Work Wherever & Whenever You Want - Digital Nomad Lifestyle

Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Loren Ross, Founder of Digital Nomad Lifestyle, located in Denver, CO, USA.

What's your business, and who are your customers?

My business is a travel brand targeted to inspire and assist people who want to build their careers while traveling the world. My customers are people who don't fit into the traditional mold of working your way up a company for years, taking 1-2 weeks off per year for a short trip to Mexico, then enjoying the world after retirement. They also don't fit in the group of people who quit their jobs and wander around on savings or money from their parents.

Digital Nomad Lifestyle is for people who want to see the world and experience life in its fullness while creating a lifestyle & career that fulfills them mentally, spiritually, and financially. They recognize that they don't have to choose between traveling the world and creating a meaningful career or making money. They suspect you can do both, and they come to me for inspiration and tips on making that happen.

Tell us about yourself

I was sleeping on my buddy's couch with no job, money, car, or real career prospects. I had just returned from teaching English for a year in Vietnam, and it would be reasonable to say I was a loser. At that point, I was 25 years old, and while I had left the US multiple times only to come back and rebuild my life, at 25, that game wasn't so fun for me anymore. I finally found a job cleaning construction floors for money (money I never got paid, by the way). The last morning at that job, I recall playing basketball with my boss early in the morning. The reason we were playing basketball was that he needed to do some exercise to sober up enough to drive the truck. I could see my future in his face. He had been enjoying life for a long time, and in his late 30s, still hadn't realized that no one was left at the party but him. My desire for novelty and excitement may not have led me to alcoholism, but I could see how I could live in a sort of Peter Pan world like him. Never fully taking responsibility for my life, constantly chasing the next exciting thing, and working random dead-end gigs where I could barely afford to pay my bills. That morning when he sobered up enough to get to the job site, I made a choice. I wasn't going to leave that construction site until I found a career and a direction in life.

I must've gone through 20 different jobs throughout that 8-10 hours of sweeping the floor. Fireman, construction management, psychologist. But the job I kept coming back to was marketing. I had always been interested in psychology and persuasion but was too idealistic in college to really pursue marketing; it didn't seem like a meaningful enough job back then. When I left that worksite I decided I would do whatever it took to become a marketer. It was a long, arduous process, but a year and a half later, after doing marketing for free for businesses, I bartender at I finally landed an internship at a marketing firm in downtown Denver. I dressed nicer than anyone else in that office. I was committed to becoming a successful businessman, driving X car, and wearing X types of pants and shirts. After some time at that firm, they weren't promoting me quickly enough, so I had to leave. After all, how am I supposed to become a successful businessman if I keep the same job title for over a year? So I found a larger firm that would give me the job title and salary I felt I deserved. I was on my way! This firm was much bigger; they had much sexier services, solutions, and clients. However, a couple of months after that job, I recall spending my lunch break in my car frantically trying to find a way out. I would think and think about how I could fix the way I felt at that job, but no amount of thinking could fix it.

The job felt soulless; my heart wasn't in it. My heart didn't want to continue working that job regardless of what social status came with it. My heart wanted freedom, wanted choice, wanted to be able to fully express myself, and I couldn't do that at a traditional office job. Then one day, my manager came to me to have a chat. It was a Friday, and I thought that meant the dress code was casual, so I wore an obnoxiously tight and bright Hawaiian T-Shirt. She told me that if I continued wearing that T-Shirt, I would lose my job, and she mentioned that my heart was re-invigorated! This is a sign! Whoever is running this world or universe is telling me it's time for me to go, man! So I put in my notice and started working at Uber while building my business. I would work on my business during the day and Uber at night. I worked harder, which was much more difficult than my previous job, but I felt so alive that it didn't matter. Even today, I can feel the excitement creeping up in my chest when I reminisce on those days. I had a clear purpose, I was broke, but dammit, I was free!

That was three and a half years ago, and due to a lot of help from people in my network and a lot of luck, I now make more money than I would've if I had stayed at that 2nd firm. While I had setbacks like anyone, I recognize the amount of advantages I had being born in the US as a white man and having a mom as supportive and incredible as she is. That being said, I know most people can do what I did if they're honest with themselves about really wanting to do it. For more info on this, check out my about page.

What's your biggest accomplishment as a business owner?

Making enough money to invite my Mom on a 5-month trip around Europe and the Caribbean.

What's one of the hardest things that comes with being a business owner?

Self-Discipline, it's not like weight training, where you can retain your strength from day to day. In my experience, self-discipline is very hard to build and incredibly easy to lose, and it feels like you start from zero every morning.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

Take time to understand what you really want, vision boarding, therapy, talking with friends about it, journalling spending time alone. Figure out what you really want and the lifestyle you really want, then build a career around that. If you don't do that, you'll find yourself stuck in a new, more shiny set of shackles, maybe nicer shackles than before but shackles nonetheless.
The people I know with the most followers on Social media tend to make the least amount of money. So be careful who you listen to, including me, and figure out what YOU want, then you can't be sold bullshit from other people.
细水长流 - this is a Chinese saying. Small streams run long. You're gonna make mistakes, have lazy days, lose lots of money, waste lots of money, fuck up in everyday imaginable, but keep moving even a millimeter a day toward your goal for your life, and it will all work out.

Where can people find you and your business?

Website: https://digitalnomadlifestyle.com/
Facebook: https://www.facebook.com/groups/327920982044468
Instagram: https://www.instagram.com/officialdigitalnomadlifestyle/
LinkedIn: https://www.linkedin.com/in/loren-ross-356a03123/

If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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