The new year is not real. It’s an artificial, made up event. Nothing has really changed. Nothing has actually happened.

We know this because there are so many different ways of tracking ‘the year.’ There is the fiscal year. There’s the academic year and the agricultural year. There are regular years and leap years. There’s the Chinese year, which varies each year, typically starting somewhere between January 21st and February 20th and lasting until a similar date the following year.

In actuality, every single day is a new year…because one year has elapsed since that day, one year earlier.

But still, there is something to the New Year. Even the Stoics acknowledged it. Seneca started each year by plunging into the frigid Tiber River in Rome—I think he was washing off the old year and starting fresh for a new year, as well as starting by doing something challenging and difficult.

Sure, you could start fresh any day, but would you? Do you know?

So let’s use the close of 2023 and the beginning of 2024 as an opportunity—however forced, however artificial—to reexamine, reorient and restart. That’s what Epictetus said, “First say to yourself what you would be; and then do what you have to do.” He asked how much longer we were going to wait to demand the best of and from ourselves?

Here are some habits, some things I am going to ask of myself in 2024, many of which were inspired by The Daily Stoic New Year New You Challenge, which starts on January 1st. It’s a big part of my year each year—kicking things off with something that challenges me—and I hope you’ll join us on January 1st. (Sign up here, more info below).

Think Small

The writer James Clear talks about the idea of “atomic habits” (and has a really good book with the same title). An atomic habit is a small habit that makes an enormous difference in your life. He talks about how the British cycling team was completely turned around by focusing on 1% improvements in every area. That sounds small, but Clear emphasizes that repetitive actions accumulate and add up in a big way over time.“Well-being is realized by small steps,” Zeno would say looking back on his life, “but is truly no small thing.” If you want to start reading more—don’t promise yourself you’re going to read more books this year; instead, commit to reading one page per day. If running a mile seems daunting—that’s fine, start with a walk around the block. If your eating habits are a mess—start by making one healthy food choice a day. Just focus on getting started, because once you start, you can build.

Embrace Hofstadter’s Law

Starting small only works if you have patience, though, if you stay at it. Hofstadter’s Law says it always takes longer than you think it’s going to take…even when you think it’s going to take a long time. As I wrote about a little while back, I’ve learned this repeatedly throughout my career. I started blogging in 2005. My first book came out in 2012. The Obstacle is the Way came out in 2014…and took six years for it to hit any bestseller list. I didn’t hit the New York Times Bestseller list until 2019, on my 13th book. My wife suggested we open a small-town bookstore back in the fall of 2019. We were delayed opening by a year because COVID, then for another year we didn’t feel right opening, then a freak storm (and political incompetence) shut down the power grid, leading to burst pipes and a busted roof, then books were unavailable due to a global logistics crisis. It was, you might say, one damn thing after another.

That’s life. That’s how success works. And that’s not even getting into my actual journey as a person and as a writer, progress in which has been slow to say the least! I feel like I’m just becoming capable of stuff that I set out to improve on years ago.

The point is: It always takes longer than you want. So, one of the most important habits is the habit that makes all other habits possible: patience. It doesn’t matter if it’s writing a book, opening a small business, getting in shape, establishing a reading or meditation practice—it always takes longer than you expect. It takes longer than you’re willing to wait. In any case, it takes however long it takes. We want our progress now. We want our success now. We want our rewards now. But if you can practice delayed gratification, if you can understand that all good things take time, that it’s a process, you’re almost always going to be more successful.

Make A Commitment

In 2018, we did our first Daily Stoic New Year New You Challenge, full of different challenges and activities based on Stoic philosophy. It was an awesome experience. Even I, the person who created the challenge, got a lot out of it. Why? Deciding what we want to do, determining our own habits, and making the right choices is exhausting. Handing the wheel over to someone else is a way to narrow our focus and put everything into the commitment.

To kick off 2024, we’re doing another Daily Stoic New Year New You Challenge. The idea is that you ought to start the New Year off right—with 21 great days to create momentum for the rest of the year. If you want to have better habits this year, find a challenge you can participate in. Just try one: it doesn’t matter what it’s about or who else is doing it.

Cut Out The Inessential

One of the challenges in last year’s New Year New You Challenge was to pick a word for the year. The word of 2023 for my wife Samatha and I is the word we’re choosing again for 2024: LESS. Less stuff. Less distractions. Less screen time. Less commitments. Less so we can have more—more presence, more peace. Matthew McConaughey told me he shut down his production company and his music label because “I was making B’s in five things. I want to make A’s in three things.” Those three things: his family, his foundation, his acting career (you can listen to our conversation here). Marcus Aurelius would say that doing less “brings a double satisfaction.” You figure out what’s really essential and you do those things better. Along the same lines, Maya Smart told me she had to start saying “No” so she could say “Yes” to writing her first book (which you can pick up at the Painted Porch Bookshop). “I had to start setting boundaries,” she said “Steven Pressfield writes about this idea that you do this shadow work. For me, it was volunteering…So I started resigning from boards and telling people, ‘I’m no longer able to do this thing that I used to do because I’m focused on this book.’” Me? As I wrote about last week, I surround myself with physical reminders that make it impossible to avoid considering each opportunity and each ask carefully. What’s at stake is my finite resources. So are yours!

Treat The Body Rigorously

Adopting a new habit always seems daunting at first. As I write about in Courage is Calling: Fortune Favors The Brave, we can’t just hope to be brave when it counts. Courage has to be cultivated. To do the big things that scare you, start with smaller things—start with developing the ability to push yourself to do stuff you’re reluctant to do. To be able to endure the cold reception of a bold idea, start with enduring a cold shower. To be able to step forward when the stakes are high, regularly do that when the stakes are low. To be able to embrace the discomfort of a major life change, accustom yourself to minor discomforts. We treat the body rigorously, Seneca said, so that it may not be disobedient to the mind. We push ourselves in little ways so the big ways stop seeming quite so big, quite so out of character. We minimize fear by making the act of overcoming it routine. We test ourselves to prepare for the tests of life. By methodically and deliberately exposing ourselves to small challenges, what once seemed daunting becomes manageable, even routine.

Do The Essential Things First

​Hugh Jackman reads right after he wakes up (early) in the morning. For many years, he and his wife would read outloud to each other for thirty or so minutes. “It’s the best. I recommend it to anyone…It’s the greatest way to start the day. Right now I’m reading Stillness Is the Key…I’m really into philosophy. So we read, and we talk, because stuff’s on your mind…That way, no matter what happens through our day, we know that we’ve had quality time together. You always think, tonight; after work; after this; when we put the kids to bed, but that doesn’t always happen.”

​Camilla Cabello told me she starts her day by reading the Daily Stoic email (which you can sign up for here) and then one page from The Daily Stoic. I like to read from Tolstoy’s A Calendar of Wisdom or Robert Greene’s The Daily Laws.

I try to get some exercise in the morning, and I for sure write in the morning. My assistant knows not to schedule calls or meetings in the morning because they make it too easy to let the day get away from you. They sap your willpower early. By tackling writing first, by getting some time outside (with the kids usually) first, I already won the day. Everything else is extra from there. Well-intentioned plans fall apart. Our willpower evaporates. So it’s key not only that we prioritize the essential things, but that we habitualize doing them first thing.

Get Help

Whenever I speak to military groups, I like to tell them about one of my favorite quotes in Meditations,

I like the way he says that with a shrug. So what? There’s nothing shameful about needing help. Whether that’s going to therapy, asking for advice, or hiring someone to work for you, ‘help’ is the secret to getting better—to unlocking potential breakthroughs, gains or efficiencies.

Tim Ferriss has a great question related to this, What would this look like if it were easy? The idea is that things don’t need to be hard if you’re doing them right. Just as with managing a business, forming new habits often requires putting in place the right kind of support and building a supportive infrastructure around you. Identify the barriers that make a habit difficult and find ways to remove them. If you need a helping hand, so what? If you need a coach or a trainer and you can afford it, hire one. It’s not a moral failure to have childcare or an accountant. If you don’t know exactly what to do or how to do it, ask someone who does. We’re in this mission together. We’re comrades. Get help.

Go The F*ck To Sleep

All the other habits and practices listed here become irrelevant if you don’t have the energy and clarity to do them. We have to follow the advice of a book I love to read to my kids: Go the F*ck to Sleep! What time you wake up tomorrow is irrelevant…if you didn’t get enough sleep tonight. In the military, they speak of sleep discipline—meaning it’s something you have to be good at, you have to be conscious of, something you can’t let slip. We only have so much energy for our work, for our relationships, for ourselves. A smart person knows this and guards it carefully. A smart person knows that getting their 7-8 hours of sleep every night does not negatively affect their output, it contributes crucially to their best work.

Don’t Just Read, Re-Read

I’ve always loved Seneca’s line: “You must linger among a limited number of master-thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.” Because the world is constantly changing, we are changing, and therefore what we get out of those books can change. So I re-read Marcus Aurelius’ Meditations (check out the leatherbound edition of my favorite translation) every year. Before I start any book project, I take a few hours and re-read The War of Art by Steven Pressfield, maybe the greatest book ever written on the creative process. Kressmann Taylor’s Address Unknown was something I re-read in light of the alarming rise of anti-semitism. This year, I’ll re-read some of my favorite novels, and I’m going to re-read some books that I think pertain to the subject I’m writing about now. When I re-read, I learn things I wasn’t ready to learn before, and I gain things that I missed the first time. We never step in the same river twice, Marcus Aurelius said. The books don’t change, but you and your circumstances do. If you want to get better this year, don’t just read…re-read.

Pick Yourself Up When You Slip Up

The path to self-improvement is slippery, and falling is inevitable. You’ll sleep in and not be able to read that page, you’ll cheat on your diet, you’ll say “yes” and take on too much, or you’ll get sucked into the rabbit hole of Twitter. That’s okay. It doesn’t mean you’re a bad person. You’re only a bad person if you give up.

​I told Dr. Edith Eger I felt guilty about how I had lost touch with someone and only recently reconnected with them. She cut me off and told me she could give me a gift that would solve that guilt right now. “I give you a sentence,” she said, “One sentence—if I knew then what I know now, I would have done things differently.” That’s the end of that, she said. “Guilt is in the past, and the one thing you cannot change is the past.”

No one is perfect. We all have bad days. We can’t change that. When we mess up, we can’t go back and fix it. But we can move forward. We can be better here and now. We have to. “Disgraceful,” Marcus Aurelius would say, “for the soul to give up when the body is still going strong.”

All of us have fallen short in the last year…and the years before that. We broke our resolutions. We lost touch with people we care about. We made the same mistakes again and again. We were “jarred, unavoidably, by circumstances,” as Marcus said. But now it’s time to pick ourselves up and try again. It’s time, Marcus continues, to “revert at once to yourself, and don’t lose the rhythm more than you can help. You’ll have a better group of harmony if you keep on going back to it.”

In other words, when you mess up, come back to the habits you’ve been working on. Come back to the ideas here in this post. Don’t quit just because you’re not perfect. No one is saying you have to magically transform yourself in 2024, but if you’re not making progress toward the person you want to be, what are you doing? And, more importantly, when are you planning to do it?

I’ll leave you with Epictetus, who spoke so eloquently about feeding the right habit bonfire. It’s the perfect passage to recite as we set out to begin a new year, hopefully, as better people.

They cost me a lot of money.

It’s a pretty weird thing to collect.

But they help me every single day.

They are a bunch of historical documents of minor historical significance—it’s probably a stretch to call them artifacts—that remind me to do one of the most important but most difficult things in the world. A thing that most of us are not very good at.

As it happens, they come from the office of President Harry S. Truman.

You see, shortly after he became president, Truman was invited to the fifth annual Roosevelt Day in Chicago.

His secretary wrote an inner-office memo to ask if they should start saying no to these sorts of requests with all the demands he had on his schedule.

“The proper answer underlined, HST”, he wrote back.

It’s this last document that I have framed and hung in my office next to two pictures of my kids. It’s the idea that the proper response is to say no because everything we say yes to is, in fact, saying no to something else. No one can be in two places at once. No one can give all their focus to more than one thing. But the power of this reality can also work for you: Every no can also be a yes, a yes to what really matters. To rebuff one opportunity means to cultivate another.

I have some other mementos from Truman’s correspondence, too. One comes from 1969 when Truman was 85 years old, still working, and world famous. Sensing his time is limited, he’s explaining his long-standing policy to not answer questions from every random person who contacts him.

My editor gifted me this memento as a reminder to stay on task. Writing demands that we be a little selfish, it requires that we tune out and tune in, otherwise we can’t do what we do. But I think it’s important to realize that Truman wasn’t some selfish jerk. First, he was polite in the way he (or his secretary) declined. And second, as this other document I have demonstrated, he found a way to scale his efforts.

Truman was realizing that his book(s) were a way to help the most people most effectively. He knew that to be of service to one person at the expense of a large audience was a mistake and that it wasn’t rude to say no to one person if it meant he could say yes to more.

Anyway, I have all these reminders because I need them.

I once heard someone say that early in our careers, we say yes to everything so at one point we can afford to say no. As I’ve been lucky enough to succeed as a writer, I’ve seen my inbound requests go way up. The Daily Stoic email alone goes out to 750,000 people every day. It gets hundreds and hundreds of replies (not all of them nice!). I get requests for speeches and advice and consulting opportunities and to be on podcasts. I get invites to dinner. I have friends who want to do things. Fans come into my bookstore wanting to talk. Neighbors have things they need. Trolls try to provoke me on social media. I have my kids, my wife, and my own interests.

It is literally impossible to do it all. Especially if I want to do any of them at a high level. As I wrote a little while back, I’ve passed on everything from trips to the Super Bowl, a vacation on Necker Island, and more than a few different ghostwriting opportunities. I’ve turned down large amounts of money to do books for people, to travel and speak at events. I turned down a job in a presidential administration (although, as I wrote at the time, there were multiple reasons for that).

A younger me would have thought these things crazy to pass up on. In fact, I used to have trouble saying no to far less crazy things. I used to get Daily Stoic email replies directly to me. I used to post my email address on my website, and I would respond to everyone and everything. I would reply when people tagged or messaged me on social media. And I loved doing it—years after I replied to a reader’s email, they’d follow up with how my reply helped them. That felt great, but I’ve had to realize that saying yes—whether to an all-expenses-paid trip to a remote island or even to a short email inquiry—takes away from something.

A few years ago, Dr. Jonathan Fader, an elite sports psychologist who spent nearly a decade with the New York Mets, gave me a picture of Oliver Sacks in his office. Behind Sacks, who is speaking on the phone, is a large sign that just says, “NO!” I have that photo hanging on the wall in my office, just a few feet from those Truman memos. Above it there is a photo of my youngest son, and below it, a photo of my oldest. I can see them—all three photos—out of the corner of my eye even as I am writing this.

It’s my constant reminder that everything I say yes to is taking me away from the two people I’ve already promised so much of my time to. And from my writing, which is not only the thing that is most meaningful to me and how I make my actual living, but it’s how I can help the most people. So if I say yes to one random person, I’m saying no to a lot more people by taking that time and energy away from my writing.

In tech, they speak of “feature creep”—when a founder or a project manager isn’t disciplined enough to protect the core concept of an idea and allows too much to be jammed in it. Trying to please everyone, they end up pleasing no one. To try to do everything is to ensure you’ll achieve nothing.

This weaker part of ourselves that cannot say no to requests for our time, the part that tries to go along with everyone, perhaps deep down wants that same excuse—if we agree to their thing, then we don’t have to answer for the poor performance of our thing when it’s time for a full accounting. It allows us to say, “Well, if only I weren’t so busy . . .”

The self-disciplined part of us, on the other hand, says, like the Queen’s motto, “Better not.” Or maybe we borrow the quip from E. B. White, when asked to join some prestigious commission: “I must decline,” he said, “for secret reasons.” A clerk of Sandra Day O’Connor once said with reverence, “Sandra is the only woman I know who doesn’t say sorry. Women would say, ‘Sorry. I can’t do that.’ She would just say, ‘No.’”

No, Sandra liked to point out, is a complete sentence.

Say no. Own it. Be polite when you can, but own it.

Don’t say maybe. Don’t give a bunch of reasons (which invite an argument). Don’t push it until later.

Say NO.

Help the people who work for and with you to do the same. Jony Ive, the designer at Apple, once recounted that Steve Jobs was always asking Ive and other Apple employees what they were focused on and specifically, “How many things have you said no to?” because to focus on one thing requires not focusing on other, less important things. A device can’t have every feature.

Life is about tradeoffs.

And this is your life. And saying no is your power.

By seizing it, you become powerful. More powerful in fact, than some of the most powerful people in the world who happen to be slaves to their calendars and ambitions and appetites. The conquerors who rule over enormous empires but are slaves to solicitations. The billionaires who fear missing out. The leaders always chasing the shiny new thing. Who cares if you have achieved extraordinary things when you are punished for it by having even less freedom day to day?

It feels like you’re free because you’re choosing, but if the answer is always yes, that’s not much of a choice.

I remember learning how to play the recorder in elementary school. I remember square dancing. I remember cursive. I built a model of a Spanish mission out of sugar cubes.

Some of this was fun. Some of it wasn’t. Some of it probably contributed, in some indirect way, to my general ability to learn and function in the world. Most of it, I think it’s safe to say, did not.

Something I don’t remember learning about at all? Money. Even our math problems were mostly about potatoes and trains, not how to calculate the interest rate on credit cards or the return on an investment. There was the occasional—and now very politically incorrect—remark from teachers about how if you didn’t do well in school, you’d end up working at McDonalds. But even with all the pressure to go to college, school provided very little in the way of discussion about what kind of careers paid what, how to live within one’s means whatever that career was, let alone how one might create their own business and work for themselves.

This is sad and strange and hardly rare. We leave it to kids who become adults who then have kids to just figure it out for themselves. Not everyone does. I’ve since met high income earners who were terrible with money. I’ve met people who were quite rich by every financial metric but whose relationship with that money was quite terrible, (you’d never want to trade places with them). I’ve met people who have been the victims of scams and frauds because they lacked the basic knowledge needed to protect themselves.

To the Stoics, the solution to these timeless problems—the way to be better with money, to improve your relationship with money, to not fall for every smooth talker, Marcus Aurelius said—is the same: get smarter. Become better educated on the topic of money. “Wisdom,” as Seneca said, “offers wealth in ready money.” It’s something I’ve been thinking a lot about in my own journey—growing up with two civil servant parents, dropping out of college, succeeding in the corporate world until I dropped out of that as well to work for myself. I’ve been thinking about it a lot now that I have kids.

And I’ve been thinking about it a lot in researching and writing what is the most in-depth course ever built over at Daily Stoic: The Wealthy Stoic. It’s a 9-week course packed with the best wisdom from the Stoics, as well as today’s leading money experts, on how to be rich, free, and happy. Along with ~30,000 words of exclusive content, there will be 3 live video sessions where I’ll be joined by bestselling authors, pioneering businesswomen, and investing and finance experts. I’m really excited about this course. I think it’s going to be one of our best, and I would love to have you join us—you can learn more at thewealthystoic.com.

Here are 31 lessons I’ve learned about money…

–I’ve never met a person who ever reached ‘their number.’ You know, people say, ‘When I hit $Xm, I’ll be good.’ They say, ‘Once I have X years salary in the bank, I’ll be good.’ No one ever seems to get to that number. We’re never ‘good’ because we move the goalposts…(or because we set a preposterous and unrealistic number to begin with).

–It’s important to remember what once seemed like a lot of money to you. When I dropped out of college to work as an assistant in Hollywood, I took a salary of $30,000. I remember saying to myself–no joke–”What am I going to do with all this money?” It was enough for an apartment and all the books I wanted to read. Remembering that as an anchor point has not only kept me humble, it’s kept me grateful. Think about what your parents made, think about what you used to get paid per hour to make smoothies or mow a lawn. People manage to live on that–you yourself once did.

–Seneca said that poverty wasn’t having too little, it was wanting more. He wasn’t talking about poor people. He was talking about rich people. He was talking about people who are insatiable. ‘Rich’ is having enough–as this story illustrates.

–My work is unpredictable, and even success comes in the form of lump payments. So when it comes to savings and investing, I have always favored things that are dependable. My wife and I invested quite a bit in different real estate things over the years, with the idea being to eventually create enough annual income that we could be independent from my creative/entrepreneurial/artistic decisions. This strategy is not for everyone, but it worked for us. I could stop writing tomorrow and know the spigot isn’t going to be turned off.

-My parents did a good job modeling how to be responsible with money. They also taught me how to be savvy at investing and growing one’s money. I wish they had done a better job modeling generosity and the proper value of money (that is to say, that most things are more important than money). There have been lots of other opportunities since to learn the skills I got from them, the others much less so…

-Pick the low hanging fruit. I’ve had to remind the Daily Stoic employees several times to be sure to sign up for their 401k/matching we offer. I’ve left money for too long in checking accounts when the easiest of transfers would have significantly increased the interest I was earning. Don’t get overwhelmed by the whole of life, the Stoics would say, do easy things first.

–If you don’t take the money, they can’t tell you what to do. That’s what Bill Cunningham said: If they pay you, they get to tell you what to do. Remember his words: “Money’s the cheapest thing. Liberty, freedom is the most expensive.”

–The trope that a day job takes away from your art or your hustle is stupid. There’s a great exhibition at the Blanton Museum right now about artists who had day jobs. I wrote 3.5 books while I was the Director of Marketing at American Apparel. I started my own marketing company while I was a writer. I have my bookstore. A job for someone coming up is like a trust fund you’ve earned. It helps.

–Learning is priceless. Robert Greene used to have to nag me to submit my hours when I worked for him. To me, the money was an afterthought, I knew the real return was my access to him, that he would answer my questions, that I could see how a real pro did the job.

–That doesn’t mean internships should be free. When you make it, you have an obligation to try to support the people coming up (which is why Robert insisted on paying me even though I didn’t care). It just means sometimes you have to accept a bad deal to learn what you know you need to learn…and also to walk away if you stop learning.

–I’ve had the privilege of talking to many, many extremely wealthy people. They are not that rare. Rarer is the one who actually likes what they do for a living (for instance, half the ones I meet all seem like they’d rather be writing books for some crazy reason). Rarest is the one you’d want to trade places with.

–When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.

–I had this idea that I wanted to be a millionaire by 25. Where this number came from, I don’t know. I made it up, it was ego, and I didn’t hit it. But you know what the difference of getting there a little later was? Nothing. No one throws you a party. Accomplishments don’t change who you are.

–I talked with Tim Ferriss when I was starting my marketing company. He asked me what I was working on and what I was trying to accomplish, and I gave your typical answer: I wanted to be financially successful. Then he asked me something I’ve never been asked. “Ryan,” he said, “What do you do with your money?” Basically, I just put it in the bank, I told him. “Then why are you doing so many things you dislike to earn more of it?” he replied. This insight changed the course of my business as well as my life. Making money is easier than most people think—knowing why and what for, and not being driven in the wrong direction to get it? Much harder.

–You work really hard to get money…and then once you have it you spend time worrying whether you’re putting it to work right. James Altucher once pointed out that you don’t have to make your money grow. You can just have it. It can just sit there. You can spend it. Whatever. You don’t have to whip yourself for not investing and carefully managing every penny. The reward for success should not be that you’re constantly stressed that you’re not doing enough to “capitalize” on that success.

–At the same time, I love Charlamagne’s “Frugal Vandross.” The less expensive stuff you have, the less there is to worry about.

–Be responsible. I have a life insurance policy. I have money saved. If something happens to me, people I care about will be taken care of.

–But not too responsible. The reason they will be taken care of and that I feel creatively and professionally satisfied, is that I have taken a lot of big risks. I dropped out of college (this gave me a two year head start on a lot of people). I left a good job. I bit off more than I could chew many times. Why could I take those risks? Because I had been responsible. I had money saved. I knew what was important to me. I had built a support network. I eliminated the tiny risks so I could take the right ones. If you cover your bases, then you can afford to bet on yourself.

–The best decision I ever made was taking a pay cut to write The Obstacle is The Way (less than half what I got for my first book). I knew it was what I wanted to write. I thought it could sell. I had my day job. It still seemed like a TON of money to me. Sometimes you have to take a step back to go forward,

–If you can, pick up the check. If you can, tip amply. It feels good, it’s nice, it also normalizes not sweating small amounts of money.

–As I wrote recently, a couple years ago, I made the decision to stop basically all the advertising that my business does. I decided to put that money into making content instead—videos, articles, etc. I did this because it occurred to me that the money I was spending on ads made basically no positive impact on the world (if any impact at all), but articles and videos could at least be enjoyed by people (for free no less), even if they didn’t drive the same amount of ROI. In the long run, this content will be around forever and have a bigger and more meaningful reach. This is a small-scale decision given the size of my business, but if people spend more time trying to maximize the positive externalities of what they did instead of optimizing for short-term profits, I think they’d be happier…and ultimately do better…and the world would be better.

–But if I am content with what I have, won’t I stop getting better? No. We play better with house money. Feel better too.

–A wise person once told me…if it’s a problem that can be solved by money, you don’t have a problem.

–If you never hear no from clients, if the other side in a negotiation has never balked to something you’ve asked for, then you are not pricing yourself high enough, you are not being aggressive enough.

–Anticipate the fact that maintaining discipline is hard. Automate. I’m always amazed when I check the balances of accounts where we’ve set up automatic transfers for investing, for our kids’ college, for our emergency reserves–things I set up a long time ago have been doing their job, a far better job that I would have done had I put it on my monthly to do list.

–Don’t compare yourself to other people. Caesar famously wept at the feet of a statue of Alexander the Great. “Do you not think it is matter for sorrow that while Alexander, at my age, was already king of so many peoples, I have as yet achieved no brilliant success?” he said. Um, you were both fucking terrible. And now you’re both gone. Who cares whether so-and-so did this or that earlier than you? Who cares that so-and-so had more?

–Acceptance is a difficult thing, but it’s an important skill as you become successful. Accepting that there will be a certain amount of your investments that fail, accepting that mistakes will cost you, there will be fees and other costs of doing business. Taxes are another thing you have to come to terms with. We must pay all this stuff gladly, the Stoics say, otherwise success will be a form of misery.

–If you live somewhere cheap, you’ve got a head start. Moving to an expensive, popular city ‘to make your start’ is a tough gamble. There is more opportunity…but less runway. I’m grateful to New Orleans in 2011 for giving me plenty of runway as well as friendships and inspiration.

–Yes, it’s true that money is better spent on experiences than material possessions. But, I will say that just because an experience presents itself doesn’t mean you have to feel obligated to do it. Remember, there is a cost to saying yes. And not just a monetary one, but it will take your most precious, non-renewable resource–your time.

–They say that if you think professionals are expensive, try hiring an amateur. This is true in the sense that being cheap or looking for a bargain on services has come back to bite me many times. HOWEVER, I have also been disappointed with how many professionals are actually amateurs. Sometimes, if you want a thing done well, you have to do it yourself. It’s very rare that you’ll just be able to hand stuff off–and don’t be fooled by high priced experts and consultants. You may end up still doing the job yourself in the end…after having shelled out for their fee.

–If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success. If starting a business makes you a worse person—if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives. It’s not successful.