Chris Ducker on Being Courageous and Authentic

Chris Ducker is a serial entrepreneur and bestselling author. He’s also launched and grown three businesses that house over 400 full-time employees, internationally. In this interview, Chris explains the connection between being a Youpreneur and who you are, how you’re working, how you want to work and who you want to work with.

This episode also explores:

  • What the Youpreneur movement means and who a Youpreneur is.
  • The role that courage, and sometimes permission, plays in becoming an entrepreneur.
  • Why authenticity and personal brand matters, and how it’s connected to relationships.
  • What it means to market like a magnet.
  • A few exercises from his book!


Also mentioned in this podcast:

Full Transcript

Michael: I’m Michael Bungay Stanier. This is The Coaching Habit Podcast. Thanks for listening in. You know what this is about. I get to talk to smart people about how they think about coaching, how they use coaching, their journey to become more coach like. And my guest today is unusual for me because I’ve not spoken to somebody who’s an expert in this realm before. Chris Ducker, based in the Philippines, shortly to be moving back to England, his home country. He’s a serial entrepreneur, and a two time author. Author of the best-selling Virtual Freedom, and that’s a clue to what he’s about, and more recently, actually this week, his new book Rise of the Youpreneur.

Now, he is based in Philippines as I said, shortly to move to Cambridge. And he owns several businesses that have crossed the border, about 400 full time employees internationally. He’s a trusted international business mentor, a speaker, writer, podcaster, blogger. He’s in all of that space, and the founder, and this is where you can find him on the web, founder of, the leading personal brand business, education company in the world. He’s the host of the Youpreneur Summit, which is held in London, UK every November and, I’m just reading from his bio here, the self-proclaimed proudest Brit doing business online.

Now, he’s an Australian, I mean, I mock him merciless for that, but we’ll get into that a little later on. But I’m really interested to be speaking to Chris about virtual businesses and what it takes to lead, run, influence, coach people through that virtual business lanes. So, Chris, welcome.

Chris Ducker: Thank you for having me, man. Very much appreciate it. It sounds like I need a holiday after that.

Michael: Yeah, I know. I need a holiday after having a hard time read out that bio, but let’s jump into this. So, we’ve talked about where you’ve from a little, but one of the things that I’m always interested in is, what’s the big game you’re up to right now? You know, at Box of Crayons, we often talk about how do we help people do more great work? Work that has more impact, work that has more meaning. So when you think about great work for you right now, Chris, what is it?

Chris Ducker: Well, I think it’s still … I mean, for me personally, everything Youpreneur focused, it’s my life’s work. I mean, I’m 100% sure that I have now dialed down, after 15 years of entrepreneurship, I’ve dialed down into what I want to be doing for the next 15 years and hopefully even beyond that if people still pay attention to me. But I still feel that the work that I did with Virtual Freedom, and outsourcing, and team delegation and things like that, I still feel that that is something that is very, very close to my heart. Obviously, I still employ hundreds of people. I still help other people employ virtual employees and staff as well. But ultimately for me now moving forward, it’s all about that youpreneur movements of helping people ultimately become future proof by building businesses around them, what they stand for, and what they want to be known for.

Michael: That’s what youpreneur means, which is that ability to have people take that bold step into what does it mean to be an entrepreneur, kind of based on their own thought leadership piece, is that what it’s about?

Chris Ducker: Mm-hmm. Well, yeah. I mean, that’s one way to look at it, absolutely. Ultimately, a youpreneur is somebody who builds a business based around them and the people that they want to serve. So it’s people like coaches, and consultants, and speakers, and authors, and content creators, and anybody really, like I said, building their business around their expertise and their personality.

Michael: Nice. So part of what I love is how you frame this, because it’s taken me a while after 15 years, but I’ve dialed down to this thing that’s like, here it is. This is the sweet spot between something that I have some passion around, some kind of engagement and heart and mind, something that there is a market force so I can make a living from it, and something that … Actually, you have a point of difference so to say. You’re like different from the way other people think about it or put it out into the marketplace. But I’m curious to know how you got there because this thing probably didn’t land fully locked and loaded in your lap. It was a journey. And we talked about this great quote, I wish I knew who said this to me because I use it in every podcast interview, which is inspiration is when your past suddenly makes sense. So what were the past moments that made youpreneur sense firm up for you?

Chris Ducker: I think for me it was … Good gosh. I mean, we’re talking many years ago. Now, 16 or so years ago, I was working in the infomercial business. So my background is actually in publishing and event organizing. I did that. That was kind of my career so to speak, in the UK. And then I came out to the Philippines in 2000, did some consultancy work here for a couple of years before being hired as an exclusive consultant on a two month, or rather a two year contract with an infomercial company based out of Miami Florida. And after a year, I had had enough. I mean, it was so clear to me that I was done “working” for somebody else and I had to go out and set up my own thing full time.

And I remember like it was yesterday, I was literally 37,000 feet in the air. I was on a plane coming back from Miami to the Philippines via Hong Kong, and it hit me and I said, “That’s it. I’m done.” Even if it means breaching contract and having to pay a penalty or whatever it was, I was not going to work for this guy anymore. I’d been in Miami for a month with the guy; he drove me nuts the entire time I was there. Lovely guy away from work, by the way. It never ceases to amaze me how many people can be so chilled and so easy going away from work, but once they step into work environments, they become this hideous fire breathing dragon. You know what I mean?

Michael: Yeah, I do.

Chris Ducker: So I was done with the guy. I wrote an email to him in the air, landed in Hong Kong and hit send. And that was the day I became an entrepreneur. That was it. Now looking back, so to speak. And so for me, that was like the biggest realization. And then looking forward or fast forward-

Michael: Actually, Chris, let me-

Chris Ducker: Go on.

Michael: … let me jump in and get nosy about this, because my guess is that as you teach people about this approach to youpreneurness, there is this moment where people have to leave their familiarity and the comfort of the place they’re in at the moment and take a leap. Now for me, I was fired. I mean, I was basically in a job, struggling, couldn’t get traction, wasn’t making any impact, and I had the good luck, turned out that my boss, basically the week I got my landed immigrant status so I could actually work in Canada independently, she fired me. And that was the push that I needed to start Box of Crayons.

But I’m curious to know, as you look at the people, the hundreds and thousands of people that you’ve worked with, do most people have to find the courage to take the leap? How does it work?

Chris Ducker: I think a lot of people need the courage. A lot of the time, they actually need the permission, and that’s a word that I use quite often in my coaching with my clients as well, because I often find that, I don’t know about you but a lot of my coaching clients, they figured out what they need to do. They know how to solve the problem even before sitting down and working with me. But a lot of the time, for whatever reason, maybe it’s fear of rejection, maybe it’s fear of earning less money for six months or whatever the case may be, whatever it is, they need the permission. And so, a lot of the time that’s what I’m doing, I’m writing out the permissions, you know what I mean?

Michael: Right. You should do that.

Chris Ducker: Yes. “That’s a great idea. Why have you not done it already?” “Well, I don’t know.”Well, I’m telling you, you need to do it right now.” There’s the admission you quite clearly are needing to take the action you need to take. And so, I think a lot of the time though, when I look back, and I think of my own personal youpreneur moment where I decided it was actually about the personal brand rather than just business building. I clearly remember when I had back surgery in 2012, I had to take a month or so off to recover. And I clearly remember doing a lot of, and it sounds very clichéd and everything, but a lot of soul searching, a lot of deep down thinking about how I was running my businesses and how I wanted to continue to grow them going forward, and it became so darn apparent to me that people were doing business with me, with Chris a long time before they ever did business with one of my companies.

It was all relationship based. It was the fact that I had done the hard work, and gone to the conferences, and sat at the dinner tables, and handled the coffee meetings. It was all me. And so I realized there and then that that personal brand element of me, what it meant as an entrepreneur was huge. And I think once I see other people have that realization and they get that catalyst moment, that youpreneur moment as well, it’s like the bloody floodgates opened up, and I can just go at a 180 miles an hour. The issue is though, a lot of people wait too long to almost allow those doors to swing open. They want to keep them sharp because, like I said, of fear of rejection, or making less money, or upsetting somebody, or uncertainty or whatever the case may be.

And so my role as a coach and as the founder of youpreneur, is to help people swing those doors open and have that one defining moment where it says, “It’s okay to be center stage. It’s okay to build a business around you but not rely on you. This is how you can do it.” And when have when that moment happens for people, it’s a beautiful thing obviously.

Michael: I love that. For the folks who are listening in, part of what I’m taking out of that, is this key lesson for me is around, look, you may or may not want to be an entrepreneur. That’s not the lesson that’s here for me. What the lesson is, whenever that thing is that you’re waiting to do, often what you’re waiting to do is hear permission from someone. So two things, either give yourself permission and do it, or hire somebody to give you permission. If you really need to hear that external voice to go, “No, you should do that,” then there’s a way of you hiring somebody to give you that permission. But so often, we get bamboozled by a hero, or the reason that I’m not allowed to do this. So find a way to allow yourself to take that next step towards whatever it might be.

Chris Ducker: Couldn’t agree more. And I find that when people get older, when they’re in their, you know, I hate to use the word old, but like a lot of my clients for example, are mid-30s and above. That’s kind of my sweet spot. Mid-30s to mid-50s is what I’m all about. And so when I see people getting older and getting further into their careers, they are more scared to take that leap because of things … They got family, they got children, they’ve got responsibilities and everything. But what they also have, a lot of them, almost all of them, is a good 15 years of experience under their belt, and people are going to pay to access and download that experience more so today than ever before.

I mean, I’ve got people who are clients that are in the financial industry, they’re in the health industry, they’re in the coaching industry. I mean, it doesn’t matter what you do and who you’re doing it for, there are people that are quite happy to pay to access your experience. And yes, you have to take a little bit of a leap of faith, but I am steadfast in my approach of helping people become youpreneurs because I know that it leads to fantastic opportunities now.

Michael: So Chris, to swing the spotlight back to you, one of the things that I’ve learned about myself on this journey is rather than having a thousand different lessons to learn, I probably got about three lessons that I just continuously learn, and relearn, and relearned because I’m a little slow. But actually, my guess is that for most of us, we’ve all got our own patterns that we keep working through and working with to try and elevate ourselves to whatever the next step might be. So when you think about the journey you’ve taken and what’s got you to where you are right now, is there a hard lesson that you’ve had to learn, or you keep having to learn along the way?

Chris Ducker: I don’t necessarily know whether it was a lesson, but it was a realization that I made probably about five or six years ago. I started blogging and podcasting in 2010. And like I said, I had that little 2012 back surgery moment where a lot of soul searching went. And I realized actually through the content that I was creating and ultimately building an audience in a community, creating, or rather attracting eyeballs onto me and my work, I realized actually that I wasn’t being me all the time. I was actually smoke and mirroring it quite a bit, not in a wrong way. I wasn’t trying to deceive anybody but I wasn’t being me all the time.

And when that realization hit and I realized that, nowadays I call it marketing like a magnet to attract the best and repel the rest. So when you are yourself all the time and you are marketing like a magnet, you will attract the people to you that are more likely to work with you, more likely to fall in love with you, more likely to hold you in esteem and to hold you in their heart as a favorite of some variety. But at the exact same time, you’re going to repel the people away that are going to suck your time, that are going to be a pain in the butt for one reason or … You know, the type of people that are … They’re going to want a 99-dollar discount on day 29 of a 30 days discount period.

We don’t need those kind of customers. We don’t need those kind of people. They’re always quite depressive or quite negative with what you’re saying and what you’re doing. So for me, it was about really being me all the time. That’s huge. And I think at the very core of what we do as entrepreneurs, particularly entrepreneurs, and a coach is an entrepreneur. If you’re running your own business you’re an entrepreneur, whether you’ve got one employee or 100, it doesn’t matter. As entrepreneurs, what we do is solve problems. That’s it. We shouldn’t get any delusions of grandeur about that. That’s all I do every day, and that’s all you do, and any other successful entrepreneur that I know.

But once you accept that, and you take it on board, and you know that you can do it by being you all the time, people will love you for it. They will love you for it. And at the end of the day, that’s what we want to do. We want to become somebody’s favorite.

Michael: Well, I love that. It’s a perfect segue to the next question that we have, because people talk about, “be authentic, be yourself” quite a lot but there’s quite a distance between proclaiming, “I want to be myself,” and actually doing the work to figure out what that means, and what that looks like, and how that shows up on a day by day moment. So when you’re working with people and you’ve laid down the challenge, be yourself because when you’re being yourself you get to market like a magnet. For these people who are listening who are like, “Well, I’m not an entrepreneur so I don’t need to market like a magnet.” Well, if you’re working for an organization, you’re still wanting to work with the right people, you’re still wanting to build a personal brand, you’re still wanting to solve problems and make an impact. So these lessons apply to you as well.

Chris, how do I figure out who I am? How do I, once I figure that out or at least got close to it, how do I stay the course and not get blown off and start showing up in a fake authentic way?

Chris Ducker: Yeah. So the good news is that this podcast is at least six hours long, so we’ve got plenty of time to cover it.

Michael: Yeah, exactly.

Chris Ducker: Now, in a nutshell, it really comes down to two very key exercises that I talk about in the book and that I’ve been talking about quite frankly for years, and that is-

Michael: This is the new book The Rise of the Youpreneur?

Chris Ducker: Yep, correct.

Michael: Then perfect. I think that-

Chris Ducker: So the first exercise is what I call the self-awareness test, and we’ll go through that in a minute because it’s a real eye opener. And then the second really is actually figuring out or almost designing your perfect customer. See, I’m a big believer that I should only do business with people that I can genuinely help, like my time is precious. I don’t want to waste other people’s time either. So if we’re not a good fit, I shouldn’t be chasing the money just for the sake of making money. I know that I will find another client who will be all about me and what I can help them with. So that’s why … That kind of perfect customer or perfect avatar, as some people call it, figuring out who that perfect customer is, is huge. And you want to do that as early on in the journey as possible.

But getting back to the first exercise in terms of that youpreneur self-awareness test, so what you can do is, actually anybody can do it, you get a piece of paper, you draw a line down the middle. And on the left hand side, you write down what I call the flatter yourself list, and this is a list of all the things that you know that you excel at. Like you’re a really, really good at these things. Funnily enough, Mike, generally speaking, people don’t have a problem talking about how great they are. So that list is actually filled up pretty quickly. But on the other side of the page is the keep it real list, and this is a list of all the things that you know that you’re not that great at. This is the one that people potentially struggle putting together, particularly entrepreneurs because of our Type-A, individual mindset. “Well, I’m great at everything. No one is better than me.”

That can be sometimes a little tougher to put together, but the goal here is actually not really to figure out what you’re not great at. The goal is actually to figure out what you really, really excel at and what you enjoy, and then do more of that. You do more of the stuff that you’re great at and you just almost eradicate the rest of the tasks or the rest of the things that you’re not very good at all, so that you can focus on helping the right kind of people. And for me, that’s been the game changer, not only in the effect that I can cause while working with somebody, but also the effects of my life, my business, and my own mental bandwidth as well. At the end of every day now, at the end of every day, I can close a laptop screen and go spend time with my family and I know I have had an amazing fricking day, like a really good day because I know I’ve done great work with great people.

Six, seven, eight, nine, 10 years ago, I didn’t feel like that. And the reason is because I’m working with the right people now.

Michael: So, Chris, I like where you’re taking us here. You’ve got two insights. One is know thyself, and the other is know the person you’re best suited to serve. And you’ve taken us through the know thyself exercise: draw the line down the middle, and then on one side, stuff you’re great stuff at, on the other side, the reality check. To make that more real for me, can you give me an example? Perhaps of your own life around what are one, or two, or three things that fall into the, “I’m really good at this,” and what are some of the things that might fall into the, “I’m not so good at it?” Just so I know it’s just about technical skills. This isn’t it about how you be and show up in the world. I mean, I’m just curious to know what that might look like as examples.

Chris Ducker: Well, I think it’s all of that and a bag of chips as well. It’s pretty much everything in regard to how you’re working, how you want to work, who you want to work with, and so on and so on. So if I can read directly from the book, page 20 to be precise, I actually share my own-

Michael: How perfect.

Chris Ducker: … my very own results of the youpreneur self-awareness test, or a few examples on each of those as well. So on the left side of this page, I talk about my flatter yourself list, which is: I’m a strong leader, I’m a compelling communicator, I’m a high achiever, I have high competitive drive, and I’m an independent worker.

Michael: Nice. Okay.

Chris Ducker: Okay? So that’s my flatter yourself list, or the beginning of it anyway. And then on the other side, I’ve got my let’s be real list, right? So I’m a micro-manager, I’m a perfectionist, I’m impatient, I’m tech incompetent, and I’m easily unimpressed.

Michael: Right. And you’re British.

Chris Ducker: And I’m British.

Michael: Sorry. That’s just — It’s the Australian thing I told you I was going to do that Perfect.

Chris Ducker: So that gives you a little bit of an insight. You see what I mean?

Michael: Yeah, I got it. And to find that person you best serve, and as you say like, this is impossible to cover in a quick podcast like this, like, I need six hours or eight hours. But give people a clue as how they can start figuring out who is their best person that they can show up and serve.

Chris Ducker: Well, it’s looking at things like, what are they up to right now? What stage would this perfect customer be in, in their lives? What situations are they handling? How old are they? Where do they live? Are they married? Are they single? What’s their background? Do they have children? But the big question you have to ask yourself is, what are they struggling with right now? And that’s where the problem solving incubus of the entire business world comes into play. Our role is to then, not only figure out what they’re struggling with, but then figure out a solution to that problem for them. And if we can package that solution in some way shape or form, whether it be an online course that will create and sell via our blog or our podcast, maybe it’s live one day workshops that we’ll run with a collection of people that are all within the same situations, possibly it’s writing a book or whatever. It doesn’t matter. It doesn’t matter at all.

Once we’ve figured out what that solution to the problem looks like, if we answer those questions, if we solve those problems properly, then we get the ability to put a price tag on it. So we’re happy, we make a living, and we know that whatever it is that we’re creating is obviously being consumed and it’s helping people along the way as well. So, that’s like the very core of everything when it comes to figuring out who that perfect customer is.

Michael: Yeah. It’s a really interesting mix of being entirely self centered, so grounded in who you truly are, but entirely customer centric at the same time, which is being entirely grounded as to what they’re really up against and what their real struggle might be.

Chris Ducker: Absolutely. Yeah.

Michael: Chris, it’s been a great conversation and there are people who are going to want to find out more about who you are and how you do it. Where can they find you? Where can they find the new book?

Chris Ducker: Well, they can find me over on my blog, which is, and the book is available obviously on Amazon, but if they want to short link, they can just go to That’s Y-O-U-preneur.

Michael: Perfect. Chris Ducker, it’s a pleasure. Thank you.

Chris Ducker: Thank you, mate.

Box of Crayons helps organizations transform from advice-driven to curiosity-led.