Derek Sivers

Interviews → Amy Jo Martin / Why Not Now

on slow thinking, how actions reveal your true values, goal-letting vs. goal-setting

Date: 2019-11

Download: audio (mp3)

Link: https://amyjomartin.com/2019/11/whynotnowdereksivers/


Amy Jo:

Derek Sivers is on the show today, and he really was not on my radar until recently. Several months ago, I listened to a podcast episode where Tim Ferriss interviewed Derek and immediately, I knew this was someone I wanted to start researching and get to know better because I was drawn to the way that his brain works. I was drawn to the way he thinks. So immediately, I started researching, went to his website, and sure enough, I was able to get Derek on the show. I’m so excited about this.

For a little background, although you will not hear Derek talk about this at all, he is the founder of a company called CD Baby, which really became the largest seller of independent music on the web with over 100 million dollars in sales, servicing 150,000 musician clients, yada, yada, yada. You won’t hear Derek talk about that at all, really. But he does draw on his life experience, of course. And he’s the type of person who challenges his own thoughts. He challenges his own thoughts all day, every day. And that’s what made me so curious about him. He defines himself as a slow thinker, and we talk about that throughout the interview a bit because we live in a world where speed is everything. Instant gratification is held so high. And I think it’s an interesting conversation to be had. Should we be slowing down a bit? Thinking things through more. And so you’ll hear Derek and I discuss that a bit. He’s definitely convinced me to start experimenting with that a little more.

And Derek’s take on “why not now?” is unique. It’s one we’ve never heard. And some of his suggestions in the way you view that question, I think will be extremely helpful and beneficial for you to hear. One of the points that Derek really doubles down on is that no matter what you say, your actions reveal your true values. So, if you think about your “why not now?” idea, if you haven’t acted on it yet, and it’s been quite some time, maybe you don’t want to do it. Maybe it’s as simple as letting go of this goal you thought you had. So we talk that through as well. And I encourage you to check out sivers.org where Derek recaps all the books he’s read, and he writes daily. He also has a new podcast. Each episode is just a minute or two long, maybe three. And he encourages you to reach out to him directly. So definitely you take a look at his site. All the information is there and enjoy this convo – a very different convo with Derek and I.

Amy Jo:

Derek, welcome to the “Why Not Now?” show. Thank you so much for joining me today.

Derek:

Thank you!

Amy Jo:

I am excited to dive in. Also, I want to touch on our prep process after we get through the first question because it’s been unique and very valuable for me at least, and so, let’s hop right in.

Can you tell me about a time when you had a big decision to make and you had to ask yourself, “why not now?” We’ll dive into that day, that minute, that hour, that season, and kind of dissect how you did navigate from idea to action.

Derek:

Okay, or not [laughs].

Amy Jo:

Or not [laughs]. Great point.

Derek:

I really like to doubt things. Some people value consistency. I think I value looking at things from another point of view, but we could talk about that later. So my “why not now?” moment that we always begin with is the day that I decided to sell my last company called CD Baby. I remember just by coincidence, it was my sister’s birthday, so I remember the dates. It was January 18th – we had a handshake deal. I knew there was going to be a few more months of paperwork before the company was sold, but it was basically done.

And that night I went to bed with just a clear head like, “Wow, I’m no longer [email protected] anymore. Wow!” This was like ten years of my identity. Right? So, the next morning I woke up, had breakfast, and then over breakfast, I had the idea for my next company. It was like, oh my god, I just had the best idea.

And I did that wonderful thing where I immediately jumped into action. I thought, “Oh, this idea is so good! I so want to do this.” And I immediately started typing it up. I started like I opened up the database – I’m a programmer, so I actually tend to start things from a database point of view. I’m like, “OK. Create. Table. Users. Log in here. Create account, and then create a new project, and every project is going to have tasks!”

For three months, I was on a tear. Just making this thing happen. I hired somebody as the manager. And after three months though before I launched anything, I had this realization that if I do this thing, my life is not going to change. I’m going to remain on the same trajectory I have been on for the last 10 years, which is just this like maniacal, single-minded focus on running a company and serving my clients. I had been doing that for ten years straight and it was wonderful! But, I felt like I was at a crossroads where I could make a real change in my life, and so I made myself stop. Sorry, this isn’t the “why not now?” moment yet...

Amy Jo:

That’s OK!

Derek:

This is the flashback of the story. If this was a movie, it would first have the little title screen that would have said, “Nine Years Ago...”

Amy Jo:

Gotcha. I Love it.

Derek:

Everything I’m telling you is from nine years ago. People are dressed in their ‘80s clothes and there’s an old something playing on the TV. So, I made myself stop even though it went against my instinct. I thought, “I’m really in the mood to make a real change in my life. I’m almost 40 years old. I feel like making a real change.”

So I started doing this deliberate process of saying “no” to things I used to say “yes” to and saying “yes” to things I used to say “no” to – just doing the opposite of whatever my instincts were. I did that for a number of years and I made a lot of changes in my life. But the whole time I kept telling myself, “I really want to make that company idea happen, like now that I’ve made some changes. OK, I got that out of my system. I’ve explored the world. I’ve scratched itches. I really want to make that company happen.”

Anybody who knows me heard me talk about how I really, really, really want to do this thing. You know, that company idea I had back on January 19th, 2008. I really want to make that happen. Like that’s really a top priority of mine. But as soon as I finish these other things, I just gotta, you know, just gotta to whatever, make dinner and do whatever. And then, tomorrow!

Amy Jo:

Ohhh, tomorrow.

Derek:

God, I love tomorrow.

Remember the musical, Annie? We should make that the theme song of the Amy Jo Martin “Why Not Now?” Podcast! [Laughs] [sings “Tomorrow” from Annie].

Amy Jo:

The antithesis of “Why Not Now?” [laughs].

Derek:

It’d have to be the instrumental version behind the scenes to just see who actually catches the subconscious.

Amy Jo:

Ooooh yeah, yeah.

Derek:

Anyway, after 9 or 10 years or so of saying “I really want to do this thing,” a dear friend who knows me really well about a year ago heard me say, “Okay, well, now that I’ve finished my book and now that I’ve finished this and now that I finished that. Now my top priority is to finally make that idea happen. I really want to do this thing.”

And my friend said, “No, you don’t.”

I said, “The hell, I don’t?! You can’t just ignore what I’m telling you. I’m telling you. This is my top priority. Now, I really want to do this.”

My friend said, “Yes, I can ignore what you’re telling me because no matter what you say, your actions reveal your true values.”

I said, “I don’t know about that. What? No, hold on a second. That’s not true. What about those people that really do want to quit smoking? They’re just having a really hard time with it?”

He said, “Then they don’t really want to quit. If they really wanted to quit, they would do it.”

I’d say, “Okay, hold on. What about people that really want to lose weight? Like they’re overweight, they really want to lose weight. This is really important. They really do want to do it. They just haven’t done it yet.”

He said, “If they really wanted to, they would have done it by now.”

We’ve all felt the difference between yeah, I’d like to, yeah. I want to, and shutting up and actually jumping out of your chair and doing it and making something happen.

There are things that happen in your life that make you jump up and do it right now without telling people, without writing it as a goal, without affirmations in the mirror or whatever it may be. You just do it because you want this more than anything. It’s more important than eating lunch, you know?

So I have to admit, he changed my mind on that. I reflected that evening and I was writing in my diary like, huh? Actually, there are a whole bunch of reasons why I don’t really want to start that company. For one, it’s very labor intensive. It was very much like a customer service company. Once I started, I am really on the hook to my customers and I can’t just disappear for a month. It was a service business idea that would require me to be on call.

Amy Jo:

Very dense?

Derek:

Yeah, and there were a lot of reasons why I didn’t actually want to make it happen. But in theory, I did. In practice, I didn’t. God that idea just comes up over and over and over again. The difference between in theory and in practice.

So this is it: that was my “why not now?” moment, but it made me realize a couple of things: that for one, if your words are disagreeing with your actions – if you’re saying you want to do something, but you’re not actually doing it – I think there are two smart reactions to this situation.

Number one, stop lying to yourself and admit your real priorities. Or number two, just shut up and start doing what you say you want to do and see if it’s really true.

Because I think a lot of things just are nicer held in theory. I like daydreaming. Daydreaming is fun to just lie down on the couch sometimes and just daydream. Where else would I like to be today? What if I was here? Or what if I was doing this other thing? Sometimes it’s just nice to close your eyes and daydream free.

I’ll just pick a specific example because I was thinking of it two days ago. I was thinking it might be really nice to ride my bike across New Zealand. I lived in New Zealand for seven years. I’m a New Zealand citizen. I love cycling. I think I might want to really ride my bike across New Zealand!

I sat there daydreaming about it for a while and that felt really nice. Of course, it was only maybe 5 or 20 minutes later before I realized – oh, right. The actual reality of cycling across New Zealand involves often being on highways with trucks running by you and riding in the rain and freezing and your third flat tire in one day. Then maybe I don’t actually want to do this, but it’s really nice in theory.

So reaction number two to this situation was you just make yourself shut up and start doing what you say you want to do and see if it’s really true because maybe it’s not really true. Then you could re-categorize it as a really nice daydream because – and this is the grand conclusion I was getting to – is that I figured out that goals are here to shape your present moment, not shape the future.

We often think of goals as something that exists to shape our future, but a good goal is something that drives you to take action in the present moment. Not to get new agey, but the present moment is all we really have, right? The past is the term that we call our memories. The future is the term that we call our imagination. The thing that’s really real is the present moment. So if a goal doesn’t change your actions in the present moment, then it’s not a good goal, no matter how impressive it seems or how nice it is in theory. If it doesn’t make you take immediate action then it’s not a good goal, and I find that getting rid of goals is freeing.

Amy Jo:

Whoa, there’s so much here to double down on. I’m like, double click, double click [laughs]!

Derek:

[Laughs] I’m one of those people. You say, “Hey, Derek, how are you?” And I’ll sit you down and give you a 20 minute answer. That was like my way of saying hi.

Amy Jo:

Well, Hello! We are on now! I have so many questions for you. I just love this relationship that you have surfaced between “why not now?” and really good goal setting or identifying if it’s a good goal. If it doesn’t make you take immediate action, it’s not a good goal. That’s really interesting. Where does fear come into this? Where does “I’m scared” fit in?

Derek:

For me, I think fear should be heeded. It should be paid attention to – it shouldn’t be ignored. I often get emails from strangers. For some reason, this common question comes up, “How can I get over my fears?” I think they’re disappointed in my answer. My answer is don’t! If you’re scared of something, pay attention to that.

I found it really interesting when psychologist, Daniel Kahneman, a Nobel Prize winning psychologist – he and many other very smart psychology people have said repeatedly that when people are depressed their world view is actually more accurate. That most people are over-optimistic, and people, when they’re depressed, actually have a more realistic view of the world. Which is a really weird, strange concerning fact.

I think that fears aren’t something we should get over. I think when we’re feeling our most scared is probably a temporary glimpse at reality. It’s not an encouraging thing to feel. It’s not a very helpful thing if you’re defining helpful as something that makes me get up and go, then it’s not helpful. But it can be helpful if you address it. That’s the word that I use – if you were to do word association, you say, “fear,” I think, “address it.”

If you list out your fears and you say, “Okay, what am I actually scared of? Let me let me address those fears one by one. Let me mitigate the downsides that what I’m scared of will happen.” Ideally, I’d like to get to a point where even my depressed, pessimistic, scared self would have to admit that the odds are in favor of this thing working out for me.

Amy Jo:

Interesting. There is a sense of information. Fear is informative and helpful when you address the fears one by one.

So to back up here, I would love to talk through the process we went through in prep for our conversation, and how you consider yourself a slow thinker, and when a friend says something interesting to you, you usually don’t have a reaction until much later.

I’m going to bookmark that for a second, but my curious mind will not let me forget to ask: with this company idea that you had, the day after you knew you were exiting your company nine or ten years ago – you mentioned that what was really stopping you, your “why not now?” was because it was service-based, it was going to be heavy, and not give you the map freedom that you wanted. Did you feel that you couldn’t outsource those types of things and still have a piece of that romantic passion fulfilled of this idea? Or it sounds like it was an all or nothing. But why wouldn’t you maybe move forward with the idea and potentially glean the components that you are interested in versus decide, “Okay. This is not for me.”

Derek:

It was like my New Zealand cycling example where I think the three months of work I did to make that company happen starting from the minute I had the idea – I literally gasped, dropped my breakfast, ran to my computer, and started typing. I think that was the equivalent – we’ll just keep using the metaphor of cycling across New Zealand – that was the equivalent of somebody going down to the bike store, loading up on gear, and reading a bunch of books or watching a bunch of videos about beautiful New Zealand.

It was still all detached from the reality of it from things like rain and flat tires, heavy winds, or not being able to find a place to sleep. I think what happened after three months is that I was hit for the first time with going, “Oh, right! Customers, demands, people getting upset at me!”

My approach to business has never been arm’s length. I wrote this book called Anything You Want. I never intended to do a book, but Seth Godin started a book publishing company and he called me up and said, “I’d like you to be my first author.” And I went, “Okay…”

Amy Jo:

Okay, Seth! Whatever you say. Yes, sir [laughs].

Derek:

Seth picked the cover, and Seth named the book. I just wrote the contents, but it was because of him that that book happened. In the book, I talk about how my approach to business has never been hands-off. It’s never been something I did for the money. It was always very personal. I see it like art. The way that I approached my songwriting as a musician, I don’t see creating a company as that different from creating a band. You do it because it’s personal expression. It’s an extension of yourself.

To me, if I were to start this company idea I had, it would be an extension of me, and if customers were upset that the company wasn’t fulfilling its promises, I would take that very personally. It would hurt. So, it’s when the idea hit the air – I often think of the metaphor of airing out ideas – putting something out into the sunlight. I think of that with my writing, too. When I’ve written something, and it exists on my laptop only and then I put it out into the world, it’s like you air it out, or you see it in the sunlight.

So once this idea was out in the sunlight, I realized how on the hook I would be with the customers, it stopped me. That’s what that’s why I couldn’t just outsource it.

Amy Jo:

That makes a lot of sense. It’s just down to the way you operate and it’s self-expression. Thank you for answering that.

Well I heard Tim Ferriss interview you, and I immediately went to go look at your website and your list of books. For those of you listening, Derek is an avid reader and he takes notes on everything he reads and then shares them and ranks the books. It’s an amazing curation and such a good way to decide what you want to read next. I’ve read a few books since listening based on your site and your summaries and notes.

Derek:

Cool.

Amy Jo:

I think we connected over Twitter because I made some comment about how your voice because it’s just a soothing, awesome voice, and it reminds me of Matt Mullenweg, who’s actually been on the podcast as well. As we started bantering back and forth, you mentioned you’d love to dive into the discussion and the topics that we would be exploring on the show prior.

What’s ironic is just last week, I work with a variety of female entrepreneurs, and last week one of them was talking about preparation for this podcast she’s launching and she asked me and said, “Do you have discussions with people prior to them coming on the show?”

I said, “You know what? Out of more than 150 episodes, I’ve had two.” You are one, and Kenny Tomlin’s the other. I’ve only had two people request that. Which got me thinking and really exploring more about the preparation and the pre-thought.

So, as you’re listening and you’re tracking along here, I started a Google Doc for Derek and I. I really just wanted to talk a little bit about your approach to your slow thinking process because it’s oddly rare in my experience so far.

I wonder if we are putting too much romanticism around spontaneity in conversation? So let’s dive in and you can start wherever you want, but there’s a softball your way because we do have a Google Doc here. Your first answer to “why not now?” is much different than your second, and your second much more interesting. So, I’m tossing the ball your way [laughs].

Derek:

This is such a pet subject of mine. It’s one of those things I could just talk about forever. As I said earlier, I really like doubting things. I write a lot in my journal. I reflect a lot. To me, I think everything I’ve ever really learned, I’ve learned in reflection. When you first take something in, it’s just information. Unless the information somehow blew your mind, it’s just information. It doesn’t really become wisdom until you reflect on it and you connect it to the other things in your life and you ask yourself what you feel about this, or do I really believe this is true? Am I just going to echo it back as I heard it? Which a lot of people do.

It annoys me when you read a non-fiction book. That’s all just, he said, she said. This famous person said this, and that person said this, and this great philosopher said that. I think, “Well don’t just echo!” If you’re echoing that reflection stage hasn’t happened yet. If you’re just echoing, telling me what you heard, then you haven’t really internalized it yet. You haven’t taken it into yourself and connected it with the other aspects of your life.

So, I spend a lot of time in my journal reflecting on what I’ve learned, and whenever something feels like an undisputed fact, I write it a second time with a question mark. If you catch yourself saying, “Well of course, such and such.” Then, you write it a second time and you go, “Of course such and such? Is that really true? Now, what if that were false? Could it be false? Why do we think it needs to be true?”

I’m saying “we” because we’re talking, but it’s more of a private “I,” in my diary. I’m never trying to figure out what other people should do, I’m just doing this all for myself. So, that’s what happened with your “why not now?” question. It was assuming this idea of procrastinating from your true calling –from the thing that you need to do. If you’d just get over your mental hurdles, then you need to do this thing. So at first, of course, I had fun and wrote down a whole bunch of answers to “why not now?” But they all had that base assumption, and then I thought about it a little more and I put a question mark on that. Well, I guess a second question mark [laughs].

I thought, “Well, maybe you don’t really want to. Maybe that’s ‘why not now?’ Maybe you shouldn’t. Maybe you should let it go.” Why do we assume that just because we had an idea once that we need to follow it through? Maybe we should let it go. It can be really freeing. Marie Kondo talks about getting rid of old clothes. What about getting rid of old goals? It’s so liberating to let go of old goals.

I’m sorry! I got distracted. You wanted to talk about the slow thinking too!

Amy Jo:

But you are! That’s the name of the show – we can spend the whole time on it. As you’re talking it through, you are answering that question. I’m just going to rattle off some of your first answers to “why not now?”

Derek:

No wait! How about this? Ask me “why not now?” and I’ll give a few answers and then ask me again and I’ll give a few more.

Amy Jo:

Okay, okay. Hey, Derek [laughs], why not now?

Derek:

[Speaking quickly] Because tomorrow is better! And I haven’t thought it through entirely, and I haven’t finished answering my emails, and there’s other stuff I need to do today, and I didn’t get enough sleep last night, and let’s just face it, Monday is a better time to start a new habit, and in fact, the first of the month is really the best time to make something happen. In fact, look where we are in the year, January 1st… that’s when I’m going to make it happen! That’s “why not now,” because January 1st is coming and that’s why I’m going to do it!

Okay…. Now ask me again?

Amy Jo:

Hey, Derek, why not now?

Derek:

Because I need new photos first!

Amy Jo:

[Laughs]

Derek:

[Speaking quickly] I haven’t picked a good name for the new project. I’ve got the idea. But I mean, look, also, I’ve got a kid! My kid’s obviously more important. Also, my best friend is going through a really hard time, and honestly, it’s kind of exhausting. I’m drained and I haven’t finished the other stuff I started and it’s freezing in here and I got to eat first and I’m in a bit of a foul mood. The world hasn’t been very nice to me today…

You want to ask me again?

Amy Jo:

Hey, why not now? Derek. Why not now?! [Laughs].

Derek:

[Speaking quickly] Because let’s not be hasty about this! Why the need to jump into things? There are a lot of things to consider first. Besides, the whole stock market seems ready for a correction and I think I’m going to move next year and I want to lose weight first. I’m not feeling my best right now and I have a bit of a stuffy nose and there’s a cold coming on and let’s just see what happens with the next election because I think that’s going to change things. But really, there are other things that are more urgent. I’m still thinking it through. I need to run it by some people first. You know what? I need to follow my gut on this one because my gut doesn’t feel ready yet and procrastination is a natural filter. If I want it bad enough, it’ll happen. You want to hear the best reason of all?

You have to ask me one more time.

Amy Jo:

Why not now, Derek?

Derek:

Because the longer you wait, the smarter you get. Uh, huh...I outsmarted.

Amy Jo:

[Laughs] Okay, can I just first highlight “I need new photos first.” And I think food is involved here. I’m seeing a theme. If you look back at what you mentioned earlier, “It’s more important than lunch” – if you know you have a good goal, it’s more important than lunch. If you’re making the excuse that you have to eat first, it’s a really good sign that this is not a good goal. So, I think food is very interesting.

Now, let’s go to your phase two, after some thought of “why not now?” Because the first response was the obvious. Did you stop then and take more time? Put down the pen or stop typing and go do something else and then arrive at this next wave? What’s the time lapse there?

Derek:

It wasn’t much time. I spent some more time thinking about pirates and ninjas and who has more fun.

Amy Jo:

Which we have to get to.

Derek:

No, I spent some more time just thinking and then I thought, you know what? I was giving the cute, fun answers to your “why not now?” But it’s just a natural thing to me, where you ask a question and after a while I can’t help but question the question or question the statement or question the assumption.

Amy Jo:

Interesting. Conceptually, this is important for us to hear. Taking the time to give things more thought and to question and to doubt. I don’t know if you’re familiar with Colby. It’s kind of like Myers Briggs. It’s a personality test.

Derek:

No, I don’t know that one.

Amy Jo:

There’s four categories, one of which is called quick start. It’s like the innovation category, and I’m a ten out of ten. It’s interesting. The consultant that was reading back my results and explaining to me, she said, “I think I’ve met three tens in the 20 years I’ve been doing this.”

I was like, “What?!” But what I found is that I can often false start. I’m so quick to start, and so this process that you’re highlighting is so valuable, and it’s worth us taking more time on it.

Derek:

Here’s another angle to it: I know I’m in a bit of a role as a “content creator” or whatever you want to call it. I don’t like that term, but It’s kind of the normal term. Whenever I’m doing an interview like this, you and I are putting something out into the world, and we’re going to tell a lot of people that they should stop what they’re doing – that they should take the time to listen to this.

I always want to feel that whatever I put out into the world is worth someone’s time, and if I’m just saying the same stuff they’ve heard already, it’s hard for me to feel it’s worth their time. I feel like I have to be adding something new that hasn’t been said already. Like I said before, if it’s just more information then nothing’s really changing your mind. There are plenty of books that I’ve read where it’s like eh, yeah, okay it gave me more information, but nothing really changed the way I think. It’s also me trying to live up to my role as somebody putting something into the world. I’m trying to find the un-obvious angle.

It’s realizing that if somebody asks you a question and you answered too quickly, I think your answer is not thoughtful. I think it’s just a reaction – usually an outdated reaction. It usually means you thought this through long ago, and now you’re just giving this rote answer whenever somebody asks the question like seven times four – 28! Are you sure? Have you counted lately? Maybe it’s changed.

It makes me want to stop and ask myself if these things are still true. I don’t remember this, but a conference organizer recently told me that when I spoke at his conference years ago, his favorite moment was when somebody from the audience asked a question about how they can they can grow their business. The organizer said, “Do you remember your answer?”

I said, “No.”

He said, “I’ll never forget your answer. Cracked me up!”

I said, “What was it?”

He said, your answer was, “Why do you want to grow your business? That doesn’t sound very fun. Are your customers asking you to grow your business?”

The audience member said, “No.”

I said, “Then why? Why do it?”

The organizer said, “You just blew that whole question apart.” It was a non-event to me, but it was flattering that it meant a lot to him because he felt that was something truly new and fun instead of yet another answer to how to grow your business. Why don’t we just question the whole assumption? Why do we think we always need to grow our business?

Amy Jo:

I actually want to touch on that in a second because I have a follow-up question for you as well. Before we go there, a lot of people listening are considering a pivot in their career. I’d love to hear what you have to say about this concept of pivoting and people who are wanting to pivot.

Having somewhat touched on this subject prior, my question to you was – what advice would you give someone who is looking to pivot their career and your feedback was, “What’s looking to?”

I thought, “Yes! That’s great point.” There is a lot of emotion in that phrase, “looking to” or “lack of,” but share your thoughts and even your tip because it’s very unique and tactical.

Derek:

I actually had more time to think about this since I sent you the email. So first, let’s take two things we’ve mentioned earlier in this call and apply it to this. First, maybe if you’ve been thinking for a long time that you want to make a change in your career, you need to make a change in your career, you’re looking into starting to make a change [laughs] – maybe you need to say, “OK, maybe I don’t really want to.” Maybe that’s just a plan, and you need to let it go. Man, that might be so liberating!

There was a point in my life where I kept saying I was going to move, “I want to leave this place. I’m going to move. I’m going to move. I need to leave this place. I’m going to move.” And at some point, I remember I thought, “Maybe I won’t move. Maybe I’ll just stay here.”

Suddenly, I gasped. I thought, “That would be so exciting! To just stay here? Oh, my god. And not have to move all this? I could just stay here! Wow, why did I not consider this idea before that? Just staying here and not moving? Oh my god, this is way more exciting now.” I just didn’t consider not moving.

So that’s one thing. Consider not pivoting your career, and think about how exciting that could be. To not. Look at your situation and decide to make the best of it. Look at all your advantages. Take the gratitude point of view about your current situation instead of the crumble.

Amy Jo:

And gaining more space, right? Imagine the amount of space that takes to have a goal that you’re not acting upon?

Derek:

So then let’s compare the cycling across New Zealand idea. Maybe changing your career is something that’s nicer in a daydream. Your listeners might like this: Five or six years ago, I used to make lots of plans every day. I used to make lots of plans every day. Very specific plans. I would suddenly get an idea.

We’ll just keep using the same one. I’m going to cycle across New Zealand. I would think “Yeahhh this is what I’m going to do!” I would open up my diary and I’d start writing and doing research. I’d say “I’m gonna do this thing! I get to cycle across New Zealand!” I’d make lists and think about how I’m going to make this happen. And then, after a week or a month, the idea would fade, but that’s okay because a new idea would show up. I’d say, “Oh, I just had a great idea for an app. Oh my god, this is the best idea!” Then I’d start making a plan of how I’m going to do this app. I’d think, “This is a great idea for an app!” I’d call my friends and say, “Oh my god, Amber! I just had the best idea for an app. Listen to this.”

She’d say, “Oh my god, that’s a great idea!”

I’d think, “Yes, it is, isn’t it?!” I’d get all excited, and then after about a month, the idea would fade and then something else would jump in.

Friends would sometimes give me grief about this. They’d say, “Oh, is this yet another one of your ‘I’m going to do it’ plans?”

I’d say, “I know, I know. Well the last 25 haven’t happened, but this one!”

So the point is, about five or six years ago, I realized I’m just enjoying daydreaming. Instead of calling each one of these things a plan from now on, I’m going to call it a possible future, and I’m going to completely indulge in this possible future as some kind of a middle ground between purely daydream and a specific plan. I’m going to enjoy that middle ground and take it for what it is.

I started a folder on my computer called “Possible Futures.” Each time I have one of these ideas, instead of putting it in today’s plan, I open up a new file in “Possible Futures” and I write down all the details about how I would make this happen if I wanted to. Then I can just leave them there. I review them every now and then I look through and I go, “Oh, yeah, I forgot about that one,” and every now and then I make one happen.

So this is a real specific concrete one. About three or four years ago, I put aside a few weeks to finish a programming project that I thought would take me another three weeks to finish, and my kid and his mom were were out of town for two weeks. I was like, “Ok, I’ve got three solid weeks to work, and two weeks with no daddy responsibilities.” And after four days, I finished. I was like, “Whoa, that went way quicker than I expected.” Programing is like that sometimes. Sometimes things take way longer than you expect; sometimes way faster than you expect. It was way easier than I thought.

Suddenly, I had two weeks of free time, and I opened up my “Possible Futures” folder. One of them was to do three of the official great hikes of New Zealand. I was living in Wellington, New Zealand at the time, and New Zealand has nine hikes that the government has labeled the official great hikes of New Zealand.

There were three in particular that I wanted to do, and I opened up this possible futures at 3 in the afternoon on a Wednesday. I said, “Yeah! Now’s a perfect time to do that. I’m gonna do it.” First, I went to their website. It said they were leaving tomorrow, and there is one slot left. Usually you have to book these things a year in advance, especially if you’re a group, but if you’re a single person, sometimes there is a single gap.

So I called them up and I said, “Is it true that you’ve got one space tomorrow?” They said, “Yeah, mate. If you can get here by nine a.m., it’s all yours.”

So I pulled up Air New Zealand and looked at flights. “Oh my god. There’s a flight leaving in 90 minutes down to Queenstown. I think I can make it!”

I called back the the tour company. I said, “Save that spot for me. I’m going to the airline. I’m going to call you from the airport with my credit card, but save it for me. My name’s Derek. Here’s my phone number.”

They said, “Alright, mate!” I hopped quickly on the bus to the airport. I made the plane just in time, flew down to Queenstown, and I made it. I went on this ten day hike of the three great walks of New Zealand, and it was because I had written out this specific plan in my “Possible Futures.”

Amy Jo:

“Possible Futures.” Wow…

Derek:

So that is now their role in my life. I don’t feel bad about indulging in my detailed plans. I’ve just now labeled them as a “possible future.” Coming full circle, I am drawing a circle in the air with my hand [laughs]. Coming full circle back to your question, a piece of advice for someone who is looking to pivot their career – besides considering that maybe you don’t really want to – consider that maybe it’s just a “possible future.”

You write your resignation letter and keep it in your desk, plan out the details of exactly how you will do this thing, do it wisely instead of impulsively or emotionally. There’s a book called So Good They Can’t Ignore You by Cal Newport where he tells a great story. He studies people’s careers, and how people change or build their career. He points to this great example of two lawyers he met, separate lawyers that didn’t know each other. Two lawyers that both wanted to quit their jobs and start a new career, but they did it two very different ways.

One of them wanted to be a ski instructor, and the other one wanted to start a yoga studio. So the one who wanted to start the yoga studio just decided one day she’d had it. She’s going to follow her dreams. She quit her job at the law firm and opened up her yoga studio.

The other one decided to approach it smart and savvy. She first started telling everyone that she was going to do ski instructions. She started telling her clients, “I’m going to take you on a ski trip.” She started telling her partners at the firm about her ski instruction, and she phased into it over a year or two until it was clear that her ski instructor idea was going to be a success. All of the initial enthusiasm turned into real customers. It was profitable. It was already starting to go well. Then, she quit her job at the law firm, and her ski instructor business was a success.

Whereas, the woman who just impulsively quit and started the yoga thing, her yoga studio flopped because she didn’t phase into it. In the book, he calls this “career capital”. He said, you build up “career capital”. Think of it as saving up gold coin – that version of the definition of capital. When you want to make a pivot in your career, you spend it so you can make a sideways leap, not start from the bottom, and he uses that example of the two different lawyers. That’s a good example, and if you still decide that you want to do it, plan it out in detail, do it wisely, but consider you might not really want to.

Amy Jo:

I love the tactical, actionable idea of writing your resignation letter and keeping it in your desk. I have this picture of an “Possible Futures” Evernote. A detailed plan of what the plan looks like and then phasing into it. I think that first action – even the act of writing a resignation letter out – physiologically, you probably are getting some body intelligence that’s clueing you into if you really want to do this or not. It’s a really interesting exercise. How cool is that? I want to write a resignation letter. I don’t even have anything I want to resign from, but I just want to do it just to try and see what it feels like. I’m gonna resign from something [laughs].

Derek:

Podcasting [laughs]. I’ve had it with you!

Amy Jo:

Thank you so much for touching on that. I keep getting this question in my mind, and it might have sparked from something that you mentioned to Tim Ferriss when you spoke with him on his podcast about it.

I might be piecing it together here, so correct me if I’m wrong – back during the CD Baby days, thinking about when people ask you for advice about company growth, which you just touched on. The whole idea of why you want to grow your business. It’s interesting because Tony Shea, the CEO of Zappos, actually asked me that one time about ten years ago, and I wish I would have listened closer because it’s a really good question.

When people come to you and someone’s in this mentality of “I need to grow, I need to grow,” which to me feels like a push and a force versus self-expression, pull, and the “it’s more important than lunch” feeling. What has been your experience? Maybe it’s reflecting upon CD Baby, which we haven’t even talked much about, and I’d love for the listeners to get some more color around that. Can you tell me about the two and your philosophy when you’re in that spot where you feel like you need to grow something and push it? Maybe a better way to look at something and your own personal experience with your company. I’m going to stop there, and there’s ninety-seven questions in one, but any thoughts on that?

Derek:

I think it is worth questioning, “why do you feel you need to grow it?” Is there something that you need to buy that you can’t afford to buy? Do not have enough savings? If you really need the money, well, then that’s one answer. Okay, I do need to grow my business because I really need the money, and if you really need the money, then that’s a good, valid answer. But a lot of people don’t need the money. They feel the need to grow because it’s just something we hear. It’s a cultural norm, some kind of, “That’s how I get my value from society. I can’t just not grow my business. I need to feel I’m growing in order to feel that life is getting better.”

Maybe ask yourself if it would be a really good time to look at the balance of your whole life. Maybe instead of continuing to amplify the thing you’ve already amplified, it would be time to look at the other things that are unbalanced. I think a lot of people that are experts in something and are very successful in one aspect of their lives are very fragile. They’re like pedestals. They have this one thing in their life that is so much of their identity that they become really easy to topple. If that one thing is not going well then they just crumble like a pedestal. Whereas, I think that if you have a lot of different aspects of your identity, well, then you’re like a 12 legged table – even two or three of the legs could break and the table is still fine.

If your business is doing well, but you’re feeling a need to grow, grow, grow it more, I’d ask myself if maybe I’m ignoring those other legs of the table because I just want to do the safe thing – the thing I know how to do instead of the scary thing– which is to address my relationship or my health, or all these other things that I’ve been ignoring in the name of making my one pedestal higher.

First, there’s that base questioning to yourself, like, “Why do I think I need to grow this thing?”

Sorry, I think I might have forgotten the other aspect of the question. That was a big one to me.

Amy Jo:

Maybe one area that, as a case study, with CD Baby, it seems that there wasn’t a push. There wasn’t a need or an indicator that said, “Oh, I need to grow this.” It just was happening. Right?

Derek:

Right. You’re right. You just reminded me of the other half of your question. When I hear people say they want to start a business, but they don’t know what to do. I hear it as somebody saying I want to wear a bandage, but I don’t have a wound. A business is a solution to a problem. If there’s no problem, then you don’t need a business – you’re doing it for others. A business is an act of service. It’s a generous act of service for people with a problem, and if the problem goes away, well, then lucky you, now your business can go away.

You don’t have to do this thing anymore. So you’re right, that is the other question, when somebody says, “I want to grow my business.” Well, are your customers asking you to grow your business? If you were to ask your clients or your customers if they have a wish list of what you could do for them, I don’t think any of them would say, “Please grow your business. Make it bigger.”

No. All of them would say, “here’s how you can serve me better,” not, “here’s how you can serve yourself better.” If your customers wouldn’t ask you to grow your business then don’t put any attention on that. That’s not something you need to do. Just keep your focus entirely on the customers and solving their problems.

Amy Jo:

That’s the romanticism around starting a company. Getting funding, growing, pushing, grinding, chasing, and grasping. That’s such an important question to ask. What an indicator – if you feel like you need to grow your business, is that an indication that you should be looking at something else? Is there something else going on? Thank you for for touching on that.

Let’s get to pirates and ninjas [laughs]. I mean, we can’t ignore the elephant in the room here.

Derek:

[Laughs] What? Okay, will you tell me your reason why first?

Amy Jo:

Yes. I will tell you the root of this question and where it came from. I started my first company in 2009, and it was the wild, wild west days of Twitter, and brands and people trying to figure out social communication and how to make money off it. The algorithms were starting to surface – these little monsters called algorithms? All I knew was that you could warm up the engine a bit if you would ask a question and get people talking. Then, you could serve them up the message you really needed to share.

So, when you ask someone, “Pirates or ninjas: Who’s tougher?” They have an opinion. I learned that people want to talk about this, and usually it’s a very passionate opinion. You could get the engagement going. You could get the conversation rolling. So my theory, and I didn’t know this for certain, but it seemed like content would perform better if you started there versus just putting something out there. It’s not as fun of an answer as you might have hoped for the genesis of the question, but here we are today, and I would like to ask you, “Derek, pirates or ninjas? Who’s tougher and why?”

Derek:

Well, it’s funny. My reaction to your question was, “Oh, actually, I don’t know. I have no opinion. I’m not sure of the origin of ninjas. Who are ninjas, really? I know they’re like the shadowy guys that wear black, right? Or is that some cartoony misunderstanding? So I had to go back and read about the history of ninjas and pirates to understand the origin. The impression I got after nerding out for 20 minutes is that pirates attack ships and they steal cargo by boat and ninjas were for espionage and surprise attacks.

I thought it was interesting that they said samurai would do things in the honorable way, and the samurai culture still continues in Japan to this day. Ninjas were the irregular, dishonorable ones. They would always act in secret, and they would get no honor or glory. So they were usually anonymous. To answer your question, pirates act tougher, but ninjas don’t act. They just get it done. So ninjas have to be tougher since they act alone.

Pirates need a boat, but ninjas just have to do their job without any social recognition. They don’t get any of that identity or camaraderie. Right? So pirates have the camaraderie. They have the brotherhood. I hear that there’s a fascinating book out there on the history of pirates. Somebody told me that there is that the history of pirates is actually surprising. In pirate culture, there are a lot of rules, and it’s all about the brotherhood and the social reciprocity. Maybe like the John Wick movies where there’s a code of conduct that everybody has to adhere to. Somebody said it’s a fascinating book. I have it bookmarked somewhere.

I imagine if somebody is a pirate, they get to flaunt their identity as a renegade pirate. So it’s more shallow fun, right? You’re doing crime. You’ve got your mates around you. But ninjas act in secret. They don’t get any social validation, and I thought of a ninja at night going out in secret assassin ways, but in the morning has to just show up to his regular job again. I thought that ninjas must, in their own mind, have to have a deeper intrinsic motivation to do what they do because they need to internalize their reasons why they’re doing this. So, my prediction is that ninjas are also more deeply happy. It’s more fun than fun.

Amy Jo:

Gosh, this is deep. This is good. Do you think ninjas are just extremely humble? Maybe pirates are more egocentric? I’m getting Ryan Holiday’s book Ego is the Enemy in my head, and how he talks about “Do you want to be the important person or do you want to do the important thing?” Maybe pirates want to be the important person and ninjas want to do the important thing, but sneakily?

Derek:

I almost never watch TV, but thanks to an old girlfriend years ago, one of the few shows I’ve ever binged on was Dexter. Remember Dexter?

Amy Jo:

No.

Derek:

Dexter was an HBO show for six or seven seasons. When Dexter was a child, Dexter’s dad, who worked for the police, recognized that he had violent, murderous tendencies. Dexter had a lust for blood. He killed rabbits or something like that, and so his dad decided to channel it. Otherwise, Dexter was going to end up in jail. He taught his son the code of conduct. He said, “Look, I can tell you’re going to murder whether the world likes it or not. So you can only murder other serial killers that are causing the world harm.” So, Dexter became a serial killer of serial killers. He would kill bad people that the police system was not catching. His day job was to work in the police force in forensics. He was often investigating his own crime scenes. Everything, of course, had to be secret. I imagine the ninja would be Dexter where maybe they’ve got their normal job as an accountant, but they have a lust for danger and killing, but they’re going to just do it in secret.

Amy Jo:

Okay, whoa.

Derek:

Whereas pirates would be like the serial killer that wants the attention.

Amy Jo:

Arrgh.

Derek:

Yeah, they want the identity of, “Look at me. Look what I did.”

Amy Jo:

We could just have a whole conversation for an hour on this one. Oh, my gosh.

Derek:

Do you know the phrase bike-shedding?

This makes me want to look it up, but I don’t want to click while we’re recording [laughs]. Bike-shedding is what programmers call it if you’re having a big discussion about something deep and difficult. A difficult decision in programming – how we’re going to implement this database and it’s memory management or calls? If it’s important stuff, it’s hard to get people to take a strong stance, but when you get to something shallow and pithy and meaningless, like what color should we paint the bike shed? Suddenly everybody’s got an opinion.

Amy Jo:

Oh, it’s safer. Oh, yes.

Derek:

So programmers call it bike-shedding. I think I’m getting the story right. So the shallow, unimportant stuff, everybody has an opinion. That’s why I was smiling when you were talking about the origin of pirates versus ninjas. It’s like oh, first ask them a bike-shedding question.

Amy Jo:

That’s easy. I love it. What’s one lesson you find yourself learning over and over, Derek? We’ll wrap up with this question.

Derek:

I think it’s still the one I mentioned earlier about how actions reveal your true values. I figure that I’m still learning this. As much as you hear me spout out, and I sound like I’ve got it all figured out – even just a week or two ago, despite every other story you’ve heard me say here, I had two guitars hanging on the wall and a nice 88-key electric piano, and almost every day I told myself, “I’m going to put aside time to make some music again.”

Almost every day, I went to bed a little disappointed that I didn’t quite find the time to do it. This was going on almost every single day for the last few years, and just two weeks ago, I thought about that thing again – about how actions reveal your true values. I keep saying I want to make music, but I’m not actually doing it, am I? How about I just let go of that goal? A friend of mine here in Oxford, where I’m living, is a full-time professional musician. I asked him, “Hey, any need for a Stratocaster and the Native Instruments 88-Key Keyboard?”

He goes, “Holy shit, dude, are you serious? Oh, my god, dude, I would love it! You’re gonna give me your guitar?!”

I said, “Uh huh.”

He said, “Oh my god I was about to buy that keyboard. Are you serious? You just want to give it to me?”

I said, “Dude, it’s yours. In fact, hearing you so excited; I’m going to give you my speakers, too, and my acoustic guitar.”

He’s like, “Oh my god, this is a dream come true!”

He’s using it every single day. He’s making his living with the stuff that was just hanging on my wall that I wasn’t using. I feel so much better now. I have let go of my goal of making music, and actually just this morning – nothing to do with our conversation – this is just the kind of journaling nerd I am. I was asking myself this morning, “What other goals can I let go of now?”

So, actions reveal your true values. I have to learn that lesson over and over and over again and remember to keep applying it to when there’s a difference between what I say I want and what I’m actually doing. How’s that for full circle?

Amy Jo:

Love it. Love it! Especially as we are getting ready to enter a new decade. What if we look at goal-letting-go-of versus goal-setting?

Derek:

Goal-letting instead of goal-setting [laughs]!

Amy Jo:

Letting! Yes [laughs]! Goal-letting. There we go.

Amy Jo:

Oh, wow. I do want to mention your new podcast. Do you mind sharing just a glimpse into what it’s all about?

Derek:

Sure. It’s basically just me reading my articles in audio form. I call it a podcast, but it made me question the format. I’m glad that you’re doing this, but I’m glad that I’m not doing this. I don’t want to do the conversation in podcast form. I’d rather be the guest not the host. It’s too much responsibility to line up guests and schedule everything.

People have been asking me for years to make a podcast and a lot of people prefer to listen instead of read, but I put a lot, a lot, a lot of work into the articles I write. I’ll work for 10 hours on one little article even though it’s just two minutes long. I like crafting things, so when they’re done, I just thought that I should also record an audio version of it. If you go to my site to sivers.org, you can either read it if you prefer reading or you can subscribe and listen to it.

Amy Jo:

Absolutely. Just to touch on one of the one podcast episodes – I’m going to call it that just because it is. It’s innovating the distribution right?

Derek:

I didn’t mention that the average episode is only two minutes long.

Amy Jo:

Yes, I was about to because it’s so good. You feel so accomplished. I listened to four this morning. The one that I wanted to touch on is on mentorship. I can’t remember the exact title, but it was basically how you get feedback from a mentor, and the process you go through. I absolutely loved it because there’s a bit of a freak out right now around mentorship.

People say, “I need a mentor to tell me how to do something and to guide me.” I think of my mentors, and they will never give me any answers ever, ever, ever, and I rarely go to them anymore because I know what they would say. So that was the gist of it, but it was two, three minutes max? It’s great. I love it.

Derek:

Do you want me to say it?

Amy Jo:

Yes

Derek:

How to ask your mentors for help?

Amy Jo:

Yes [laughs]. That’s click bait right there.

Derek:

I have three mentors, and this is true. Seth Godin is one of them. So when I’m stuck on a problem, and I need their help, I take the time to write a good description of my dilemma before reaching out to them. I summarize the context, the problem, my options, and my thoughts on it. Because the goal is that I want to make it as succinct as possible so that I don’t waste their time – especially somebody like Seth Godin. I don’t know if you’ve ever emailed him, but he will reply to most emails. He tells people, “please don’t email me.” But if you do, he’ll often reply with just a few words. So I know that I need to make this as succinct as possible.

Before sending it, I try to predict what my mentors would say. I say, “Okay, well I know he’s probably going to say that,” so then I go back and update what I wrote to address these obvious points in advance, and finally, I try and predict what they’ll say to this based on what they’ve said to me in the past, and what I know of their philosophy.

Then, after the whole process, I realize I don’t need to bother them anymore because the answer is now clear. If anything, I might just email to thank them for their continued inspiration. The truth is, I’ve hardly talked with my mentors in years. None of them know they’re my mentors, and one of them doesn’t even know I exist.

Amy Jo:

Wow. Powerful. I absolutely love that.

Wow. Thank you so much, Derek for sharing your thoughts.

Honestly, just from learning about you and then studying and following along in this conversation, you’ve really encouraged me to think differently and challenge my own thought process, and that’s such a gift. I’m sure many people listening will feel similar. Thank you!