Derek Sivers podcast

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Solitary socialite Dec 27, 2016

Show notes

For the past ten years, I’ve answered up to two hundred emails per day. I sit alone in my little office for hours, engaging with everyone’s stories and questions for a few minutes each.

Then when friends want to hang out with me, I say I need some me-time first. They wonder why, since I’ve been alone all day, so I explain how I’ve actually been very social and connected with so many people.

I like what I do, so I’m not complaining — just explaining. It’s unusual to be physically alone, but extremely social. A solitary socialite.

At first I thought this was a new internet thing. But for decades, there have been people who talk on the phone all day. Before that, there were people who just answered paper mail all day.

It works for me. I love people one-on-one. When I’m not answering emails, I’m often talking on the phone with one of my dear friends across the world, getting into great conversations for hours.

But it’s a strange life. The solitary socialite.

How to do what you love and make good money Dec 19, 2016

Show notes

People with a well-paying job ask my advice because they want to quit to become full-time artists.

But full-time artists ask my advice because they’re finding it impossible to make money.

(Let’s define “art” as anything you do for expression, even just blogging or whatever.)

For both of them, I prescribe the lifestyle of the happiest people I know:

Have a well-paying job.
Seriously pursue your art for love, not money.

Let’s look at the ingredients of this plan. First: balance. You’ve heard about balancing heart and mind, or right-brain left-brain, or whatever you want to call it. We all have a need for stability and adventure, certainty and uncertainty, money and expression.

If you have too much stability, you get bored. If you don’t have enough stability, you panic. So keep the balance.

Do something for love and something for money. Don’t try to make one thing satisfy your entire life.

Each half of your life becomes a remedy for the other. You get paid stability for part of your day, but then need creative time for expression. So you push yourself creatively, expose your vulnerable art to the public, feel the frustration of rejection and apathy, and then long for some stability again. Each half is a remedy for the other.

About the job: Be smart, and choose something that pays well with a solid future. Look for statistics in your area about what pays the best when factoring in the required training. You’ll probably need to study for a few years to build up the rare skills that are well-rewarded. This is a head choice, not a heart choice, since you’re not trying to make your job your entire life.

About your art: Pursue it seriously. Take lessons. Make weekly progress. Keep improving, even if you’ve been doing it for decades.

If you don’t progress and challenge yourself creatively, it won’t satisfy the balance. Release and sell your work like a professional. Find some fans. Let them pay you. But your attitude is different than someone who needs the money. You don’t need to worry if it doesn’t sell. You don’t need to please the marketplace. You don’t need to compromise your art or value it based on others’ opinions. You’re just doing this for yourself — art for its own sake. And you’re releasing it because that’s one of the most rewarding parts — important for self-identity — and gives you good feedback on how to improve.

Your main obstacle to this amazing life will be self-control. You’ll need good time management to stop addictions like social media and video-watching, and make your art your main relaxing activity. You’ll need good mind management to not think of your job after you leave the office.

Most full-time artists I know only spend an hour or two a day actually doing their art. The rest is spent on the boring work that comes with trying to make it a full-time career. So skip the art career and just do the art.

And that’s my advice for a rewarding life. I’ve met thousands of people over the last twenty years — many of them full-time musicians, many of them not — but the happiest people I know are the ones that have this balance.

Don’t expect your job to fulfill all your emotional needs. Don’t taint something you love with the need to make money from it. Don’t try to make your job your whole life. Don’t try to make your art your sole income. Let each be what it is, and put in the extra effort to balance the two, for a great life.

Tilting my mirror (motivation is delicate) Dec 05, 2016

Show notes

Motivation is delicate.

When you notice your motivation fading, you have to seek out the subtle cause. A simple tweak can make all the difference between achieving something or not.

An hour outside my city, there’s a little mountain range. The other side is gorgeous. But the road that crosses the mountains is very twisted, with sharp turns every few seconds. The first two times I drove across, my kid threw up in the back seat. It’s also stressful because I’m surrounded by mountain scenery but I can’t take my eyes off the winding road. Though I drive at a normal speed, the other cars follow impatiently on my tail, because many of them drive this road every day.

Crossing the mountains takes only half an hour, but I always arrive exhausted. The stress was affecting my motivation enough that I wanted to stop visiting.

So one day I tried a new approach: I drove really slowly. Now the turns didn’t make my kid sick. Now I could afford to take a few seconds to glance sideways and appreciate the scenery. Now it wasn’t stressful, except for one thing: the impatient queue of cars behind me. I care (perhaps too much) about other people, so just seeing them in my mirror made me go back to driving faster than I wanted, which brought back all the original problems.

So I made one simple tweak: I tilted my rear-view mirror up towards the ceiling so I couldn’t see anything behind me.

That little tweak changed everything!

Now it feels like I’m almost alone on this gorgeous mountain drive. Going at my own pace, not influenced or stressed by anyone else.

There’s a passing lane every few minutes, so when it comes, the other cars whiz by me. But for thirty minutes, they’re not my problem. When I get to the other side of the mountain, I put my mirror back.

Now I visit all the time — no stress at all.

You know I’m going for the metaphor here:

Social media comments
Distracting environments
Discouraging family members
Your email inbox

Even the toughest of us have delicate motivation.

When you notice that something is affecting your drive, find a way to adjust your environment, even if that’s a little inconvenient for others.

Why are you doing? Sep 05, 2016

Show notes

It’s crucial to know why you’re doing what you’re doing.

Most people don’t know. They just go with the flow.

Social norms are powerful. The inputs that influence you are powerful. A great talk, book, or video can instantly change how you think.

But on your death bed, you don’t want that horrible regret, feeling like you spent your life pursuing what someone said you should want, instead of what you actually wanted.

For example, if you want to make a lot of money, you need to admit that. If you want to be famous, you need to pursue that. If you want freedom and no responsibilities, or want to learn as much as possible, or whatever else, you need to realize it and embrace it.

Whatever you decide, you need to optimize for that goal, and be willing to let go of the others.

You can’t diffuse your energy, trying to do a little bit of everything, or you’ll always be in conflict with yourself.

For example, one way to make money is to take on a lot of responsibility, which means letting go of some freedoms.

One way to get famous is to let others make more money, while you take the spotlight. I learned this while living in Los Angeles, when I got to know some famous Hollywood actors and realized they’re not as rich as you’d think. The richest people in Hollywood are the ones you’ve never heard of, because they’ve optimized their careers for money. They know that others are willing to take less money in return for more fame, so they profit from the other side of that deal.

Maybe the most important thing to you is learning, or creating, or giving. Maybe it’s how many people’s lives you can influence. Maybe it’s how deeply you can influence just a few people’s lives.

Once you realize what you really want and admit it, you need to pursue it.

If you want freedom, then own a business but delegate all the work. You won’t be learning or creating or giving as much as you could with a different strategy, but that’s OK. You know freedom is what you’re after.

Sometimes your best strategy is counter-intuitive. If you have a high paying job, but realize that charitable giving is what matters most to you, then the best strategy is not to quit your job to go hang mosquito nets in Africa, but actually to keep your job and make as much money as you can, while funding organizations in Africa that hang thousands of mosquito nets. (Unless your goal is just to look charitable. Then admit that to yourself, too.)

But whatever you choose, brace yourself, because people are always going to tell you that you’re wrong.

That’s why you need to know why you’re doing what you’re doing. Know it in advance. Use it as your compass and optimize your life around it. Let the other goals be secondary so that when those decision moments come, you can choose the value that you already know matters most to you.

I’m a very slow thinker Aug 26, 2016

Show notes

When a friend says something interesting to me, I usually don’t have a reaction until much later.

When someone asks me a deep question, I say, “Hmm. I don’t know.” The next day, I have an answer.

I’m a disappointing person to try to debate or attack. I just have nothing to say in the moment, except maybe, “Good point.” Then a few days later, after thinking about it a lot, I have a response.

This probably makes me look stupid in the moment, but I don’t mind. I’m not trying to win any debates.

In fact, I’ll tell you a secret. When someone wants to interview me for their show, I ask them to send me some questions a week in advance. I spend hours writing down answers from different perspectives, before choosing the most interesting one. Then when we’re in a live conversation, I try to make my answers sound spontaneous.

People say that your first reaction is the most honest, but I disagree. Your first reaction is usually outdated. Either it’s an answer you came up with long ago and now use instead of thinking, or it’s a knee-jerk emotional response to something in your past.

When you’re less impulsive and more deliberate like this, it can be a little inconvenient for other people, but that’s OK. Someone asks you a question. You don’t need to answer. You can say, “I don’t know,” and take your time to answer after thinking. Things happen. Someone expects you to respond. But you can say, “We’ll see.”

And maybe, through example, you can show them that they can do the same.

Keep earning your title, or it expires Aug 04, 2016

Show notes

Until yesterday, I called myself an entrepreneur. Now, I don’t.

It’s been years since I started a company, so I can’t keep using that title.

Someone who played football in high school can’t call himself an athlete forever. Someone who did something successful long ago can’t keep calling himself a success.

You have to keep earning it.

Holding on to an old title gives you satisfaction without action. But success comes from doing, not declaring.

By using a title without doing the work, you fool yourself into thinking that future success is assured — thinking, “This is who I am!” But that premature sense of satisfaction can keep you from doing the hard work necessary.

Stop fooling yourself. Be honest about what’s past and what’s present. Retiring outdated titles lets you admit what you’re really doing now.

And if you don’t like the idea of losing your title, then do something about it! This goes for titles like “leader,” “risk-taker,” and “good friend,” too.

Today I updated my website to reflect which of my accomplishments are in the past. It’s liberating to speak in the past tense about what you’ve done, and only speak in the present tense about what you’re actually doing.

When you’re extremely unmotivated Aug 02, 2016

Show notes

Like everyone, I get those times when I’m unmotivated to do anything. Brain dead. No energy. Everything feels like, “Why bother? What’s the point?”

But I’ve finally figured out what to do with those times.

Like everyone, I have a list of boring chores that need to be done but that I’ve been putting off for years. I never do them because I’m always more excited about something else.

During my last unmotivated funk, I realized that because nothing is exciting me, that means nothing is exciting me more than this boring necessary stuff. And since I don’t want to waste my inspired times on brainless work, this is a perfect time to do those dull tasks.

So I made a list of these necessary things. I grumbled and complained, but I used some caffeine and got through them. It actually felt pretty good.

Conventional wisdom tells us to do the important and difficult thing first. But doing this boring work moves me from a state of doing nothing to doing something. It makes me feel like doing something important again.

So the next time you’re feeling extremely unmotivated, do those things you never want to do anyway.

Disconnect Jul 27, 2016

Show notes

All the best, happiest, and most creatively productive times in my life have something in common: being disconnected.

No internet. No TV. No phone. No people. Long uninterrupted solitude.

When I was twenty-two, I quit my job and spent five months alone in a house on a remote part of the Oregon coast. Practicing, writing, recording, exercising, and learning. No internet. No TV. No phone. No people. I drove into the city only once a month to see friends and family. The rest of the time, I was completely disconnected.

In those five months, I wrote and recorded over fifty songs, made huge improvements in my musicianship, read twenty books, and got into the best physical shape of my life.

When I was twenty-seven, I moved to the woods of Woodstock and did that again. Months and months of lovely solitude. That’s how I started CD Baby.

It’s not that I hate people. The other best times in my life were with people. But it’s interesting how many highlights were just sitting in a room in that wonderful creative flow, free from the chatter of the world. No updates. No news. No pings. No chats. No surfing.

Silence is a great canvas for your thoughts. That vacuum helps turn all of your inputs into output. That lack of interruption helps you flow.

Every business wants to get you addicted to their infinite updates, pings, chats, messages, and news. But if what you want out of life is to create, then those are your obstacles.

People often ask me what they can do to be more successful. I say disconnect. Even if just for a few hours. Unplug. Turn off your phone and Wi-Fi. Focus. Write. Practice. Create. That’s what’s rare and valuable these days.

You get no competitive edge from consuming the same stuff everyone else is consuming. It’s rare, now, to focus. And it gives such better rewards.

Don’t add your two cents Jul 25, 2016

Show notes

“My two cents” is American slang for adding a small opinion or suggestion.

An employee says to the boss, “I’ve been working for the past two weeks on this new design. What do you think?”

The boss says, “Good job. Maybe just change the blue to gold, change the word ‘giant’ to ‘huge’, and get rid of the border. Other than that, it’s great!”

Now, because the boss said so, the employee will have to make those changes.

But there’s a big downside: The employee no longer feels full ownership of their project. (Then you wonder why they’re not motivated!)

Imagine this instead:

The employee says, “I’ve been working for the past two weeks on this new design. What do you think?”

The boss says, “It’s perfect. Great work!”

This slight change made a huge difference in the psychology of motivation. Now that person can feel full ownership of this project, which is more likely to lead to more involvement and commitment for future projects.

The boss’s opinion is not necessarily better than anyone else’s. But once you become the boss, your opinion is dangerous because it’s not just one person’s opinion anymore — it’s a command! So adding your two cents can really hurt morale.

A business should not focus on the boss, so this restraint is healthy. You shouldn’t give your opinion on everything just because you can.

Obviously, if there’s more than “two cents” worth of stuff that needs to change, then this rule does not apply. But if your contribution is small and just an opinion, let it go. Let the other person feel full ownership of the idea, instead.

Possible futures Apr 27, 2016

Show notes

I occasionally get a big vision for my future — a huge project that will take many months or years. Something exciting and very worth doing.

I’ll do a bunch of research, make a bunch of plans, and feel like I’ve made a big decision on a new direction in life.

Then a month later, I have a completely different vision. Something unrelated to the previous one. Something I’m more excited about.

And the process repeats.

I used to feel bad about this. Like I should stop having new ideas for the future, and just stick with one. I used to feel bad for not acting on them.

Then I made a little change that made a big difference: on my computer, I made a folder called “Possible Futures.” For each big plan, I make a new file in that folder and put all of my ideas and research into it.

Now I can daydream all I want, not feeling bad that I’m not taking action, because it’s clear that each plan is just one of many possible futures.

This collection of plans also reminds me that I love daydreaming, just for its own sake.

I’ve got seventy-two different futures in there as of today. A few times a year, I read through them all. Some seem stupid now, but some get more and more enticing with time.

When I finish a big project and I’m feeling ready for a new future, I open this folder and pick one to make real.