Tribe Of Mentors: Short Life Advice from the Best in the World

by Timothy Ferriss

If you could have a gigantic billboard anywhere with anything on it, what would it say and why? “We need a new diversity—not one based on biological characteristics and identity politics but a diversity of opinion and worldviews.”

Many students come to me full of wonderful intentions hoping to change the world; they plan to spend their time helping the poor and disadvantaged. I tell them to first graduate and make a lot of money, and only then figure out how best to help those in need. Too often students can’t meaningfully help the disadvantaged now, even if it makes them feel good for trying to. I have seen so many former students in their late 30s and 40s struggling to make ends meet. They spent their time in college doing good rather than building their careers and futures. I warn students today to be careful how they use their precious time and to think carefully about when is the right time to help. It’s a well-worn cliché, but you have to help yourself before you help others. This is too often lost on idealistic students.

The private sector teaches important skills like entrepreneurship that can then be applied to any area of work later on.

Sam Barondes’ book Making Sense of People has had a big impact on my thinking, and I sometimes give a copy to people in the midst of hiring someone or even deciding whether to get engaged.

The killer combination is high open-minded, high conscientious, low neurotic.

The third mental model I find myself recommending lately is found not in a book, but on a slightly obscure website: workwithsource.com. This work is based on a European management consultant who studied hundreds of startups and realized that even when there are multiple “co-founders,” there is always a single “source”: the person who took the first risk on a new initiative. That source maintains a unique relationship with the gestalt of the original idea and has an intuitive knowledge of what the right next step for the initiative is, whereas others who join later to help with the execution often lack that intuitive connection to the founder’s original insight. Many organizational tensions and power struggles often revolve around lack of explicit acknowledgment of who the source of the initiative is. A prominent angel investor observed to me recently that many founders seem to hire friends as co-founders more to quell their own anxiety during the early, highly ambiguous days of a new company than to fulfill a specific role. This can work fine as long as everyone is clear on who the source is. The responsibility to fully own the role of source rests in large part with the source themselves.

Often the responsibility to make the room for a real transition is in the hands of the source. It’s the lesson from the George Washington song in the Hamilton musical, as Washington declines Hamilton’s plea to run for a third term and sings, “We’re going to teach them how to say good-bye.”

Today when I speak with anyone about anything, I try to hold their perspective with a “light grip”: the knowledge that they, and I, have very incomplete maps of reality.

I don’t think it’s useful to see a “fund” or a “product.” These are just temporary collections of flawed, brilliant people, who in any given year decide to make a sequel to the movie they made the prior year. The only product is the set of future decisions the portfolio manager makes. If they get divorced or depressed, if their second in command leaves, the “product” completely changes. Calling it a product ignores the reality that the only source of stability is whether the mindset of the team leader is resilient or even antifragile (Nassim Taleb’s notion of actually getting stronger with volatility).

In the last five years, what have you become better at saying no to? I have my assistant Google pictures of people I’m considering meeting or calling in the next two weeks and put them in Trello cards. I see meeting new people as the opportunity to open a new door to a new world that could change my or their life in some way. Seeing someone’s picture allows me to visualize their intentionality and unleashes more creative ideas about what we can discuss and how I may be able to help them. It also lets me access whether I have a “full-body yes” to actually seeing them and opening this new door, and if I don’t then I take my hand off the door handle.

I ask myself “what would be the worst thing” about that outcome not going the way I want?

I like the question because it often surfaces a hidden assumption.

When I came back to Silicon Valley, I didn’t get a general partner offer from the venture firms I cared most about, so I ended up starting one called Floodgate. Floodgate is doing awesome, and I am thankful every day that I didn’t get what I “wanted.”

What advice would you give to a smart, driven college student about to enter the “real world”? Life will go faster than you know. It will be tempting to live a life that impresses others. But this is the wrong path. The right path is to know that life is short, every day is a gift, and you have certain gifts. Happiness is about understanding that the gift of life should be honored every day by offering your gifts to the world. Don’t let yourself define what matters by the dogma of other people’s thoughts. And even more important, don’t let the thoughts of self-doubt and chattering self-criticism in your own mind slow you down. You will likely be your own worst critic. Be kind to yourself in your own mind. Let your mind show you the same kindness that you aspire to show others.

Your time is limited, so it’s best to spend it with people who will make you feel like you made the most of your gift of today.

In general, whenever I feel things are moving too quickly, I find the right instinct is almost always to slow down and get my thoughts back in order. It ends up speeding things up because we get better decisions and more alignment of everyone on the team. If someone on the team needs to be replaced because they don’t have the right skill set, we should face that problem too, but only after we have done our best to seek the truth of the situation. Ego is about who’s right. Truth is about what’s right.

“Diversity in counsel, unity in command.” –Cyrus the Great Founder of the Achaemenid Empire, known as the “king of Persia”

“I can’t give you a surefire formula for success, but I can give you a formula for failure: try to please everybody all the time.” –Herbert Bayard Swope American editor and journalist, first recipient of the Pulitzer Prize

A Little Life by Hanya Yanagihara. The greatest work of fiction I’ve ever read, with the simplest theme: All of us come with baggage and wounds and pain; all of us. But recognizing that common, human bond is what helps us transcend that pain.

It was the most valuable lesson I ever received. Don’t let someone knock you off course before you reach your destination. Trust the work. Always trust the work.

What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? Mother Dirt: It cured my acne and skin problems permanently. It’s a $49 spray with oxidizing bacteria that you use in place of soap, and it restores your skin to its natural balance. If I could buy this for every teenager in America, I would.

Advice I’d give: Make sure you have something every day you’re looking forward to. Maybe it’s your job, maybe it’s a basketball game after work or a voice lesson or your writing group, maybe it’s a date. But have something every day that lights you up. It’ll keep your soul hungry to create more of these moments. Advice to ignore: A little part of me dies every time someone tells me they’ve taken a job as a “steppingstone” to something else, when they clearly aren’t invested in it. You have one life to live. Time is valuable. If you’re using steppingstones, you’re also likely relying on someone else’s path or definition of success. Make your own.

Feeling unfocused, on the other hand, usually means I haven’t quite locked into whatever I’m working on yet—that a part of me still thinks I can pull the ripcord and bail. It usually happens in the first three months of writing a new book. In the end, a lack of focus is usually just fear: fear that whatever project I’m attempting will go nowhere or fail miserably. Early on, I used to give in to that fear. Four books later, I know it’s just a ghost, and I can blow right through it without looking back.

“You can be a juicy ripe peach and there’ll still be someone who doesn’t like peaches.”

Guns, Germs, and Steel by Jared Diamond: This text helped rid me of the nagging incompleteness in my understood connection between the successes and failings of ancient and modern civilizations. Power needs tools and circumstance. Neither need be earned.

Transcendental Meditation is something I’d long heard about but only stepped into this year, and it’s transformed my ability to center my mind and recharge in short periods of time. The David Lynch Foundation has made it so digestible without any of the rigidity or easier-said-than-done elements that I expect many of us find intimidating about beginning a meditation practice.

What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life? The 15 Commitments of Conscious Leadership by Jim Dethmer and Diana Chapman. Though most people will typically blame other people or circumstances in their life when they are unhappy, Buddhists believe that we are the cause of our own suffering. We can’t control the fact that bad things are going to happen, but it’s how we react to them that really matters, and that we can learn to control. Even if you don’t accept that this is true in all cases, giving it consideration in moments of unhappiness or anxiety will often give you a new perspective and allow you to relax your grip on a negative story. This book is an approachable manual for how to do that tactically, and the lessons it teaches have transformed the way I engage with difficult situations and thus reduced the suffering I experience in big and small ways. Though it is written with leaders in mind, I find myself recommending it to everyone, and we give it to every new employee at Asana.

The Back Buddy by the Body Back Company is my favorite purchase from the past five years, bar none. Most basically, it allows you to administer self-massage anywhere on your back with the full leverage of two hands, but I’ve also really gotten to know and appreciate all the little knobs and other features over the years. I’ve even learned how to manipulate parts of my skeletal structure (i.e., self-chiropracty) and incorporate it into my yoga practice. It only costs $30, so I have purchased several: one for the living room, one for my desk at the office, and a collapsible version for traveling (though I do bring the full-size one if I’m checking a roller bag). With 4,500 reviews and a 4.5-star average review on Amazon, I’m far from alone in my appreciation of this product.

The first no is by far the easiest and cleanest.

It takes time, but if you are consistently good at what you do, at least you get to call your success your own.

Looking at the larger picture gives you perspective. Like when a plane takes off, you realize how small your little cocoon of problems, in fact, is.

The education system, by and large, gears everyone up to adhere to set industry standards. While this is a foolproof way to get a job and live a normal life, very few people can break out of the cycle of the mundane to be adventurous, inventive, and selfless. The safety net of a regular job is too comfortable.

I have been blessed with “well-wishers” and “advisors” throughout my career. They teach me what not to do. People make recommendations based on what they think is safest for you, or based on their understanding of who you are and what you ought to be. They set invisible limits on how much you can achieve in your life and pass those limitations on to you inadvertently.

When I am straightforward and sincere about my needs, I find that no one is offended when I say no. Those who are offended perhaps don’t value my needs.

I have a few approaches. First, I journal. It gives me clarity. I have had a diary ever since I was about ten. Today, when I look back at my scribbles from when I was in high school, it gives me great joy to notice how far I have come intellectually and career-wise. I am living my dream.

I meditate. This is a challenge when I feel like my head is in turmoil. I generally start by focusing on my breath. I could count back from ten to one while exhaling and I drift into meditation. It takes about 20-odd minutes to become somewhat thoughtless. Sometimes I feel like I am asleep, but I realize that lucidity is meditation. It always helps. There has not been a single time in my life when I have meditated on something and it hasn’t been useful. I meditate either first thing in the morning or post-lunch if I am at a stressful film shoot.

The Master and Margarita, by Mikhail Bulgakov (translated by Pevear, et al.), which is I think is one of the finest works of fiction of the last century. It’s a fairly short novel, remarkable in its exceptional depth, exploring everything from fundamentals of Christian philosophy to the fantastical (and hilarious) satire of soul-corrupting 20th-century Soviet socialism. I usually buy M&M in batches of five or ten and give as gifts to new friends. There are always a few copies on my desk at work, just in case someone wants to borrow one.

Next, not a book, but a movie. I’ve watched the Kurosawa classic Seven Samurai more than 100 times (really), and used to give DVD copies of the Criterion Collection remaster to young CEOs I mentored. I love the movie (and am generally a bit of a Japanophile), but I recommend it to new managers and CEOs especially because it is fundamentally about leadership: A small band of courageous leaders risks everything to organize a ragtag group in a fight for its life. Sound familiar? To me, this timeless story is a near-perfect metaphor for startups. What would Kambei Shimada do?

“Whenever there is any doubt, there is no doubt.” The line is from the inimitable David Mamet, a quote from Ronin, one of my all-time favorite movies. A laconic reminder to always be decisive in battle and in business, and at a most basic level, to trust your gut. In my line of work, this often enough translates to “fire early,” too. When you aren’t sure about a key employee or a co-founder, odds are exceedingly low your mind will be changed for the better.

“The difference between winning and losing is most often not quitting.” This famous line from Walt Disney on willpower cannot be more true when it comes to entrepreneurship. The only predictable thing about startups is their unpredictability, and powering through the lows of the startup roller coaster ultimately just takes grit—yours and your team’s.

“Look for a partner you’ll try to impress daily, and one who will try to impress you.” Over the last couple decades, I’ve noticed that the best, most enduring partnerships in business (and in life) are among people who are constantly growing together. If the person you choose to depend on is constantly striving to learn and improve, you too will push yourself to new levels of achievement, and neither of you will feel like you have settled for someone you eventually outgrow.

When the time came to start another company, my wife (who continues to impress me every day!) pointed out that I was happiest when working on building PayPal, not when it went public or was acquired. She suggested I consider going back to my entrepreneurial roots in financial services. Having stayed far away from financial services for over a decade, I co-founded Affirm. Very different from PayPal, but with many overlapping concepts and related challenges. Daily work at Affirm can be just as challenging and difficult as it was during PayPal, but I am once again working in my sweet spot and loving every minute of it.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? [My advice is to] take risks, now. The advantages that college students and new grads have are their youth, drive, lack of significant responsibilities, and, importantly, lack of the creature comforts one acquires with time. Nothing to lose, everything to gain. Barnacles of the good life tend to slow you down, if you don’t get used to risk-taking early in your career. I started numerous companies in my early 20s only to see them all fail, but I never thought twice about starting the next one. I knew after the first one that I loved the feeling of starting something, and I had almost no other responsibilities. Eventually, one of the startups did work out, but I was prepared to try as many times as it would take to win. If you are your sole responsibility, this is the time to step outside of your comfort zone, to start or join an exciting, risky project; to drop everything else at the chance to be part of something really great. So what if it fails? You can always go back to school, take that job at an investment bank or a consulting company, move into a nicer apartment. The advice to ignore (in certain situations) is to strive to become “well-rounded”—to move from company to company, looking to pick up different types of experience every year or two, when starting out. That’s useful in the abstract, but if you find that strength of yours (as an indi...

We are in an arms race against distractions. Our devices and technology have gotten to know us so well that we now need devices and technology to protect us from them. Especially our time. So what’s helped me say no to distractions is the app Freedom on my computer, which I’ve set to block the Internet 22 hours a day, and a Kitchen Safe [now called kSafe], which is a timed safe I can drop my cell phone into. What’s helped with saying no to others is asking myself first if I’m saying yes out of guilt or fear. If so, then it’s a polite no.

My favorite failure is every time I ever ate it onstage as a comedian. Because I woke up the next day and the world hadn’t ended. I was free to keep fucking up and getting better. I wish at least one catastrophic failure on everyone pursuing the arts. It’s where you’ll get your superpowers from.

The year of poverty-level living I did, burning off three years of savings (which wasn’t much to begin with), from the summer of ’92 to the summer of ’93 in San Francisco. I got onstage at least once a night and grew ten years as a comedian in a year. I burned off any safety net I had becoming proficient. If you can swing it—and I know a lot of people can’t—and you can scam a way to live off of nothing, it almost always pays off.

Daily meditation, twice a day. Just giving my brain a chance to power the fuck down and refresh. Makes all the difference.

Embrace the suck for a while. Chances are your first job is going to stink and your living conditions won’t be much better. Enjoy the scrappy years, ’cuz they’ll make you self-sufficient way faster. Ignore anyone who tells you to go for security over experience.

When you feel overwhelmed or unfocused, what do you do? I meditate. I sit for 20 minutes and meditate. Best thing I ever learned how to do.

The Making of the Atomic Bomb by Richard Rhodes is a masterpiece of explaining the sequence of discoveries that led to the development of the atomic bomb in an historical context. During my graduate studies at Cornell, I minored in theoretical physics and took courses from Hans Bethe and other luminaries, so I had met several of the physicists in the book. Yet I learned more physics from the book than I did in my courses.