On Our Final "Virtual Route 66" For Feburary 2024: On Career Advise ((Courtesy Ryan Holiday))

 

​37 Pieces of Career Advice I Wish I’d Known Earlier​

From my first desk job working at my college newspaper.

​Today’s newsletter is brought to you by Sidebar. Read more at the bottom.

My first job was working at a small deli and grocery store in Lake Tahoe when I was 15. It was a job that came full circle some twenty years later when my wife and I bought a place called Tracy’s Drive-In Grocery in 2021, a little place that’s been in business since 1940.

I’ve had my fair share of gigs in between.

I worked in fast food. I was the director of marketing for a publicly traded company. I’ve been a lifeguard. I dropped out of college to be a research assistant to an author. I worked a desk at a talent agency in Beverly Hills. I’ve started multiple businesses. I’ve freelanced. I’ve been lucky enough to speak and consult with multi-billion dollar companies and Super Bowl winning sports franchises, family offices and law firms.

I wouldn’t say I’ve done it all because that’s one thing you learn–how much you have left to learn–but I have done a lot. I’ve had to think a lot about how to be a good employee as well as how to be a good boss. I’ve seen what makes good companies succeed and bad companies fail. I’ve seen how people get ahead…and how people get stuff.

I’ve also written a lot about this over the years, as I was figuring it out. In fact, many times I had to talk to bosses about this “little thing I do on the side” which was writing until eventually, the business stuff itself because of the stuff I do on the side. And now I have to have the conversation the other way with the people who work for me at Daily Stoic or Brass Check or at The Painted Porch or at Tracy’s: Ok, but what do you really want to do and how can I help you get there?

Anyway, this post is about that. The best of those lessons—things I wish I’d been told when I was just starting and things I still tell myself. Some of them might be exactly what you need to hear right now. Some might not apply to you yet, or ever. That’s okay. Whether you’re just starting out, looking to make a big change, or aiming to reach new heights in your current role, I hope you’ll find something here that helps you navigate your own unique path.

1. Be quiet, work hard, and stay healthy. It’s not ambition or skill that is going to set you apart but sanity.
2. I remember once I called Dov Charney, founder of American Apparel, about some little success I’d had on some project. He was very busy and frustrated that I’d interrupted, but politely, he said, “Ryan, you are calling me to tell me that you did your job.” I thought of that conversation when I saw that famous scene in Mad Men where Peggy complains that Don never says thank you. “That’s what the money is for!” he tells her.
3. The thing that’s wrong about imposter syndrome is that for the most part no one is thinking about you at all. They’re too busy with their own doubts and their own work.
4. When I was starting out as an assistant in Hollywood, someone told me that the best thing I could do was make my boss look good. Don’t worry about credit, they said. Forget credit so hard that you’re glad when other people get it instead of you. It ended up being pretty decent advice, but it was nowhere near the right wording. I think a better way to express it would be: Find canvases for other people to paint on. Come up with ideas to hand over to your boss. Find people, thinkers, up and comers to introduce them to. Cross wires to create new sparks. Find what nobody else wants to do and do it. Find inefficiency and waste and redundancies. Identify leaks and patches to free up resources for new areas. Produce more than everyone else and give your ideas away. The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.
5. Very rarely have I ever let anyone go because they did not have the skills to do their job. It’s almost always their unwillingness to learn those skills or their inability to take feedback.
6. When I was 20 years old, I was working at this talent agency in Hollywood, and I got invited to this important meeting. As they were talking about stuff, I interjected and said something. My mentor took me aside after and he said, why did you say that? Did you think it actually needed to be said or did you just feel like you wanted to have something to say? I think about that all the time. It’s in The 48 Laws of Power — Always say less than necessary. Saying less than necessary, not interjecting at every chance we get—this is actually the mark not just of a self-disciplined person, but also a very smart and wise person.
7. The boss/mentor/biz can’t want you to succeed more than you want it. You have to be the driver of your own life/career/advancement.
8. I was working full time at American Apparel but planning my next move, saving my money and thinking about writing a book. Over lunch one day, Robert Greene told me, Ryan, while people wait for the right moment, there are two types of time: Dead time—where they are passive and biding and Alive time—where they are learning and acting and getting the most out of every second. Which will this be for you?
9. When you’re lacking motivation, remind yourself: discipline now, freedom later. The labor will pass, and the rewards will last.
10. When I first moved to Austin in 2013, I went out to lunch—fittingly—with a writer named Austin Kleon. I was a longtime fan of his book Steal Like an Artist (his book Keep Going is another favorite). After we ate, he drove me around the city, showing me things and giving me advice. Austin was a little older than me and already married with kids. I remember asking him how he made time for it all. “I don’t,” he told me. “Life is about tradeoffs.” And then he gave me a little rule that has stuck with me always: Work, family, scene. Pick two. Your creative output, your personal relationships, and your social life—balancing all three is impossible. You can excel in two if you say no to one. If you can’t, you’ll have none.
11. Lengthen your timeline. Opening my bookstore, The Painted Porch (delayed a year by COVID) taught me that it always takes longer than you think it’s going to take. That’s Hofstadter’s law. And even when you take the law into account, you’re still surprised.
12. ​All success is a lagging indicator… all the good stuff (and bad stuff) is downstream from choices made long before.
13. Lyndon Johnson said that the way to get things done was to get close to those who are at the center of things.
14. Robert Greene’s metaphor for mastery is being on the inside of something. When we start a new sport, when we get our first job, when we approach a field we haven’t yet studied, we are on the outside of. But as we put in the work, as we familiarize ourselves with every component, as we develop our intuitive field, we eventually make our way to the inside. This is a metaphor from Robert I think about constantly. I don’t want to be an outsider on anything I do, I want to make my way inside it.
15. Focus on effort, not outcomes. Just try to make contact with the ball. Give your best effort, make contact with the ball. Let the rest take care of itself.
16. In 2013, I started a business with a partner that my wife warned me against working with. I remember explaining to her why she was wrong and that I couldn’t possibly not do this because of some vague gut instinct of hers. The business turned into a nightmare, and it turned out that this partner was not someone I should have worked with. This shares a commonality with almost all my mistakes and regrets: Not listening to my wife from the beginning. You have to learn whose judgment to trust. You have to learn who knows you better than you know yourself, and you have to be able to trust and defer to them.
17. The trope that a day job takes away from your art or your hustle is stupid. There was a great exhibition at the Blanton Museum a couple years ago 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.
18. 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.
19. My career in Hollywood came to an end when one of the talent managers took a dislike to me (I told this story at the beginning of my appearance on Joe Rogan). When I ended up at American Apparel, I asked Robert Greene about how to prevent that from happening. He pointed out my problem before was that I had only had one ally or patron. I needed to cultivate relationships with multiple decision makers/power brokers at the new company, especially a place as political and full of intrigue as American Apparel. So that’s what I did–you don’t want to be dependent on a single thread or a single vote of confidence. You need redundancies. You need relationships.
20. When you’re building a business, salaries/staff can feel expensive. But if you succeed, you’ll regret giving up equity so cheaply.
21. Dov Charney said another thing to me that I think about a lot. I was pointing out that some store (which had just opened) wasn’t doing well. He said, “Run rates always start at zero.” The point there was: Don’t be discouraged at the outset. It takes time to build up from nothing.
22. There is a story about an exchange between Jerry Seinfeld and a young comedian. The comedian approaches Seinfeld in a club one night and asks him for advice about marketing and getting exposure. Exposure? Marketing? Seinfeld asks. Just work on your act. Your work is the only thing that matters.
23. Talking about what you’re going to do makes you a lot less likely to actually do it. Keep your plans to yourself.
24. The distinction between amateur and professional is an essential piece of advice I have gotten, first from Steven Pressfield’s writings and then by getting to know him over the years. There are professional habits and amateur ones. Which are you practicing? Is this a pro or an amateur move? Ask yourself that. Constantly.
25. Peter Thiel: “Competition is for losers.” I loved this the second I heard it. When people compete, somebody loses. So go where you’re the only one. Do what only you can do. Run a race with yourself.
26. The idea of “Fuck Yes…or No” is far too simple and has caused me quite a lot of grief. Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. Right now I’m about to do something big that I am both excited and terrified about. The point is: The certainty comes later. The truly life-changing decisions are never simple. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my “Fuck yes’s” because I was caught up in a fit of passion or bias. The whole point of risk is that you don’t know.
27. There is a story about the manager of Iron Maiden, one of the greatest metal bands of all time. At a dinner honoring the band, a young agent comes up to him and says how much he admires his skillful work in the music business. The manager looks at him and says, “HA! You think I am in the music business? No. I’m in the Iron fucking Maiden business.” The idea being that you want to be in the business of YOU. Not of your respective industry. Not of the critics. Not of the fads and trends and what everyone else is doing.
28. If you can afford to, delegate it. If you can’t yet afford to, automate it. Time is the most precious resource.
29. The best coaches and CEOs aren’t the ones who succeed just on the field or in the boardroom. The true greats are measured by their coaching tree—what the people who worked for them, who they mentored, who they inspired go on to do.
30. The thing I’ve learned about leveling up in your career, or breaking through different ceilings, is that you really only realize that it happened in retrospect. Just like you don’t notice your hair growing or your face aging, you can’t really feel it as it’s happening. Be patient—evaluate later. Don’t kick yourself now because you think you’re stuck. You might be the opposite of stuck and just not know it.
31. Be able to adapt and make use of new tools. I have no idea what the long term implications of artificial technology will be, all I know is that the best approach as an individual is to find a way to use it to get better at what you do.
32. Having now been in pro locker rooms and boardrooms and briefing rooms with special forces operators and the Senate dining room—all very different worlds—I have come to believe that elite performance is elite performance is elite performance. While these folks all do very different jobs at very different levels of fame or fortune, they’re all basically thinking about the same handful of things, accessing the same core mental skills: Resilience. Creativity. Focus. Collaboration.
33. 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.
34. 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.
35. 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.
36. If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success. If starting a business 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.
37. A friend of mine just left a very important job that a lot of people would kill for. When he left I said, “If you can’t walk away, then you don’t have the job…the job has you.”

On Our Virtual Route 66: On Our World

 

We present a set of Random Thoughts on the Education Front courtesy of Stanford University and the Visual Capitalist as we look forward to the continued privilege to serve:

IN THIS EMAIL:  Upcoming Events: Forugh Farrokhzad (Feb 22) | Iranian Masculinities (Feb 29) Around Campus: Mahan Esfahani Concert (March 6) For Stanford Students: Norooz celebration (March 5)

The United States, the West, and the 1979 Revolution, with Dr. Abbas Milani On the 45th anniversary of the 1979 Islamic Revolution, this Iran International episode of "Witness to History" features an interview with Dr. Abbas Milani analyzing the policies of the United States and Western allies toward the final months of the reign of Mohammad Reza Shah Pahlavi. In Persian/Farsi.

Narratives From the Victims of Flight PS752 October 26, 2023. In Persian/Farsi.  Dr. Hamed Esmaeilion, Ms. Moniro Ravanipour, and guest Ms. Azadeh Heydaripour

UPCOMING EVENTS

Forugh Farrokhzad: A New Edition of Her Collected Works Domenico Ingenito Thursday, February 22th, 6:30-8:00 PM PT | In Person

Professor Domenico Ingenito discusses his new book offering a critical edition and Italian translation of Forugh Farrokhzad’s entire poetic production. Farrokhzad (1934-1967) is the first female Iranian poet who playfully renegotiated the formal rules and dominant imagery of classical Persian poetry and wrote about sex and desire from the perspective of women. Until recently, due to censorship and editorial misunderstandings, no reliable editions of Forugh Farrokhzad’s collected works were available on the market. Dr. Ingenito’s new book features the Persian text of all the original collections of poetry published by Farrokhzad during her lifetime, along with pieces published posthumously, verses co-authored with Yadollah Roya’i, lines extracted from the film Khāne siyāh ast, as well as Farrokhzad’s proto-feminist afterword to Asir (1955). This edition includes a literary biography of Farrokhzad’s life and works as well an annotated critical study that traces the editorial development of Farrokhzad’s poetry collections until the time of her death. Domenico Ingenito is Associate Professor of Iranian Studies and Persian Literature at the University of California, Los Angeles Part of the Stanford Festival of Iranian Arts

RSVP to attend in person

A History of Iranian Masculinities During the Late Qajar and Early Pahlavi Period Sivan Balslev Thursday, February 29th, 6:30-8:00 PM PT | In Person

The transition from Qajar rule in Iran to that of rule by the Pahlavi dynasty set in motion a number of shifts in the political, social, and cultural realms. Focusing on masculinity in Iran, Dr. Sivan Balslev's book Iranian Masculinities: Gender and Sexuality in Late Qajar and Early Pahlavi Iran interweaves ideas and perceptions, laws, political movements, and men's practices to spotlight the role men as gendered subjects played in Iranian history. It shows how men under the reign of Reza Shah dressed, acted, spoke, and thought differently from their late Qajar period counterparts. Furthermore, it highlights how the notion of being a "proper Iranian man" changed over these decades. Demonstrating how an emerging elite of western-educated men constructed and promoted a new model of masculinity as part of their struggle for political, social, and cultural hegemony, Dr. Balslev shows how this new model reflects wider developments in Iranian society at the time including the rise of Iranian nationalism and the country's modernisation process.

Sivan Balslev is a historian of modern Iran, focusing on the cultural and social history of the 19th and 20th centuries. Her fields of interest include gender, sexuality, childhood studies, and everyday life. Her current project, funded by the Israel Science Foundation, focuses on the history of children and childhood in Iran, circa 1870-1970. Since 2018, Dr. Balslev has been a lecturer (assistant professor) at the Department of Islamic and Middle Eastern Studies at the Hebrew University of Jerusalem. Iranian Masculinities: Gender and Sexuality in Late Qajar and Early Pahlavi Iran (Cambridge University Press, 2019) is her revised dissertation. The book offers the first study of the emergence of a new model of hegemonic masculinity in Iran. In addition to Iranian Masculinities, she published two translations to Hebrew from the work of Iranian poet Forough Farrokhzad: Another Birth and Let Us Believe in the Beginning of the Cold Season.

RSVP to attend in person

AROUND CAMPUS

Global Dialogues: Indigenous Data Sovereignty Friday, February 23 at 12:00 pm Pacific, via Zoom

Mahan Esfahani In Recital  Stanford Live Wednesday, March 6, 7:30 PM PT | In Person

Mahan Esfahani has made it his life’s mission to rehabilitate the harpsichord, bringing it into the mainstream of concert instruments. Performances by the Iranian-born harpsichordist leave critics breathless and audiences rapt—his light touch and superhuman agility conjuring interpretations that are “exquisite beyond measure” (Los Angeles Times).

Which Countries Recognize Israel or Palestine, or Both? In this visualization, we look at how international recognition of Israel and Palestine breaks down among the 193 UN member states. > Read more   SPONSORED   Visualizing the New Era of Gold Mining Where will our future supply of gold come from? This infographic highlights the need for new mining projects, to make up for a lack of recent major gold discoveries.  > Read more Ranked: The World's Top 25 Defense Companies by Revenue With billions in defense contracts handed out annually, who are the key players profiting? View this graphic to find out. > Read more   The World's Most Powerful Passports in 2024 The most powerful passports have changed over the last decade, driven by political and economic factors. Here are the top 30 worldwide.   >> View more

Notations On Our World (Special W-End Edition): "Why go to the moon?" - John F. Kennedy at Rice University

Notations On Our World (Special Friday Edition); Saving Ourselves

 

​How to Save Your Family from the Algorithm​

Why my wife and I don’t post pictures of our children online

This piece was initially published on December 31, 2023 for The Free Press, you can read and share it there. I did another piece for them on parenting back in June, which you might also like!

Before we get into the article, I want to share some very exciting news. I’m doing two LIVE events in Australia where you can see me discuss big ideas and answer your questions from the stage. We’re calling it The Stoic Life. Join me in Sydney on July 31st and Melbourne on August 1st. We’ll have a limited number of slots of a VIP meet-and-greet as well if you want to chat afterward. It’s going to be great. Learn more and purchase tickets here.

There in the hospital in 2016, when I held my first child for the first time, I had a feeling common among new parents. I was overwhelmed by the sense that I had been entrusted with something very special. Your kids are so vulnerable and defenseless, so innocent and new. You hold them for that first time and think, this is the most wonderful and special thing in the world. You think, this is my purpose now: to protect, to serve, to teach.

What I was not thinking was: I bet this will get a lot of likes on Instagram.

My wife felt the same as I did. So, there and then we made a decision: we would not post pictures of our children online—and if we did, we would obscure their faces. We would also ask that their grandparents and our friends respect that choice and avoid doing so, too.

The reason I don’t post pictures of my sons, who are seven and four, on the internet is not because I am a private person. It’s not because, after writing a handful of bestselling books over the last decade, I have managed to achieve a fraction of the fame of the average beauty influencer and now worry about my family’s safety.

I mean, I am private and I do worry.

But we have kept them offline because it is the only way to stop social media’s skewed incentives from distorting our family life.

I see what the social networks are getting out of it. But what’s in it for the kids? And what’s it doing to all of us?

In my line of work, we talk about “audience capture.” It means that performing for viewers who like and respond to what you post can change a person. Across my handful of social media accounts, including in my writing and thinking on parenting at DailyDad.com, I have a few million followers and many hundreds of millions of views across them and YouTube. You can feel the pressure to give the audience what they want, or to obsess over how your content will be received.

That’s what algorithms do, they seduce and corrupt. Fame and the demands of an audience are wicked forces in the life of an artist or a political thinker—it’s not something you want acting on your personal life too.

I know a couple, a man and a woman, who are both popular influencers. I watched with fascination and horror at how perfectly their expanding family fit into their social media lifestyle. The announcement. The baby bump. The gender reveal. The trip to the hospital. The public registry. The recommended products (complete with affiliate links). The sponsored content. It was almost as if, a cynical person might say, they had a kid for the content.

And the content is big business. It’s algorithmic gold—especially for other parents, scrolling on their phones in the middle of the night while feeding their baby, or sitting in the sun during soccer practice. And it’s the social media companies making money off the clicks.

On top of these distortive effects, there’s the hostility of social media. Trolls who tell you what you’re doing wrong. Haters who question your parenting decisions. Creeps who have opinions on what children wear and how they act. This is no place for babies! It’s no place for a parent either—not if one wants to cultivate the traits that parenting requires: Presence. Unconditional love. Patience. Respect. Humility.

***

Last Thanksgiving, as we took a family photo at the beach, my seven year old was acting crazy. He was running around in circles. He was making weird faces. His four-year-old brother was laughing while cowering, trying to avoid getting smashed into. Then they teamed up to lunge at the camera in an effort to knock it over, repeatedly, each time the timer was about to go off. I caught myself saying, “You’re ruining the picture!”

But they were not. The picture was not for anything. In fact, the phone was capturing an actual moment, and our actual family life—with its fair share of insanity and complete meltdowns never far away.

This is not what you see on social media. No one posts about life’s mediocrity, or their own deficiencies as parents. They don’t share their mistakes, or their unflattering angles.

“Family blogging is the grossest thing that has ever existed,” the filmmaker and vlogging pioneer Casey Neistat told me recently. “If you’re a parent, you know: it is hard to get your kid to behave, to do those performances and to act happy all the time. For every smiling kid, for every one of those videos, there’s six hours of the kid crying and screaming and the mother cutting all that footage out.”

The grossest example of the grossest thing ever? Four months ago this clip of a mom appeared on Reddit, where she asks her devastated son to perform for a video she’s making about their dog dying.

“Act like you’re crying,” she tells him brusquely.

“I am crying!” he wails.

And then he gets to watch his mom trying on a series of facial expressions to see which would pop out best as a thumbnail for her YouTube channel.

That is the screwed up part not just of family vlogging but of all the ordinary exploitation of children via social media. I wouldn’t wish having a stage mother on any kid, but child actors are at least protected by some regulations. Income is put in trusts so greedy parents can’t steal it all.

What happens to the ad revenue from the videos like the boy with the sick dog? Who protects kids from those kinds of parents? The answer, as a court just found in the child abuse case of popular mommy blogger Ruby Franke, is basically no one.

But the impact of social media on families is usually more subtle than this. Last year, we were standing in line at Disneyland when we got talking to a large family behind us. The young children and the adults were wearing color coordinated outfits perfect for social media.

What rides have you done so far, we asked.

“Oh, none,” their eight-year-old daughter told us in frustration. “We’ve been posing for photos for our parents all morning.”

Mom and Dad weren’t doing it for the money. Certainly the kids weren’t enjoying it. But personal boundaries and common sense were no match for the thrill of appearing to be the perfect family to friends, relatives and strangers on the internet.

***

In the ’70s, long before social media, the novelist Joan Didion dressed her daughter in perfect outfits for photographs. They would take her out to be seen in restaurants, the perfect literary family. “Only later,” Joan Didion wrote of parenting her daughter long before social media, “did I see that I had been raising her as a doll.” Heartbroken and grieving over the loss of both her husband and only child when she wrote those words, Didion was almost certainly being too hard on herself. But she was right to recognize that our kids are not props. What right do we have to turn them into fodder for our feeds, whether we have a few dozen followers or many millions?

Because we spend a lot of time together as a family and I show footage from my own life on social media, my kids do occasionally appear in the background of videos I’ve posted (if they turn toward the camera, we blur their faces). When I launched the Daily Dad email in 2018, it became inevitable that I would have to share at least some of my parenting experiences, whether in my own content or when asked about them in interviews, but still, I try to keep pretty clear boundaries between their lives and mine. I don’t want them to be dolls or props, unpaid accessories.

Yet even with the anonymizing we’ve done with our kids, I still felt strange including them without their consent, and so my wife and I set up retirement accounts for them that we deposit into each month as compensation for these background appearances. When they get older, they can decide whether they want to be included more or less in the work I do and they will at least have been compensated for their work as background actors when they were younger.

One of my other rules is that I don’t post any of the content myself. It goes through a social media team, so I don’t have to be an editor of my own life. I don’t have any of the social media apps on my phone either—preferring not to get unsolicited feedback from strangers about whether I am interesting or not. Because if this data and its demands are acting on you, shaping what you post or how you experience moments in your life, it bears asking, do you have an audience or does the audience have you?

If you need more convincing, just look at what the social media titans are doing themselves. Mark Zuckerberg, the founder of Facebook and the owner of Instagram, who has made billions encouraging other people to live their lives out on his platforms, made a powerful admission on July 4 of this year. He posted a photo of his lovely family celebrating together . . . with the faces of his kids blurred out.

The only way to win is not to play.