“I started out basically imagining I was writing for a stadium full of replicas of myself—which made things easy because I already knew exactly what topics interested them, what writing style they liked, what their sense of humor was, etc.”

TIM URBAN is the author of the blog Wait But Why and has become one of the Internet’s most popular writers. Tim, according to Fast Company, has “captured a level of reader engagement that even the new-media giants would be envious of.” Today, Wait But Why receives more than 1.5 million unique visitors per month and has over 550,000 email subscribers. Tim has gained a number of prominent readers as well, like authors Sam Harris and Susan Cain, Twitter co- founder Evan Williams, TED curator Chris Anderson, and Brain Pickings’ Maria Popova. Tim’s series of posts after interviewing Elon Musk have been called by Vox’s David Roberts “the meatiest, most fascinating, most satisfying posts I’ve read in ages.” You can start with the first one, “Elon Musk: The World’s Raddest Man.” Tim’s TED Talk, “Inside the Mind of a Master Procrastinator,” has received more than 21 million views.

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 Fountainhead, by Ayn Rand, because of the two main characters in the book —Howard Roark and Peter Keating. Neither of the characters is like a real person—they’re both too one-dimensional and extreme. But to me, if you put them together, you get each of us. Roark is a totally independent reasoner. He reasons from first principles—the base facts at the core of life like the limits of physics and the limits of his own biology—and uses that information only as the building blocks of his reasoning to construct his conclusions, his decisions, and his life path. Keating is the opposite—he is a totally dependent reasoner. He looks outward and sees contemporary values, social acceptance, and conventional wisdom as the core facts, and then does his best to win the game within those rules. His values are society’s values and they dictate his goals. We’re all like Roark sometimes and Keating other times. I think the key to life is to figure out when it makes sense to save mental energy and be like Keating (I’m super conforming in my clothing choices because it’s not something that’s important to me) and when in life it really matters to be like Roark and reason independently (choosing your career path, picking your life partner, deciding how to raise your kids, etc.).

The Fountainhead was a major influence when I wrote a long blog post about why I think Elon Musk is so successful. To me, he’s like Roark—he’s tremendous at reasoning from first principles. In the post, I call this being a “chef” (someone who experiments with ingredients and comes up with a new recipe). Musk is unusually cheflike. Most of us spend most of our lives being like Keating, or what I call a “cook” (someone who follows someone else’s recipe). We’d all be happier and more successful if we could learn to be chefs more often—which just takes some self-awareness of the times we’re being a cook and an epiphany that it’s not actually as scary as it seems to reason independently and act on it.

Note from Tim Ferriss: I asked Tim to share a fun piece of related background. Here it is.

In early 2015, Elon reached out to schedule a call. He said he had read some Wait But Why posts and was wondering if I might be interested in writing about some of the industries he’s involved in. I flew out to California to meet with him, tour the Tesla and SpaceX factories, and spend some time with the executives at both companies to learn the full story about what they were doing and why. Over the next six months, I wrote four very long posts about Tesla and SpaceX and the history of the industries surrounding them (during which I had regular conversations with Elon in order to really get to the bottom of the questions I had). In the first three posts, I tried to answer the question, “Why is Elon doing what he’s doing?” In the fourth and final post of the series, I examined Elon himself and tried to answer the question, “Why is Elon able to do what he’s doing?” That’s what led me to explore all these ideas around reasoning from first principles (being a “chef” who comes up with a recipe) versus reasoning by analogy (being a “cook” who follows someone else’s recipe).

What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)?
The NYTimes crossword puzzle app. I’ve always liked crossword puzzles but I kind of sucked at them. Since getting the app I’ve gotten much better (started off mostly doing Monday through Wednesday puzzles and now I do every day of the week) and doing the puzzle is a delightful part of my day every day. I love waking up and working on the day’s puzzle in the morning—in bed, while eating breakfast, on the subway, while standing in line at a coffee place, etc. But I have to be careful—the later it gets in the week, the longer the puzzle takes me, and I often don’t have the discipline to put down a hard puzzle until I finish it, which can bleed badly into my planned workday and make me hate myself. Or sometimes I’ll open the app when I’m taking a five-minute work break, and then that turns it into an 82-minute work break and I again hate myself. So I now try to keep my puzzling to nighttime.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
My senior year of college, I decided to apply to write the music for an annual student-written musical called The Hasty Pudding. When I went to the orientation for people applying to be the composer, the session was run by the head of the program and a fellow student who worked at the program and who was assisting the head in the audition process. The head talked us through how applying worked, and the student assistant got on the piano to give some examples of what kind of music they’d be looking for. I left super excited about this—I wanted to compose music for a living after college and was dying to get the gig.

Later that day, they emailed all of the applicants the schedule for when we’d be coming in to play our sample songs for the program head as our audition. On the schedule, I noticed the names of both the person who had written the music for the show the previous year (and I knew the same composer often wrote the music multiple years in a row) and the student assistant himself—the one who had given us advice about what they were looking for! Totally deflated, I decided not to apply. Clearly either last year’s composer (who already had a relationship with the program head) or the student assistant would end up with the job.

A few months later I saw the show being advertised around campus, and the composer was . . . neither of them. Some other guy got it. I had massive regret and self-loathing for not applying. But a cheap lesson—don’t get daunted out of shooting for something you want, especially by potentially unfounded assumptions.

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
It would be a magical billboard that would display something unique for each person who looked at it. The billboard would be able to mind-read, figuring out which group of people the viewer was most one-dimensionalizing, demonizing, and dehumanizing in their heads. For one viewer today, that might be Trump voters. For another, it might be Muslims. For another, it might be black people, or wealthy white people, or sex offenders. Whichever the group, the viewer would see an image of a member of that group doing something that reminded the viewer of that type or person’s full, three-dimensional humanity. Maybe it would be that person sitting by the deathbed of their parent, or helping their child with their homework, or doing some silly hobby that the viewer also happened to like.

I think humans can only feel real hatred of people they’re able to dehumanize in their heads. As soon as someone is exposed to reality and reminded of the full humanness of someone they hate, the hatred usually fades away and empathy pours in.

What is one of the best or most worthwhile investments you’ve ever made?

My first year out of college, I started a small test prep company (tutoring for SAT, ACT, etc.). Over the next nine years, I put a large portion of my time into growing that company. Early on, my co-founder and I realized it was an advantage to be two single dudes in our 20s with no real financial obligations, so we decided to keep our lifestyles at the same level even as the company grew. After a good year, instead of giving ourselves a $25,000 raise each, we’d keep our salaries in the same place and hire a $50,000 employee. After a great year, we’d keep our salaries where they were and hire three or four new employees.

I can credit my co-founder mostly for this, as he’s the more disciplined one of the two of us, but it turned out to be a good strategy. By the time I turned 30, the company had 20 employees and was generating probably ten times the revenue it would have been generating had we kept upping our salaries each year. We traded the fun of having fancy lifestyles in our 20s for being far more free people at the age of 30. This freedom is what led me to start Wait But Why and become a full-time writer.

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

I have a toy box at home. Well, I actually just have a lot of toys, but my fiancée finally got fucking sick of my shit being everywhere and brought home a box where she insisted I keep all my toys. The toys are all mechanical, tactile, fidgety things—the same toys I liked when I was five. I have a bunch of different kinds of magnets, a wide array of silly putties, fidget spinners, fidget cubes, bouncy balls, etc. This isn’t just because I’m a child—it actually helps me focus. I’m a kinetic thinker—the kind of person who paces constantly when on a phone call. And when I’m working—brainstorming, researching, outlining, or writing—I do a lot better with a toy in my hand. If I don’t have one, I’ll end up biting my nails down until they bleed. I have problems.

In the last five years, what new belief, behavior, or habit has most improved your life?
Working as a writer on your own hours, it’s tempting to get into the romantic notion that you don’t play by society’s rules—you work from home in your underwear, you do your most inspired writing at 3 A.M., you never set an alarm, etc. I’ve always prided myself on doing things unconventionally, and I’m very physically lazy, so I was definitely a believer in the unconventional work schedule/environment.

The only problem is that it doesn’t actually work well for me at all. I’d get stuff done when I had a deadline, but when I didn’t, I’d be horribly unproductive. I also found myself in a permanent state of kind of working. I was rarely in a long period of full work focus, and I was rarely just carefree off work.

I realized at some point recently that there’s something to the “go to an office from nine to five” thing. I stopped writing from home and started putting clothes on and writing from a coffee shop. I started going to bed at a normal human hour and setting an alarm. And I’d try to compartmentalize, being dead serious about work until the late afternoon or early evening and then stopping entirely until the next day. I’ve even tried taking weekends (or at least one weekend day) off work. I’m not perfectly on this schedule and sometimes fall off the wagon, but when I can manage to pull it off, it’s better for me for a few reasons:

Most people do their best work in the morning, and I’m no exception. Working later in the day kills your social life, since most social life happens between 7 p.m. and 11 p.m. on weekdays and on weekends. If you’re working in that time you suddenly become that friend who’s never available, which is horribly shortsighted and unwise.
As I detailed in my TED Talk, I think we all have two main characters in our heads: a rational decision-maker (the adult in your head) and an instant gratification monkey (the child in your head who doesn’t care about consequences and just wants to maximize the ease and pleasure of the current moment). For me, these two are in a constant battle, and the monkey usually wins. But I’ve found that if I turn life into a yin-yang situation— e.g., “work till 6 today, then no work till tomorrow”—it’s much easier to control the monkey in the work period. Knowing he has something fun to look forward to later makes him much more likely to cooperate. In my old system, the monkey was in a constant state of rebellion against a system that never really gave him any dedicated time.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? You can kind of group all careers into two major buckets—careers where you’re the CEO and careers where you work for a CEO.

Careers where you’re the CEO include anything where you’re trying to start your own company, anything where you’re trying to make your name in the arts and win fans, anything where you’re doing freelance work—paths where you’re driving the ship of your own career and making the big decisions.

Careers where someone else is the CEO are where you’re on an existing ship that’s being driven by someone else, and you’re doing a job on that ship. This includes obvious situations where you’re an employee at a company, but also a situation where the career itself is a predefined ship, like being a doctor or a lawyer.

Society loves to glorify the “you-as-CEO” paths and make people who don’t want to be the CEO of their own career feel inferior about their path, but neither of these paths is inherently better or worse than the other—it just depends on your personality, your goals, and what you want from a lifestyle. There are some super smart, talented, special people whose gifts are best expressed as CEO and others whose are best expressed when someone else is worrying about keeping the lights on and you can just put your head down and focus on your work. Likewise, there are some people who need to be CEO to find their work fulfilling and others for whom being CEO and having their work bleed into everything is a recipe for misery.

For some people, they want one thing specifically—like someone who needs to be a singer-songwriter to be happy—but most of us leave college pretty torn about the kind of work we want to do most. For those people, I’d recommend thinking hard about the CEO question and experimenting in your 20s to see what it feels like on both sides.

What are bad recommendations you hear in your profession or area of expertise?
I’m a writer, and I find that a lot of advice to young writers—especially those trying to make a name for themselves online—centers around trying to win readers over. If you think of your potential readers as pegs, this advice is about trying to mold yourself into the right-shaped hole—a hole that will fit a lot of readers or draw in a bunch of readers quickly, or some other means of getting a writing career going.

I think the opposite advice is better. Obsess over figuring out the funnest, most exciting, most natural shape of yourself as a writer and start doing that. There are a lot of people on the Internet, and they can all access your work with one tap on the phone in their pocket. So even if only one in every thousand of them—0.1 percent—happens to be a reader peg that perfectly matches the shape of your writing hole, that amounts to over a million people who will absolutely love what you’re doing.

I started out basically imagining I was writing for a stadium full of replicas of myself—which made things easy because I already knew exactly what topics interested them, what writing style they liked, what their sense of humor was, etc. I ignored the conventional wisdom that online articles should be short, frequent, posted consistently—because I knew the Tims in that stadium didn’t care about those things—and instead focused on a single type of topic. And it worked. Four years later, many of those people who happen to like my type of writing have found me.

By focusing inward on yourself as a writer instead of outward on what you think readers will want to read, you’ll end up creating the best and most original work, and that one-in-a-thousand person who happens to love it will end up finding their way to you.

In the last five years, what have you become better at saying no to? What new realizations and/or approaches helped?
I’ve learned to make my “no” list by starting with my “yes” list. The “yes” list should be centered around what’s important—but how do you define a vague concept like “important”? I use a couple of simple litmus tests:

When it comes to my work “yes” list, I think about what I might call the Epitaph Test. When I find myself with an opportunity, I ask myself whether I’d be happy if my epitaph had something to do with this project. If the answer is a clear no, it probably means it’s not actually very important to me. Thinking about your epitaph, as morbid as it is, is a nice way to cut through all the noise and force yourself to look at your work from a super zoomed-out perspective, where you can see what really matters to you. So I try to make my “yes” list by thinking about the Epitaph Test, and potential time commitments outside of that definition fall on my “no” list. For me, the Epitaph Test is usually a reminder to focus my time and effort on doing the highest-quality and most original creative work I can.

For my social life “yes” list, a similar test could be called the Deathbed Test. We all hear about these studies where people on their deathbed reflect on what they regret most, and the cliché is that nobody ever says they regret spending more time in the office. That’s because a deathbed offers people a level of zoomed-out clarity that’s hard to get to in our normal lives, and it’s only when we’re lacking that clarity in the fog of our day-to-day rush that we’d think it makes sense to neglect our most important personal relationships. The Deathbed Test pushes me to do two things:

Make sure I’m dedicating my time to the right people with the question, “Is this someone I might be thinking about when I’m on my deathbed?”

Make sure I’m spending enough high-quality time with the people I care about most with the question, “If I were on my deathbed today, would I be happy with the amount of time I spent with this person?” An alternative is thinking about other people’s deathbeds—“If X person were on their deathbed today, how would I feel about the amount of quality time I’ve spent with them?”

The people who matter most are always in competition for your time with both your work and with other people, and the Deathbed Test can be a good reminder that the only way to dedicate the proper amount of time to your key people is by saying no to a lot of other stuff and a lot of other people.

The point of both the Epitaph Test and the Deathbed Test is that by the time you’re on your deathbed and your epitaph is being drafted, it’s too late to change anything—so we want to do whatever we can to access that magical end-of-life clarity before the end of life actually happens.

Of course, actually saying no to your “no” list is a struggle of its own, and I’m still working on that—but having good mechanisms for defining what’s important has helped a lot.

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