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Ep: 190: How this productivity strategist helps online entrepreneurs avoid the burnout with Erin Elizabeth Wells

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In this episode, I speak with Erin Elizabeth Wells who is The Intentionality Expert and founder of Chosen Course. 

She works with location-independent entrepreneurs to stop the borderline burnout, 24/7 overworking hustle, and start creating scalable, business, and productivity systems so they can enjoy their freedom-loving lifestyle.

Listen on to find out how Erin has been able to help remote entrepreneurs become more productive while enjoying their freedom.

Listen Below:


Ep: 189: How this Ex Corporate Executive left his 9-5 to do a social experiment as a homeless man traveling the world with Mark Philpott

My Offbeat Journey: The Morning Routine

Ep: 188: How this former teacher became a successful remote photographer with Jennifer Brazeal



Hey everyone! Thank you so much for being here. I am so excited to be speaking with my guest today. Hey Erin, how are you? 


Hey, Debbie! I’m great. How are you? 


I am wonderful. Can you tell us about you and why you live an offbeat life? 


Absolutely. So I have been living an offbeat life, I would say, for many years but really for the last year-and-a-half, my husband and I decided that we were going to finally take the plunge that we had dreamed about since we were first dating and become a full-time digital nomad family.

I had traveled a fair amount when I was younger: when I was a kid and in college and all of those kinds of experiences. I took a long four-months wander through Europe while I was in college. Basically, right after my junior, a  year abroad. 

And I always knew that I love to travel. That was something important to me and those things that start showing up on, what most people call, a bucket list. I tend to prefer the term life list, a little more focus on life as opposed to death. All these items about spending three months here and spend three months there in this country, in that country, on this island, and that location.

And finally, after he and I had talked about that for many many years, we decided that there was no time like the present. And so in October of 2018, we gave away and sold everything we owned and we have been exploring around now for the last year-and-a-half. 

At the moment we are currently restricted to staying in the United States which is kind of sad in my opinion because of my husband’s corporate job. He works remotely for a US-based business and they do require us to stay in the United States. 

But it’s a huge country and there are many many areas of it that I had never had an opportunity to really visit and spend a lot of time in. So at the moment, we are US-based but once we can retire him from that corporate job, I already have my list of all of the amazing places we will be heading off to next.

We travel the country at the moment in our little Mazda 6. No RVs for us. We stay in furnished rentals and usually in any place for 3-4 months at a time. Actually, we’re currently in Santa Fe, New Mexico for just one more week. 

This is the longest place we stayed in. We’ve been here for almost six months now because unsurprisingly the land of quarantine, covid, and such.


Yeah. But surprisingly for most remote entrepreneurs, this has not really done too much to their lifestyle. I mean, it obviously stops us from traveling but other than that we still make money. We still do pretty much what we’ve done before and a lot of us always stay indoors anyway.

I love that we stay indoors. I mean, we work from home so yeah, in some ways we have been blessed and not be nearly as dramatically affected as many other families. I do recognize and honor my privilege in that and that’s huge. 

We haven’t taken any massive financial hits, it’s a lifestyle more than anything. We haven’t been able to go to all of the museums we would have liked to go to while we’re here. For anybody who’s ever visited Santa Fe in New Mexico, there’s this really awesome place called Meow Wolf which is like an interactive, live alternate reality, art installation, art experience.

We had gotten our memberships figuring we would go pretty darn frequently and halfway through our visit here, actually a little less than halfway through a visit, everything shut down. So we haven’t been able to go and have those kinds of adventures and those kinds of fun but we do what we have to do. 

We take care of ourselves. We take care of our community. We wear our masks and we keep on with our lives in the best way that we can.


And thankfully things are starting to open up. So this is definitely not something that’s too long term and we can get back to our semi-normal life hopefully sooner rather than later.


We’re planning our next road trip. We’re actually leaving one week from today, literally. So probably by the time this goes live, it already has happened. We were supposed to be leaving Santa Fe at the end of April and we were going to be flying back across the country to visit friends and family in New England leaving our car behind for a few weeks. 

And obviously, that trip got canceled and so we just decided to stay and extend. But we are leaving next Friday and heading on a road trip up through the Rocky Mountains to Yellowstone National Park and Grand Tetons before we start heading west because we’re going to be spending the rest of the summer and fall in Portland, Oregon.


So many beautiful things that you can do and it’s pretty much doable as long as you can get this going, right? 

Now, how were you able to start becoming a remote worker, remote entrepreneur, Erin, and really start to make this come to life, this life that you want?


So my story begins back when I was actually in graduate school and I started my first business which was called Living Peace Professional Organizing when I was 23 and still in graduate school. 

And that was a definitively hands-on, non-location Independence. Very much you have to show up and go to your clients’ home or workspace and you’re digging through their stuff. It was professional organizing. A lot of people are familiar with Marie Kondo – that kind of staff.

Basically, I was doing that work long before anybody ever heard of Marie Kondo and it was wonderful and lovely and I loved doing it. And then after a few years, I was fully booked and I realized that either I was going to have to start turning clients away or I was going to have to grow.

And so I made a decision to grow that business and I hired on other organizers. First as contractors and then as employees and I started to grow my team. And I, in fact, grew one of the largest organizing firms in New England over the course of the next several years.

Soon after that point in time, basically, I started pulling myself out of doing the hands-on and having my team members basically doing most of the client work. So I was responsible for marketing and growing the business and they were responsible for delivering services.

And it was somewhere right around that point when I began to realize that I really didn’t want to run a local service business. I really did want to be able to do work I love, that I was passionate about but be able to do it from anywhere in the world. 

And that was kind of the beginning of my realizing that I needed to figure out a different way. 

Long story short: over the next several years, I began to realize that my personal passion was beyond what I referred to as tangible organizing – moving around stuff in someone’s place and more into the intangible organizing. 

How do we organize our information? Our plans are decision-making. How do we prioritize? How do we get clear on what is most important to us and make sure we stay focused on that and take action on that on a regular basis?

And blessedly, since I was shifting my attention to intangible organizing, that makes going online a heck of a lot easier. Because, essentially, what ends up happening was I started my second business concurrent. I was still running my original company Living Peace but I started my business Chosen Course back in 2011, we’re almost at my 10-year mark on that one.

Initially, I was primarily working with corporations. So I was doing corporate consulting, corporate training, primarily working with C-level Executives and doing productivity work with C-level Executives from Fortune 500 companies and beyond. 

And that was really fun and really engaging but also often meant that I was still hopping on a plane to fly out to a particular client site to do an all-day intensive with one of my corporate clients or to do a training for their team. 

There’s a point in time at which flying persistently to Cedar Rapids, Iowa is not necessarily your favorite thing to do and particularly because my husband and I decided we wanted to start our family. I knew I didn’t want to have to be hopping on planes to get paid. 

And so that was when I decided it was time to shift entirely and basically stop it with any of the in-person work even if it was travel-related, which was fun for a while and then exhausting, and instead really focus on what I knew best which was entrepreneurs.

By that point in time, I’ve been an entrepreneur for, my God, decade-plus and now I’m at 17 years that I’ve been running my businesses. 

So I realized the best thing I could do was serve the people I knew best and really support entrepreneurs in building their personal productivity and the business systems that allow them to make running a business easier, that allow them to get the things off their plate that aren’t the best use of their time and skills. 

So that was essentially that’s the final piece that fell into place. And then when we became location independent almost a year and a half ago, almost two years now, that was when I decided to niche even further and really focus on working with other location independent and digital nomad businesses.

Because the needs of these types of online businesses in particular around productivity are somewhat unique. We’re dealing with timezone things in far more dramatic ways. Many of us are running fully remote companies where we’re managing teams of people that are spread across the globe. 

My team is currently on three different continents and then four different countries. So it’s how do we navigate those kinds of challenges? There’s the whole story bringing us up to today. I was drafting a contract for a new hire literally today. So, here we are.


When you decided to do that pivot where you left your organizing company to solely focus on entrepreneurs and now really niched into digital entrepreneurs, remote entrepreneurs, how were you able to land your first few clients? because that’s really one of the big questions a lot of newbies ask, right? How do I make income from this? And how do I make this sustainable? 


Sure, absolutely. Well, I have used so many different strategies over the years because at 17 years, you tried a bunch of different things and you see what works. And the answer is all of them work depending. 

So, as I was transitioning out of my organizing business and I did end up selling that business back in 2015, sold it to a colleague, I no longer run it although it does still run and many of the same staff members are still working for it, essentially I realized that they’re kind of two approaches that happen for a lot of people in kind of the remote work, freelance, online entrepreneur space. 

They’re the folks who figure out what they’re good at doing and then they try and figure out how to find a whole bunch of clients doing it which usually involves posting on Upwork and applying for Upwork jobs or any number of those kinds of online remote job database, connection services, that kind of stuff.

I tried that out once or twice. Honestly, I tried it out after my maternity leave ‘cause I was like, “Alright, I really don’t want to fully restart my business,” ‘cause I virtually shut my business down for about 6 months after my daughter was born.

I knew I didn’t want to get full-time back up to speed ‘cause it just wasn’t realistic, that wasn’t what my family needed. And so I decided I’d kind of test things out on Upwork a couple of times. I got a couple of clients. And you know what? Those were not the best relationships on the planet.

Not that you can’t find great employers, great clients, and everything on Upwork but a lot of times you can’t charge the premium prices. And think about it: I was working corporate prior to all of that and my clients were paying five figures for contracts with me. And most of my Upwork clients were like, “You want to charge what?!” 

I did a project with one client for about 3-4 months and then I had another client that I worked with – kind of ongoing consulting basis. But it was not as lucrative as it should have been. 

So the better answer to your question: podcasts are great. I’ve gotten plenty of clients from this kind of conversational, putting yourself out there, and helping people get a sense of who you are and what you can do. 

But more than anything, it’s really about learning the skills in online marketing and learning how to be able to connect with people, solve a problem that they are experiencing and get them interested in why your approach is different than the guy they can hire for $6 an hour on Upwork.

I’m a big fan of Marie Forleo and Amy Porterfield and kind of that whole approach to establishing yourself, establishing your expertise.

The other thing is, I’ve mentioned, my husband works for a US corporation, he actually works for Hubspot, which is an online marketing software company. And part of what they’re known for is what’s, classically now, referred to as inbound marketing. 

It’s how you establish yourself as an expert in something and then show up in enough of those various places that when people are looking for an expert in that, they end up coming across you.

So, personally, I really do believe that that’s a stronger and better approach to getting really quality clients. 


And you’re not constantly chasing, right? It’s more of attracting than chasing. So that is such a great way to be able to put yourself out there and so much better for yourself too in the long run.


Absolutely. No question. 


What are some of the best resources that you’ve used for your business and to make it easier for your tasks and more productive? 


Now that is a huge question, Debbie. Before I go into the answer to that, I have a feeling you’re looking for I need to preface because I personally, in my expertise as a productivity consultant hasn’t done this work for a lot of years, have a very strong opinion about the fact that most people think, “I just need the right app.

If I can just find the right tool. All I need is the right software. If I had the right software then all this would be easier and it would be magically organized.” And I very strongly believe that that is a myth. 

That is something we need to shake off because the reality is that I could tell you about my favorite tools, the coolest tools that I use that I’ve used for a decade or more. But if you don’t have the rest of the system as I say that allows you to use the tool effectively, the tool itself will do nothing for you.

It’s kinda like the classic, people say, “Oh, I need to get organized, go into the physical realm.” This makes so much sense to most people, “I need to get organized. So I just need to go and buy some bins”. 

And then you go to the store and you buy these pretty bins and you toss a bunch of stuff in it, and then you can never find anything because you really are not more organized than you were before. You just hid it all. It’s like, “It’s all in one of these bins, which one of these bins is it?”

Because if you don’t take the time to actually go through the stuff, create clarity about: this belongs here and this belongs here. And you are kind of the organizational system that defines how the bins are working for you. Then it’s not really gonna do much for you, is it?

And the same things are true with our digital systems. So I can tell you, yes, I use Asana, I use Evernote, I use Slack. Those are things that I basically live in on a daily basis. 

Asana is for our project management with my team, Evernote is where we keep a lot of the contents. So like content for video scripts, for blog posts, for email drafts, all of that kind of stuff. That’s where a lot of that gets drafted and organized. And slack is obviously where we manage a lot of our team communication conversations.

You have to have the tool and then, as I say, there are usually three parts to a system. You need the tool, you need the habits, the human behavioral element of how it gets used. And then finally, the piece that most people never even think about is the mindset 

Because if you have beliefs about for instance your ability to stay on top of your tasks. I had a client once who used to say, “My to-do list is a horror.” And she had this personal limiting belief that she could never be on top of her to-do list. 

And until we addressed that, until we kinda dug that out and helped her to overcome and remove, uninstall that limiting belief, there was no system or habits that were going to stick. So it really does take all three: it’s the tool, it’s the habits, and it’s the mindset. That’s what actually makes the difference and that’s part of what I incorporate into my work.


Yeah. And it becomes more sustainable when you are able to start putting all of those things together and for the long term whether you have this business. And then you start something else completely different if you are able to take that with you, it’s always going to work. 


Exactly. I’ve run two different companies now, two different six-figure organizations. And both of them, I used roughly the same kinds of systems that I use now in my current business 10 years ago in my previous business. Little modification here, a little tweak there, slightly different roles.

In my previous business, we had a lot of professional organizers and I was working on helping them manage their client work and those were systems that were important. Now in my current business, I’m doing almost no one-on-one work now. I focus exclusively on my course, which just launched the first time this year.

So now it’s all about marketing and the course delivery and those kinds of things. So my team, the virtual assistant, the copywriter in the graphic design person, the video editor, and all of those kinds of roles. As your team’s roles change, the system will adjust with it but the core functionality and the core structure of it are the same and are basic.


So let’s fast forward to 40 years from now, Erin, and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


Oh, this is such an amazing question and it’s awesome because one of the things that I love to do with my clients is to help them ask this question. And so, my answer is I want to inspire people to live a life with intention. 

I want them to question the norms, the things that have been assumed as this is what success looks like, these are the steps that you just go through: first, I graduate high school and then I go to college and then I get a good job and then I work my way up the corporate ladder and then I get the big house then I get married – all of these things that we were, particularly as Americans, told that I think there is some level of this that extends beyond the US, this is what the good life looks like.

And I have just heard so many people who walk that road and still ended up miserable. And I genuinely believe that the more we ask ourselves questions as early in life as possible, I mean, honestly, whenever you come to the questions is the right time to come to the questions.

These are questions I want my daughter to be asking herself by the time she’s 12, by the time she’s 15. It’s: what do I want in my life, what’s the impact that I want to make. 

My desire to help people both ask and find answers to those questions and then design a life whether that’s building a company for themselves or whether that’s finding a company with which they feel highly aligned and be able to do that work.

We’re a generation where what we can do now has never been possible before. Our ability to work remotely and be able to have the same work wherever we happen to be on the planet. No other generations had this chance.

And we have the ability in doing this and then living this way to essentially become like a beacon that shows others what’s possible. So, my core is about helping people to live with intention and part of that is about asking different and bigger questions. 

And that’s truly what I hope that I will help many, many hundreds and millions of people to do.


Yeah. And it’s also great that you’re trying to teach this to the next generation like your daughter. And then hopefully she’ll also take it with her. So it’s such a great type of legacy, right? Like what you’re giving to your children and the next generation, it’s pretty incredible when that happens.


It really is. That’s why it’s been fascinating to me since becoming a digital nomad and really steeping myself far more into the community of location independent entrepreneurs and digital nomads to realize that there’s kind of almost a separation between what is considered the digital nomad community versus the world schooling community.

Because worldschooling is focused on families and kids. And it’s focused on bringing kids out into the world and giving them a global education. And a lot of digital nomads are single or maybe they’re couples.

And there’s like this division between the two and I would personally love to help bridge that division. Because I see them as just a larger group of people who are questioning the norm and who are figuring out how to live their version of life that feels aligned, authentic, powerful, and purposeful in a very offbeat way.

It’s outside of what kind of the rest of our common culture or mainstream culture tells us is what life needs to look like. For a lot of digital nomads who get into their early twenties, I’ve seen these comments and soul-searching that goes on. It’s like, “Well if I get married and I have kids, I probably have to settle down.” It’s like, “No. You don’t.” Don’t assume that.

Question everything, figure out how to make it work in the way that you want to make it work. I mean, I knew when I met my husband and when I was first starting dating that I wanted to travel to be a big part of our life. And that was something, blessedly, he was very much in agreement with and it’s I think one of the reasons why we clicked.

And even though he hadn’t had as many opportunities to travel as I had, that was a value that we shared. That’s I think what makes our current life possible: to find people who have that shared value and who want to live the offbeat life as you say, Debbie. 


It’s great when you find a partner that shares that same type of value like you were talking about, Erin, because it goes a lot better in life when that happens.


Yeah. I do acknowledge that I think it made it a little easier than at the time we met and we’re dating, I was not yet a digital nomad. We met, we dated, and we have lived together in one place for quite a number of years. We’re coming up on our tenth dating anniversary actually this fall.

We had that time to establish a relationship. And so I have a whole lot of respect for the digital nomads who try and figure out how to both travel and have a committed relationship if their partner can’t travel with them yet. 

I will say however that I did have, prior to meeting my husband, a long-distance relationship for 6 years. So I know it’s possible. Like I know what’s possible even if you, and I would say, come back and hang out with your loved one for a period and then you disappear for a couple of months and then come back – it is possible. 

But yeah, the time helps.


It’s good to see that it actually can be possible by listening to your story, Erin, that we can do this as well. 

So if our listeners want to know more about you, where can they find you? 


Well, you can find me at Otherwise, I’m on IG @chosencourse or on Facebook, same thing, Chosen Course. Find my Facebook page and those are awesome places to connect with me. 

Then, we do a weekly video. You can actually find us on YouTube as well ‘cause now we just started doing our weekly videos which most weeks are focused on productivity-related topics. But once a month, we also do a video of our course update which is basically what we have been up to and where we visited. 

And we’re now doing those in a video format that I’m very excited about. That’s fairly new, I used to do them all written. 

So that’s the best place, best ways to follow my journey, follow our journey, and as well as essentially get some good ideas and guidance about how to improve yours. 


Perfect. Well, thank you so much, Erin, for being here with us and sharing all of these amazing tips with us. We really appreciate you. 


Thank you so much. I’m happy to be here with you Debbie.

Listen to Erin’s extended interview where she shares how to move from freelancer to entrepreneur.

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Show Credits:

Audio Engineer: Ben Smith

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