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How Joanna Penn Designed the Lifestyle (and Career) of Her Dreams
7th July 2016 • The Digital Entrepreneur • Rainmaker Digital LLC
00:00:00 00:37:24

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Joanna Penn was a self-proclaimed “cubicle slave” who had a nagging feeling that she “should” be happy with her life, even though she wasn’t. So many digital entrepreneurs face similar feelings on their path to freedom. How did Joanna get from there to where she is now as a very successful, bestselling author entrepreneur? In this episode, Joanna shares her digital entrepreneur origin story.

It s a story all of us who are aspiring, and even current, digital entrepreneurs can learn from.

In this 36-minute episode, you’ll discover:

  • How Joanna started and failed numerous businesses before one stuck
  • The book she read that changed her life
  • What eventually inspired Joanna to become unwilling to live with the pain of having a job she didn t love
  • Why Joanna decided that she was NOT going to go up the career ladder (and what she means by a Pizza Hut job )
  • The importance of embracing movement and the zig-zag
  • How Joanna dealt with her inner frustrated creative who had a NEED to do something that mattered
  • How Joanna got into self-publishing … without any publishing experience at all
  • Why Joanna is now seriously happy in her new life … and how work-life balance doesn t really apply when you love what you do

And more. You can get more from Joanna at, and you can see her speak this October at Digital Commerce Summit. Early bird ticket prices go away later this month! For more information, go to

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The Show Notes

The Transcript

How Joanna Penn Designed the Lifestyle (and Career) of Her Dreams

Voiceover: You are listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs.

DCI features an in-depth, ongoing instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/DigitalCommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur. I’m your host Jerod Morris, the VP of marketing for Rainmaker Digital, and this is episode No. 22.

In this episode, we are going to continue our interview series with the esteemed panel of digital commerce practitioners who will be speaking at Digital Commerce Summit this October in Denver. If you missed our recent episodes with Brian Clark and Chris Garret, Joanna Wiebe, Sonia Simone, and Pamela Wilson, they are easily accessible as the previous five episodes in your Digital Entrepreneur feed.

How to Take Your Digital Business to the Next Level

Jerod Morris: If you enjoy those episodes and if you enjoy today’s discussion with author, entrepreneur extraordinaire Joanna Penn, then I highly recommend that you consider joining us in Denver this October at Digital Commerce Summit, where you will discover smarter ways to create and sell profitable digital products and services from some of the most successful digital entrepreneurs in the world. People like those that I’ve already mentioned, as well as folks like Rand Fishkin of Moz, Jeff Walker, Laura Roeder, Tara Gentile, Chris Lema, Chris Ducker, and many others.

Plus, of course, you’ll get to spend a few days hanging out in a theater full of like-minded people who are pursuing the goal of building a successful business around digital products and services–like you may be right now–and, of course, people who want the financial and professional freedom that can come from doing that.

It’s a great way to build your network, and it’s a great way to build your notebook with ideas that, who knows, might change the course of your business. That can happen at conferences like this. I know that because it’s happened to me at conferences that I’ve gone to.

Early bird tickets are still available for the conference for at least a few more weeks, at least as of July 7th, 2016, when this episode first goes live. The early bird tickets aren’t going to be there forever. In fact, we’re taking them away later this month, so don’t miss out on getting the best value. You can go to Rainmaker.FM/Summit for more information.

All About Joanna

Jerod Morris: Well, today on The Digital Entrepreneur, as I said, you’re going to be learning from Joanna Penn. Joanna, if you don’t know her already, is a New York Times and USA Today bestselling fiction and nonfiction author. She’s done it all independently. She’s not just an author. She was also voted one of the top 100 creative professionals in the UK by The Guardian in 2013, a recognition of her success as a not just a creative, but also a businesswoman.

Clearly, Joanna has an impressive professional life and so many essential lessons. She can teach so many essential lessons that we can all learn when it comes to the power of creating ‘intellectual property assets.’ This is a buzz term that Joanna uses a lot, and it makes so much sense once you hear her explain it. This concept is how she’s built her thriving business and how, in her words, she’ll still be making money 70 years after she’s dead.

Well, I had the chance to chat with Joanna about this and much more on a recent members-only case study inside of Digital Commerce Academy. What surprised me about our conversation is that I was actually more fascinated by her origin story–how she went from being a self-proclaimed ‘cubicle slave’ who ‘should have been happy with her life but wasn’t’ to where she is today because it certainly didn’t happen by accident.

She made a series of intentional, strategic, and well-thought-out choices to systematically transition out of her IT consulting job and into being one of the world’s most successful independent authors. It’s a story that so many of us who are aspiring or even current digital entrepreneurs can learn from and relate to because I know there’s so many of us. Maybe we’re in a current job, but we have this dream of doing this over here, this business idea, maybe something creative, and we can’t seem to get to that point, to get to that transition point.

Well Joanna did it, and there’s so much that we can learn from her story. I’ve decided that for this week’s episode of The Digital Entrepreneur, I’m going to play you an excerpt from that conversation because I got a lot out of it, I got a lot out of re-listening to it as I prepped for this episode, and I think that you’ll get a lot out of it, too.

We discuss how Joanna started and failed numerous businesses, actually, before one stuck. We talk about the important decision that she made about how to view her job that actually set the stage for her growth as an author and to her becoming an entrepreneur. We also talk about the book she read that changed her life, how she dealt with her inner frustrated creative–and I think a lot of us deal with a inner frustrate creative–and much, much more.

I will tell you real quick that what I’m going to play for you here right now, it’s audio that is recorded from an GoToWebinar session, so it’s not perfect. Fortunately, Joanna comes through much clearer and much better than I do, so please just suffer through my short question interjections. They’re very short, and Joanna does most of the talking because, as I said, the audio for her is much better than me.

She provides some incredibly useful insight, so I didn’t want less-than-perfect audio to keep me from bringing this to you here on this podcast. I really hope you enjoy it. Here now is an excerpt from my Digital Commerce Academy chat with Joanna Penn.

How Joanna Started and Failed Numerous Businesses Before One Stuck

Joanna Penn: Like many people, I went to university and did a random degree. In England, you can do random degrees. I did a degree in theology at Oxford, and out of Oxford, you tend to get recruited to these big firms, like a bank or a consultancy firm. I became an IT consultant straight out of university in order to pay off my student loan.

Like many people, getting that first job, you’re not so much worried about what it is. It’s just making a living. I never thought, back in 1997 this was, that I would end up doing that job for so long. So many of us, we don’t even make a decision, or we just do something by default, make a choice, and then wake up years later and go, “What the hell just happened?” That’s basically what happened to me. I had a fantastic time. I certainly appreciate my years in business, but it was 13 years before I got out.

Basically, I ended up implementing accounts payable in large corporate financial departments, which is just not at all creative. I did this across Europe. Pre-2000, I did a lot of the Y2K bug, which everyone will laugh about now, showing my age, and traveled all over Europe, Asia Pacific, came to America. Basically, I was paid very well to do a, as we said, corporate-slave-type job.

As I put on the screen there, I should’ve been happy with my life because I was paid well. I traveled. I was doing a job that my mum thought was great, that society thinks is great. I was paying my taxes early. I was the epitome of what a good girl should do out of Oxford University or any university–get the right degrees, do the right job–but I was basically really miserable. I almost felt ashamed of being miserable at work because I had a good job. I should’ve been happy, but I just wasn’t.

I started to try and figure what the hell was wrong. I actually left my job a number of times. I was a consultant, so I could come and go on projects. I started a scuba diving business briefly in New Zealand, which didn’t go very well because the price of fuel, insurance, a boat, and skipper and crew–recommendation, don’t start a scuba-diving business. Then I also did property investment and really just didn’t enjoy that and lost money on that as well.

The Book Joanna Read That Changed Her Life

Joanna Penn: Before I started considering what do I actually want my life to look like, and we’ll get into this in a minute, the turning point for me was always implementing more accounts payable into a train company, rail company in Australia. I was just crying every day. I just couldn’t work out why I was so miserable, so I started reading a lot of self-help.

Just one book–well, I’ll probably mention a lot of books as we go through this–but the book I read that changed my life was The Success Principles by Jack Canfield. The very first principle is take 100 percent responsibility for your life. This is a big deal because I thought I was taking responsibility, but what it said was, all the choices you make over your lifetime that mean you’ve ended up where you’ve ended up. The continued choice to choose a job for money and stability over my happiness was part of the big deal. That was the as-was situation and the point at which things changed.

Jerod Morris: You said to me that you found that you weren’t willing to have the pain any longer, and you’re talking about existential pain here. I think that we find that, for a lot of us, whenever we want to make a big change, we have to get to that point where the pain of the status quo, of not acting, becomes so great that we just can’t, and that forces us to do the hard work of change. You talked about this book being a big influence.

Were there any other moments, big moments that really signaled, “Hey, this is the time I’ve got to really start being intentional about designing the life I want because I’ve got all these things–but yet I’m not as happy as I should be, and I’ve got to do something different”?

What Inspired Joanna to Leave the Job She Didn t Love

Joanna Penn: As I said, I was listening to a lot of self-help audios. I was reading a lot of books, and I guess I just looked at how short life is as well and just wanted to do something that would make me happy. I started researching how to enjoy what you do with your life. It was at that point where I thought I should write a book.

Although I’ve always been a reader and I’ve written journals, I’d never written a book. I started researching that and finding out a bit about that. Probably, another big deal was I got into affirmations. This was around the time of The Secret. I want to say that The Secret was missing a big thing, which is the action that you have to take.

But one of the things that they did introduce me to was this idea of an affirmation. I wrote down, “I am creative. I am an author.” At the time, I couldn’t even say that out loud. So I wrote it down on a little card, and I would say it in my head “I am creative. I am an author.” This is going back to 2006 now. Then, eventually, I started whispering it on my route home when I was out walking and things. Eventually I could say it out loud. I certainly wasn’t creative, and I wasn’t an author at that point. But there was this point where I was like, “I just have to make this change.”

Why Joanna Decided That She Was NOT Going to Go Up the Career Ladder (and What She Means by a ‘Pizza Hut Job’)

Joanna Penn: Around then, I also decided that my job was not going to be a proper career anymore. Everybody knows that, when you’re in a job that you want to stay in, you do extra stuff. You go above and beyond, generally, but you don’t work eight hours a day at most normal jobs. You work longer hours. You do certain things in order to go up the career ladder.

I made the decision that I was not going to go up the career ladder. I was going to treat this job like a Pizza Hut job. I can’t remember where that phrase comes from now. But basically, it was a job to pay the bills, but I was not doing anything more than the basic amount of work in order to keep my job. I did a good job, but I didn’t do anything more than I should have.

If there was a chance to leave early, like at four o’clock in the afternoon, I would go home, and I would start. I was writing, and I was learning and all this type of thing. Essentially, that crux point came when I was crying at work, and I just went, “That’s it. I have to transition out of this,” but it did take quite awhile to transition.

Jerod Morris: I think it will for a lot of people. It’s one thing to have this realization, to start making these affirmations, and it’s quite another thing, then, to take the next step of being truly intentional about what steps you want to take next.

Obviously, you don’t just want to quit your job, have nothing, make this rash decision, and don’t have anything set up. This is what I love, that you did that. You asked yourself, “Okay, I know I need a change. I’m realizing there’s these other things that I want to do more than what I’m doing now, but it’s more than just what you’re going to be doing. It’s what type of life do you want to live.”

As you told me, you decided that you wanted to indulge your inner introvert. You wanted to travel. You wanted to be location independent. You wanted to create things in the world. How important was it that you actually sat down and figured these things out in terms of helping you actually create that reality, which you have now?

The Importance of Embracing Movement and the ‘Zig-Zag’

Joanna Penn: Firstly, I would say it’s very easy in hindsight to look back and figure out these things, but when you’re actually in the moment, I normally tell people it’s a bit like skiing down a hill. Even if you haven’t skied, you know what it’s like in that you don’t just go straight line, top of the hill to the bottom of the hill where you wanted to end up. It’s really zig-zag. You have to zig-zag down the hill, so you’re not always pointing in the direction you think you’re going.

Also, you need to be moving in order to turn, so you actually need some momentum before things appear, before you can turn and try the next thing. For me, the mistakes I’ve made before that–so for example, the scuba diving business–the location-independent decision came from running a location-dependent business, where we’re dependent on a physical boat, a physical island, physical people.

That decision on location independence happened earlier on when making a living on the Internet was not such a big deal. That