Rosie’s Rules for Success, Happiness, and an Awesome Life

Oh, Adolescence.

A locked bedroom door meant a moment of peace and quiet. 

Solitude, an escape from trivial stress and an entrance to the black hole of YouTube searches, video games, and blogs. 

On one Saturday afternoon spent in my room in late 2012, I stumbled through the vortex of the fitness internet and landed on an article titled “How to live an Awesome Life: Roman’s Rules for Success, Happiness, and an Awesome Life” on John Romaniello’s blog.

As I read each rule, I noticed which ones I related to like rule #18, “Sun’s out, guns out” (this was the onset of my cut-off t-shirt phase). I determined some weren’t applicable like an aside on rule #8 on cologne, “have a scent for each girl you’re dating” and rule #30, “A man can never have too many leather jackets.” And, I recognized rules I should be following like rule #50 “Floss your teeth for better fitness.” Finally, I noted novel rules, like Rule #35 “Read as many books as you can.” This rule marked the first time I’d heard someone I looked up to, someone I perceived as cool talk about reading books.

In addition to changing the course of my dental health (and probably the rest of my life also), Roman’s rules inspired me to ponder the rules I lived by, to outline my own. On that day, I organized a list of—mostly really stupid—rules you’d expect from an 8th grade boy. Yet, like any brainstorm of ideas, there’s usually a diamond or two in the pile of shit. One of my rules was, “don’t drink alcohol until you graduate high school,” In addition to steering me away from drugs and alcohol, it framed my thinking towards making generally healthy, responsible decisions.

I scraped the initial draft of Rosie’s Rules for Life and updated it. I consider this an ongoing list, subject to tweaking on a regular basis. 

And John, of course, is now my mentor, my obi-wan, and one of the most important people in my life, so actually writing out this list made it feel like it’s all come full circle.

Rosie’s Rules for Life (updated: February 2020)

1. Always have someone you’re learning from and someone you’re teaching. This comes from Peter Attia in Tribe of Mentors. Continual, consistent improvement starts with erecting an environment where you’re always learning. Naturally, having someone to learn from ensures constant growth. Teaching may seem altruistic, a way to pass on the lessons I’ve learned, but I also do it for selfish reasons. When you teach something, you have to explain it well. And if you don’t know something thoroughly, you won’t be able to explain it well. Teaching forces me to review, question, and refine my thinking.
2. Write. As with teaching, writing forces another examination of my thoughts. Getting it down on paper opens it up to criticism, feedback, improvement, and action steps. Also if I don’t write,  I’ll forget my good ideas and hate myself for it. 
3. Dress comfortably and fashionably. I cringe at people who dress so fancy they can only walk or sit down with subtle movements. Yet, I recognize good style is necessary for all human interactions—we all subconsciously make judgments about people based on their appearance. Fortunately, Levi’s stretch jeans and lulu’s ABCs accomplish both. 
4. Never sleep in too late. Even after nights out, wake up at a reasonable time (For me it’s 9am), do something productive, then reward yourself with a nap.
5. Floss. I’m stealing this from John because it’s the reason I floss. The lesson is a reminder to also learn the basics first. Here’s what he said:

“Floss your teeth for better fitness. I feel that you need to have the basics down before you start adding things intended for ‘advanced’ reasons. I have friends who don’t floss but go out of their way to use whitening strips or see a dentist for teeth bleaching. This is stupid, to me—if you just took care of your teeth on a daily basis, you’d have to worry a bit less. In the fitness context, people ignore basic nutritional needs, but try crash diets or supplements; they can’t take the time to foam roll, but want the hottest training strategy. If you can’t make a habit of flossing your teeth, you shouldn’t bother with supplements—likely, you don’t have the basics figured out.”

6. Embrace varying temperatures. We evolved to resist both heat and cold and maintain homeostasis. Constant comfort shrivels this ability. If you shudder inside when it’s 32 degrees that’s a you issue. If you hate sweat that’s a you issue too; life is messy. If it’s a little chilly, leave the winter coat and opt for a sweater. Your body will adjust and after a few minutes you won’t feel cold. (Disclaimer: Please don’t take this to an extreme and do something stupid.) 
7. Talk to strangers. They’re just friends you haven’t met yet, and you can likely learn something from them. Additionally, it flexes our courage muscles. Approaching a stranger makes you realize most of our fears are largely unfounded and prepares you for hard conversations in your everyday life. 
8. Ask for shit. The worst they can say is no, and the world just might reward you. This is another great comfort zone breaking exercise. Next time you go to a coffee shop, ask for 10% off and give no justification.
9. Learn another language. It will give you—literally— a whole new way to think about the world. And, the process will teach you how to learn anything. 
10. Travel. Get out of what you think is the whole world and see shit that’s completely different. The more perspectives you can foster the more strategies you’ll have to process and make sense of problems. 
11. When you travel, do all the tourist attractions in a few hours and spend the rest of the time with locals. Do what they do; eat what they eat; talk how they talk. This is how you learn their language and understand their perspective. Win-win. New Yorkers don’t hang out at Times Square, Barcelonians don’t chill at plaça catalunya. This will also make traveling affordable because your new local friends will show you the places to eat, shop, etc that don’t jack up the prices for tourists. 
12. Don’t work so hard. Working smart is more rewarding, and saves your battery for when you need it. Anytime you feel like you’re working hard but getting nowhere, ask yourself, “what would this look like if it were easy?”
13. Work hard. Once you’ve mastered rule twelve, and you’re working efficiently, pull out the work boots.
14. Keep a journal. One, your memory sucks. Two, it clears your mind for thinking the rest of the day. Anything you meant to remember, like the good advice you got, should be discussed in your journal so it can be freed from your mind. 
15. If a girl doesn’t read, don’t bother dating her. If you’re the kind of person who just doesn’t see the value in digesting the wisdom of people smarter than you, it’s simply not going to work out long term.
16. When choosing projects, prioritize learning. Tim Ferriss often relays how he chooses projects based on the skills he’ll learn, and the relationships he’ll develop. I’ve mimicked the same approach, and I credit this advice for leading me to my internship with Devan, my education at NYU, and my apprenticeship with John. Focus on this over financial gain. Inevitably over time the skills you learn and the people you meet will lead you to financial opportunities. 
17. Practice radical open-mindedness. We’re all wrong about a lot. Columbus died thinking he was in India. We laugh at this now, but there are metaphorical continents all around us in plain sight we haven’t uncovered. Further, in arguments remember that it’s not about who’s right, but what’s right. If it turns out you’re wrong, you just learned something. Make a habit of not being married to your ideas, and always stay open to changing your mind.
18. Showcase what makes you different. The first twenty years of my life, I was embarrassed to tell people my favorite kind of music was pop-punk. If people asked, I’d say “I like everything” or “you wouldn’t like my music.” What made me unique is precisely what I wanted to hide. In a world where it’s hard to stand out, we should do the opposite. Embracing your uniqueness attracts people who share those interests. And remember, everybody is so worried about themselves, they rarely judge what you like. More frequently, it will plunge us into a conversation about what pop-punk is and a conversation about something interesting to me. Because it stands out, people are often curious. 
19. Make listening your first instinct. This takes time and practice and is a rule I’m still doing my best to follow.
20. Learn something in every conversation. Every person has experiences we don’t, and therefore knows things we don’t. By following rule #19 we open ourselves up to learn from others. 
21. Real maple syrup only. Seriously, all other breakfast syrups should just be thrown in the trash. (As I no longer live in Vermont, I carry maple syrup with me nearly everywhere. If you’re a native Vermonter in foreign land, I recommend you do the same).
22. Spend outrageously on the things you love and be stingy on the things you don’t care for. This is advice from Ramit Sethi. I limit my spending on transportation (I’ll walk or take the subway), new technology, or trending fads. But I throw the bank at things like plane tickets, concert tickets, and eating out with friends because those experiences give me disproportionate happiness compared to what I spend on them. Money at the end of the day is meant to be spent so spend it on what makes you happy. 
23. Don’t be a donkey. From Derek Sivers. 

“Are you frustrated that the world wants you to pick one thing, because you want to do them all?

The problem is thinking short term — assuming that if you don’t do all the things now, they won’t happen.

The solution is to think long term. Do just one thing for a few years, then another for a few years, then another.

You may have heard this story: Buridan’s donkey is standing halfway between a pile of hay and a bucket of water. It keeps looking left and right, trying to decide between hay and water. Unable to decide, it eventually dies of hunger and thirst.

A donkey can’t think of the future. If he could, he’d clearly realize that he could first drink the water, then go eat the hay.

Don’t be a donkey. You can do everything you want to do. You just need foresight and patience.”

This is another one I admittedly struggle with. 

24. Don’t judge what people do in the bedroom. It doesn’t matter with who or in what ways, as long as it’s consensual and safe. It doesn’t affect you. I’m wondering what it’s like to have your life so put together you worry about where other people put their genitals. Must be nice. 
25. Don’t sleep with someone the first time you meet. You don’t know much about them, or what they could under the influence of. I prefer to wait until we can have a proper conversation about consent and boundaries. Additionally, it always builds tension so if the person does pass the tests, it’s much more rewarding. See rule number #26. 
26. Delay gratification. Do the difficult, important work, and then reward yourself. A workout always feels better when you know you put the effort in, and the feast afterwards always tastes better because of it. Watching Netflix while you have important work to do never feels as good as watching your favorite show after finishing the essential work. The fast always makes the feast better. 
27. Listen to The Tim Ferriss Show. Honestly, I can’t imagine where I’d be without it. If you hate podcasts read Tools of Titans and Tribe of Mentors.
28. Read The 48 Laws of Power. Honestly, read all of Robert Greene’s books.
29. Listen to audiobooks. Books are the gateways to communicate with the smartest people in history. If you’re allergic to actual physical books, then use audiobooks as your entry point. 
30. Prioritize sleep. “Sleep when you’re dead,” is one of the worst mottos of all time. Sleep improves your attitude, alertness, and thinking capabilities. Without it you become a useless sack of shit and you know it. This doesn’t mean on the micro you can’t lose a night’s sleep, but in everyday life prioritize it. 
31.  Make decisiveness your default. When people ask what time, suggest a time. When they ask where, suggest a place. Often, people don’t want to make decisions and will go along with whatever you suggest. Secondly, it makes taking action your default and limits the likelihood you’ll put off decisions. Start with the small decisions, and then the big decisions become much easier. 
32. Don’t hit the snooze button. It sets the tone that you’re in control of the day and provides a small win to build momentum. If you can’t help but hit the snooze button, get a dog. Unless you want them to pee in the house, you’ll get up.
33.  Offer to pick up the check. There’s no better way to cap off a great meal than thanking the other person for their time by grabbing the check. When you buy someone a meal, they’ll often insist on returning the favor next time.
34. Don’t put all of your self-worth into one thing. If your identity intertwines with one thing, what happens when you have a setback in that? How many athletes go crazy when injured from their sport, or sink into depression when their career ends? There’s more to you than that one sport, talent, hobby, or piece of art. 
35.  Foam roll.
36. Learn how to drive stick. You never know when you’ll be somewhere in Europe looking to rent a car but only manual cars are available. Then your whole friend group will go, “uhh who can drive manual?” and you’ll save the day (this happened). 
37. Maintain a mindfulness practice. In a world where our attention is called to so many places, electing where to place it is one of the most valuable skills. Fortunately, this doesn’t have to be boring. My practice involves emo music.
38. Train for athletics before aesthetics. An athletic body looks good because it is good. Good athletes have good physiques. As Dan John says, train movements, not muscles. Once you’ve got the important boxes checked, do all the biceps curls you want. Aside: Beach body day is always a suitable replacement for conditioning if you feel like you’ve earned it. 
39. Find some hobbies unrelated to your vocation. For me, chess and playing guitar in front of my dog fit the mold. They stimulate my mind in different ways, give me joy other activities can’t. They also keep me from putting all of my self worth into one thing (see rule 34). And even though I suck at both of those things, it’s fun.
40.  Assume formlessness. This is the last law of Robert Greene’s 48 Laws of Power. It means you can break all of the rules if the situation calls for it. Don’t be married to any rules or laws. There are situations where all of these laws should be broken. It also aligns with rule #17. I am open minded that I might think these rules are ridiculous in just a few years. 

Now that I’ve made my list, of course I’m going to ask you to do the same. Establishing a set of rules to live your life by forces you to examine what actions and attitudes are important to you and to narrow this down into a list of rules. 

You’ll likely have virtues you value, but don’t actually follow. You can identify incongruencies in your character, and use your new rules to improve yourself, developing self awareness drastically increasing your accordance with what you believe.

Additionally, rules eliminate decisions. Because I have a rule to never hit the snooze button, I never do. It’s a categorical no, and so I avoid the inner contemplation of what to decide. In high school, peer pressure to drink is something nearly everyone goes through. But my rule made it easy to say no. “I don’t drink,” was a simple response. My rule not to drink always made the decision for me. When pressed further, I’d say, “it’s a personal rule.” No amount of peer pressure would affect me, because I had my rule, and I wouldn’t break it. 

Structuring decisions in this manner allows you to categorically eliminate what you don’t need, but also forces the opposite for others. “Learn something about someone in every conversation” makes my default to ask questions about the other person, to lean into the moment, to drive away my instinct to talk about myself. The rule elevates every conversation I have. 

Rules also create structure, and this structure often carries into other areas, such as choosing what to eat, what to do, et cetera. As Jocko Willink says, discipline equals freedom. Rules create structure and therefore the discipline to create the space for what you care most deeply about.

The list will increase your awareness about everything in your life. 

“And I think that’s worth writing a list.” – John Romaniello