25 Rules For Living From A (Semi-) Successful 26-Year-Old

October 9, 2013 — 14 Comments

I’m not saying I have everything figured out. In fact, I’m saying the opposite. My parents were good to me growing up, at least in terms of my physical well-being and my material wants. But the one thing I didn’t get was advice. I don’t recall many situations where my father took the opportunity to use a particular instance to give me general advice. Which of course, is the best way to learn about the world.

Now that I think about it, they didn’t really teach much how to do a lot of basic things either. I’m not talking about how to fix a flat tire or how to change your oil–you can pay someone to do that. This is embarrassing but I remember checking into my first hotel as an adult, during college probably, and getting assigned to room 1214 or something and actually thinking for a second: “How am I supposed to know what floor that’s on?” All I’m saying is that it would have been really nice if one of my parents, during the several dozen times we’d stayed in a hotel as a child, had taken two seconds to say, “Hey six year old, this is how this whole system works.” You know, instead of hoping I observed everything (which in the case of the elevator thing, I probably should have but clearly did not).

That being said, I turned 26 this week and all things considered, I’ve done pretty well for myself. Stumbling and fumbling through the dark, I’ve managed to become a bestselling author, work for some pretty cool people, start my own company, not fuck up my relationship with a girlfriend I love, and for whatever reason, now people come to ME for advice.

I’m sure many of you will disagree with these rules and shortcuts. You’ll say they’re cheating or wrong or inefficient. You may be right. They are, after all, the rules of someone who is completely self-taught. All I can say is that they work for me.

[*] Talking about what you’re going to do makes you a lot less likely to actually do it. Keep your plans to yourself.

[*] If it’s less than 2 floors, never take the elevator. Take the stairs. Nassim Taleb talks about this too: Carry your own bags. Take the stairs. Walk instead of taking a cab. You were already planning to go to the gym later, don’t be an idiot. Exercise is exercise.

[*] Always pull the car up to the very end of the curb (never waste a parking spot)

[*] Public speaking is only hard or scary if you don’t think you know what you’re talking about. That’s relatively simple to fix.

[*] Never recline your seat on an airplane. Yes, it gives you more room–but ultimately at the expense of someone else. In economics, they call this an externality. It’s bad. Don’t do it.

[*] After you’re done eating at a restaurant, just hand the waiter your card. You don’t need to see the receipt first (99% of the time it’s right and if it isn’t–it’s their fault. Send them back to fix it). Also, there’s no need to calculate the tip. I just enter the final number I’m paying. I’m paying them, they can do the math for me. (Provided you actually tip well.)

[*] If someone wants to go faster, let them pass.

[*] When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your work out clothes and go for a long run. You get to see the sights, get a sense of the layout and then you won’t waste an hour of your life in a lame hotel gym either.

[*] Never correct someone’s pronunciation of a word with the more appropriate ethnic accentuation. Only small people care that much about grammar or pronunciations.

[*] Everything your doctor, school and parents said was healthy is probably bad for you. Whole grains, soy, corn, wraps, milk. Ask yourself: does what I am about to eat even remotely resemble something my ancestors evolved to eat? If the answer is no, put it down. If, like me, the allure of these foods is too much, save them for one day a week where you splurge (and then hate yourself and swear them off for another week).

[*] Unless it’s an atrocity, take responsibility for it. You’re probably more at fault than you know.

[*] Get a dog, not a cat. One will make you a better person, the other is just an animal that lives in your house.

[*] In business situations, your first instinct is to start negotiating. Stop that. How much is significantly less important than whether you truly, truly want to do this thing. If you do–and I know this advice is controversial–just take the deal, provided its half way decent. Don’t look a gift horse in the mouth. Bird in the hand. Blah blah. If you don’t want to do it–don’t let money sway you. Take the deal, do a good job, get more money on the next one. This is the philosophy of doers. Sharks and sociopaths care about squeezing every penny because they’ve confused money with their worth.

[*] Shame is a powerful emotion that can be used for good. If it’s something you want to hide or are embarrassed about, think twice about whether it’s actually the right thing. (Two good one liners about this here).

[*] Be in the middle of a book at all times. Better still, carry one with you at all times–a physical one. You’ll be amazed at how impressed people are by this.

[*] Frequent Flyer Miles are for people whose time is worthless. Here’s what I do: I use a Southwest Visa card. It means I get a few extra free domestic flights a year without ever having to do anything. And then on everything else? I never, ever think about it–even though I fly close to 50,000+ miles a year. If I am going to have to juggle a bunch of arbitrary, meaningless numbers for piddly rewards, I’d rather juggle sports stats or play games on my cell phone. At least those are entertaining.

[*] Most people are lying when they describe what their life is like. Don’t listen, don’t use what they say as a baseline, don’t get jealous, just nod and then forget it.

[*] Speaking of which, people are constantly trying to bribe you to be like them and take on the same burdens as them. DO NOT ACCEPT.

[*] Traveling for the sake of traveling is stupid.

[*] If there is a long line and you don’t want to wait in it, walk up to the front (or walk through the back or opposite way) and pretend you didn’t know you were doing things incorrectly. It almost always works. And when it doesn’t, no one thinks it was malicious. After all, you were just turned around. Note: pretending you forgot something–like you were just walking up to grab silverware at the buffet line–works well too. Grab your stuff and make a getaway.

[*] The best way to flirt is to ask provocative questions. And provocative is anything people aren’t expecting to be asked–it doesn’t have to be sexual.

[*] Eliminate options, concentrate your forces. Here I am combining two lessons from Tim Ferriss and Robert Greene. For example, in terms of clothes and meals, just pick a few favorites and then stick with them. This means less time is wasted thinking about choices on a daily basis. But more importantly, concentrating your limited dollars/time on fewer entities gives you more leverage. I mostly eat at the same restaurants over and over–and you know what, they always hook me up. The fastest way to VIP status on anything is to cheat by going or buying a few times in a row. There’s a saying behind this too: More wood behind fewer arrows. It applies to more than just dinner perks.

[*] Conference calls and meetings are mostly a waste of time. If the person is more important or successful than you, consider going. If not, beg off as best you can.

[*] Current events/the news should be followed only if it fits one of the following criteria 1) It directly affects you in someway. 2) Knowing about it would make for interesting conversation. If you’re watching something and you can’t tell yourself that you either plan to do something with that information or it will make you seem smart, turn it off. Or flip it over to Comedy Central because you may as well be watching pure entertainment.


This isn’t conclusive. It’s just some stuff that occurred to me and that I think about often enough to have a policy on. I don’t think it’s a coincidence that a lot of them line up with sayings or cliches. Those are cliches for a reason–namely that they’re true for a lot of people and have been for a long time.

All I know is that I wish I hadn’t figured them out on my own (or in some cases, heard from mentors and other smart people, but only well into my twenties.) Because missing these rules was painful. It wasted time, money and energy.

Hopefully they save you some trouble. And I guess, the message, at the end of the day, is that it’s never too late.

This article originally ran on ThoughtCatalog.com. For my thoughts on the response and any of the more controversial rules, read the comments there.

Ryan Holiday

I’m a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

14 responses to 25 Rules For Living From A (Semi-) Successful 26-Year-Old

  1. Not sure i understand how you say its unacceptable to put your seat back in an airplane, but cutting in front of people in line is encouraged. Both cases come at someone’s expense, but in the case of cutting in line it is coming at many other people’s expense. Just seems like a much bigger dickhead move.

    • If only I’d addressed this in the comments like 40 times…which I linked to at the bottom of the piece. In other words, you would be the kind of person I would cut in front of in line because you don’t listen to instructions.

      • I don’t get it and I don’t have time to read the comments. If it’s unclear, why did you republish the same text without further clarification? Why would I not think that you’re a jerk after reading it?

        “If there is a long line and you don’t want to wait in it, walk up to the front (or walk through the back or opposite way) and pretend you didn’t know you were doing things incorrectly.”

        You’re doing something incorrectly and pretend that you didn’t know it. That’s what egotistic jerks do.

        “It almost always works. And when it doesn’t, no one thinks it was malicious.”

        No one thinks it was malicious. So you fooled everyone because what you wanted to do was malicious. Again, that’s what jerks do.

        If a message is unclear to many of the intended recipients, it’s the fault of the person who sent the message, not the audience.

  2. For anyone who has not taken the time to read the comments in the original posting of this article, you should. They are hilarious.

    Whenever I see that Ryan has posted an article on another site, I immediately skip to the comments section because the dogmatism that spews from that site’s community is more entertaining than anything Ryan could write.

  3. Ryan-

    Are you straight or gay? You have a gorgeous smile.

  4. What about using social pressure to push yourself to complete your plans? For example, I was reading Tucker Max’s blog and he was writing posts about crowd funding. At the end of his last post, he wrote that he was going to write some more posts about this topic and even explained that at the end he was declaring this in order to use social pressure to get him to do these posts. I was actually going to use this tool and post on my Facebook that I was going to finish the first draft of my book by the end of the month.

    • It doesn’t make a difference if you announce what you’re going to do or if you don’t. All it ever comes down to is yourself. There’s always going to be a hundred factors that get in the way of what you want to do- You need to get paid from your real job before you can write, you need to take care of your family before you can write- No, it’s you. You can take Ryan’s advice and talk about it to no one and see if that helps, maybe it does or you can follow Tucker Max’s example and boost to the world that you’re going to write a book, but no matter what it always comes down to is just you doing it. There is no simple answer, there is no answer at all. Just write.

  5. Sandeep Gourkanti October 12, 2013 at 6:04 pm

    Thanks for sharing your observations Ryan. It has had a profound impact on how I approach the value I want to receive from media, entertainment, and books.

    I’ve been reading the books on your “Life” section and I can see where you got some of these tips/strategies from.

  6. This is an amazing post. I wish I heard each of these points years ago! Great compilation of important life lessons, Ryan.

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