I never thought I would make it to 40

2017 was an unusual year for me. The first six months were a slow simmer, and then, within a matter of weeks, I turned 40, my first book (The 4-Hour Workweek) had its tenth anniversary, several people in my circle of friends died, and I stepped onstage to explain how I narrowly avoided committing suicide in college.

Truth be told, I never thought I’d make it to 40. My first book was rejected 27 times by publishers. The things that worked out weren’t supposed to work, so I realized on my birthday: I had no plan for after 40.

As often happens at forks in the path — college graduation, quarter-life crisis, midlife crisis, kids leaving home, retirement — questions started to bubble to the surface.

Were my goals my own, or simply what I thought I should want?

How much of life had I missed from underplanning or overplanning?

How could I be kinder to myself ?

How could I better say no to the noise to better say yes to the adventures I craved?

How could I best reassess my life, my priorities, my view of the world, my place in the world, and my trajectory through the world?

So many things! All the things!

One morning, I wrote down the questions as they came, hoping for a glimmer of clarity. Instead, I felt a wave of anxiety. The list was overwhelming. Noticing that I was holding my breath, I paused and took my eyes off the paper. Then, I did what I often do — whether considering a business decision, personal relationship, or otherwise — I asked myself the one question that helps answer many others . . .

What would this look like if it were easy?

“This” could be anything. That morning, it was answering a laundry list of big questions.

What would this look like if it were easy? is such a lovely and deceptively leveraged question. It’s easy to convince yourself that things need to be hard, that if you’re not redlining, you’re not trying hard enough. This leads us to look for paths of most resistance, creating unnecessary hardship in the process.

But what happens if we frame things in terms of elegance instead of strain? In doing so, we sometimes find incredible results with ease instead of stress. Sometimes, we “solve” the problem by simply rewording it.

And that morning, by journaling on this question — What would this look like if it were easy? — an idea presented itself. Ninety-nine percent of the page was useless, but there was one seed of a possibility . . .

What if I assembled a tribe of mentors to help me?

More specifically, what if I asked 100+ brilliant people the very questions I want to answer for myself? Or somehow got them to guide me in the right direction?

Would it work? I wasn’t sure, but I did know one thing: If the easy approach failed, the unending-labor-in-the-salt-mines approach was always waiting in the wings. Pain is never out of season if you go shopping for it.

So, why not spend a week test-driving the path of least resistance?

And so it began. First, I scribbled down a list of dream interviewees, which started as one page and quickly became ten. It had to be a list with no limitations: no one too big, no one too out-of-reach, and no one too hard to find. Could I get the Dalai Lama? The incredible Temple Grandin? My personal white whale, author Neil Gaiman? Or Ayaan Hirsi Ali? I wrote out the most ambitious, eclectic, unusual list possible. Next, I needed to create an incentive to encourage people to respond, so I sought out a book deal. I figured “Be in my book?” might help. From the outset, I told the publisher that it also might not work, and that I’d return the advance if so.

Then, I started pitching my little heart out.

I sent an identical set of 11 questions to some of the most successful, wildly varied, and well-known people on the planet with “Answer your favorite 3 to 5 questions . . . or more, if the spirit moves you.”

After hitting “send” dozens of times, I clasped my hands to my chest with excitement and bated breath, to which the universe replied with . . . silence. Crickets.

For 12 to 24 hours, nothing. Not a creature was stirring, not even a mouse. And then, there was a faint trickle through the ether. A whisper of curiosity and a handful of clarifying questions. Some polite declines followed, and then came the torrent.

Nearly all of the people I reached out to are busy beyond belief, and I expected short, rushed responses from a few of them, if I got any at all. Instead, what I got back were some of the most thoughtful answers I’d ever received, whether on paper, in person, or otherwise. In the end, there were more than 100 respondents.

Granted, the “easy” path took thousands of back-and-forth emails and Twitter direct messages, hundreds of phone calls, many marathons at a treadmill desk, and more than a few late-night bottles of wine, but . . . it worked. Did it always work? No. I didn’t get the Dalai Lama (this time), and at least half of the people on my list didn’t respond or declined the invitation. But it worked enough to matter, and that’s what matters.

In cases where the outreach worked, the questions did the heavy lifting.

Eight of the questions were fine-tuned “rapid-fire” questions from my podcast, The Tim Ferriss Show, the first business-interview podcast to pass 200 million downloads. These questions have been refined over more than 300 interviews with guests such as actor/musician Jamie Foxx, General Stanley McChrystal, and writer Maria Popova. I knew that these questions worked, that they could help me in my own life, and that interviewees generally liked them.  

The remaining three questions were new additions that I hoped would solve my most chronic problems. Before taking them into the wild, I tested, vetted, and wordsmithed them with friends who are world-class performers in their own right. These three often ended up indirectly answering the “big” questions.

The older I get, the more time I spend — as a percentage of each day — on crafting better questions. In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to (when Lady Luck really smiles) 1000x returns in various areas has been a product of better questions. John Dewey’s dictum that “a problem well put is half-solved” applies.

Life punishes the vague wish and rewards the specific ask. Conscious thinking is largely asking and answering questions in your own head, after all. If you want confusion and heartache, ask vague questions. If you want uncommon clarity and results, ask uncommonly clear questions.

Fortunately, this is a skill you can develop. No book can give you all of the answers, but this book can train you to ask better questions. Milan Kundera, author of The Unbearable Lightness of Being, has said that “The stupidity of people comes from having an answer for everything. The wisdom of the novel comes from having a question for everything.” Substitute “master learner” for “novel,” and you have my philosophy of life. Often, all that stands between you and what you want is a better set of questions.

The 11 questions I chose for this book are listed below. It’s important to read the full questions and explanations, as I shorten them throughout the rest of the book. Special thanks to Brian Koppelman, Amelia Boone, Chase Jarvis, Naval Ravikant, and others for their hugely helpful feedback.

First, let us take a quick pass of the 11 questions. Some of them might seem trite or useless at first glance. . . . But lo! Things are not always what they appear.

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?

What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? My readers love specifics like brand and model, where you found it, etc.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)

What is an unusual habit or an absurd thing that you love?

In the last five years, what new belief, behavior, or habit has most improved your life?

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

What are bad recommendations you hear in your profession or area of expertise?

In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?

When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)

Now, let’s take a look at each, and I’ll explain why they appear to work. You might ask, “Why should I care? I’m not an interviewer.” To that, my response is simple: If you want to build (or foster) a world-class network, you need to interact in a way that earns it. All of the following points will help.

For instance, I spent weeks testing the order of questions for optimal responses. To me, proper sequencing is the secret sauce, whether you’re trying to learn a new language in 8 to 12 weeks, overcome a lifelong fear of swimming, or pick the brain of a potential mentor over coffee. Good questions in the wrong order get bad responses. Conversely, you can punch well above your weight class by thinking about sequencing, as most people don’t.

As one example, the “billboard” question is one of my podcast listener and guest favorites, but it’s heavy. It stumps or intimidates a lot of people. I didn’t want to scare busy people off, who might opt out with a quick, “Sorry, Tim. I just don’t have bandwidth for this right now.” So, what to do? Easy: let them warm up with lightweight questions (e.g., Most gifted books, purchase of <$100), which are less abstract and more concrete.

My explanations get shorter toward the end, as many of the points carry over or apply to all questions.

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?

“What’s your favorite book?” seems like a good question. So innocent, so simple. In practice, it’s terrible. The people I interview have read hundreds or thousands of books, so it’s a labor-intensive question for them, and they rightly worry about picking a “favorite,” which then gets quoted and put in articles, Wikipedia, etc. “Most gifted” is lower risk, an easier search query (easier to recall), and implies benefits for a broader spectrum of people, which the idiosyncratic “favorite” does not.

For the curious and impatient among you, here are a few books (of many) that came up a lot:

Man’s Search for Meaning by Viktor E. Frankl

The Rational Optimist by Matt Ridley

The Better Angels of Our Nature by Steven Pinker

Sapiens by Yuval Noah Harari

Poor Charlie’s Almanack by Charlie Munger

What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? My fans love specifics like brand and model, where you found it, etc.

This might seem like a throwaway, but it isn’t. It provides an easy entry point for busy interviewees while providing readers (and me) with something immediately actionable. Several answers have already changed my life, boosting immune function, improving sleep, and much more. The deeper questions elicit more profound answers, but profundity is the fiber of knowledge — it requires intensive digestion. To keep marching forward in the meanwhile, humans (yours truly included) need short-term rewards. In this book, I accomplish that with questions that provide tangible, easy, and often fun answers — Scooby snacks for your hard-working soul. To get the heavier lifting done, these breathers are important. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

This one is particularly important to me. As I wrote in Tools of Titans:

The superheroes you have in your mind (idols, icons, elite athletes, billionaires, etc.) are nearly all walking flaws who’ve maximized one or two strengths. Humans are imperfect creatures. You don’t “succeed” because you have no weaknesses; you succeed because you find your unique strengths and focus on developing habits around them. . . Everyone is fighting a battle [and has fought battles] you know nothing about. The heroes in this book are no different. Everyone struggles.

If you could have one gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

Self-explanatory, so I’ll skip the commentary. For would-be interviewers, though, the “If helpful…” portion is often critical for getting good answers.

What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)

This is also self-explanatory . . . or so it seems. With questions like this and the next, I’ve found it productive to give interviewees a real-world answer. In a live interview, it buys them time to think, and in text, it gives them a template. For this question, for instance, I gave everyone the following:

SAMPLE ANSWER from Amelia Boone, one of the world’s top endurance athletes, sponsored by big brands and 4x world champion in obstacle course racing (OCR):

“In 2011, I shelled out $450 to participate in the first World’s Toughest Mudder, a brand new 24-hour obstacle race. Saddled with law school debt, it was a big expenditure for me, and I had no business thinking I could even complete the race, let alone compete in it. But I ended up being one of 11 finishers (out of 1,000 participants) of that race, and it altered the course of my life, leading to my career in obstacle racing and multiple world championships. Had I not plunked down the cash for that entry fee, none of that would have happened.”

What is an unusual habit or an absurd thing that you love?

I was first asked this when interviewed by my friend Chris Young, scientist, co-author of Modernist Cuisine, and CEO of ChefSteps. Before responding, and while sitting onstage at the Town Hall in Seattle, I said, “Oooooh . . . that’s a good question. I’m going to steal that.” And I did. This question has deeper implications than you might expect. Answers prove a number of helpful things: 1) Everyone is crazy, so you’re not alone. 2) If you want more OCD-like behaviors, my interviewees are happy to help, and 3) Corollary to #1: “normal” people are just crazy people you don’t know well enough. If you think you’re uniquely neurotic, I hate to deliver the news, but every human is Woody Allen in some part of life. Here’s the sample answer I gave for this question, taken from a live interview and slightly edited for text:

SAMPLE ANSWER from Cheryl Strayed, best-selling author of  Wild (made into a feature film with Reese Witherspoon): “Here’s my whole theory of the sandwich… every bite should be as much like the previous bite as possible. Do you follow? [If ] there’s a clump of tomatoes here, but then there’s hummus — everything has to be as uniform as possible. So any sandwich I’m ever given, I open it up and I immediately completely rearrange the sandwich.”

In the last five years, what new belief, behavior, or habit has most improved your life?

This is short, effective, and not particularly nuanced. It has particular application to my life reassessment. I’m surprised I don’t hear questions like this more often.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

The second “ignore” sub-question is essential. We’re prone to asking “What should I do?” but less prone to asking “What shouldn’t I do?” Since what we don’t do determines what we can do, I like asking about not-to-do lists.

What are bad recommendations you hear in your profession or area of expertise?

A close cousin of the previous question. Many problems of “focusing” are best solved by defining what to ignore.

In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?

Saying yes is easy. Saying no is hard. I wanted help with the latter, as did many people in the book, and some answers really delivered the goods.

When you feel overwhelmed or unfocused or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)

If your mind is “beach balling” (nerdy Mac reference to when a computer freezes), nothing else matters much until that is resolved. Once again, the secondary “if helpful” question is often critical.

***

Since any greatness in these pages is from other people, I feel comfortable saying that you will love some of what’s here, no matter where you are in life.

In the same breath, I know you will find some of what’s inside boring, useless, or seemingly stupid. This is by design and a byproduct of collecting very different people with very different life experiences from around the world. Out of roughly 140 profiles, I expect you to like 70, love 35, and have your life changed by perhaps 17. Amusingly, the 70 you dislike will be precisely the 70 someone else needs.

Life would be boring if we all followed exactly the same rules, and you will want to pick and choose your own.

The more surprising part of all of this is that Tribe of Mentors changes with you. As time passes and life unfolds, things you initially swatted away like a distraction can reveal depth and become unimaginably important.

That cliché you ignored like a throwaway fortune cookie? Suddenly it makes sense and moves mountains. Conversely, things you initially found enlightening might run their course, like a wonderful high school coach who needs to hand you off to a college coach for you to reach the next level.

There’s no expiration date on the advice in this book. In the following pages, you’ll find advice from 30-something wunderkinds and seasoned veterans in their 60s and 70s. The hope is that, each time you pick up this book, not unlike with the I Ching or Tao Te Ching, something new will grab you, shake your perception of reality, illuminate your follies, confirm your intuitions, or correct your course that all-important one degree.

The entire spectrum of human emotion and experience can be found in this book, from hilarious to heart-wrenching, from failure to success, and from life to death. May you welcome it all in.

On my coffee table at home, I have a piece of driftwood. Its sole purpose is to display a quote by Ana?s Nin, which I see every day:

“Life shrinks or expands in proportion to one’s courage.”

It’s a short reminder that success can usually be measured by the number of uncomfortable conversations we are willing to have, and by the number of uncomfortable actions we are willing to take.

The most fulfilled and effective people I know — world-famous creatives, billionaires, thought leaders, and more — look at their life’s journey as perhaps 25 percent finding themselves and 75 percent creating themselves.

This book is not intended to be a passive experience. It’s intended to be a call to action.

You are the author of your own life, and it’s never too late to replace the stories you tell yourself and the world. It’s never too late to begin a new chapter, add a surprise twist, or change genres entirely.

What would it look like if it were easy?

Here’s to picking up the pen with a smile. Big things are coming. . . 

Get Tribe of Mentors at these fine retailers or at your local bookstore! Barnes & Noble | Amazon | Apple iBooks | Books-A-Million | Indigo