-middle-class or lower-upper-class income.

I hate to admit it but this journey so far has seen me have to reprioritise my interests already. Instead of focusing on technical challenges I enjoy I've had to start thinking about customers, what do they want, what will they pay for and how much?

I don't understand why commenters here are bashing this article and/or the author. Why do people see financial success as the only worthwhile goal?

Because the author is a millionaire living a millionaire lifestyle and telling other people not to try to imitate him. It just comes off as very hypocritical.

DHH is a proponent of Stoicism. This article is an argument for the Stoic concept called "dichotomy of control", which can be summarised as: "Don't worry about things you don't have any control over. Instead, try to change those things for the better you at least have a some sort of control over".

Articles like these don't have to be motivated by feeling remorseful about or by trying to do some weird kind of penance for one's success.

Marcus Aurelius probably is the most well-known adherent of Stoicism during classical antiquity and he was Roman Emperor after all. Aside from Mount Olympus itself you can't really get any more to the top than that.

You rarely hear people say Aurelius was just humblebragging because he felt uncomfortable about his success, do you?

I agree. We're all dealt different hands in life. The best thing is to strive to be the 'best you can', not 'the best'.

A motto from an old children's organization sums it up: "Do your best." It really is good advice.

This ignores the role of optimism: if you believe you will make it to the top then you are more likely to get there.

While it is true that optimism generally is a sensible approach, I really dislike how it's often used to dismiss the various factors that can make it difficult for some to reach that top, or progress towards it.

Basically, it's good advice when applied to the self, but terrible when applied to others.

"The top is full of people who hate what they had to do or who they had to become to get there."

What a great quote. There are so many things I could be doing as a blogger/YouTuber/solopreneur/whatever to try to maximize my chances of success, but I would hate myself for doing them. Things like putting horrible newsletter signup popups on my website, or gaming the system on YouTube to get more subs (because it's all about the subs, right?).

I once worked as a software developer for a marketplace-type project where they started talking about faking analytics data for profiles so people would think the platform is successful. I voiced my hesitation at the time, and thankfully I ended up off the project before I was told point-blank to implement it, but that's the kind of crap people pull in order to rise to the top.

All the privacy headaches, security breaches, UX dark patterns, and other garbage we're having to deal with online and in the computer industry is all because of people sacrificing their morals on the altar of "making it big." Silicon Valley did an excellent job marketing itself as a better capitalism than the robber barons of old, but now we see the cracks in the armor. Props to DHH for constantly and consistently pointing out the fallacies of all the entrepreneurship BS.

Eh there is a lot of “tops” and you can always find a new one. Also it’s relativley easy to ge the best programmer in language that’s 2 months old.

Seems wise but it really is built in our DNA to compete with the other lobsters

edit: this comment probably won't make it to the top