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The End of Jobs And The Rise Of Creative Entrepreneurs With Taylor Pearson

OLD POST ALERT! This is an older post and although you might find some useful tips, any technical or publishing information is likely to be out of date. Please click on Start Here on the menu bar above to find links to my most useful articles, videos and podcast. Thanks and happy writing! – Joanna Penn

Indie authors are just one part of the global renaissance in creativity and entrepreneurship.

There are now indie film-makers, indie musicians, indie gaming companies as well as maker movements in all kinds of crafts, science and tech.

Consumers are buying from small batch breweries, artisan breadmakers, Etsy crafters and farmers' markets. People are turning away from mega-corporations towards meaning and story.

Flickr CC Artisan by Quinn Dombrowski

In today's interview, I talk to Taylor Pearson about how these movements spell The End of Jobs, and the rise of entrepreneurship.

In the intro, I mention my trip to Paris (see the photos here), the new direct submission for translation site from Amazon Crossing, Jane Friedman's roundup from NINC which includes writing a series and the rise of global markets. Amazon is also having a Spanish language self-publishing promotion and Pentecostés is included in that. If you read Spanish, click here to check it out.

This podcast is sponsored by Kobo Writing Life, which helps authors self-publish and reach readers in global markets through the Kobo eco-system. You can also subscribe to the Kobo Writing Life podcast for interviews with successful indie authors.

Taylor Pearson is the bestselling author of The End of Jobs: Money, Meaning and Freedom without the 9-5. He's also a systems-obsessed entrepreneur and consultant.

You can listen above or on iTunes or Stitcher, watch the video here or read the notes and links below. Here are the highlights and full transcript below.

  • On Taylor's entrepreneurial awakening during a study abroad opportunity.
  • The shift, even in large corporations, to an entrepreneurial mindset, and the change needed in the vocabulary around jobs, 'employability' and economics.
  • How our attitudes toward work have changed, as well as our ideas about security.
  • Finding meaning in creative work vs. the old carrot-and-stick model.
  • Taylor's definition of entrepreneurship, whether being an expert matters and why a willingness to learn does matter.
  • How ‘stair-stepping' as an entrepreneur works.
  • On mindset and fear of change.
  • The way that blogs and podcasts support entrepreneurs or those considering making a change or taking a risk, and the importance of surrounding oneself with a community of like-minded thinkers.
  • The comparative risk between a job vs. multiple streams of entrepreneurial income, and the instinct that urges us to walk away from the unknown.
  • The lack in the education system for children around the skills entrepreneurs need and the two strategies parents can use to make up for this.
  • On Taylor's experience in the world of publishing and the marketing strategies for his book that were the most effective.
  • The systems Taylor used for writing his books.

You can find Taylor at TaylorPearson.me and The End of Jobs here on Amazon

Transcription of interview with Taylor Pearson

Joanna: Hi, everyone. I'm Joanna Penn from thecreativepenn.com. And today, I'm here with Taylor Pearson. Hi, Taylor.

Taylor: Hello. Thank you for having me.

Joanna: Welcome to the show. Just a little bit of an introduction. Taylor is the best-selling author of The End of Jobs: Money, Meaning and Freedom Without the 9-to-5, and he is a systems-obsessed entrepreneur, which is very cool. So first of all, tell us just a bit about you and your journey into entrepreneurship up to this point.

Taylor: I was a history major in college. And I was basically a history major because I didn't know what I wanted to do, and I liked to read and I liked to write and I studied people. And history is a very broad subject, so you can get away with doing whatever you wanted. And at least in the U.S., the default path for studying history is law school.

I think there was 25 people in my cohort of history majors and 17 of them were going to law school. And so that was very much “No,” I thought, “Maybe I'll go get a Ph.D.” But no, that's a 10-year track, and not great job prospects on the other end of it, in most cases, for humanities. So I said, “Well, I'll go to law school.”

And then on a fling, ended up going to a study abroad program in Argentina and had this cliché travel experience of, “Oh my God, look at this different culture and all these different people.” I see the world from a new perspective and everything else you've ever heard from that story, that experience, and really broadened my perspective to what I wanted to do.

And about the same time, I read The 4-Hour Workweek, which was a seminal book for me and I think for a lot of other people. It opened my eyes to this new world, and that set me off on a different path. I was an interpreter for a little while in hospitals. I worked as an English teacher in Brazil. I worked at a marketing agency and then eventually found my way to this apprenticeship position with a small entrepreneurial company based out of San Diego.

They had a line of e-commerce manufacturing companies, and I did the online marketing for them for about two years. And so that was my gateway moment into entrepreneurship. I worked in this small company. I got to hang out with the CEOs on a regular basis, learned how they ran the company, learned how this entrepreneurship stuff worked. And then I think I was working with them a couple of years ago and sat down and started writing The End of Jobs, which came out about three months ago now.

Joanna: What specifically made you go, “I want to write a book about this?”

Taylor: I think I was always attracted to writing in general, and I was actually sitting at a conference. I was in Bangkok with the guys I used to work for. They run a company or an online forum called The Dynamite Circle, which is this online forum for location-independent entrepreneurs. So I was at that conference last year. And we were sitting around, and I was talking with someone, asking, “How is this possible? We're in Bangkok, Thailand. There's 300 entrepreneurs here. They're in Bangkok, Thailand for a week. They're running their businesses from their laptops.

We were reflecting on friends we had in New York and where we grew up. “How do you explain this? How are these two groups of people…they're both intelligent. They're both hard working, but they're getting very, very different outcomes in terms of what their lifestyles look like and their incomes and their professional lives.” And that was the genesis of the book. How do we explain this?

Joanna: So tell us a bit more, because the title is very good. It's quite alarmist in a way, which actually the book isn't, in my opinion.

Tell us what is the end of jobs? What do you mean by that?

Taylor: It's an optimistic book with a very pessimistic title. So what I mean by the end of jobs is that we have this certain notion of work and certain notion of jobs, I think, that's been formed over the 20th century. This gold-watch notion that you go to a large, typically firm or corporation. You spend a long time working there. You spend most of your working life doing a relatively similar thing to what you started out with. You get your degree in accounting, you finish school in your 20s, and then you spend the next 40 to 45 years doing accounting, and then you retire with your pension. And that notion of continuous careers, those jobs, is disappearing.

Work now is much more entrepreneurial that even people working in companies are going to change roles every three to five years. They're going to have to constantly be reinventing themselves and their careers. So there's this notion of work is changing. It's becoming less…as we think about “jobs” and more entrepreneurial.

And then also there are just more and more entrepreneurs; that the national size of a firm as transaction costs go down is getting smaller and smaller. You don't have to have large corporations to get things done. You can have these armies of freelancers and entrepreneurs that can self-organize for a project, like Hollywood puts together a movie. Everyone's sitting around in L.A. and everyone comes together and makes this amazing production and then disperses. And that's more and more true of the economy at large.

Joanna: I was just listening to Unemployable podcast with Brian Clark. Have you listened to that podcast?

Taylor: I have.

Joanna: That's great. And I love the term “unemployable.” And I said it to my mum once. I'm like, “Mum, I'm unemployable now.” And she's like, “No, no.” She hated me to use that word, but what I meant was I can't work in a hierarchical organization.

And I think what you're saying is jobs in the way that they have been is different to work. Because we all need to work. It gives our life meaning.

You're not saying it's the end of work. You're saying it's the end of the traditional model.

Taylor: Yes, very much so. And it's tricky to talk about these kinds of things. There are a lot of new words, I think, that need to be invented, or at least words need to be redefined. Like you look at traditional measures of economic productivity, and people look at job reports. That's a measure of how healthy is the economy, and that made sense. That was a very logical thing to look at for the 20th century.

Job reports are a less and less intelligent way to look at the economy. A lot of people I know personally are much more productive now that they don't have jobs. They create a lot more value in the economy now that they are unemployable.

Joanna: I know what you mean. And that is interesting. And have attitudes to work as well changed? And again, I mention my mum, because she's in her 60s. She's 68, so very much of that baby-boomer generation. And she had the same, not the same job, but she worked in the same company, Hewlett Packard, a good American company, for 30 years, and got a good pension, all of that.

And she doesn't know what I do all day. She says she didn't have a choice about enjoying work. How can I say these things? Now, you're 26, I think you just said, and I'm 40. But I feel more like a millennial, I think, in my attitudes.

Has that attitude to work fundamentally changed? Do we just want more than security?

Taylor: I think so, and I think we want more because it's available. And I think because it's actually more in demand. I think one book that influenced my thinking a lot on this was Drive by Daniel Pink. There's actually a great little eight-minute YouTube video, I think, where someone sketches it out.

He cites a few studies. There are a couple of other books I reference that if you look at the work that's in demand by the economy now, work is becoming more entrepreneurial. There was a study that came out – I think it was KPC&B – and they were talking about if you look at job growth or job decline over the last 20 years, that all segments of jobs are declining except for non-routine cognitive jobs. So basically you're doing something with your mind and you're doing something new over and over. These are basically entrepreneurial jobs. You're reinventing your position over and over and over. The kind of motivation for that work is actually much different than traditional work.

The model we have of jobs and how motivation works is just like a carrot-and-stick model. You're doing this unfavorable task, and so you get a bigger carrot held out in front of you and that lets you do the task. And for industrial work, you think about putting together pieces on a factory line. That's true. That is an effective motivator.

But for this creative work, it's much more important in terms of the actual value of the work, that the person be in a situation where they find meaning, whatever they decide the meaning is, in the work, and they have the sense of freedom and autonomy to do the work they want.

There was a great study in India where three cohorts of people did some creative cognitive task, and there was an inverse correlation between monetary reward and performance on the task. The group that was paid the least but did it for the pleasure of it was actually more effective at it than the group that was paid the most.

Joanna: And I think we can see that. The audience listening are authors writing books, and you can actually see it in some of these top, best-selling authors who are forced to write the same books over and over again, who you just don't want to read anymore, because they're repeating the same crap.

Compare that to somebody who's writing their first novel or their first non-fiction book and is really driven by it. There may not be any money at the end, but they're driven by the passion of the topic. As you were, and as I am. It's the drive to create, as you say.

And interesting you mentioned Daniel Pink. I read his book, A Whole New Mind, I think it was 10 years ago now. And he predicted this rise of the creative job being the thing that you can't outsource. We can outsource pretty much a lot of things that can be done either by robots or for people who are cheaper than us, but we can never outsource creativity, right? So put the spin on things now.

What do you mean by entrepreneurship? And what can people consider as the options for an entrepreneurial portfolio income as such?

Taylor: So to answer the first question, the way I define it in the book is creating and connecting. I think non-routine cognitive work is actually a pretty good description of what entrepreneurial work is. You're using your mind in some way and you're doing something novel on a repeated basis.

It's like you have to come up with something new. And actually I wrote down this question from a professor actually. She said, “Being entrepreneurial is essentially about thinking and doing something that we have not done before in order to achieve a desirable goal or outcome. It is about assessing a situation, designing alternatives, and choosing a new way, or perhaps a combinations of ways, that we hope will lead us to something better, however we happen to define better at the moment.” I thought that was quite articulate. That was better than my definition.

Joanna: But the fact that it's the ‘something you've not done before' that I think freaks people out, right?

They think, “Oh, but you have to be an expert.” What do you think about that?

Taylor: I don't know. I think it definitely still freaks me out. I think I had lots of moments writing the book where I was like, “Who am I to write this book?” I don't know why we do that. I certainly have the same problem. I attach a certain stigma to credentials.

I remember my family are all in health care, and my sister's a physician, and she has M.D. after her name, and we attach a really high level of importance to that. I catch myself doing it as well. So I'm not sure why it is we do that. It certainly doesn't seem to be true. There seems to be a very loose correlation, if any correlation at all, between having some credentials and being competent, that those seem to be largely independent variables in a lot of domains, especially entrepreneurial areas.

Joanna: And the importance of being able to learn, that's the more important thing. Going…

“Okay, so I need to learn this,” and then learning it. That's more important, isn't it, in an entrepreneurial life?

Taylor: Yeah, I just finished reading Sapiens. Really interesting. But one of the things he said in that book that stood out to me, was that he credited the success of Europe in the last 500 years to that typically when countries or people invaded, they assumed they already had all the answers. They would tell the people they were invading how to do everything, and that the Europeans basically took this notion of, “Maybe we can learn something from everyone else.”

And so they went and took the best from everyone else in the world. It's a really interesting way to think about it. That's true on this micro-perspective as well. If you have this attitude of, “I don't know everything, but I can go out and find the people that do know everything and repackage that or redo that in some interesting way,” you can create a lot of value.

Joanna: And just in terms of the entrepreneurial possibilities, that you said you were in this mastermind group. You wrote the book because of all these people you know doing entrepreneurial things.

Give us a couple of examples of how are people making a living in this way.

Taylor: I think the more interesting examples, the ones that people have latched onto from the book; there's a guy named Rob Walling, who actually spoke at the event when I was there. His story, I think, is interesting because he's gone through so many iterations.

He was working in a large corporation and left to do software development consulting, and then started out with these very, very small products. This is one thing I talk about in this book, this idea of stair-stepping, that you can start in very small markets and very non-competitive markets, where even though you're not the best expert in the world, there's very little competition and you can still do quite well.

He was selling books about…I think his first book was about duck blinds, which is a way you hunt ducks. So he was making $500 a month selling this e-book for $27. This was maybe 10 years ago now when you could have still sold $27 e-books about duck blinds. And then he bought a job board for electricians in his local area, and he was doing a job board for electricians in his local area. And so now he had a couple of income streams. I think he had a website-building service for people that wanted to have wedding websites so you can have your wedding website set up.

Now he's doing two or three different things in fairly small, non-competitive markets, right? So there's not a lot of electrician job boards based in his city in California. And then he started stair-stepping this up into bigger and bigger businesses. Eventually he bought a business that was doing invoicing software for a very specific industry, so it was DotNetInvoice, and then a long-tail SEO software. And now, he's working on a larger email marketing software. So starting at duck blind e-books, and then he's moved up into bigger and bigger businesses.

Joanna: Yeah, and that's a really good point. And one of the things I go on and on about is these multiple streams of income. And authors in particular, we can't make a living from one book. You know this. You have one book, right, at the moment?

Taylor: Yes, it was great. For the first month, it was maybe viable. And then after that, not so much.

Joanna: It's not so much.

As someone who has a non-fiction book, how are you leveraging the book into multiple streams of income?

Taylor: I'm still very much trying to figure that out to be honest. I've done some free speaking stuff and am looking to get into more speaking. I think that would be interesting and something I really enjoy doing. But beyond that, I don't have…I have other consulting projects that aren't really related to the book at this point. I'm very much still trying to figure that out.

Joanna: Which is a great answer. And actually a lot of people do that; write the book and then figure it out later. I did notice from your website that you are doing some consulting, and you're obviously very busy because you're not taking any new clients right now. So that's great, and it's a great way to start. And then as you say, you get into more scalable things.

I wanted to ask you about the mindset side, because I know that a lot of people just are very worried about this potential shift. The shift is coming. I believe it. I've made the shift.

What can people do to change their mindset around risk, around being scared and fear of change?

Taylor: A lot of people have asked me this since the book came out, and I've been talking to other people that have gone through it, and asked what were the things that impacted them.

The big things that seem to come up over and over are content and community, which are creating this steady diet of information that is around this new world view. What I love about blogs and podcasts and all this stuff is that even if in your local area you're going to find very few people that are taking these new entrepreneurial routes, that you can read blogs and listen to podcasts. You get this steady stream of look at all these people that are succeeding at this, and look at all these different routes to how they're doing it. Which one of these would fit for me? Which one of these can I emulate?

And then I think the other thing is community, which is how can you find other people? Surround yourself with other people that are thinking in similar ways, trying to do similar things, which I think is a real challenge.

Most people's day-to-day lives, you don't walk around and find people saying things like, “Jobs are ending.” That's a very atypical point of view in the mainstream. I think if you can get yourself into some sort of online community or a personal mastermind group where you have four or five other people that you're working towards similar goals…and I think in-person is still the best. If you can find people in your local area that are trying to write and become full-time authors, can you have dinner every Saturday with those people or have a mastermind group? I think that's still really the most powerful way.

Joanna: Absolutely. And what about that fear of risk?

What is more risky, a job or the multiple streams of income approach?

Taylor: I would certainly say the job is more risky, certainly over the long-term. I think initially the entrepreneurial path appears much more risky because the cash flow is just so unsteady, up and down, as opposed to the paycheck that you know comes in every Friday, every two weeks.

The biggest thing I noticed in myself and talking to other people is just having to remind yourself of this difference between what feels risky and what actually is risky when you sit down and look at it intellectually or really think through it. Most entrepreneurs I talked to I think still feel very risky on a day-to-day basis, even if the data doesn't reflect that.

Even if the data looks like what they're doing is less and less safe, the programming from evolution of you're walking through the savannah and you hear a rustle in the bushes, even if it's food 99 times out of 100, the one time it's a lion and it kills you. We're trained to walk away from that unknown. And that's not true in most cases in the modern world, right? You start a side project. There's not really a lot of risk there.

Joanna: Yeah, I think that's the point. And most people listening will be writing as a side project, as I did. I spent three and a half years while still working my day job building this business, and then only then did I leave. But it's funny you're talking about fear.

I haven't really admitted this, so I'll admit it to you. Why not? We've never met. And to the listeners. I hired my husband out of his day job a month or so ago now. And that was a big fearful moment, because it suddenly was…we always did have his steady job as a backup, even though I'm very independent. And then it was, “Okay, this is the end. This is the end of the job as such.” And we've gone through two months of me just being, “Oh, my goodness. This is a big risk.” And now, it's so funny. It's worked out better I could have ever expected. It's just been amazing.

I think that that fear is inevitable at any point in your journey, and I dare say there'll be much more scary moments to come. But facing that, what's the worst that could happen? He has to go back to his job?

Taylor: It is always good to play out the worst-case scenario. That typically does seem to be the worst-case scenario. The worst-case scenario is I'm doing exactly what I'm doing right now.

Joanna: I think people worry that they won't be able to go back into their job. But the reality is whatever the scare mongering of the press, there's always work that you can get. I've said, “Well, I'll just go and do cleaning. I'll get on TaskRabbit and I'll be a cleaner.” At the end of the day, you can still do that. That might be the worst case. Or stack shelves until the robots do it.

Taylor: I don't know if the fear ever goes away entirely. I was talking with someone who I know his business is growing very, very fast. It's already very, very large, multiple seven-figure business. And he was like, “Yeah, two or three times a week I think it's all going to collapse and disappear and it's all over.” And I was like, “Okay, good. It's not just me.”

Joanna: Yeah. With writing, the fear of judgment, the fear of failure, we have to go through all of these things.

Have you had a backlash to the title at all?

Taylor: Honestly, not anything substantial. I've had a few negative reviews on Amazon as everyone ever has.

Joanna: You've got to have those.

Taylor: But nothing dramatic or notable to be honest.

Joanna: I wanted to ask you, again, you're a lot younger than me, but closer to the education system. For people listening who have children who are at school, or maybe they're home-schooling them or whatever they're doing. There are kids who are at the moment in the education system. It's not really designed for this new world. It's still in this shifting period of exams where you're not allowed to use Google or exams where you're not allowed to collaborate, which essentially is what we do in the grownup world now. We don't sit on our own and just come up with things without a computer. It's ridiculous.

What would you say to people with kids? What should they be encouraging the kids to learn?

Taylor: The traditional schooling system, which very much teaches this notion of there are certain rules and you win by getting good at these rules. Whereas what we're talking about in doing entrepreneurial things is a lot more about the rules are all made up, and you're successful by making up new, more interesting, more profitable rules for yourself.

So I guess the two specific things I've seen people do with their children that seem to be really effective are international travel, especially to some sort developing country, or not Western Europe or the U.S. or Canada kind of thing.

And there's organizations. One I've heard of is Woofing, which is, I think, World Wide Organic Farmers. They can go and basically live for free on a farm, work 10 or 20 hours a week, and lots of other programs like that where you can go do extended travel in the developing country, get this new perspective. So I think that seems to be really powerful.

And the other thing that I think is maybe more practical and tactical is learning to code, computer programming.

Joanna: I'm glad you said that.

Taylor: I think it's good for a couple of reasons. If you do want to have some security, if you're going to pick a job that's definitely not going to disappear, computer programming's a great choice. That if you are competent at that for the next 50 years, you'll almost certainly be able to make enough money to survive.

And it also, I think, is a really effective way of teaching this. You can actually create wealth almost instantly, right? You can sit down for four hours, and with nothing, a blank screen, and you write code on this screen. And all of a sudden, there's more value in the world than there was four hours ago. And you get this real sense of like, “I made something and it's valuable. And it didn't take anything other than me thinking hard.”

Joanna: Yeah, I totally agree with you on this. And this coding thing, what it does is it allows you to create something in the world very fast. You can literally just do some code to print something on the screen, for example, output something in a color that whirls around. And it's a demonstrable change in affecting the world, which writing a book is a lot bigger thing. I'm totally with you on that. And it's something that I've put on my list that I think I should learn at my age. And it's funny. One of my jobs before, I used to interface with the computer programmers. So I think by understanding code, even if the code is outsourced to India, for example…then if you're cognizant of the code, you can write the specs that somebody else can code. But you have to know that you can create it.

Taylor: Yeah, I can't code. I can do basic HTML. I can't do anything…

Joanna: That's something.

Taylor: …substantial. But it's interesting. I actually used to do sales for a software project. And it was really interesting. I'd go to the developer about, “Can we do this?” And he was like, “We can do anything. Anything is possible. It's just a question of time and resources.” Because I'd just talk about the opportunity cost and the trade-offs. And I was like, “Oh, right. We can do anything.” It's like, “Do we want to spend a month building this feature? Or is it better…” So you say like, “Yes, anything is possible. Now, we're just talking about opportunity cost and trade-offs and risk,” which is a different way of thinking about things. In most jobs, it's like, “Can we do this?” “No. No, we can't do this.”

Joanna: The other thing is not having to ask permission. My husband's been like, “Wow.” Because he used to work for Deloitte, which is a really big company. And he's like, “Wow, I can just say, ‘Let's do this,' and then we do it, and it's done. I don't have to write a document that asks permission to do it.” Or what was so funny is they even have a form for innovation. If you want to innovate, you have to fill in a form. And I'm like, “That's just so different.”

To teach kids that they can just come up with an idea and then make it, that, to me, seems to be the best way. And not just kids, the adults listening who are afraid.

I think I've spent the last 10 years trying to unlearn what I learned at school and university. Do you still feel that at 26?

Taylor: Well, I think about my brain as thought I'm ripping out the old wiring and trying to put in better wiring, like this wiring is no good and it's got to come out, and I need to lay some better wiring. I think blogging in a lot of ways did that for me, too. I think coding is probably better. It's a little more tangible. You can see the effects, but I think blogging did that in a sense.

Joanna: I actually think coding is just as creative as writing poetry. In fact, it is more like poetry because you have to get the exact lines and it has to be really nice. Whereas writing novels is…if you wrote code like you wrote novels, it would just be a mess, because it would be overblown. But I think coding is super creative, and that that's going to be so important in the new world.

Now, I wanted to ask you a bit about entrepreneurship in terms of the publishing world, because publishing is still so old school. I heard another podcast with Peter Diamandis – you've probably read his Bold and Abundance, which I absolutely love. He said, “Once the organizations are going to the government to ask for protection, the industry is done.” And that is what the publishing industry is doing in America right now, going and asking them to shut down Amazon, which is crazy.

Now, tell us what did you do with this book in terms of your publishing decisions? And what do you think is the future in the book world?

Taylor: I guess I can relate my experience. I'm just learning about the traditional publishing industry in the last two months, so my experience there is very fresh. I self-published because no publisher would have taken me seriously. And actually I had a meeting with a publisher after the book came out and it had already done fairly well, and they pretty much said, “If you'd come to us nine months ago and showed us how many email subscribers and Twitter followers you had, we would have laughed at you. No agent would have taken you seriously. We would have never talked to you.”

I think it seems like self-publishing might be emerging as this interesting route. I guess if you're going to write a proposal and you don't already have a large platform, it might just be better to self-publish a book and sell 5,000 copies and then go to a publisher and say, “Hi, I wrote a book. Here's my Amazon sales numbers for 5,000 copies. I'd like to write another one. Are you interested?” and come at it from this position of strength. I still don't know if I'm going to go the traditional publishing route. But self-publishing seems to be this new avenue into that if you want to do that. So I guess that's been interesting from my perspective.

Joanna: Yeah. And for me, it's about, again, not asking permission and not having to go through all that traditional hoops. I just can't be dealing with that. Let's just get on with things.

As somebody who didn't have a big platform or anything, how did you actually do the marketing for the book?

Taylor: I think the big things for me that were effective in marketing, one was I “bloggered” the book. So about 30% to 50% of the book appeared in some form on my blog before I published the book, which I was very hesitant to do.

I was like, “Oh, if everyone sees it already, no one will want to read the book.” And that was just totally wrong.

That built up a small but significant audience around the ideas in the book that was amazingly helpful when the actual book released in terms of the launch.

Other things that I did that I found really effective, I wrote a lot of personal emails. So I went into Gmail and I downloaded everyone I've emailed in the past five years. And I basically sorted those into people that weren't going to be into the book, and I obviously threw them out, and then people that I knew very well personally and had good relationships with and would be interested in the book, and then people I knew, kind of acquaintances, but that'd also be interested in the book. I wrote all of them. It was like 300 something people. I had a typical email saying, “Please leave a review on Amazon. Please share this thunderclap.it link.” So for people not familiar with Thunderclap, it's this service that lets you synchronize social sharing.

So at 12 p.m. on Wednesday, Eastern U.S. time, the day my book came out, 118 people shared the same link. So you create this surround sound effect of like, “Who is this guy and what's this book about? Why did 17 people in my Facebook feed just share it at the same time?” So I wrote all of them personal emails, half template and half like, “Hey, it was great seeing you in L.A. last year. How's this project going? Just so you know, I'm working on this book. It's going to be out in a month. I would love it if you would support this Thunderclap here and write a review when it comes out.” That wasn't a very, I guess, not scalable strategy. It took a bunch of time, but was really, really effective. And people, you can tell it was a personal email. I didn't see everyone in L.A. last year. Obviously, I took the time to write it and people really appreciate that. That was really effective.

I gave it away for free for four days, which I was also very hesitant about at first. And I think, just like blogging it out, the inverse was true. Giving it away for free let me do a lot of things I couldn't have done had I charged initially, and I think let me be able to reach more people and make more money. And so I think part of the reason that was for me is one, it let me reach out to people to support the book who wouldn't have probably supported it otherwise. So people I knew that were maybe bigger influencers, I think, to ask them to recommend a paid book would have been ….

Joanna: Difficult.

Taylor: Yeah, there's like a personal brand equity. And they're like, “Well, I haven't read the whole thing, and I don't know if it's good.”

“Free?” It's like, “Sure.” If someone downloads it and they don't like it, it's free. It let me reach out to a lot more people. And then it also let me ask the small community i had – I had a few hundred email subscribers when the book launched – to do things that were more helpful in the marketing as opposed to buying the book. Instead of saying, “Hey, go buy my book for $10, $15, $20, whatever.” Instead, “Please leave a review. Please share. Please write a post on reddit. Please write a post on Hacker News or one of these other sites where people share articles and books.”

It actually made the initial reach much, much broader, and then also catapulted it or moved it much farther, faster up the Amazon rank. For a couple of days, it was the number one Business and Money book in Amazon, and there's no way it would have gotten there had I not given it away for free for four days first.

Joanna: That's great. And I think that will encourage people. Because you only had a couple of hundred subscribers like you said. But you really mined your personal email list, which, as a blogger you probably had emailed with people who have blogs and that type of thing. So that's really great. We're almost out of time, but just that you talk about being a systems-type person, a systems obsessed-type person.

What systems did you use to get the book written? Because it is very well-organized and you're obviously an organized guy. What was your system for getting that non-fiction book done and out there?

Taylor: I think the biggest influence on me in terms of structuring creative time is an essay from Paul Graham called Maker's and Manager's Time. There's two kinds of work that most entrepreneurs do. One is this maker's work of writing or creating where you need, long, two to four hours, not interrupted, whether that's for a coder coding or a writer writing, that you need to be uninterrupted. So that was how I had two hours pretty much every morning when I was doing the writing, when I was used the time to work on the book, and then left the rest of the day either for consulting projects I was working on or marketing for the book.

Joanna: And that's what I talk about as well, diarizing the time. And for me, the morning is creating and the afternoon is doing stuff like this. And it always works really well for me being in the U.K.. Because for the U.S., I'm always doing these things in my afternoon…

Taylor: Yeah, that's convenient.

Joanna: …which works pretty well. Right. So where can people find you and your book online?

Taylor: So the book is on Amazon. You can search The End of Jobs. And then you can also go to taylorpearson.me. That's my site. You can download the first three chapters of the book there and more info about me. And then I'm on Twitter @taylorpearsonme. And I love Twitter so that's where I tend to hang out.

Joanna: Fantastic. Thanks so much for your time, Taylor. That was great.

Taylor: Thank you so much for having me.

Joanna Penn:

View Comments (7)

  • Wow what an incredible read. I loved the part on how best selling authors have to keep writing the same stories over and over because their bound to their contracts.

    In the past I've stopped reading certain books because the stories are predictable and flow in the same sequence, with the exception of different names and locations

    I love how indies are free to be creative and write what they truly want, regardless if they sell thousands and or not. It's about taking joy in what you do and finding solutions to your problems.

    The education system in America is lacking with them only teaching students to graduate and get a job. Anything outside that bubble is a no no.

    Thank you for the wonderful read. I can't wait to share it with my husband.

  • Oh! Another book to add to my to-read list. Sounds right up my alley.

    I've been seeing this more and more. The old guard model for middle-class survival by studying hard and getting a safe, secure job and retiring at 65 is becoming really bad advice. The only people I know who managed to retire comfortably had a successful side hustle or ran their own business. Minding your own business will pretty much be the only way forward from here on out. I cringe when I hear my friends and family talk about their futures when the only plan on the cards is working for 40+ years making someone else rich.

    That is also why I think self-publishing is becoming more and more popular. It is a side hustle that you can turn into a full-time income like Joanna Penn does. Everybody has the opportunity to be an author-entrepreneur, and I find that exciting. I'm working towards the end of my job through self-publishing. I just hope that my success will inspire those friends and family to stop thinking what I'm doing as risky, and start seeing that relying on a job is.

    • I think it's also that 65 or even 75 doesn't have to be "old" anymore. My Mum is super active at 68 and fitter than she was at the peak of her career. There's no way she's sitting around watching TV :) I think the Boomers are starting new things in the next third of their lives and everyone needs work really - for self-esteem and for something to do. Writing and self-publishing is a great choice for that.

  • Great interview! I am one of the boomers who is looking for a way out of the working world. I love writing and realize that everyone has a story to tell and by not doing so -- we are depriving the world of some of our well-worn wisdom. I love the fact that both of you are doing what you love and having a great time doing so and others are benefitting from your expertise.

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