Chris Englert: “Create a business out of your three favorite things”

When the hobby starts becoming the business, step back and really have gratitude that you get to do what others only dream about. Be sure to continue to do your hobby as your hobby. Once you understand how to monetize your hobby, it’s easy to forget to just enjoy it. So every once in a […]

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When the hobby starts becoming the business, step back and really have gratitude that you get to do what others only dream about. Be sure to continue to do your hobby as your hobby. Once you understand how to monetize your hobby, it’s easy to forget to just enjoy it. So every once in a while, do your hobby just for the sake of the hobby and don’t monetize that particular instance of it. Just enjoy it for the hobby of it. You don’t have to make money every time you do it.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Chris Englert, Head Motivator for Eat Walk Learn. Knowing that her successful corporate career in Higher Ed publishing was coming to an end, Chris turned inward and rediscovered her sense of adventure and love for writing. She pulled out a map of the city of Denver’s trail system and asked an innocent question, “Where do the trails go?” Then she started walking, urban hiking and hiking Denver’s regional trail system, discovering the amazing parks, interesting neighborhoods, and fascinating trails within the City of Denver. She then broadened that question to the great walks and hikes of the world. Four years later, she has published the number one urban hiking book and number one parks book in Denver, owns two blogs, leads global walking tours, circumnavigates the world, and speaks at outdoor functions globally.

Thank you so much for doing this with us Chris! Can you tell us a bit about your “childhood backstory”?

I grew up in Del Mar, California, where my parents made me walk to the bus every morning to go to school. This daily ½-mile ritual cleared my mind and became a habit I grew throughout my life. Daily morning walks helped me embrace boarding school in the foothills of Arizona and by the time I graduated from the University of California at San Diego, those walks had turned into local hikes in Torrey Pines State Park. (Fat Man’s Misery, anyone?) These hikes turned urban in New York while I attended grad school at Columbia University and have forever helped motivate my days and goals.

While growing up, my parents cajoled my sister and me into the backseat of the family car for our annual summer vacation. We’d speed through each state as fast as Dad could drive to get to our destination, only to turn around quickly to get home late Sunday night for work two weeks later. Mom and Dad felt we should see the U.S. first before we ventured internationally. By 12, I had seen 35 states. I picked up the rest on my own through personal and business travel, eventually breaking out to the rest of the world at 17. Since then, I’ve enjoyed 53 countries and now I’m revisiting the 50 states in my #50hikes50states projects. My hand-written travel journals span my entire lifetime, refreshing my memory throughout my life.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I knew my career in higher ed publishing was coming to an end. It had been a good 20-year run, but the industry was changing, and downsizing sizzled through the company. Being an avid traveler throughout my life, I had started a blog a few years prior about my travels for my family to read and follow along. With my departure from corporate life looming, I was literally sitting on the couch in my living room looking at a trail map in Denver, where I had only recently moved. I asked the questions, “I wonder where these trails go?” and then the immediate question and ah-ha movement afterward was, “Who else would want to know?” Those two questions immediately got me digging into the internet to find two things: no local info about Denver trails and several organizations that would want to know and share what I discovered. I knew that I could provide them what we both wanted through my blog.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I honestly didn’t know I was starting a business when I stepped out to my first trail. I did think I was onto something though when one of the businesses I had reached out to about my discovery idea offered me a GoPro for free. While walking, I started to see what I could say and who would be interested. It certainly wasn’t a straight line from that question to four published books, two blogs and worldwide adventures, but it was the beginning of a new career creating content about walking in the outdoors.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

When the hobby starts becoming the business, step back and really have gratitude that you get to do what others only dream about. Be sure to continue to do your hobby as your hobby. Once you understand how to monetize your hobby, it’s easy to forget to just enjoy it. So every once in a while, do your hobby just for the sake of the hobby and don’t monetize that particular instance of it. Just enjoy it for the hobby of it. You don’t have to make money every time you do it.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I particularly set aside hikes and trips that are mine alone. They aren’t for the business, my followers, or my customers. I go out and just hike or travel, leaving the business behind for the day. On these hikes and trips is when the fresh ideas pop up.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I love it when someone sends me a message from the trail about how much fun they’re having. They’ll post a great picture of the view or of themselves and tag the post with #denverbyfoot or #50hikes50states. It makes my day. The downsides of running a digital business is that sometimes I feel like I’m banging out content that is fantastic yet I don’t hear a word from anyone about it. But honestly, I know deep down that my content is good. It’s what I want to read, and it’s what makes people happy and successful being on foot in Denver or enjoying a walking vacation somewhere in the world. They may not tell me in the written word, but they’ll tell me in person when I eventually run into them on a trail or in a park.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I don’t think it’s a job. It’s just how I live. That’s the difference.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?


Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was first starting and looking for people to sponsor me somehow, I really didn’t understand what my business model would be. I made a cold call on an Executive Director, pitching what I thought she’d be interested in. She flat out said no. But thank god she was kind and also just starting her organization. She sat back a second and told me she liked my idea but that it was the wrong application.

We continued to talk and went for a walk.

And relaxed.

I began listening, for the first time. It was then that we came together and formulated the service that I could provide for her that she’d be willing to pay for. From that meeting, I’ve been able to multiply that offering out to other organizations and it has become the center of my service offerings.

Who has inspired or continues to inspire you to be a great leader? Why?

It’s not so much an individual that inspires me. It’s the feedback I get from my community. They look to me to offer up suggestions for how to enjoy Denver by foot or how to create a walking vacation in the world. They trust that my suggestions will produce high quality and value for them. It’s their feedback that inspires me to take on more projects like my current project, #50hikes50states, where I’m hiking one hike in each state. The stories I write from those adventures inspire people to get out and do their own adventures, which in turn inspires me to keep going.

How have you used your success to make the world a better place?

When people get out of their comfort zone, their cubicles, and their cars, and they get on their feet out into the air, they become better people. They say hi to strangers. Buy others coffee. Yield to traffic. I like to think my information gets them to put on their shoes and get outside. And that’s what makes the world a better place.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Listen to your gut. When I first flirted with the idea that I could make money by walking and hiking, people simply didn’t think it was possible. But I kept digging.
  2. Create a business out of your three favorite things. This is how I named my company. I love to eat, I love to walk, and I love to learn. The url for was already taken by some guy in Canada. He wanted 100 dollars for the domain, and I thought that was ridiculous and told him so. He was completely offended and told me to take a hike. I was stuck and I had to realize what an ass I had been. So I wrote him again, apologizing for my rudeness, and told him my story. Thankfully, he relented and sold me the domain. It was the best humble pie I ever had to eat.
  3. Do keyword search. When I first started my blog, I had no idea what keywords were. I renamed my blog based on my three words that were relevant to me to, but still hadn’t done any keyword search. It wasn’t until three years later that I hired someone to do some analysis for me that I realized that a good part of my traffic was people looking for hiking in Denver. I spun off a second blog,, which has niched into the heart of Denver. If I had looked at my earlier, I could have saved myself a lot of heartache and wasted content.
  4. Get a media release. I have thousands of pictures filled with people that I can use at any time because I ask them to sign a media release whenever they walk with me. I do remain sensitive to them though, and I would never use a person’s image for paid advertising unless I had personally asked them directly. I want folks to trust that I’d never abuse the privilege of getting their permission.
  5. Pet your dog. Sometimes I’ll get so wrapped up in producing content, I’ll forget to do my own self-care. Luckily, my dog knows when it’s 3:00 and time to take me for a walk. These are the best times of the day.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I’d love to take 1% of all the money used to build roads and infrastructure that’s designed to eliminate traffic and reward people for getting out of their cars and onto their feet. It’s not sitting that is the new cancer, it’s driving.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

When I was struggling to pay my way through college, my dad said to me, “You can live in your car but you can’t drive your house.” He wasn’t advocating that I live in my car. He was creatively telling me to think about how I spend money and to do it wisely. That’s still how I think today. If I have a dollar, what’s the best way to spend it and to get it to work twice as hard?

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Rose Marcario of Patagonia rocks my thoughts daily. She’s taken a giant brand and made it responsible for improving the world everyday. I’d love to partner with her to make Denver be the leader in outdoor stewardship and inner happiness, one person at a time.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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