Derek Sivers

Interviews → Vitamin Joy / Shelby Stanger

How to say “no,” the importance of reflection, joy

Date: 2020-04

Download: mp3



Derek Sivers is many things. He’s been a musician, producer, circus performer, entrepreneur, Ted Speaker, and book publisher.

He started and sold the company CD Baby for millions of dollars and then gave most of it away. He’s lived in different places around the world, often for a year at a time. He loves New Zealand, which is also my favorite country.

He’s often known for being the guy who coined the phrase, “hell yeah or no.” That’s a phrase that’s been especially helpful to me.

I’ve been wanting to interview Derek for forever. He’s philosophical and his voice is really calming.

We recorded this episode in April in quarantine, but even as we get back to a new normal, this message is more important than ever.

Derek Sivers, welcome to the show. I really appreciate you being here with me virtually.


Thanks, Shelby.


The phrase “hell yeah or no” has been really impactful for me. Saying no is so hard for so many people, including me. How can we be better at it?


To gain clarity on any subject, it’s helpful to imagine extremes. If you’re not sure where you stand on something, imagine taking it all the way to one extreme and then the other.

See how those two scenarios feel. Imagine two extremes around saying “no.”

First, imagine yourself saying “yes” to everything. Attend everything, meet everyone, read everything, watch everything. You’d be pulled in a hundred different directions.

Every minute of every day would be filled with obligations. At best, you’d probably be able to give each of them a minute or two of your time.

Imagine the other extreme, which is saying “no” to everything. Imagine yourself with no obligations. You could do whatever you want. You have all the time in the world.

Now, imagine that saying “no” is your default state. You’re free and you have lots of time and energy. Then, imagine that something comes along that’s worth saying “yes” to. A great opportunity plops into your lap.

And because you’ve said “no” to everything else, you can throw yourself completely into this one thing. You can do an amazing job. You can learn and grow. You can rise to the heights of achievement, acclaim, and fulfillment because you said “no” to everything else.

When I picture those two extremes, saying “no” becomes really damn easy for me.


This feels like a meditation [laughter].

Are there any specific examples in your life right now where saying “no” has helped you?


Goals. I have been saying “no” to potential futures. We are talking now in April 2020 and up until two months ago, I had a lot of travel plans.

As of now, I have none. I had to let go of a bunch of plans. Letting go is also like saying “no.”


Do you have any tips to make saying “no” easier?


Yes. Make a little form letter. I have one that’s only six sentences long. I put about 20 minutes of thinking and diplomatic wording into my six- sentence refusal.

I keep it in a little text document nearby and use it a handful of times a day in my emails. It’s well-written and respectful.

A few people have actually replied saying, “This is the nicest refusal I’ve ever gotten.”

Instead of having to wrench my soul and come up with the words every time, I can just copy and paste my nicely written refusal.


That’s so kind to put some thought into saying “no.”


I make it about them, not me. I say, “I really appreciate it and I appreciate you thinking of me for this. I wish I could say ‘yes’ right now,” and I give a little context.

I say, “I’m at a time in my life where, in order to get my book finished, I’m saying ‘yes’ to this one thing only and saying ‘no’ to everything else. Please take no offense. It has nothing to do with you. Don’t take this as a forever. In half a year or so, my answer might be different. Please feel free to ask me again.”

I feel good about copy and pasting it to anybody.


I love that saying “no” can add so much more joy to your life. This is so cool.


Saying “no” to me is the liberating process of letting go. This means that you can let go of old goals and make peace with the fact that you’re never going to learn Mandarin, or you’re never going to hike the entire Appalachian Trail, or you’re never going to turn that little business idea into an actual business.

You could even let go of the little plans, like meeting up with that person you can’t ever seem to coordinate with. Just let it go.

Or watching that movie everyone says is great. Or even writing a song. If you let go of all these expectations, it’s freeing. It’s so liberating.

Assume that they’ll never happen and make your peace with that.

This is like taking off a huge, heavy backpack of stuff that you didn’t need. Doing this makes me realize how little it takes to be happy and how much my load of expectations was holding me down.


Minimalism has always been part of you – philosophically and physically and philosophically.

Do you have any advice on how to cultivate a more minimalistic lifestyle?


I was not always a minimalist.

I moved my house five times in two years. If you do that a few times, I realized “Alright no more unloading and reloading this U-Haul. I have to get rid of this stuff.”

I could give some bullshit answer and say, “Ask if this thing sparks joy inside of you.”

But come on, we’ve all heard that.

You need to go through the pain process yourself. You have to feel the pain of having too much stuff.

You have to feel the pain of having too many apps on your phone, or too many browser tabs open. Feel the pain of having too many obligations and having too many plans.

Sometimes, advice is worthless because people actually need to feel the pain before they make the change.

My advice to help others cultivate a minimalistic lifestyle is to go shopping. Go read wire cutter and buy everything they recommend and then go read the book called A Thousand Places You Must See Before You Die and take it to heart. Then, listen to Shelby’s Wild Ideas Worth Living podcast and after each guest say, “I’m going to do that, too.”

Then and only then, you will feel the incredible overwhelm and have a mental snap. That’s when you can let it all go.


What are some things that you got rid of that have physically added joy in your life?


I’m going to give you a slightly deeper answer than you’re expecting. Ever since I was 14, all I wanted to do was be a musician. It was such an intense passion in my life. I was a monomaniacal, ambitious musician.

When I was 29, I accidentally started CD Baby and I poured myself into that for the next 10 years, but I still defined myself as a musician.

After 10 years passed, I sold CD Baby and retired. I still wasn’t making music, but every now and then I’d pick up my guitar and play a few notes.

I told myself, “Now that I have the time, I need to record an album full of songs. I need to put aside the time to do it.”

But another 10 years passed, and I still hadn’t done it. I moved to England last year and I told myself, “I’m going to set up a recording studio in the spare room in my house.”

I bought new musical equipment. I got speakers and a new synthesizer that has a billion sounds on it.

I said to myself, “OK, now I’m going to make a record. But first, I’m going to answer these emails. In fact, I have to finish my book first. I have to do this other stuff, but then I’m going to make a record. . .”

My two guitars and keyboard were in my line of my sight every single day. My soul was conflicted. Every single day I would look at that musical equipment and go, “I want to do that, I need to do that.”

But it was third priority after finishing my book and exercising. After about nine months, I was writing in my journal about it. I asked myself, “When am I going to record? I really need to start putting aside at least two hours a day to work on music. Oh wow, that’s a lot of hours each day that I could be spending writing my book. Listen to that thing in my gut that’s clearly telling me I don’t want to do this. I say I want to do it, but look at my actions.”

Looking at your past actions is a better indicator of values than listening to your past words. So, I took my two guitars, my speakers, and my synthesizer, and I called up a friend of mine here in Oxford who’s a full-time professional musician.

I said, “Mark, how’d you like to have my guitars?”

He said, “No way. Dude, are you serious? That Fender.”

I said, “Yep. You want it?”

Mark said, “Hell yeah, man!”

I said, “Do you want my Native Instruments keyboard?”

He said, “Holy shit. I was just about to buy one of those myself!”

He was so thrilled. He uses it every single day. He’s so happy. I thought I would have a period of mourning after giving my music away. Instead, I felt so much lighter.

Once I gave it all away, it was such a load off. No more conflicted soul. No more beating myself up about something that I thought I “should” be doing, even though I’m not.

Letting go of goals is one of the most liberating things I’ve ever done.


I really appreciate you sharing that. What a joy and gift to share that with your friend. And you can always buy another guitar.


Exactly. When I mentioned the example of letting go of your goal to hike the Appalachian Trail. It doesn’t mean never, ever, ever. First, come to peace with that “worst case scenario” that you’re never going to do it. If you can make your peace with that, then you’re liberated and free.

And if the day comes when your values realign, or you’ve accomplished some of your other goals, then maybe you revisit that.

But first, you have to be okay with the idea that you’ll never do it.


This is so helpful because I’m one of those people who wants to do everything. I want to be a podcast host, a journalist, and a surfer. Doing all these things at once has never been easy internally.


Some people have that personality type. Some people are massive multitaskers who really like switching tasks every two hours.

I tend to get really into one thing at a time. So, you have to acknowledge your personality type, too.


You’re also a dad. I feel like being a parent is like one of the greatest jobs in the world. What do you do with your son that brings you both lots of joy? And how old is he?


He’s eight and we do whatever he wants [laughter].

There’s this idea that we need to mold and train children.

But isn’t that how they make those little stunted bonsai trees?

So, he’s free to follow whatever fascinates him, and I’m his helpful companion. He bounces out of bed in the morning, and literally within a minute of waking up, he’ll say, “Let’s go make something!”

There’s a room in our house and we call it The Making Room. There are three tables in the room filled with things that he makes.

As soon as he wakes up, he goes straight to the making tables and starts creating. He also delegates some of the tasks to me.

He says, “OK, you build the Lego walls. I get to build the Lego characters.”

Then, he makes up games and adventures and tells me how to play my part.

Yes, we also do homework and practice math and spelling, and I turn him on to things that he’d otherwise be unaware of. But mostly, it’s him leading the way.


I love how kids can take us to different worlds. They’re so imaginative and free.

Where do you mostly get your vitamin joy today?


The tranquility of silence, nature, typing, and tea [laughter].

I’m answering this way because just a few days ago, I woke up and I asked myself, “Why am I so happy?”

It was one of those mornings where it was warm in the bed, but cold outside and I stayed in bed a few more minutes. I thought, “I’m really, really happy. Why am I so happy? Shouldn’t I be wanting more out of life? Shouldn’t I be wishing I was somewhere else right now? Shouldn’t I be aspiring to something?”

Then, I remembered that joy is our default state when nothing is wrong. I asked myself, “Why is nothing wrong?”

I realized I was really thankful for having a place to live, and climate control, and silence.

I asked myself, “What would be the biggest obstacles to my happiness right now?”

I imagined if I was living right above a noisy venue full of drunk people shouting into the night, that would be an objective obstacle to my happiness. That would be hard.

Or if I was living somewhere freezing cold or burning hot and I had no climate control, that would be an obstacle to my happiness.

I found that as long as I have silence, a comfortable temperature, and an OK house that’s not collapsing, it leads me to a state where I’m able to focus on the higher rungs of human development.

I also love my tea. I found an Australian tea company that is surprisingly good. They’re called T2. I used to live in Singapore, and they have a loose-leaf tea called Singapore Tea.

When I saw it in the shop, I thought, “Yeah, right. Singapore tea? Come on.”

But they had a little smelling box, so I lifted off the lid and I thought, “Oh my God, they did it! That’s the smell of Singapore tea shops. How did they do that?”

I bought a box and looked at the ingredients.

It’s made up of genmaicha, toasted brown rice, a little black tea, coconut, and some kind of oil. Oh, my God, when you put these ingredients together and drop in a little honey and milk, I can’t get enough of it.

I’m on my 12th box of it in four months. Singapore tea by T2 is the best thing I’ve tried in years.


That sounds delicious.

You are a really thoughtful human. Are there certain books you read? Have you done silent meditation retreats?

I’m wondering how you are the way you are because you’re a very unique human.


I spend a lot of time reflecting. I used to think that reading more books would make me smarter. After many years, I looked back and realized that all of my insights into life that have been the most useful have not come from the process of gathering more information, but more from the time I spend later reflecting on what I’ve learned.

I’m actually reading less and reflecting more now. I’m thinking more than ever about topics like, “Why am I happy?”

I love getting to the bottom of that answer, even if it takes me two or three hours of writing. It’s so cool to ask yourself, “What has made me happiest in the past?”

Look at your past actions. Ignore your words. What viscerally made you the happiest in the past? Is there a common thread in there?

I also play through hypothetical futures a lot. The other day I was really wishing for a hot tub and I don’t have access to one. Instead, I vividly imagined myself in a hot tub and feeling the joy of that.

After doing that for a while, I thought, “I don’t need a hot tub. I can just imagine it.”


I wonder if I could imagine getting a full body massage [laughter].


[Laughter] That’s exactly what I was doing! I shortened the story for the sake of the interview, but in my daydreaming, I was also imagining getting a massage. I thought, “Hm. This is almost as good. Not entirely. . .”



You’ve also lived in all of these places and I’m sure that’s added such a unique perspective to your life. Travel changes us because we experientially, which is a beautiful thing.

Do you think that that’s also added to your ability to reflect because you’ve had so many beautiful experiences in so many different places?


It’s the challenges that make you question your values and question who you are.

They say you don’t really know somebody until you’ve seen them lose their luggage.

Figuratively losing my luggage in different places has helped me re-evaluate what’s important to me, who I am, and what I really need in life.


That’s very timely. Do you have advice to other people on how they can cultivate their own vitamin joy?


I don’t have any advice. I come across as someone who’s got it all figured out. But here’s the catch – I only have myself figured out.

I really have no idea what anyone else should be doing.

If we think we know what others should be doing, that’s a dumb assumption. We don’t know who this other person is. We’re way more nuanced than that. I can’t really prescribe anything to anyone. So, sorry, no advice.


That’s OK. It’s been a joy to talk to you.

Derek, what’s your next book about?


The next book is How to Live. I’m not here to promote it. I’m still writing it and I am so excited about this book! It’s so fun to write.

In the meantime, go to and email me and say “hello.” I will keep in touch and tell you when the book is ready, but I’m still writing it.


Is there anything you can tell us about it?


In short, it’s 27 deliberately, one-sided arguments. One argument per chapter, each one completely disagreeing with all the other chapters.

Each chapter answers the question of how to live in 27 different ways.

There’s a really amazing book called Sum: 40 Tales from the Afterlives, by David Eagleman. It’s a massively creative little piece where he answers the question, what happens when you die?

He answers it in 40 different ways. Each chapter gives a scenario about what happens when you die, and each chapter also completely disagrees with all the other chapters.

I love the format of answering the same question 40 different times with 40 different answers, as if none of the other answers exist. So, I read Sum and loved it. Then, I read it again and loved it even more.

One day, I thought, “I want to write a book called How to Live in that same format!”


That sounds so cool. I cannot wait to read it. Derek, it has been such a pleasure to chat with you.


You too, Shelby.


You’re a gem of a human.

You can find more about Derek and sign up for his beautifully written, minimalistic newsletter at