Derek Sivers

Interviews → Gap Year for Grown-Ups / Debbie Weil

Why I respond to every email, ignoring the daily and looking at the big picture instead, why difficult times are great catalysts for personal reinvention.

Date: 2020-04

Download: mp3



Hey, this is your host, Debbie.

Welcome to Gap Year for Grown-ups, a podcast for those who believe you can take a timeout to reinvent your life, especially at 50 plus.

Today, I talk to Derek Sivers. I’ve been following Derek’s work for close to a decade. He’s something of an online legend. We talk about the task he set himself of answering 6800 emails recently. He got those in response to a very short email he sent out to the 50,000 people on his email list.

The subject line was so simple, but it was relevant. It said, “Debbie, are you OK?’ And then in the body the message he wrote, “I care and I’m really asking.” So, I wrote back and invited him to come on the show.

Derek is a breath of fresh air right now. He’s no bullshit. He’s wise. He’s eloquent. And I love his very clear diction.

Derek, welcome to the show.

Take us into a day of creating and learning in Oxford.


First, I’ll give a little bit of context of that. About 15 years ago when I was still running CD Baby, I felt like I needed a little extra help with what I was trying to achieve in life. So, I decided to look for a coach.

I called Tony Robbins’ company, and they assigned me a coach. It was this guy named Jared Rose, who was the best. He and I talked every week. One day he asked me, “What is your ultimate value?”

I said, “I don’t know.”

He asked me questions that kept drilling it down. He said, “What’s important to you?”

After each of my answers, he would say, “OK, why is that important to you? What’s the ultimate point of that?”

He asked until it finally got down to the final two, which were learning and creating. He said, “Which one is more important to you, ultimately, learning or creating?”

I said, “Both.”

Jared said, “No. One of them ultimately is going to be more important.”

I said, “Nope.”

He said, “Derek, come on, you’ve got to know what your ultimate value is.”

My conclusion was that this was a trick of language. If we were speaking German, and there was a long word in German that meant learning for the sake of creating, then that word would be my ultimate value.

Like if you were looking at teal, which is equal parts green and blue, and somebody said, “No, what’s your favorite color? Is it green, or is it blue?”

You could say, “No, teal. Teal is my favorite.”

So, learning and creating are two halves of the same thing. I think of learning and creating as a cycle. I don’t like to learn for the sake of learning. I like to learn things for the sake of creating. I like to create things because of the learning process in creating them.

My daily life is not interesting at all. That’s the reason I don’t have Instagram. You’d see nothing but me just typing all day.

I wake up at 5 a.m. and I type all day long, taking maybe one break to go running, take a bike ride, or workout for a little bit. I stop to play with my kid. Then, I just keep typing until I drop at night, at 11 p.m.

I’ll sleep for five or six hours, and I do it again. I’m basically typing most of the hours that I’m awake, whether that’s answering emails, programming, writing in my journal, writing my book or whatever it may be.

I don’t do very well with a schedule where you wake up and do an hour of this and an hour of that. I tend to get into one thing at a time for months at a time, sometimes even years at a time. I will just do one thing until it feels complete.


I don’t think that’s boring at all. It’s fascinating.

How and why do you answer so many of your emails? There is a number on your website. You’ve answered around 90,000 emails in X number of years?


Yeah. And we’re actually speaking during one of the most intense weeks of this in my life. One week ago, today, I sent out an email to my mailing list of 50,000 something people that said, “How are you? Are you OK because of all this stuff?”

And so far, 6,800 people have replied. I’m answering every single one of those replies. The only way to do it is by waking up at 5 a.m. and plowing through them as quickly as possible. I do that until midnight when I sleep for five hours and do it some more. That’s what I’ve been doing for the last seven days, so I actually just took a little break from answering emails to do this call.

But you asked why? Because it matters. It’s important to people. I think that people are in disbelief that there’s a real person on the other end. People have gotten so cynical with automation and corporate-ness that they think they’re talking into the void.

I like to show that I’m a real person. But emails are also where I get a lot of my ideas. It’s also where I’ve made some of my best friends. They’re people who have emailed me out of the blue after listening to a podcast or something like that.

I often get an introduction from somebody who sat and listened to me speak for 90 minutes on a podcast. They sent me an email afterwards saying, “Hey, my name is ___ and I live here, and that was a really cool interview. This is me and this is what I’m doing, and I have a question for you. . .”

It begins the dialogue. Sometimes we’ll go back and forth by email a few times until I say, “You know what? You’re a really cool person, what’s your phone number? Let’s talk.”

We talk on the phone a few times, and then we say, “Next time you’re passing through, let’s meet up,” and then we meet up and say, “Wow, you’re even cooler in person!” So honestly, right now, a lot of my best friends are people who sent an email to a stranger years ago and vice versa.

A couple other of my friends are people whose writing I loved so much that I sent them an email out of the blue that said, “That was a brilliant article. I ended up reading some of your work and I really liked the way you write. We should talk.”

Two or three of my friends now are people who were anonymous internet strangers whose writing I admired. I reached out and we met because of that. In fact, two of the great loves of my life are people who reached out in that same way and then turned into a romance. That in itself would be a reason to keep that channel open.

Right now, when a lot of people are really scared because of the Corona thing, I think reaching out to everybody on my list was just really, really heartwarming. It’s really nice to connect, especially with people that have just been sitting silently on my mailing list for 10 years. For the first time ever, they’re replying to one of my emails now because I asked.

I love it. It’s exhausting, but it’s worth it.


There’s something completely counterintuitive about your use of the internet for connection and learning as well as your single-minded focus on the various projects you have. This strikes me as almost what’s the word – weird?


We all have tendencies. I’ve always tended to throw myself completely into one thing at a time. And I’ve been like that since I was a kid. I’ve stopped fighting it and I’m just going with it.


Tell us about slow thinking and slow living in terms of your own philosophy and your lived experience?


Do you know that feeling when you have a confrontation with somebody, and then an hour or day later, you come up with that perfect thing that you should have said?

I feel like that a lot in life. In the moment, I’m pretty inarticulate or just not that interesting. I don’t have brilliant ideas that snap to the top of my mind, but I get them later. For years, I pressured myself to say something anyway. Somebody asks you a question, you’re supposed to say something immediately.

After years of this, I decided I don’t need to say anything. Just because somebody is asking you a question, it doesn’t mean you need to answer.

Now, often when people are trying to debate with me on something I’ll say, “Hmm, I don’t know, I’ll think about that,” and they will say, “Well, what do you think about that?”

Again, “I don’t know yet. I don’t know what I think about that. I’ll have to go think about it.”

It’s admitting that, at least for me, these things take time. This is a side effect of being a writer. It’s better for me to have a brilliant idea later, instead of an average one now. But if I was a debater, an improvisational comedian, or a radio host then I’d have to get better at being a fast thinker.

In that case, I would probably find a way to practice doing that. I’d say, “OK, this is important. This is something I need to get better at. I need to find a way to get to that interesting thought out more quickly.”

But luckily, I don’t have to. I admitted to myself that I don’t have to come up with an average, half-ass answer on the fly. It’s better for me to say, “I don’t know,” and come up with a better one later.


In business meetings, I’ve noticed that the person who speaks the least often has the most power or comes across as holding their fire because they’re only going to deliver it once.

I don’t think you shouldn’t change what you’re doing. I think it’s working.


Thank you.

I got an email about a month ago from a guy in India, who said, “Hey, I read your article, but I’m in corporate sales. I sell software to businesses. When they ask me a question about the software, I have to give them a quick answer in the moment. I can’t say ‘I don’t know,’ I would lose the sale.”

I said, “I disagree. I think it would be more impressive to the customer if they ask you a question about the software and you say you don’t know, instead of faking it and spouting some nonsense. Just show that you’re taking their questions seriously, and say, ‘Hmm, that’s a really good question.’ Pull out a pen, write it down. Then say, ‘I’m going to find out the real answer for you.’ And then go find out the real answer you return to the office. Get back to them the next day when you’ve got the real answer. I think that would be more impressive to a customer than spouting nonsense in the moment.”


How do you cultivate slow thinking? Particularly in the times we’re in right now with this pandemic?

Because that doesn’t seem to be what most people are doing as they post their latest thought or article they read to Facebook.


Debbie, I have so much to say about this. The news is freaking out. What was true yesterday is false today and vice versa. Isn’t that a perfect reason why we shouldn’t follow it? If what was true yesterday is false today, that’s a perfect in-your-face reason to bow out and say “OK, wait, let’s step back. I’m going to ignore this.

Give me the weekly update because clearly everything’s changing every day. How about I not spend my time paying attention to the flutter?


It’s an anxiety response – sort of filling the air.


I was hit with a weird situation at the age of 38 when I sold my company, CD Baby. I thought I was going to do CD Baby for the rest of my life. I never intended to be one of those entrepreneurs that exits. But I hit a certain time of reinvention, where suddenly this thing I had been doing for 10 straight years had grown toxic for me.

For personal reasons, I needed to stop. I had three different companies offering to buy my company, so I had them bid against each other. I sold the company for a ridiculous amount of money that I would never be able to spend in a lifetime. So, I had to learn about investing for the first time. I had never invested in my life. I’d never done anything in the stock market. But suddenly it’s like, “Oh my God, I’m going to have this money that I need to look after for future generations. I need to learn about investing!”

One of the key things I learned about investing from reading the wisest books that the wisest people said I should read, was that the daily stock market is something that you should ignore. In fact, you should probably ignore the weekly and the monthly too.

The wisest investors are the ones that don’t look at the daily ups and downs. One author pointed out this metaphor: Imagine that somebody is walking their dog across town. They’re walking in the northeast direction at approximately four miles per hour. But the dog is darting left and right and sniffing fire hydrants and pulling forward and then pulling back.

If you watch the dog, you’d say, “Oh now they are going east, hold on, they’re going south, no wait . . .” But the truth is, you’re watching the dog, instead of watching the bigger picture. No, they’re still heading northeast at about four miles an hour. So, the people who watch the stock market every single day are watching the dog and getting all kinds of misinformation and nonsense that isn’t even true. If you slow down and zoom out, you can see what’s really happening.

I love that metaphor for the stock market. Then, I heard that a few years back, Fidelity, the investment company in America, decided to do an analysis to find out what common thread their best performing customers had in common. They contacted their customers who had the best performing portfolios and asked them some questions. And guess what they found the best performing customers had in common? Do you want to guess first?


They traded less frequently?


The best performing customers were the ones who forgot they had a Fidelity account. It had been sitting untouched for decades. Those customers outperformed the ones that were trading every day and every week or every month.

I love those two examples. Combine those examples with the daily news – these are all the same bit of wisdom. Ignore the daily stuff and look at the big picture which is slower by definition.


I actually have an IRA with Fidelity, and I completely forgot about for about 10 years. I somehow remembered and found it, and all I can say is that you’re spot on.

You said that deliberate daydreaming is one of your favorite past times.

How are you fitting that in right now, when you’re typing all day long?


Right now, I’m not. All the way up until Christmas, I was working on my new book.

But then my assistant reminded me that there were some programming projects that she was waiting to be done that was really holding back her work. So, for the next eight weeks after Christmas, I paused the book and did nothing but programming. I got myself out of author head and dove into programmer head.

Then, I sent out that mass email we talked about, so right now I’m doing nothing but emailing people back. I’ll be done with it in a couple days, and then I’ll get back to my book again.

I’m not a well-balanced guy. I never aimed to be, but when you zoom out and you look at the things I’ve done, they’ve usually been done in bursts.


Well, you’re not convincing me, because it sounds to me like you’re very intentional.


What do you mean?


Intentional in terms of choosing. Choosing and sifting through the options. Choosing what you’re going to focus on.

In a blog post you sent me says, “Infinite options are overwhelming.”


You pick a project based on a combination of things, right? We all decide what is worth our attention. Even with you doing your second season here at Gap Year for Grown-ups. It’s probably something you feel is a personal need or curiosity.

But you also felt that the world needs this, and it suited your lifestyle now. This isn’t a major annoyance for you to be doing this. You’re enjoying it. It’s a combination of something that makes you happy, that interests you, that’s useful to others, and that you’re getting good feedback on. We all weigh those type of factors when choosing what to spend our time on.


Do you think we need to go through that exercise that the coach took you through and ask, “Why am I doing what I’m doing?” It’s so useful to slow down and reflect on how you’re spending your time.


It’s a wonderful thing to constantly ask yourself, “Wait a minute. Why am I doing this?” Even as I’m sitting here answering all of these emails – I have to admit, I got way more replies than I expected. When 6800 emails came in, I looked at my inbox with a dropped jaw like, “Oh my God, what have I done?! I’ve handled an incoming lump of 400 emails before, but 6800?! I’ve never done this in my life. What do I do? Should I send an automated reply?”


Did you have an automated copy paste?


I thought about sending out a mass email again and say, “Thank you for your reply, I got it. I’m sorry, but there’s no way I’m going to be able to reply to your reply. I just want you to know I got your email.”

I thought about that. But then I started reading them. 90% of people said, “Hey, all’s well. Thanks for asking,” but 10% said, “I’m screwed. My life is trapped. Oh my God. I don’t know how I’m going to pay next month’s rent. And my mom is sick, and I’m not allowed to see her.”

For me to say, “Hey, everybody, thanks for the reply,” would have been so heartless. I looked at the situation, and I ended up writing some macros that I assigned to the 26 letters on the keyboard. I had 26 sentences that I found myself typing very often, so I assigned them letter strokes. Now, I’m able to read and answer each email in about five to 10 seconds each. I’ve been going through the 6,800 at that pace, using macro typed out sentences.


That is perfect. That sounds like how Derek Sivers would do it [laughter].

There’s this contradiction of you being in your little house in Oxford and maintaining quiet control over your schedule, and then connecting with the whole world out there. But again, it sounds like it’s on your own terms.


You know what is funny? Go to, which is an article called “Solitary Socialite.”

It’s something that I realized I’ve been doing for many years, which is to sit alone in my little house in nature, connecting with thousands of people per week.

I’ve been doing this for many, many, many years. I didn’t realize how strange it was until friends would ask me to hang out. I’d be in my room emailing people all day long, like I’m doing right now. It’s mass-socialization with hundreds and hundreds of emails every day where people tell me about their lives.

It’s empathetic, and I’m connecting with every single one of them. But the end of the day, I’m as exhausted as if I had been at a cocktail party for 16 hours straight.

In reality, I’ve actually just been sitting alone all day, so somebody will say, “Hey, since you were alone all day, do you want to hang out?”

I say, “I can’t, I’m exhausted. I need some me-time.”

They say, “But you’ve been alone all day?”

I say, “But I’ve been social – it’s hard to explain. . .”

It’s strange. I used to think it was just a new internet thing, but then I realized that before this, I’m sure that people who worked for the Beatles and answered all of their fan mail felt the same way. And before that, there are plenty of people who would sit on the phone all day, like a booking agent. They might be sitting in their office all day long, alone, but speaking with 100 people a day on the phone.

We’ve always had versions of this. Maybe they’ve always been fueled by technology. Maybe it’s only been a 100 years or so. I think there have been versions of this for a long time, but this is our current one.


My audience age range is mostly midlife and older. What are your slow living tips for them?

People are interested in changing and reinventing their lives. They want to get off the corporate treadmill. For that particular audience who may not be terribly tech savvy, do any tips come to mind?


You and I are talking on March 25th. We are a week or so into this worldwide lockdown.

Talk about reinvention – slowing down is one way to do it. We are all forced into this lockdown. All businesses are shut, everything’s closed, everybody’s home, everything’s going to freeze.

I heard from so many people in these emails who were fired, laid off, shut down, and I felt so bad for them. I would reply back and say, “Oh God. I’m sorry. That’s horrible. The timing of this is terrible and my heart goes out to you. Let me know if I can help.”

What’s interesting is that as they started replying back to my replies, most people said that they were actually due for a change anyway. They said they were in a rut, and they can now make the best of this unfortunate situation to push them into making a change.

Most of us don’t change until we have to. Something usually has to push us. Even if you look at yourself in the mirror and you’re disgusted at who you see. Don’t we all have friends who stayed in a job way too long and really should have quit, but they never did?

And then one day, they were finally fired. They went, “Yeah, I probably should have quit years ago. Now, it’s time for me to make the change.” But most people don’t quit. They need to get fired.

That’s my thoughts on what’s going on now. I think this is going to be a great catalyst for a lot of personal reinvention.


Oh, gosh, I hope that is one of the outcomes. I agree with you. It’s scary. It’s a scary reinventing.


Getting fired in itself is pretty scary. Change is usually not comfortable. This whole thing is scary. But on the other hand, aren’t we in good company? Years from now, everybody will be saying, “2020 – that’s when I decided to take up the new career. That’s when I decided to make this change.”

The whole world is changing right now, so we’re in good company.


Derek, I think we should end on that high note.


Thanks Debbie, fun conversation.


Thank you so very, very much. This is just wonderful.