10 Life Lessons from Esquire’s “What I’ve Learned” Interviews

From 50 Cent to Julia Child, or what Apocalypse Now has to do with sperm whales.

Since 1998, Esquire magazine has conducted more than 300 interviews with artists, athletes, celebrities, entrepreneurs, musicians, politicians, scientists and writers. The series — called “What I’ve Learned” — provides a fascinating cross-section of the lives of prominent people. From Buzz Aldrin to Batman, the interview list reads like a Who’s Who of our era.

We’ve chosen 10 timeless quotes on how to live, from 10 of our favorite interviews in the series, a fine extension of these 5 guides to life from cultural luminaries, featured here last spring.

Smoke like a chimney, work like a horse, eat without thinking, go for a walk only in really pleasant company.” ~ Albert Einstein

Get yourself in trouble. If you get yourself in trouble, you don’t have the answers. And if you don’t have the answers, your solution will more likely be personal because no one else’s solutions will seem appropriate. You’ll have to come up with your own.” ~ Chuck Close

You practice and you get better. It’s very simple.” ~ Philip Glass

A big part of life is realizing what you’re good at.” ~ Alyssa Milano

Children teach you that you can still be humbled by life, that you learn something new all the time. That’s the secret to life, really — never stop learning. It’s the secret to career. I’m still working because I learn something new all the time. It’s the secret to relationships. Never think you’ve got it all.” ~ Clint Eastwood

You can’t just live in a comfortable little suburban neighborhood and get your education from movies and television and have any perspective on life.” ~ J. Craig Venter

A friend is someone who will tell you when you’re bullshitting, when you’ve overstepped a mark, or when you’re being an idiot.” ~ Sting

I think we will make it. Because one quality people have — certainly Americans have it — is that they can adapt when they see necessity staring them in the face. What to avoid is what someone once called the definition of hell: truth realized too late.”~ E. O. Wilson

The measure of achievement is not winning awards. It’s doing something that you appreciate, something you believe is worthwhile. I think of my strawberry souffle. I did that at least twenty-eight times before I finally conquered it.” ~ Julia Child

In the end, winning is sleeping better.” ~ Jodie Foster

In addition to reading the “What I’ve Learned” archives online, you can also collect the interviews in book form — Esquire published an anthology of their own favorites as The Meaning of Life: Wisdom, Humor, and Damn Good Advice from 64 Extraordinary Lives, featuring icons like George Carlin, Ray Charles, Faye Dunaway, Eminem and Oliver Stone.

Kirstin Butler is writing an adaptation of Gogol for the Google era called Dead SULs, but when not working spends far, far too much time on Twitter. She currently lives in Cambridge, MA.

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Anything You Want: Derek Sivers on the Secrets of Entrepreneurship

Why not to trust futurists, or what the entrepreneurial power of empathy has to do with the art of letting go.

Derek Sivers may be best-known as the founder of CD Baby, commonly considered the first true empowerment platform for independent musicians, but he also happens to be one the smartest, most interesting and most curious people I know. His first book, Anything You Want, is out today and makes the entrepreneurial heart sing with inspiration and insight into the business of following your dreams.

The book is the latest release by The Domino Project, one of 7 platforms changing the future of publishing.

Today, I sit down with Derek to talk about the essentials of entrepreneurship, selflessness, and forming a healthy relationship with the prospect of failure.

You’re extraordinarily good at synthesizing complex insights into digestible, bite-sized nuggets. If you had to do that with your top three learnings from your CD Baby experience, what would those be?

#1 : Delegate, but don’t abdicate.

Founders have a problem delegating, so I learned that one well, and my business took off huge because of it. But then I tried to delegate even more, even delegating major decisions inside the company that completely changed its culture. And that’s when it all went downhill. I had over-delegated. That’s when I learned the word “abdicate” : to give away authority or power. I learned it too late. The damage was irreparable. That’s why I sold the company.

#2 : If it’s not a hit, quit.

Many times before and after CD Baby, I launched projects that I thought were brilliant. But people weren’t into it. I used to persist, to try to push my idea into the world, against all resistance. But now I’ve learned from experience: starting a business is like writing a song. You can’t know which one people will like. If the world isn’t into it, don’t keep pushing it. Change the song or just write another song.

#3 : Know what makes you happy.

Too many people start business by emulating others. Thinking they need to be like the people profiled in magazines, or the last business author they read. But what you want out of life is different than them. If you prefer privacy, or are happier when your company is small, you need to know this and make a plan that accommodates it, instead of pursuing someone else’s path.

What’s the number-one quality one needs to have or choice one needs to make in translating a brilliant idea into successful entrepreneurship?

Be selfless. Do not think of yourself, your needs, your protection, your security. Think only of what would be a dream-come-true for your customers, and find a way to make that happen. Only after you design a perfect business from their perspective, should you adjust the numbers to make sure it’s sustainable. But focus entirely 100% on them, not yourself.

Other thought-leaders have previously spoken about the fear of failure and it — or, more precisely, your seeming resistance to it — seems to be a running undercurrent in much of your work. What’s been the role of failure in your career and what would you say is the key to having a healthy relationship with it as an entrepreneur?

Like the “#2: If it’s not a hit, quit” thing: You need to learn to let go, shrug it off, and try something else. Think of the life of a songwriter. They write 100-500 songs in their life. One is a hit. Who knows why? Some random combination of ingredients or timing makes it really click with people.

It’s the same with anything we do. Even if you had a big dream, pushed for it, and it didn’t happen. Learn to let it go and do something else. There are so many different things worth doing. You’ve got plenty of ideas.

Much has been said about the tectonic shifts in the music business today. Where do you see it all going in 10 years, both as an industry model and a sociocultural paradigm?

Nobody knows the future. Anyone who claims to know the future is full of shit, and not to be trusted.

Seriously. We have this strange obsession with wanting to know the future. But if you can learn to let that go, and admit you don’t know, you can stay focused on the very valuable skill of helping people here-and-now, instead of guessing what might be some day.

I don’t think about the future for one minute. Not at all. I can have some personal intentions, like, “I would like to move to Brazil in a few years.” But guessing what might happen in the world? No need.

Back in the day, you and I became friends largely through the overlap of our reading lists and our shared belief that what we choose to read plays an important role in the life of the mind and the entrepreneurial self. What books have excited you the most over the past year?

The Personal MBA by Josh Kaufman

A Guide to the Good Life: The Ancient Art of Stoic Joy by William Irvine

Seeking Wisdom by Peter Bevelin

Switch by Chip Heath and Dan Heath

Ed.: Anything You Want is out today and an absolute gem. It’s available in hardcover, mp3 audiobook, CD audiobook, shareable 5-copy and 52-copy mulitpacks, ultra-limited-edition collectible signed by Derek, and, of course, on Kindle.

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Kurt Vonnegut Interviewed on NPR Inside Second Life

What it means to be a man without a country, or what Marx has to do with improving life through technology.

Kurt Vonnegut is one of my big literary heroes, a keen observer and wry critic of culture and society. His Armageddon in Retrospect is an absolute necessity and his wildly entertaining series of fictional interviews with luminaries, God Bless You, Dr. Kevorkian is an absolute gem, firmly planted on this year’s edition of the annual Brain Pickings summer reading list.

In 2006, NPR interviewed Vonnegut from inside the virtual world Second Life, as a part of their Infinite Mind series. Recorded shortly before Second Life reached its peak and mere months before Vonnegut passed away, the interview is a rare cultural time-capsule in more ways than one, as well as a fitting meta-wink to God Bless You, Dr. Kevorkian, which is premised on the idea that Vonnegut would conduct fictional interview with dead cultural luminaries and ordinary people through controlled near-death experiences, allowing him to access the afterlife, converse with his subjects, and leave before it’s too late.

It’s actually possible to get a better life for individuals [through technologies like Second Life] and I have frequently inanimated new technologies, but I love cell phones. I see people so happy and proud, walking around. Gesturing, you know. I’m like Karl Marx, I’m up for anything that makes people happy.” ~ Kurt Vonnegut

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Sentimental Value: Shopping for Human Stories on eBay

What social psychology has to do with Victorian romance and the official White House gift wrapper.

Since 2007, Emily Spivack has been scouring eBay posts to uncover the remarkable secret stories people share about their things. The project, aptly dubbed Sentimental Value, is as much a fascinating exercise at the intersection of digital and analog anthropology as it is a vicarious journey into the lived and unlived lives of others. Today, I sit down with Emily to chat about the impetus for the project, the most curious stories she’s dug up, and the fundamental psychology of sentimentality.

The mandatory question: What inspired Sentimental Value?

I’ve been working on projects about how clothes function in society for a while, so Sentimental Value came out of that interest. I’ve also been into vintage clothes since I was a teenager, obsessed with their one-of-a-kind-ness. I’m fascinated with the little clues left behind about the garment’s former life — a rip in the knee of a pair of jeans, a handwritten name in a shirt, a lingering smell of perfume.

Victorian travel dress a newly wedded bride intended to wear to meet her husband until he was killed in a horse and buggy accident

I started looking for vintage clothes on eBay and noticed that I’d occasionally find interesting stories people would share about the garments they were selling. I started collecting them, using the site like most people, only instead of hunting down things, hunting down the stories about those things — the provenance of the article of clothing, a story about wearing it, or the reason the seller is giving it up.

I was drawn to the idea of eBay as a place that’s indirectly become a repository for sharing stories and memories. I loved how eBay could offer an unexpected window into strangers’ lives. So, with Sentimental Value, I’ve been working to cull the best stories from what’s been posted.

What are some of the more interesting sentimental treasures you’ve excavated over the course of the project?

It’s hard to pick — there are all sorts of elements that make for a good story — the story itself, the way it’s told, the actual object, the photos… Over the past few years, though, I have seen some specific themes and patterns emerge amongst what I’ve posted.

For example, there are tons of stories about relationships, like this guy who was selling sneakers with air pockets slashed by an ex-girlfriend. There are people who share transformational life experiences, like this woman, who was selling a gown she was once levitated in. At times, I learn something completely new, like the fact that these earrings had been owned by the official gift wrapper for the White House during the Eisenhower, Kennedy, and Johnson administrations. Or there tend to be loads of wedding-related stories, like this one about a drunken bridesmaid mishap.

Sequined gown worn by a woman who believed to have levitated in it.

I appreciate learning about the historical provenance of an item, especially when you get to see a photo of the garment actually worn by the owner, like this dress, which had been worn by Ann Schofield in 1903 when she was presented to the King and Queen of England. Occasionally there’s a celebrity tie-in, like these sunglasses that were touched by Michael Jackson. Or some stories I’m just drawn to purely for the way the story is told, like this handmade Vash the Stampede costume.

There’s a certain notion that digital platforms are completely devoid of the sentimentality we tend to associate with analog objects and keepsakes. Yet Sentimental Value seems to be an experiment in the opposite. What insight has the project given you into the ever more hotly contested question of whether or not technology is making us shallow and dehumanized?

With Sentimental Value, I found affirmation that the attachment I feel towards certain pieces of clothing (that had been, for instance, handed down to me, purchased on a trip, worn on a certain occasion) were echoed in the stories people were openly sharing on eBay.

Earrings worn by the official White House gift wrapper for presidents Eisenhower, Kennedy and Johnson

I love that this online platform, based on transactions and consumption, has indirectly become a trove of stories, albeit ephemeral ones. I really appreciate eBay as an anonymous marketplace where hundreds of millions of people all over the world are buying and selling goods alongside the rich storytelling by-product that has evolved from it. People are craving an online space to share memories. As a result, they’re finding ways to make digital platforms, like eBay, less sterile or shallow, incorporating personal elements into what might have once been relegated to an offline context.

We tend to think of sentimentality as highly personal, confined to the individual. And yet platforms like eBay, and certainly networks like Facebook and Twitter, are making it highly social. Do you think there’s any ‘sentimental value’ lost in broadcasting these intimate stories to the world? Is there any found?

The reasons we hold onto things (or get rid of them) are usually quite personal. As we continue to feel more comfortable putting more of our lives online, we wind up sharing those stories publicly with less hesitancy.

K-Swiss sneakers worn by Suge Knight, a.k.a. Big Suge, founder of iconic rap label Death Row Records

I think there is significant value to airing those feelings in a public forum. It provides an outlet to more easily document our attachment to the objects in our lives , something that’s often lost generation-to-generation. It allows us to process why we hold such an attachment to certain objects. It turns the sensation into less of a solitary experience and instead, into one that can be more community-driven and interactive.

This may be idealistic, but I like to think that perhaps, with this increasing sense of fondness expressed online and in open spaces, people will become less interested in fast, disposable fashion, feel less inclined to buy the newest, coolest, fanciest ‘thing’ and instead hold onto the object that’s already been imbued with a different kind of value.

What’s next for Sentimental Value?

For about a year, I’ve been buying quite a few of the items with more unique provenances that I’ve posted on Sentimental Value with the intention to put together an exhibition or gallery show. One of my favorites pieces that I now own is a 1920s gown with blood splatter from a mob-related murder. I’ve also collected a rayon blazer owned by a woman who sold her clothes to join a nudist camp, a pair of K-Swiss sneakers that belonged to Death Row Records’ Suge Knight, and a Victorian travel dress that a newly wedded bride intended to wear to meet her husband until he was killed in a horse and buggy accident. The garments will be shown alongside their stories.

Rayon blazer owned by a woman who sold all her clothes to join a nudist camp

I’m also working on creating a Sentimental Value book. I’m excited about working in that format as I’ll have the opportunity to organize the stories by common themes, draw connections that are more difficult to make in its current online format, and add perspective by distancing the anecdotes from the proximity of the platform from which they’ve been culled.

Ed.: You can follow the project on Facebook for a delicious feed of found sentimentality.

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