Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

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The Nitty Gritty:

  • How purchasing a tanning salon when she was 18 set Emily on a track for entrepreneurship
  • Why extremely detailed process management will help you feel more productive
  • How Emily balances the demands of running two businesses

This week, my guest on the Profit. Power. Pursuit. podcast is Emily Thompson, founder of Indie Shopography and co-host of Being Boss, a podcast for creative entrepreneurs who want to up their game. At Indie Shopography, Emily helps creatives build and run online businesses from the design and development of their business websites to marketing and education products. Emily and I talk about the time she bought a tanning salon at the ripe age of 18, why her extremely detailed process management helps her feel more productive and how she balances running two businesses.

Lessons from owning a tanning salon

I remember thinking this would not be my last relationship with business.

– Emily Thompson

When Emily was 18 she worked at a tanning salon one night a week in exchange for getting to use the tanning beds herself. Even though she had never taken a business course and was young, she could tell the business was in trouble. Then, thanks to a combination of moxie and mettle she made a call to the owner and ended up buying the salon and owned her first business at age 18. During our conversation, Emily shares insights about this opportunity and although it was a relatively short period of time, she credits it with giving her the bug to be a business owner. Today, she is very intentional about building a business that really allows her to do work that works for her.

Detailed {often painstaking} to-do lists for optimum productivity

My trick for myself is breaking down those tasks so minutely that sometimes I can check off 5 things in 5 minutes because I really broke them down that small.

– Emily Thompson

Whether Emily is designing a website or developing a new educational product, her process is very much the same. She outlines her entire process in the podcast and emphasizes the power of her detailed to-do lists that break down tasks into bite-size chunks. Once she has that very detailed plan, she schedules it out by using Asana. Even though her to-do list may seem super overwhelming for every project, she knows that tackling each of those individual tasks—that are small and manageable—she will ultimately get to the end of it. When those to-dos are marked off, the end result is a new product or website has been created.

Secrets to juggling two businesses

I don’t have to wear too many hats. They’re the same hats, just different colors.

– Emily Thompson

In the podcast, Emily shares her experiences and thoughts about how to juggle being the boss for two different businesses. She loves that she doesn’t have to put all of her energy into one thing, and that makes having more than one business appealing to her. The two businesses give her enough structure to not pigeon-hole herself creatively into one creative endeavor. She and her partner at Being Boss put together a very detailed marketing calendar annually so that they have a clear view of what’s happening in all three of their businesses so nothing gets lost.

In the full episode, we talk more about Emily’s passion for Asana, the structure of her team, as well as what’s on the horizon for both of her businesses, plus a book launch next spring! I hope you’ll tune in to receive all her valuable insight.

Learn from today’s most innovative and inspiring entrepreneurs every week by subscribing to the Profit. Power. Pursuit. podcast on iTunes when you want to know how small business owners really manage their time, develop outstanding products, build their teams and get new customers.

Finding Momentum & Engineering Productivity with Jodi and Jason Womack

Jodi and Jason Womack on Profit. Power. Pursuit. with Tara Gentile

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Tara:  Hey everyone, welcome to Profit. Power. Pursuit.  I’m Tara Gentile, your host, and together with CreativeLive, we explore the unique strategies that creative entrepreneurs use to take control of their lives, profit from their passions, and pursue what’s truly important to them. 

This week, I’m joined by both Jason and Jodi Womack.  Jason Womack is the CEO of The Womack Company, an international training firm, and the author of Your Best Just Got Better.  Since 2000, he’s coached leaders across industries and trained them in the art of increasing their workplace productivity and achieving personal happiness.  Jodi Womack is the CEO of the Get Momentum Leadership Academy, and the founder of No More Nylons, a coaching program providing women business leaders with professional networking expertise.  I spoke with Jason and Jodi about the importance of offline relationship building in an online world, the unique challenges of wooing corporate clients, and what they do to create momentum when even they get stuck. 

Jason and Jodi Womack, welcome to Profit. Power. Pursuit.  Thank you so much for joining me.

Jason:  Hey, delighted to be here, everybody.

Jodi:  Good to see you.

Tara:  Awesome.  So I’d love to start with how you both transitioned from careers in education to starting an international consulting firm.  What inspired you to start your business and kind of how did you navigate that transition?

Jason:  You know, Tara, the short answer is we … we both make really bad employees, because we always had great ideas about what the companies we used to work for could be doing, and so in education, as a high school teacher back in the 90s, I really felt comfortable making up lesson plans, developing project-based learning, taking a look at portfolio assessment over time education.  Jodi, meanwhile, was in the counseling office dealing with the kinds of issues that a high school campus might encounter when it comes to students who weren’t performing well on tests, doing their homework, or being quote/unquote good students, and so there were several stones in the river that got us from one side to the other side, and one of them was we both left education and worked for a private, very small at the time, consulting business, where we got to explore and start to take a look at, okay, who out in the world needs to know something, what do they need to know, and are they willing to pay for it.

Tara:  Brilliant.  Awesome.  So what misconceptions did you have when you first started your business?

Jodi:  Well, we had a good start, because we were working in a company that was also run by a married couple, and while we were there, we sort of got to look at what parts do we like and what parts do we don’t … we don’t like, and my thing was I never wanted to have a company where a whole bunch of employees came to my house, and that’s what I was going to every day, and I just saw what it did to their personal relationship, and I said I didn’t want to replicate that.  But there were parts that I really did like, so my hope and goal was to be able to run an international company from a laptop and travel wherever the work was and not need staff, and I think the misconception for me was that we could do it all on our own, even with all the apps and tools and things, and so over the last nine years, we’ve evolved.  We have a team of about twenty-four people now, but again, holding back to that original standard of not having people come to us.  It’s a virtual team that’s located all over the U.S., and some people around the world, and we had to kind of build that ourselves to figure out what was going to work.

Jason:  And on the content side, and I say this with a big smile, I was under the misconception that if I provided really, really good content and really, really good work, that that would speak for itself, and so what I’ve had to learn is a very delicate balance between creating the great material that when someone sees, they’re going to be naturally drawn to share it, and mapping that to what can be perceived as self-promotion.  Oh, there’s Jason talking on his Facebook wall again about his new book.

Tara:  Got you.  So can … I want to talk more about the team piece in a little bit, but let’s … let’s start with this content piece, because I think that’s really juicy and it’s really relevant to a lot of people who are listening.  So what have you noticed about content that actually helps you drive revenue without having that kind of self-promotional piece to it?  How do you make that balance?  What does that look like for you?

Jason:  Everyone’s looking for … when they’re … when they’re reading something, listening to something, watching something that’s content-based, they’re trying to answer three questions.  Who is this person I’m reading, listening to, or watching?  What do they know that I don’t know?  And can they help me with a problem I have right now?  And so the best content that I think Jodi and I come up with, and it’s weekly that we can come up with things like this, is going to our user-base.  Going to the clients that we just coached last quarter.  Going to our current academy members.  Following up when I do a workshop on site, and asking them, what are you dealing with in the next 90, 60, or even 30 days, and I really like that time period, Tara, because I think once we start getting into over the next year or over the next three years, for me, it gets really fuzzy, but if I can get someone to tell me a challenge that they know they’re going to face in the next 90 days, then all of a sudden, it gives me my own homework, and then I can go back to them and say, hey, you know, based on that conversation we had six weeks ago, I’ve created a white paper, a short video course, a new podcast episode.

Tara:  Brilliant.  That is incredibly juicy, and I hope everyone’s taking notes on that, because that’s really awesome.  Can you tell me how you kind of parse that information that you get back?  Because if you’re following up with people that often, you’re getting a lot of information.  How do you decide what to focus on when you are creating that white paper or that video course or whatever, you know, kind of content you’re … you’re producing?

Jodi:  Well, we find, number one, we put it in people’s hands directly.  So it’s a personal email, it’s not just a giant blast that goes everywhere, because we find people just have become numb to that, and I don’t know about you about, you know, if you have a read later folder in your emails, but we find that we send something, we call to follow up, and we do, we hold people’s hands, because we’re the ones with the real interest.  You know, that we want to be able to provide service.

Jason:  And I know Jodi went digital really fast.  I just want to make sure that we spotlight this.  We’re just as apt to send a handwritten letter, a photocopied article.  I’ll print up an article that I post over on or, and I’ll pull that content over into a Word document, I’ll make it a two-column Word document.  Up on the top left, I’ll put a big title.  On the bottom right, I’ll put a picture and my bio.  I’ll make it look like an article, and I’ll actually put that in the mail, and then there’s always a call to action, so if I … if I do mail you something, and by the way, for those of you who are listening to this right now, the easiest way to do this is for the next two weeks, listen to the questions that your customers ask.  If you’re running a boutique, listen to the questions they ask you when they call you on the phone.  If you run a restaurant, if you’re an artist, if you’re … I could keep on going.  If you’ll come up with the five or ten questions that people ask you, then over the next two weeks, find out which of those two, three, four that you get asked over and over again.  That’s where we find, if we can give someone some content, if we can copy … if we can write copy on something, if we can record a video on something, if we can give them something that they can use right away, all of a sudden, we become the source.  I think, I think, Jodi, if you were to talk about for a moment your women’s business social, and how you gathered people together and became a hub of women in business, that could be a story people could walk away with.

Jodi:  I literally printed up postcards at Vistaprint.  You know, just online, overnight, and started walking around my community and hand, personally inviting people to my networking event, and it was one of those things that it just handled so many questions all at once.  It was actually more time efficient, even though it seemed like it took a long time, but people then felt like they really knew me.  And I love that expression, like, oh, what are you waiting for, a personal invitation?  It’s like, yes, I kind of am.

Tara:  Yeah, that’s great.  I … I so love that you guys are highlighting this offline example, because for as wonderful as online business is and all the tools that we have now, we tend to forget that there’s all these techniques that have worked for time immemorial that are absolutely applicable to a business that’s run virtually as well.  So I love this … this kind of juxtaposition of you guys running a distributed team in a virtual, you know, in all but virtual business, but also using these on-the-ground marketing techniques.

Jason:  I’ve got a quick story on that.  My third book is called Your Best Just Got Better.  Someone wrote a review of the book, this is a few years ago now, maybe three or four years ago.  This woman named Rongenie wrote a review of Your Best Just Got Better, and while I was up at my parent’s house up in Northern California, I took her name, and I pasted it into Google.  It turns out that she was in charge of a NAWBO, National Organization of Women Business Owners organization, she was very prominent in her community.  I called her at work to say thank you for writing the review.  You would have thought like the president of some country had called her.  And I tell you, to this day, she’s probably one of our longest-term members of our academy.  She’s been to two of our three retreats in Ojai, and she continues … she hired us to come up to Pleasanton and run a program last year.  So you know, someone can say, “But Jason, is it cost-effective to call everybody who writes a review of your book?”  Well, my answer is yes.

Jodi:  Well, and the other part is we’re not doing it as a sales technique.  We do this to build our community, and people remember us, and that’s really what we want is a whole community of people who want to take our calls and who do in fact open our emails, because it’s … there’s … it’s just really noisy out there, and it’s really easy to hit that delete button, so it … the human experience, you just can’t underestimate how far it’ll go, whether it is with, you know, building clients, or just that word-of-mouth and people who are willing to speak on your behalf.

Tara:  Yeah.  Well, and Jason mentioned that, you know, first question that people are asking themselves when they’re reading new content is who is this person, and I think when you’ve got that offline connection, whether it’s a phone call or a postcard or something hand-delivered that, you know, you’re answering that question pretty … pretty definitively right there and then.

Jodi:  Yeah.  And I’ll share … I’ve also added it on the flip side where I put people’s images, I’ll Google them and find pictures of people that I’ve never met but have been long-time clients and put them in the phone app in the contacts, and I love when I see their face pop up on my phone.  It’s like how human can we make this?  How … you know, it’s like I know that person.  I know them by their look and by their name, and it’s … it’s really very fun.  It sparks so many valuable conversations that lead to more things.  That’s really what we’ve learned in business.  It really is just Jason and I making the whole company run as far as the marketing and the experience with … you know, we don’t have a sales staff.  We don’t have people going out into the field on our behalf.  That’s all us, and people, our clients will tell you they know us well.

Tara:  I love that.  How human can we make this?  That’s a brilliant question for people to ask themselves.  So let’s talk about the company and how you guys actually make money.  What are all the different ways that your company generates revenue today?

Jason:  There’s three, and what we found over the years was that having a multiple streams of income was absolutely significant.  And for this, Tara, I’m going to take out the investing that we do, I’m going to take out the more passive income, and go to what we do actively.  So there’s three streams.  One is we run an online academy.  It’s called Get Momentum.  We also put on workshops and seminars.  That’s under the Womack Company.  And then we help companies build internal information, content delivery, and kind of white label content.  We write it, but they get to use it on an annual, and they just re-up every year, whether or not they want to use that information again.  So with the academy, it’s a membership program.  People jump in for a year at a time.  We say that it’s for recently-funded entrepreneurs, people starting up a company where they’re going to be put in a position of leadership, and then of course, on the corporate side, recently promoted managers.  And really, what winds up happening is people join Get Momentum, and then they find out about what we do, so then they have us come in and do a workshop.  We come in and do a workshop, someone hears about the content, they ask us if we can do a four to seven to twelve video series for their intranet, for their side of the firewall.  So I don’t see it as much as three columns, as much as a triangle, where each one gets to lead to the next, to the next.  The last thing I’ll say on that, because I know you’ll have a follow up question, is that recurring revenue model we knew we had to jump into a few years ago.  So the idea of someone joining Get Momentum for twelve months, at the end of those twelve months, I’m going to look at Jodi, what do we have, eight?  Probably 75-80% of retention.  Meaning people sign up for another year.

Tara:  Nice.

Jason:  So where everyone in the world will always look at us and go, well, you know, what are you doing about … what’s that word?  Attrition, right?  I just always smile.  It’s like, well, people come in, and I mean here’s the deal, you know, for example, in April, we study time management.  Look, everybody should probably spend a month a year studying time management.  Later, in October, we’re going to study relationship management.  I can’t find anybody who would say, “Oh, yeah, I studied that last year.  I’m done.”

Tara:  Brilliant.  I love that.  And I love how you … you really illustrated how the business model works.  Like you said, it’s not three different columns, it’s not three different streams, they’re all related.  They all feed each other in a system, and that’s … that, to me, is sort of the holy grail of setting up a really effective business model. 

So I do have a follow-up question, clearly, and that is around the corporate clients that you work with and how you woo those corporate clients, because it’s something that often, my audience, my clients ask me about is, you know, how do I get in front of decision-makers at a, you know, companies larger and small.  So what have you guys done to connect with the corporate market and develop relationships to book deals?  Whether it’s for speaking or for executive coaching or the content marketing that you do.

Jason:  So this is hindsight.  This is, you know, we’re nine years into this together, and then I’ll get to the foresight on the other side.  The hindsight is it’s referral-based.  It is absolutely, you know, I could probably do a numbers game where 9 out of 10 pieces of work we get is because, you know, Bob at company Acme was just speaking with Sarah from company whatever.  The real question is how did we create that in the first place, and what we did is … and we’re actually doing it again this summer, I’m … I moved … I put that in air quotes, I moved to New York for about two weeks, and in New York, using LinkedIn, Jigsaw, the New York Times, using anything I could do to find real, actual names of people who were at all involved in learning, leadership development, training, classes, I invited them.  I invited them to coffee, to lunch, to happy hour, to dinner.  Of those fourteen days I was in New York, Tara, I think I had about forty meetings over that time, and we have a story we tell internally, but one of those meetings over coffee was the most expensive coffee I’ve ever bought in my life.  For three of us to get coffee, it was about $28.  That has turned into nearly half a million dollars in booked business.

Tara:  Nice.

Jason:  Building that relationship, maintaining that relationship, and then the real big thing is making it easy for people to refer you.  The first chapter, the first stage of momentum, we just published a book a couple of weeks ago, the first stage of momentum is motivation, and what we mean by that is what do you want to be known for?  What motivates you?  So our clear and present job is to let people know here’s Jason, here’s Jodi, here’s what we want to be known for, here’s what motivates us.  Your people on your staff being better leaders motivates me to want to be a better coach, let’s work together.

Jodi:  Let me jump in, also, and it goes to this humanizing effect.  Really understanding what people in the hiring position really value is so important, because a lot of times as vendors, we think, oh, our pricing is too high or too low.  A lot of times, the cost of a speaker is about the same as the cost of a coffee break, you know, at a large conference, so it’s really not the significant factor, but you know, they’re putting their name on you.  Like, they’re betting their reputation on you, if you’re the keynote, if you’re the person that they hire, and so our job is to always make them look good, and to make it really easy to work with us, and I think that’s part of the reason why we’ve had the same clients for the whole time.  They take us with them when they jump jobs either sideways or up as they get up the ladder in the HR and training and development departments.  We’re a known quantity, you know, a known entity, and they know they can trust us.  That we’re going to be easy to work with, we’re going to do what we say, we’re going to show up when we say we’re going to show up, we’re going to make them look really good, and you don’t realize how much of their reputation is really on the line when they bring in an outside vendor, and understanding that game, and again, it goes to these real-life conversations and coffee chats and happy hours and asking good questions and listening to what they really value.

Tara:  You know, Jason, you said something about making it easy for people to refer you.  Do you have, you know, referral information?

Jason:  Really tough.  So after I do an event, if there’s any kind of good feedback at all via email or face-to-face or someone follows up, the question I ask is who do you know who has similar challenges to you, and would you connect us via email, I’d like to tell them what we do on the phone.  That’s it.

Tara:  So simple, so important, right?

Jason:  And you know what, I mean, there’s probably three layers to that little process that I just gave you, that each one will scare people away.  You know, I mean look, at bottom line, what I do, what Jodi and I do is very scary to some people.  Jodi will look at me every now and then, because I’ll see her typing an email, and she’ll look over with this knowing look, because you know what I’m going to say.

Jodi:  So the idea is like get away from hiding behind email and pick up the phone, and you would not believe how much time it saves from going back and forth and then wondering if they read your email, wondering what they’re doing with the email, all that.  Just pick up the phone and make a call.  Even if it’s a call to make an appointment to meet in person or you know, something, but set … put a real person behind it, because people like doing business with people they like and they know and they trust, right?  So if you can be that person, and you know, it’s … the referral base is also all reputation-based.  We … we’re only as good as our last gig, and everybody is connected, so we know that we have to really shine every single time, and handle anything.  Like the more we talk with clients, the more we get to know where their pain points are, and anticipate it so we don’t drop the ball or we don’t let them look bad in any part of the whole process, and that’s really been our business model is stay in touch and don’t mess up.  Stay in touch, do great work.

Tara:  Oh, I love that.  I love that.

Jodi:  That’s our system.

Tara:  That’s excellent.  All right, so you guys mentioned that you’ve got a new book out called Get Momentum.  I’d love to talk about the … just even the idea of momentum for a little bit, and specifically kind of the obstacles that we face, or even that you guys face in getting momentum for your work, for, you know, your day-to-day life, your productivity.  What obstacles do you see to gaining momentum, getting a hold on things for your work today?

Jason:  You know, I gave my first TEDx talk about a month and a half ago, and I led it off, I started off, I asked the audience a rhetorical question, and I asked, I said what if everything they’ve told us about achieving success is incomplete?  What if there’s something more for us personally that we need to know, we need to do, we need to be, we need to have?  And so if I look at the one thing, and I’m kind of giving Jodi a moment to think here, if I look at the one thing that blocks momentum, that forward motion, that get up off the couch and do what it is that you think should be different, do what it is you’re complaining about, do what it is that you know could be better, and look at any time I say, “Someone should …” or any time I hear someone say, “Why doesn’t someone just …” that to me is an indicator that I am someone.  That they are somebody.  So the number one thing that I think blocks momentum is that trust inside that they way other people have done it may not be the way I do it.  That I will add my unique spin to it.  People ask me all the time, Tara, “Jason, you’ve written a bunch of business books, you teach productivity tips, you talk to people about how they could be better managers and better parents.  You know, what makes you different than anybody else?”  And I go well, you’re listening to me right now, so I’m different than everybody else.  That’s it.  Where are you going to put your attention and where are you going to step into and do what it is that you know needs to be done?

Jodi:  Okay, so my answer to that is we absolutely could not have written a book called Get Momentum: How to Start When You’re Stuck without having been stuck ourselves over the years.  Personally, professionally, all that good stuff.  And so a lot of it comes from our experience and our stories, and then we also pull from the Get Momentum membership, and people have shared some really big events that they’ve worked on in their lives and what they’ve been stuck on, and we found themes.  So there’s activities, it’s very practical, but you know, for me, it’s about getting out of the day-to-day and looking up and out.  You know, it’s having a more executive experience in my own business, and not being in the weaves and the day-to-day so much.  Bringing in all these people to help support us and have this virtual team means that I end up being the bottleneck more often than I’d like.  People are waiting for me to decide and give feedback and give the green light, and so my next challenge and real opportunity is how do I act more like an executive and let other people, you know, for me to set the vision and allow other people to step up to help and support us that way.

Tara:  Okay, so I want to talk more about that for sure, because that, I think, is a very, very common problem, and I love that you guys are so far along in your business, you’ve already created all the success, and that’s still something that you’re wrestling with, but I want to back up for just a second, and Jodi, you said, you know, you couldn’t have written this book if you guys hadn’t been stuck before.  So could you tell me about a time when you guys were stuck, or when you personally were stuck, and how you found momentum again?

Jodi:  That’s a stumper.  We’re both looking at each other.

Jason:  Yeah.  Daily?

Jodi:  Well, the Get Momentum program came out of this feeling of being stuck where we were doing these executive coachings, we were doing … Jason was on stage doing these workshops, and it was like having a day job.  If we didn’t go to work, we didn’t get paid.  You know, we had to show up and be there in order for the work to happen.

Jason:  The writing was on the wall for me.  There was one year I … I took 168 flights in 12 months, and I was in hotels just shy of 300 nights that one year, and you know, where I was stuck, and this is going to sound ironic or weird, but I was stuck making a lot of money.  I mean, don’t get us wrong, you know, we were living fine, but as Jodi just said, if I wasn’t on stage, we could not submit an invoice to a client.

Jodi:  We didn’t have a company, we just had our own jobs that we had created.  So that was the stuck of not being able to figure out how to get out of that successful loop, but there was really no end to that.  We were in our 30s.

Jason:  So let’s … let’s … let’s do how we got out of it.

Jodi:  Okay.

Jason:  Because I think that’ll be … there’s a couple lessons that we can share with that one.  So Tara, it was back in two-thousand, and I want to say eleven (2011), and I ran an experiment, and we did an email campaign, we sent emails out to about 6000 people, our list was small.  We sent an email out to 6000 people, we actually sent 12 emails out to 6000 people over one month asking them what is it that you need information, education, coaching wise that would be of service to you?  Long, long, long story short, we created a one-month pilot Get Momentum program that was a class a week, it was a call with your coach a week, and it was a workbook that each member had to fill out of worksheets a week.  Now, because it was so intensive, I could only take ten people in this program.  Tara, when we opened registration for that ten-person spot, we sold out in 36 hours, and we opened the cart on December 27th.  So with everything that was going on, with holidays, with New Years, with all of this, there were ten people who within 36 hours, they wrote us a check, and they said Jason and Jodi, we’re all in.  So we did that one-month program, we reached out to those ten people, so this is the iterative process, we reached out to those ten people, and we said look, we can’t keep doing this, the numbers won’t work, but what if we did a monthly program?  Not a weekly one, but a monthly one.  And so you know, for anybody who is interested to see how we’ve created an online recurring revenue information/education-based business, you can get all those details at, but it’s what we had to do that would pull me off the road while maintaining this thought leadership domain expertise that Jodi and I have.

Tara:  And how did you manage that transition?  Because I think a lot of people, you know, you mentioned you’re constantly on an airplane, you’re constantly in a hotel, you’re constantly on stage.  How did you find the space to create even the idea of this monthly coaching program, this monthly academy, and navigate the transition between those two things?

Jason:  So there’s a term that people use for when people are playing pool and there’s one person who can really play pool well, but they don’t let everybody know that they can play pool well until they start betting for money.  You know that saying?

Tara:  Yeah.

Jason:  Tara, I’ve been studying personal productivity and time management for 19 years.  I’ve taught more than 3000 classes on personal productivity, project management, time management.  I’ve read hundreds of articles, dozens of books, if there’s a class out there, I’ve taken it.  So what I’ll say is there’s a tactic I came up with a long time ago that I’ve been using ever since.  Let me explain it, and I’ll ask everybody who’s listening to this, do this for a month, and your life will change.  So Tara, I call it the 30/30 rule.  30 minutes a day I work on anything that’s not due for 30 days or more away.  So what I’ll do is I’ll open up my calendar in the morning, and I’ll go three, I’ll go four, five, six, seven weeks into the future, and I’ll pick something.  Here’s my question I ask: What will I wish I had started working on sooner?  And look at personal or professional.  Right?  Maybe five weeks from now, I’m planning to throw a surprise birthday for my sister.  Maybe six weeks from now, Jodi and I are going to take a long weekend vacation.  Maybe nine weeks from now, I’m … I’m rolling out a brand new product to a client that we’re working with for the first time.  If I’ll spend 30 minutes today working on that, if I’ll spend that little bit of time where I carve out not working on what’s due tomorrow, in 30 or 60 or 90 days, I’m going to be ahead.

Tara:  I love that.  I love that.  I’m going to start doing that.  That’s such a great question to ask.

Jason:  30 minutes a day, and look, you know, I’m going to pull in on all the people that you and I know.  There’s so many guys out there that are saying, look, for the first 30 days, maybe you need to get up a half an hour early, maybe you need to forego one episode of that one TV show that you want to binge watch over the weekend.  I don’t care how you buy or borrow or beg or steal or find these 30 minutes, but if you’ll do this, within 30 days, that’s the bad news, right?  If you start doing this today, you won’t know if it works for 30 days from today, but I can all but promise you get to 30, 45, 60 days from now, and over that period of time, you’ve been working a half hour a day on the things that are already coming at you, you’ll be shocked.

Tara:  Yes.  I think that’s a really … that 30-day bet is a really good bet to take.  All right, let’s talk more about this executive experience piece, and how you guys are setting yourselves up to do that, because Jodi, I love that you mentioned that you’ve noticed that you’re really the bottleneck, or can be the bottleneck in your business, and I find that with my clients a lot that, you know, they’re getting better at delegating, they’re hiring more people, they’re investing more in the structure of their business, but at the end of the day, everyone still reports to them.  Everyone, you know, still needs something from them to make value happen, to make progress on their to do list.  So what specific things have you been doing to eliminate that bottleneck from your business?

Jason:  So two things, and I think I’ll have Jodi come in on the second one, which is the Monday meetings.  So I’ll have you talk about that.  Here’s the first one: we are the cumulative …

Jodi:  Average.

Jason:  The cumulative average of the people that we spend time with the most.  Way back when, before I knew I needed a coach, I had a coach, I didn’t know she was coaching me until later on she told me, “I was coaching you.”  But Martha, a woman who helped me a long time ago, she had me make a really easy, quick spreadsheet, it had five rows, and it had about a half a dozen columns.  In the first column on the left-hand side, she had me write down the five people that I had been spending the most time with.  The next column, how much money each one of those people made per year.  The next column, how many books they read per year.  The next column, how many days of vacation they made per year.  You’re getting where I’m going with this.  Well, what wound up happening is when I took those five people that I had been spending the most time with, and I averaged out how much money they made, how many days of vacation they took, how many books they read, I was living the average of those five.  So here’s what I’ve done over the past nine years, I continue to add another C-level, executive, founder, entrepreneur.  Basically, I look for people who are busier than I am, and I get coaching from them, even if it’s a hike in the woods, a chat over a coffee.  I’ll fly around, literally, I flew to Singapore last Thanksgiving so I could have two dinners with a guy over there that I knew if I could hang out with Mark for an extra 48 hours this year, that influence was going to carry me to the next level, and it did.

Tara:  Wow.  That’s incredible.

Jodi:  Yeah, and having those mentors in your life, even like Jason was saying, if it’s over coffee.  Learning how to be an executive, nobody teaches you that.  They teach you how to be a good employee and competent worker, but learning how to hand things off, follow-up, and train people along the way, that’s … that’s big … that’s big learning to do.

The other thing that is really a surprise to me because nobody likes meetings and I’m especially one of those people that don’t like meetings, but I found that people let me down or I … I don’t like being surprised by people when they come up with something that wasn’t what I wanted, right?  And I find that it’s usually my fault not guiding them better along the way.  So we’ve created these Monday meetings with each of our teams, and they’re fast, they’re painless, everybody needs to come in with their agenda or they’re not allowed in, and then we have one person that tracks all of the action steps and who’s doing them.  That was not a great strength of mine, and that’s one of the things about being executive is learning to find somebody who’s really great and wants to do things that you don’t want to, and so you know, it’s basically a glorified note-taker, but someone who’s really acute to following along and capturing who said they’ll do what, and if nobody claimed it, they’ll say near the end of the meeting before we break, “Well, who’s going to take that one?  Who’s owning that piece?”  And I’ll tell you, at the end of meetings, everybody always walks away, before we had this piece, saying, “Oh, so and so’s handling that,” and it’s like all the fingers were pointing to somebody else.  Nobody knew.  So really clarifying who’s going to do what by when has helped us keep projects on time, on schedule, on budget, and that there’s few surprises, and you know, people don’t want to disappoint.  I think people work really hard.  I work really hard.  I don’t want to disappoint anybody, and so just building in a couple more touchpoints, and again, making it a human experience for the staff and the … the freelancers and all the people helping us out, making sure that every … I know that they know that I know that everybody’s on board.  That’s really been a big learning curve for me, because my go to is like I’ll just do it.  I’ll figure out how to do a WordPress blog site or something, you know, and I have no business doing that.  And that’s really the hardest part about being in this executive type space is not going to that go to belief or core inside of like I’ll just do it, and training people so that they can help us along the way.

Tara:  Yeah, I love it.  So what’s next for you guys?

Jason:  Let’s see, I’ll date stamp this thing.  We’re in Ohio right now. We’re speaking at an Agile … I’m speaking at an Agile conference in healthcare, and I really am fascinated by, if I look at what’s next, if I look at the next three, four years, you know, 2020 has always been something, I just like the numbers put together, 2020, but Jodi and I spend a good portion of our time working with clients, asking them what will your workplace look like in 2020?  Now, in many instances, it acts as a conversation stopper, because people are like, “Dude, I can’t think about this weekend, let alone 2020.”  But it’s what I spend my … it’s what I spend my free time looking at.  So the big thing that’s next for us is the Get Momentum Leadership Academy, it’s growing.  We’ve opened up another level of membership to make it easier for people to get access to our information, without having to commit to the monthly one-on-one coaching calls, because all of that was a staple of our program, and Jodi and I both know how powerful it is to schedule a meeting with each one of our members.  There were people out there that said, “Jason, A, I don’t have the time, I don’t have the budget, or right now, I simply need to read and listen to and watch what you create.”  So you know, with a big smile, I’m studying very closely business schools, specifically executive education at business schools, because I see in the 2020, 2025, there’s going to be a lot more self-ownership of letting creativity, letting intuition, and letting curiosity guide their learning.  And just to kind of, you know, as I know we’re bringing this to an end, it’s why I see CreativeLive being the support system and structure that it is.  People are very … I don’t think we’re going to be moving toward a future where people are told as much what to learn, but they’re going to have to figure out how to, because there’s so darn much information to go get.

Tara:  I love that, and that is a great place to leave it, but I think that’s also a great jumping off point for another conversation that we’ll have to have sometime soon, I think.

Well, Jason and Jodi Womack, thank you so much for joining me.

Jodi:  Thanks, Tara.

Jason:  Absolute pleasure, and please, everyone out there, we’re huge CreativeLive fans.  If there’s anything we can do for this community or your friends, just reach out.  We’d love to stay in touch.

Tara:  Check out Jason and Jodi’s new book, Get Momentum, and their executive education academy at, plus find Jason’s class, Think Bigger, Make More, at

My guest next week is feminist wedding photographer and founder of Catalyst Magazine, Carly Romeo.  Carly and I talk about how being a feminist wedding photographer helps her stand out in a crowded industry, why she decided to pursue a print magazine in the digital age, and how she manages her time to make sure all her projects actually get done.

That’s a wrap for this week’s episode of Profit. Power. Pursuit., a CreativeLive podcast.  Download more episodes of this podcast and subscribe on iTunes.  If you appreciate this kind of in-depth content, please leave us a review or share this podcast with a friend.  It means the world to us.

Our theme song was written by Daniel Peterson, who also edited this episode.  Our audio engineer was Kellen Shamezu.  This episode was produced by Michael Karsh.  We add a new episode of Profit. Power. Pursuit. every week.  Subscribe in iTunes, Stitcher, or wherever you love to listen to podcasts so you never miss an episode.

Personal Productivity & The Future of Digital Publishing with Chris Guillebeau


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Tara:  How do you balance the pursuit of art and ideas with the pursuit of profit?  That’s the fundamental question we tackle on Profit. Power. Pursuit.  I’m Tara Gentile, your host, and together with CreativeLive, we explore the unique strategies that creative entrepreneurs use to take control of their lives, profit from their passion, and pursue greatness.

Today, I sit down with Chris Guillebeau, the New York Times bestselling author of the $100 startup.  An accomplished travel hacker, he has visited every country in the world 193 in total, before his 35th birthday.  Every summer in Portland, Oregon, he hosts the World Domination Summit, a gathering of remarkable, creative people.  Chris and I talk about how he still manages to do a lot of the work in his business, what systems he has in place to make sure everything gets done, and the key way he sees online publishing changing.

Chris Guillebeau, welcome to Profit. Power. Pursuit. Thank you so much for joining me.

Chris:  Awesome. Thank you so much for having me, Tara.

Tara:  Absolutely.  So let’s just get started by kind of talking about what all the different moving pieces to your business are.  You’ve got … You’ve always got a lot going on, so I’d love for you to just kind of explain to everyone what are all the different ways that your business or businesses are generating revenue right now.

Chris:  I do always have a lot going on for better or for worse.  I don’t know if that’s a good thing.  I can’t always keep track of it myself, but I would say maybe first and foremost, I’m an author, I write books, and I actually like the process of writing books.  I like everything associated with the publishing process and going on tour, seeing the books translated around the world, so that’s probably my main business.  It’s not something that I do to accomplish, you know, something else, but then maybe for the past 10 years or so, I’ve also produced a number of products.  I’ve done digital products, I’ve done eBooks and courses.  I have a business called unconventional guides that I operated for a while.  It’s still around, although I’m kind of phasing out of it.  I have a membership site called Travel Hacking Cartel, and I also do a lot of different events.  And there’s probably some other stuff in there, too.

Tara:  Yeah.  How about speaking?

Chris:  I do speak.  It’s not really a revenue model for me.  It’s more something that I do to kind of connect with readers, and you know, just to be out and about around the world.  But once in a while.

Tara:  Got ya.  Nice.  So you’re in Jakarta right now, and I think a lot of people know that you do a lot of traveling, and one of our listeners asked me specifically, you know, she just really wanted to know how people like you manage their time, and so I was trying to think about, like, how do I ask Chris Guillebeau how he manages his time when there is probably not a typical day in your life.  So instead, I’d love to know what are some of the systems that you have in place to make sure that everything gets done?

Chris:  You know, the greatest system that I have is that I love my work.  Like, I absolutely love what I do, and I feel very fortunate that I have the ability to write books and to publish the blog and connect with people, and so I’m very motivated by that.  Like it’s what I want to do.  If I won the Powerball, I’m pretty sure that tomorrow, I’d be doing exactly the same thing, and so that helps a lot.  I mean, when I say that’s the greatest system, it really helps a lot, because I get up in the morning, and I’m like let’s get to work.  Let’s do fun stuff, and yeah, I’m on the road all the time.  I’m traveling.  So I like to take time to see the cities and, you know, go on walking tours and have different experiences and discoveries, but then I’m also eager to kind of get back and do my stuff.  So you know, I always have my laptop with me.  I’m always kind of working on the next thing.  I’m a big list person.  You know, I love kind of writing things down and checking them off, and I always carry a notebook with me where I’m outlining stuff and planning ideas.  And so I get behind on things, it’s because I have too much going on, but I’m really motivated to keep going.  So that’s really the greatest system.

Tara:  Nice.  Is there any software systems that you use to kind of manage your day or manage your to-do list?

Chris:  Sure, sure.  Yeah.  I mean, I use Omnifocus.  That’s my number one, like, task, you know, program.  I don’t think it really matters which one you use as long as you have something that works for you, but that’s what I do, and then I have a lot of stuff in Evernote as well, which is great, because as most of the listeners probably know, you can access data from all kinds of different locations and devices, and it becomes more helpful the more you use it, so there’s that, and there’s some other stuff, but it’s all kind of cobbled together.  There’s no, like, one master system.

Tara:  Perfect.  So I’m sure, I know, actually, that another system you have is a team around you in your various ventures, and I’m privileged to be friends with a couple of people that are on your team.  So can you tell us a little bit more about what that team looks like and how they’re organized?

Chris:  Yes.  I should say, I am kind of a classic solopreneur.  You know, I was always doing my own stuff for a while, and I like working independently, so I don’t have like a huge team.  I have one employee, one full-time assistant, and she’s wonderful.  She’s been with me for a year now, but you know, for all the time before that, I was kind of doing a lot of stuff myself.  For the events that we do, we definitely have a team.  That’s not something I can do on my own, so I’m really grateful for them, but a lot of them are volunteers, some of them get a stipend, but maybe there’s 10 of those people.  We all work virtually, and then when I’m home in Portland, Oregon, most of them are based in Portland as well, and so we do have regular meetings either every other week, or once an event is approaching, every week, but everybody kind of does their own stuff, and everybody manages themselves for the most part, which is great, because I’m not a good manager.

Tara:  Yeah, that’s excellent.  I love the sense of independence that they each have, and I think it brings kind of a sense of creativity to your team as well.  I can see that, you know, in the different events that you do and just the way they talk about the ownership that they have over the work that they do with you.

Chris:  That’s good.  No, I’m glad to hear you say that.  I think it can be frustrating for some people.  That kind of work style doesn’t work for everyone, so it’s really important to get the right people, you know, in place for that, but for me, I think it’s a tremendously valuable skill whether you want to be an entrepreneur, whether you want to think entrepreneurially in another career working for someone else or working for a company.  It’s an extremely valuable skill to be able to kind of figure stuff out, basically, and to have a project or to have a responsibility, but not necessarily be given, like, here are the steps, you know, one through eight that you have to follow.  And so if you can find people like that, there’s just so much value there. 

Tara:  Yeah.  I think that’s a great point for everyone, because team-building is also a huge thing that our listeners are really interested in figuring out and finding out what’s working for people, and so I hear you saying essentially that you need to put together the team that’s going to work for you, and that that doesn’t mean that it has to look like a conventional job, or that it has to look like a conventional employee relationship, or that it even has to look like a conventional, like, management relationship.  That it can be something that works for you and works for a very specific type of person, and it doesn’t have to be a great fit for everyone.

Chris:  Right, exactly.  I mean … so it has to work for you as the business owner or the entrepreneur or whatever, but then it also has to work for that person, you know, as well.  So it’s not necessarily the easiest thing to find, but I think it’s something that’s kind of worth … worth investing in, you know, because anybody can follow a list of tasks, but it takes creativity, as you said.  It does take some entrepreneurial thinking to kind of figure stuff out and decipher it, and that I think is a skill that everyone can improve on regardless of your field, your industry, it doesn’t matter what you went to college for.  This is something that kind of sets people apart in life in general.

Tara:  Got you.  So you mentioned that you’re still doing a lot in your business or at least with the writing side of the business now.  What are some of the tasks that we might be surprised to learn you still actually do?

Chris:  Huh.  I mean, pretty much any sort of administrative task I still do it from time to time.  I mean, just putting together newsletters, I do all of my own social media.  I don’t know.  I guess … I guess there’s not much that I don’t do, but I also don’t want to take anything away from the people who, you know, work on stuff with me.  Like I’m very grateful for them.  I just don’t have much of a separation between like here are like these top level task and here are like these low-level administrative tasks, and maybe that’s something I need to work on, but at the same time, it’s also kind of helped me not get too distant from things.  It’s helped me kind of, you know, have direct contact with people and understand, like, where they’re going, what’s going on with them, and how I can hopefully be helpful or be of service in some way to them.

Tara:  Mm.  Do you have any kind of automation in place in your business, or are you pretty hands on with the day-to-day, you know, this needs to get done, that needs to get tweeted out, etc.?

Chris:  Very little.  I mean, I don’t have a problem with scheduled tweets or something.  Like that’s fine.  Like, we might like put up some posts or something that go out at different times, but I … I think, like, it’s important to not be disingenuous with it, you know?  If you’re sharing some content that you’ve written at some point, you know, nobody cares whether you’re like live-tweeting that or something, but otherwise, I try to be pretty, pretty hands on.

Tara:  Got you.  And you said you’re not a great manager, but I’m curious how you manage your team, if at all.

Chris:  Correct.

Tara:  You know, what … how do you set expectations?  How do you communicate with them on a regular basis?

Chris:  Well, we talk pretty much every day.  I mean, we talk by email, usually, or by chat or something.  The WDS team, we use Slack, which is a great network for keeping in touch with people in different time zones and things.  But I don’t like I said, I really don’t think I’m a great manager, so I try to focus on … I try to focus on the goal.  Like, okay, what are we actually trying to achieve here?  What are we hoping to do?  And then there’s lots of moving parts, and you know, as we said, the right people kind of pick up those parts and run with it, because you know, to go back to where we started, if you’re motivated by what you do, if you enjoy what you do, then you’re probably going to do it a lot better than if you’re just doing something because you have to do it.  So wherever you can find that magic fix, you know, between your own skills and the people that you’re working on, that’s where you’re going to see far greater success.  So that’s what I try to do.

Tara:  So the next question is one that I’ve asked just about every one of our guests, and the answers have been very different, and I’m really interested to see how you’re going to answer it.  So how do you balance the roles of writer and executive in your business?

Chris:  I think there’s a big tension there, and I think it’s a natural tension, it’s a healthy tension because I do enjoy, like, doing more than one thing.  I’m not good, you know, just working on one project at a time, but then, of course, there’s a cost to that.  So I think, you know, every year, I kind of evaluate, like, am I happy with the balance?  Am I, you know, am I creating art?  Am I actually writing?  That’s how I got started in this.  Or am I focused too much on business stuff?  And I think maybe a year or so ago, I went away and felt like I had, I wasn’t writing enough, and so I tried to focus more on that, but then I miss the other thing.  So I don’t know, I just go back and forth.  I guess every day I try to make progress on the things that I believe in.  I have these, it’s like kind of values-driven.  It’s like I’m not happy if I’m not writing on a regular basis, and so I know if I get away from that, I have to go back.  So I don’t know if it’s 50/50, I don’t know if it’s a precise balance, it’s more of like on a general basis, am I making progress on these things that I’ve identified are important to me?  If yes, I’ll be happy.  If no, I won’t be.

Tara:  Yeah.  I’m really intrigued that you mentioned kind of it being values-driven.  What are some of the values that you put, that you prioritize in your business and the way you work?

Chris:  I would say the, you know, the number two, the number one and number two values, and they’re interconnected, is these questions that I asked myself, like you know, what am I making, what am I creating, and whom am I helping?  Right?  And so it’s like every day, because most of us, like there’s all kinds of stuff that we could do, and the beautiful thing about this kind of creative work is there’s so many opportunities, but the tragedy of this, you know, creative work is that there’s so many opportunities, and how do we choose to focus, and so whenever I become overwhelmed, I try to go to these questions.  Like okay, am I making something, or am I just kind of spinning my wheels?  And if I’m spinning my wheels, I need to get out of that and focus on creating something, you know, that I can identify and point to and have some value for people, and then hopefully, I’m not just doing something that’s self-referential or, you know, self-glorifying, but it’s actually making a difference in people’s lives.  So am I making something?  Am I helping people?  If I’m doing that, that’s great.  If not, I need to adjust.

Tara:  Mm.  So continuing along that thought, every year, you post an annual review to your blog, and I know it’s a really popular post, and you know, it’s less about the kind of income reports that a lot of people put out at the end of the year every month and a lot more about the exact questions that you’re asking and the kinds of goals that you’re setting for yourself, and kind of a check-in on the goals that you did set for yourself and all of that good stuff, and as I was reading over this past year’s annual review to prep for the interview, I saw that you mentioned that you see a big change in online publishing coming, and I would really love to pick your brain on this, because I know what I think I see coming, but I know that you’re in a lot of different areas than I am.  So what is this change that you see coming, and how do you think you’re going to adapt your own approach to ride that wave or to take advantage of it?

Chris:  Well, don’t give me too much credit here.  I don’t think I’m a futurist.  I don’t think I’m like, “Hey, here’s what’s coming.”  I think I’m more of an observer that’s like, “Hey, here’s what’s already arrived.”

Tara:  Yeah.

Chris:  Like, you know what I mean?  Like this has actually happened, and I actually feel like I was kind of late to observe this, and I feel like everything that we have said for years, all of the great advice, you know, at least that I’ve dispensed, I don’t know if it’s as relevant as it once was.  I wrote a manifesto a few years ago called 279 days to overnight success.  It was one of the things I did when I was kind of first building my career, and it was like this case study model of how I, you know, built a sustainable business doing online writing, and so for years and years, like, that’s been out there, and you know, for years and years, I’ve said I think those lessons are still kind of relevant, and now I’m starting to think, like, well, the strategy of connecting with people and creating is still very much, you know, relevant.  That’s never going to change.  But I do think there have been so many changes in online publishing.  I think the thought leader space is incredibly crowded.  Everybody has a message; everybody has something to offer.  I think formats have changed.  I think platforms have changed a lot.  And it’s not just a matter of like, you know, this network is going down and this network is on the rise.  I think, you know, some of the traditional advice, which was, you know, well-meaning and accurate for a long time was all about this like hub and spoke model of like okay, so you got to, you know, built your hub, and like everything else is kind of a, you know, an anchor or something that drives people, you know, to your blog, but you really want to make sure everybody is on your site, and I think that’s still … that’s still great if you can make it work, right?  But you know, I think more and more people are choosing to be deliberate and engaging with platforms directly, and they actually want more of their stuff to be just on Facebook or on Instagram or Snapchat or whatever it is.  I don’t think the specific platform is as important as this overall trend.

Chris Guillebeau on Profit. Power. Pursuit. with Tara Gentile

I think, you know, maybe to kind of sum up what I see as either coming or has arrived, I would say the next big thing is small, and you know, the next big thing is far, far more focused on connecting with maybe not hyper-specific, but you know, much more intentional, smaller groups and going deeper than going broader.  And the thing is, people have said this for years, but I don’t know that they really believed it.  You know what I mean?  Like they were always like, “Oh, it’s far more important to have this small group of people and really focus on them than to like try to build a huge email list or a huge social media following or whatever it is, but in reality, I think most of us were like, oh, yeah, but it’d be really awesome, you know, to have the really big list or the really big social following.  And so you know, even though we said, okay, we’re going to focus small, but you know, our strategy is still kind of big.  I feel more and more and more that the people who are actually going to be successful on a scalable level, like, are intentionally and deliberately focused on that small group to the exclusion of anything else.  And that’s something I think you’ve done really well.  That’s something I see a few other people doing well, but I think a lot of people are still kind of behind.  A lot of people are using tactics that, you know, may have worked five years ago, but not necessarily going to work now, you know?

It’s like … I’ll tell you a quick story, and if this is going on too much, just tell me.

Tara:  No, it’s great.

Chris:  But when I first started, you know, online business, like so long ago, it’s like 17 years or something, you know, there was this new website called  I went on, and I could like buy and sell, and it was a seller’s market at the time.  At the time, when EBay first got started, you could go to the store and buy things, and then put them on EBay, and people would pay more for it because it was like this new thing.  It was like, “Wow, I’m buying stuff on the internet.  Isn’t that cool?”  You know?  So that was fun, obviously, but it didn’t last because it’s a gold rush, you know.  It’s like this arbitrage thing that happens when something is new.

So the same thing has been true in online publishing, internet marketing, whatever you want to call it.  A number of years ago, you could, like, I’ll write an eBook, and I’ll write an eBook on, you know, I don’t know, how to clean my house better or something, and everybody will, you know, spend $100 on it.  That doesn’t work anymore.  You know.  I think things have changed so much because everybody has an eBook, everybody has a course, blah, blah, blah.  So I have a lot more thoughts, but I just talked for like three minutes, so I’ll stop now.

Tara:  No, I loved it.  Well, okay, so that got me … Actually, let me back up.  I love what you said about how people are being intentional about spreading their content out in a lot of different, or maybe not a lot of different places, but several different places now where they’re not putting quite as much value on the hub, although I do think people are still putting a lot of value on email lists, it’s less about the particular place people are going as long as there’s some way for them to get back on their email list eventually, but they’re putting content on Medium or they’re putting content on Facebook, and that doesn’t seem to be letting up at any time soon.

Chris:  Sure.  Sure. 

Tara:  But I also really liked and appreciated the way you talked about going small and how that’s going to help people create stronger connections with the people that they’re looking to serve, but I also think, as you kind of alluded to, that this idea of passive income, or at the very least, leveraged income is so attractive that people keep getting off-track with this idea of going small.  So could you talk a little bit about what you might see the relationship being between a small, focused, highly-engaged audience and this desire for passive or leveraged income?

Chris:  I think, I mean, this just relates to a classic, you know, business idea of what problem are you trying to solve, and I think a lot of people who are starting out now really don’t have a clear answer for that, and it’s probably our fault, the people who have been around for a while, you know.  I would say it’s our fault because, like, we didn’t necessarily have to have great answers for that many years ago.  I mean, we could, obviously, like, we could still focus on solutions, and focus on being helpful and genuine.  I don’t think it was, you know, fraudulent or something, but you know, I do think it was much broader and much more scattered, and I think, you know, the people who are successful now, whether it’s smaller pockets or bigger pockets, they really do have a clear and specific answer for that, and they’re not trying to be like this big thought leader, you know this online celebrity or whatever.  I mean, some people with really small email lists or social media followings or whatever can do very, very well.  You know, as you know.  I mean, you know lots of folks with stories and examples like that, whereas, you know, there’s many people who have very large followings who are actually struggling a bit, or not nearly as successful as you might expect them to be, and I mean, just a quick point on the email list, it’s like I totally agree that an email list is super, super valuable.  It’s one of those things where, yeah, if you could do only one thing, sure that’s great, but I also think we have to be mindful of giving people what they want, and I think what people want is changing quite a bit, and not everybody wants to give you their email, you know, sadly.  It’s kind of like the way I think about Facebook, because for years, I didn’t really like Facebook very much, and I was just kind of like Facebook is not my platform, I’m just not going to go there.  What I kind of realized over time was it’s not really about me, you know?  Because if my community, if a lot of people in my audience or whatever, if they like Facebook, then that’s where I should be.  You know, I have to find, I have to like adjust because it’s not like, you know, going to my readers and saying, hey, readers, like stop, stop, you know, this behavior or this pattern that you like.  You know, come and join my email list, right?  And so what’s interesting is you can look at lots of people who’ve been very, very successful, you know, just building businesses on social, which I understand is completely the opposite of the advice, you know, that we’ve given to people over the years, and I have, too.

Think about something just briefly before we go on, like Humans of New York.  I would say probably everybody listening to this is familiar with Humans of New York.  If not, obviously, go and look it up.  This guy has, you know, millions and millions of followers.  Does he even have a website?  I don’t know.  I mean, I guess he probably does, but I would say 99, you know, percent plus people, you know, have become familiar with this project and become passionate fans of this project simply through the stories that he shared through social.  So it’s a totally tricky thing because I guess it relates to where we started, it’s a whole new world, and it’s not like everybody should like shut down their website and their email list, but I think people should pay attention, because, you know, change is coming, change has already arrived, and the people who went are the ones who are aware of that and can adjust going forward.

Tara:  Yeah.  I love your point about giving people what they want, being very mindful of what people want as well, and I’m sure you can make decisions that work for you in that paradigm as well, but really being intentional about understanding and delivering on what people want, and I’m really glad that you mentioned Facebook, too, because I had totally forgotten about that, but I’ve noticed recently, maybe within the last four or five months how much your Facebook strategy has completely changed.

Chris:  Yup.

Tara:  Can you give us a little bit more detail on that?

Chris:  Yeah, you’re so kind when you say it completely changed.  You mean, like, all of a sudden I started posting.

Tara:  Yes, that’s what I mean.

Chris:  That was the change of strategy, right?  Before, I had a Facebook page and people could like it, but I didn’t do anything there, and then I had this great idea of like actually posting, you know, to my page.  That was the big insight I had last year.  And you know, historically, I loved Twitter.  Twitter was like, that’s my network.  I’m so … I’m comfortable there.  I like that, you know, but what I noticed was, you know, people were engaging less and responding less, and so that’s when I was like, well, I have to figure out where the people are, and so just as an experiment, I started posting more on Facebook, started seeing much more, much greater responsiveness and engagement, so I just followed them there.  I don’t think the lesson for listeners, necessarily, is Facebook is better than Twitter.  That’s not the point because that’s going to change again in two or three months or six months or whatever.  Again, the lesson is where we started, like give people what they want.  Figure out where they are and go to them, as opposed to saying like here’s where I am, you should come to me.

Tara:  Yeah.  I have done the exact same thing over the last six months.  You know, my whole Twitter life has changed, and I can be sad about that personally, but businesswise, I know the best decision is to go to where my people are, and you know, since realizing that and being very intentional about that, I’ve seen my Facebook following really explode, and I’ve really enjoyed creating content for, specifically for Facebook, but I also really appreciate you saying that you need to give people what they want and go where they want to go, but you know, be intentional about it.  It’s not about following whatever the latest, greatest thing is, it’s about making real decisions for your business.

Chris:  Absolutely.

Tara:  Awesome.  So let’s talk a little bit about the live events that you have been hosting for the past five years.  I’ve told you before that I was at the very first World Domination Summit, and it literally changed my life.  I am so thankful for that experience and the people that I met there.  I am still just a such … I mean, they’re my best friends in the whole world.

Chris:  That’s awesome.

Tara:  Yeah.  So hosting live events has really become a big part of your brand.  It’s something that a lot of people know you for.  Perhaps as much or more so than travel hacking.  So what do live events help you accomplish in your business because I bet it’s not profit?

Chris:  Well, you just said it.  Your kind introduction there of talking about how you came to WDS and it, you know, connected you with greater people, and you know, it’s something that you remembered, and of course, you’ve been part of our stuff for years, which is great.  I think that’s why I do it.  That’s the motivation.  You know, and the motivation for everything I do is to have some sort of impact, and you know, hopefully to, you know, maybe not necessarily be a catalyst in people’s lives, because I think people come to my work when they’re already in a place of like being pro-change or wanting to do something different or wanting to follow a dream or just looking for greater support, but hopefully being like an amplifier to that, and being able to say like, oh, that’s awesome that you’re doing that.  You know, here’s some other people that are also doing awesome things, and you’re not alone and let’s support one another.  So I think that’s very powerful, and it’s not completely like a selfless thing.  It’s not sacrificial.  I benefit from it, too.  I really, really enjoy it.  You know this process of hearing stories like that, so that’s why I do it.

Tara:  Got you.  So I’m going to ask you a selfish question now.

Chris:  Okay.

Tara:  Which is I’m putting on my first event in April, and I would love to know if you had one piece of advice to give me about putting on a live event, what would that be?

Chris:  Hmm, well, one piece of advice, okay.  Yeah, it’s just the problem … the problem is being succinct.

Tara:  Well, I’ve already hired Isaac, so that part is covered.

Chris:  Okay.  That’s good.

Tara:  So something else.

Chris:  Okay, okay.  No, I mean, you’re in good hands with Isaac, of course.  I would say that one thing, maybe, like you kind of touched on is like to really be clear on what your intention and goal for it is, and I’m sure you’ve done that.  You know, you’ve been to many events.  I mean, you’ve spoken at many events, you’ve been on teams for events, so I think you understand, like, what you hope to get out of it, and you understand that it’s probably not profit, or at least that’s not the primary goal.  If you have some kind of, you know, mission-driven focus for it, then I think that’s great.  If you can challenge your attendees in some way, I think that’s also great, you know, leave them wanting more, but of course, you know, try to excel in everything you do.  I’m sure it’ll be great.

Tara:  Wonderful.  Thank you so much.  So let’s talk a little bit more about World Domination Summit for a minute because you’ve made the decision after five years to change up the format in a really big way.  Can you tell us a little bit more about that and why you made that decision?

Chris:  Yeah, so I announced this at last year’s event, and I don’t think I did a very good job, because ever since then, people have been asking about it, and what people are saying is like, oh, you’re making the event smaller, and that’s not necessarily what I was trying to accomplish.  What we’re doing is we are kind of scaling the mainstage component of the event back, which is the weekend focus of like a, you know, Friday to Sunday.  That is going to only 1000 people now instead of 3000 where it’s been the past three years, but then we’re also expanding everything else that happens throughout the week, and so we’re moving to more of like a week-long total experience where I actually hope that we can serve, I don’t know, 3000-5000 people this year probably, but then for the, you know, the immersive portion, we are focusing on a smaller audience.  So it’s kind of a two-prong strategy to better serve the people who are like yes, I want to be fully immersed, you know, I want this kind of special, you know, special high-touch experience, but then also serving people who aren’t able to come to that or who just want to kind of connect with other people but actually formalizing that process so that they have a way to do that.

Tara:  Again, you’re giving people what they want, right?

Chris:  We’ll see.  We’ll find out.

Tara:  All right.  So you’ve got a new book coming out that should be out I think right about when we’re going to be releasing this episode.

Chris:  Awesome.

Tara:  And the book is called Born for This, right?

Chris:  That is correct.  Yeah.  New book is to help people find the work they were meant to do, and this is the culmination of many years of research with all kinds of people who have forged or created unconventional careers, and I found a lot of people who use phrases like I feel like I won the career lottery, you know?  I love what I do, I can’t believe I get paid for this, you know, I would do it for free, but you know, I actually do get paid for it, so that’s even better.  So how did those people, you know, find that work, how did they create it, whether they’re entrepreneurs or whether they think entrepreneurially, but you know, find their best path within a corporate structure or some kind of organization.  Like my mom, for example, was a rocket scientist for NASA.

Tara:  I didn’t know that.

Chris:  Yeah.  Fun fact.  And if you want to be a rocket scientist, you’re not really freelance most of the time.  You know, most of them work for somebody, and I talked to the first female firefighter in Mississauga, Ontario.  She’s one of my case studies for the book, and so the same kind of story there is like okay, if you want to be a firefighter, like, you have to, you know, do that with other people.  So how do these people like find that work, what lessons do they have that they can offer, and how can readers, you know, find the work they were meant to do.  So I’m excited about that.

Tara:  Brilliant.  I’m excited about that, too.  So beyond the book, what’s next for you?

Chris:  Well, the book is a big thing right now, because just as it’s out, I’m going on the road.  I’m doing thirty cities.  Would love to have, would love to meet up with people.  If you go to, you can get free tickets to any number of events.  That’s about a two to three-month process, then we go into the new WDS, then I hope to just keep doing what I’m doing.  I hope to keep traveling, I hope to keep writing, I hope to keep connecting with people and learning, changing it up as we go, because as we’ve discussed, change is the only constant, but again, I feel very fortunate, so I hope I can keep doing it.

Tara:  When, specifically, is the book coming out?

Chris:  April 5.

Tara:  Love it.  Chris Guillebeau, thank you so much for joining me.

Chris:  Thank you so much.

Tara:  Chris’s CreativeLive Bootcamp, Make Your Dream Trip a Reality can be found by going to 

On the next episode, we’ll sit down with Natalie McNeal, author of She Takes on the World and the Conquer Kit.  We went behind the scenes on how she plans her year, grows her email list, and works with her team.  Don’t miss it. 

That’s a wrap for this week’s episode of Profit. Power. Pursuit. CreativeLive podcast.  Download more episodes of this podcast and subscribe on iTunes.  If you appreciate this kind of in-depth content, please leave us a review or share this podcast with a friend.  It means the world to us.

Our theme song was written by Daniel Peterson, who also edited this episode.  Our audio engineer was Kellen Shemezu.  This episode was produced by Elizabeth Madariaga.  You can catch up on older episodes in the iTunes store, where new episodes are added every week, and learn more by going to

The 3 Kinds of Work (including 2 you should be doing less of)

There are three kinds of work you do a regular basis.

First, there’s work that gets immediate results. It might be actually delivering the service you provide or creating the product you sell. It could be writing on your blog or updating product descriptions. It could be ordering supplies or promoting your work.

Second, there’s work that should be done by someone else. This varies depending on your business and your strengths within that business. It could be fiddling with your website, sending out emails, or scheduling clients. It could be writing copy or creating advertisements. It could be shipping packages or bookkeeping.

Third, there’s the work that contributes to long-term growth. Often this is work that requires your expertise but that isn’t the hands-on work that you sell. It’s systems work. It’s process work. It’s relationship building. It’s working on the vision (and the byproducts of it).

You probably do a lot of the first and second kind of work. You are constantly after immediate results (they feel good, right?) because immediate results are better than no results. And you do a lot of work that you really have no business doing because you have chosen not to invest the time or money in having someone else do it.

That means that the work that contributes to long-term growth gets the short shrift. When you don’t work towards the future, you leave yourself in the hamster wheel of constant hustling. Sound familiar?

…while you’re doing it, doing it, doing it, there’s something much more important that isn’t getting done. And it’s the work you’re not doing, the strategic work, the entrepreneurial work, that will lead your business forward, that will give you the life you’ve not yet known.
— Michael E Gerber, The E-Myth Revisited

If you’re beginning to lose faith in the dream of having a business that takes care of you (instead of you taking care of it), then it’s probably because you find yourself doing so much of the first two categories of work. When that type of work is disproportionate to the results you see, frustration is the natural byproduct.

When you exercise your responsibility to long-term growth work, even if you’re not seeing immediate results, you can better weather the ups and downs of entrepreneurship. If a particular idea doesn’t work out, you have the systems or relationships in place to get you through. Or you have the comfort of knowing your next idea or opportunity is already in the works.

If you’re ready to do more long-term growth work and less of the rest, you need to schedule it. Put it on the calendar. Honor it like it was a client appointment or a project deadline. This is the work that will keep your business in business – respect it.

Once you’ve got that kind of work on the calendar, make sure that you’re creating systems that reduce the amount of other work you’re doing. Use your scheduled time to create a training or on-boarding process for an assistant or business manager. Also use that time to plan for new products or services that require less effort or active time from you. Plan to shift your business model to one that leverages your time & talents.

Bottom line: how would you spend your time if doing work that contributed to long-term business growth was your primary responsibility?

‘Cause it is.

— PS —

Kick Start Labs designed a brand-new Lab to help you get out of this rut and into strategic product development. It’s call Product Development 101. It’s available for a limited time on its own or as part of a Kick Start Labs membership. Click here for more info.

Busyness is the enemy of business.

The road from follow-your-passion to thriving business can be a bumpy one. Once you realize “if you build it, they will come” isn’t a business strategy, it’s tempting to spend every waking hour tweaking, writing, emailing, networking, and trying to push through.

“…while you’re doing it, doing it, doing it, there’s something much more important that isn’t getting done.”
— Michael E Gerber, The E-Myth Revisited

Busyness isn’t business.

Don’t confuse the two. You can work until you’re blue in the face and still not succeed. That’s not to say that hard work doesn’t or won’t pay off. But is what you’re spending your day doing really getting you one (or better, a few) steps ahead? Are your daily actions tuned to the goal you’ve set in front of you?

Check yourself.

Your goal can’t be to work yourself to the bone. The sense of accomplishment you’ve been missing won’t come from just checking tasks off a list.

What you’re missing is progress, the sense that what you’re doing matters in the larger scheme of things.

Being busy doesn’t level the learning curve. Being busy doesn’t create ease. Being busy doesn’t create satisfaction.

Know where you want to go and create a plan to get there. Remove any and all unnecessary tasks and busy work. Take time off, explore, enjoy.

Have faith that your plan will take time and that doesn’t mean that you have to fill it with work that is meaningless.