Digital Nomad Lifestyle: “Pursue it all-out.” An interview with Ryan Chaffin.

This week I had the privilege of interviewing Ryan Chaffin, a digital marketing consultant with 15+ of experience advising clients from small businesses to personal brands and large tech companies. Ryan recently launched a new digital marketing agency (KAHA) focused on helping small businesses across America during these unprecedented times. Ryan has dedicated himself to […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

This week I had the privilege of interviewing Ryan Chaffin, a digital marketing consultant with 15+ of experience advising clients from small businesses to personal brands and large tech companies. Ryan recently launched a new digital marketing agency (KAHA) focused on helping small businesses across America during these unprecedented times. Ryan has dedicated himself to helping as many fellow entrepreneurs and digital nomads as possible grow their businesses and reach their full potential.

What was your inspiration for living and working nomadically? What factors inspired you to leave the stationary lifestyle and start earning money remotely?

I had just returned to work from a long weekend, and hated the feeling I had inside. I had just spent four amazing days with my wife and two young children, and felt so connected to them for the first time in a while. It was so hard to leave our tiny New York City apartment and return to my job on Wall Street that morning. I felt like I was throwing away all the progress I had made in those relationships over the weekend. It was at that moment that I knew I could not continue to pursue a career on Wall Street at the expense of my relationships with my wife and kids. I was tired of the early mornings and late evenings, often not even getting to see my kids while they were awake, and feeling like a visitor in my own apartment.

I didn’t have a plan on what I was going to do after Wall Street. I just knew it was time to leave. And after I left, we decided to move the family to Hawaii to “recover” from life on Wall Street in NYC. We felt the change of pace was in our family’s best interest. We also knew there weren’t many options in Hawaii that would allow me to use my skill sets and adopt the family lifestyle we wanted, so I started brainstorming ways I could earn money remotely.

What unexpected challenges and hurdles have you encountered so far as a digital nomad?

While being a digital nomad with a young family is definitely possible, it does introduce some unique challenges. For example, I always thought if I had a home office, then I could escape in there and get work done and have any calls I needed in peace and quiet. Anyone with kids will tell you that was wishful thinking. Fortunately, given that we were in Hawaii and just steps from the beach, it wasn’t hard to get the kids out to play. However, it did take planning between my wife and I. We finally got in a groove, and I was able to schedule my days to maximize working during their nap times and daily activities.

Another unexpected challenge I’ve encountered as a digital nomad was the internet stability. If you’re earning money remotely, never leave it up the internet of where you will be. Always have a backup. For example, I always have a global hotspot with me. There’s many providers and options, so just find one that works for you. If you know where your adventures will take you, then simply check the coverage map to make sure your destinations are covered, and what speeds you can expect there so you can plan accordingly on where and when you do video calls versus just checking emails.

Do you have any personal anecdotes or stories about the hardships you’ve faced as a location independent worker? How did you overcome them?

While I have several different ways to make money working remotely, my primary source of income is as a digital marketing consultant. I work with clients ranging from growing personal brands to small businesses, and even large tech companies on things such as websites, search engine optimization, online reviews and press coverage. At the time, a client had asked me to come present to thirty of their biggest clients, to help teach them about digital marketing, and how they could grow their individual businesses, which would in turn grow my client’s business. There was one condition: I had to complete a sample project for my client, so they could show it off at the conference. This is when I learned to never trust the internet of where I would be.

I had two days before my flight to the event, and had given myself plenty of time to complete the project under normal circumstances. The project was 90% done. However, no one could have planned for what was to come. A storm hit the island, and there were frequent internet and power outages. I did not have a Wi-Fi hotspot at the time, and was trying to use my personal cell phone as a backup hotspot. What I didn’t know was that those networks were greatly impacted by the storm as well, and were overloaded with people using the network capacity that was intact. I was scrambling and desperate. Not only was my client counting on me, but this event provided the opportunity for a partnership that could generate a significant amount of business for me.

I called the client, apologized and let them know I wasn’t sure I could get the project done on time. It crushed me, but I asked if they would prefer I not come. Fortunately, the client believed in me and asked if I could get it done once I was at the destination for the conference where the internet was reliable and fast. I ended up flying out to the event and pulling an all-nighter to complete the project just an hour before it was presented to the group. It wasn’t ideal, but I survived.

Fortunately, I learned my lesson from that experience, and have always had a mobile hotspot with me that provides me consistent internet access, and that has helped me avoid being in that position again.

Has any aspect of the lifestyle and career been easier than expected? Is there anything that you thought would be difficult but, in reality, hasn’t been?

Overall, the entire lifestyle is way better than I ever imagined. I no longer feel guilty about not spending enough time with my kids, because I’m around them all the time. I’m in complete control of my schedule and get a significant amount of meaningful time with my family. I get to eat every meal with my family, and work when they are busy playing, learning or napping.

I thought it would be difficult to attract clients working remotely, but in reality, it hasn’t been an issue at all. In fact, it actually helps attract some clients. I’ve also found that if I offer to travel once a year to meet a client, it resolves any concerns that they may have around me working remotely.

What character traits would you say are the most important or essential for successful digital nomads?

When it comes to important character traits or attributes, accountability is essential. If you’re not great at holding yourself accountable, find someone that is. It can be a business partner, a significant other, or even a client. If you don’t have accountability, you won’t be a digital nomad for long.

If you were starting over from scratch today, what would you do differently?

If I was starting from scratch today, the first thing I would do differently is get rid of all the excuses and just start. Figuring it out and improving isn’t really that difficult. Oftentimes, our biggest struggle is actually getting started. If you’re serious about your dreams, why would you keep pushing them off? Wouldn’t you rather start down the path to achieving them sooner?

I dreamt of spending more time with my family while still providing for them. I put it off for years and stuck with an unfulfilling career on Wall Street. As soon as I got on the other side and started earning money while spending time with my family, I couldn’t believe it took me so long to make the change.

What would you say to aspiring digital nomads looking to get started on a similar career path? Any words of wisdom or cautionary tales?

If you’re considering being a digital nomad, pursue it all-out. That doesn’t necessarily mean quit your job today with no plan, like I did. Sure, I’m living proof you can do it. However, you can test your idea on the side while keeping your day job. I’ve met many people that actually built the foundation for their digital nomad lifestyle while holding down a full-time job. Once the money they were making online was enough to cover their desired lifestyle, they left their full-time job and therefore never really assumed any significant risk in starting.

What I mean by “pursuing it all-out” is to put all your spare energy and time into starting now and figuring it out. You talk to any successful digital nomad and they all say they wish they would have started sooner. Time is a great asset, so start now and test your idea. It may take-off faster than you expect, or you may learn you need to try another remote option.

In the early days, what initial strategies did you use to gain visibility and get your business off the ground?

Being a digital marketing consultant, and having 15+ years of experience in this field definitely helped me get started. Additionally, new potential clients liked that I had Wall Street on my resume, among other achievements. The point here is that you don’t want to focus on “being new” to whatever it is you’re pursuing. You want to do the opposite, and show that you have a strong track record. Even if you don’t have years of experience doing whatever it is that you do as a digital nomad, you do have years of experience with achieving results. Find the experience and results from your past that aligns with what you are doing as a digital nomad, and use them to help promote yourself or your business. People don’t care about your history, they care about the results you generate.

Once you’re clear on the results you can generate for clients, you need to get in front of as many people as possible. As Grant Cardone says, “Promote! Promote! Promote!” and “Where attention goes, money flows.” The point here is that if you don’t promote your business, you will never get the attention of prospective clients, which means they cannot purchase from you. My favorite strategy to do this is to find keywords that your potential clients are searching, and create amazing content around that keyword that educates the reader and provides a ton of value. Then you want to rank that content in search engines so that people searching for those keywords find your content and are introduced to your brand. The goal here is to answer their questions and become the trusted authority in their eyes, so that when they need your product or service, they buy from you. The great thing about this, is that it doesn’t cost any money! You can do this simply by investing sweat equity.

I’ve helped many brands do this, and it works really well. One of my clients went from getting less than 100 visitors per month from Google, to over 16,000 visitors from Google in just six months. Not only did they get more visitors, we knew it was higher quality traffic because the percentage of website visitors that converted to a lead (submitted their information) increased by 600% as well.

For more insights, you can follow Ryan’s digital nomad journey on socials by following @realryanchaffin across the major platforms.

    Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

    You might also like...


    Digital Nomad Lifestyle: “The solution was to stop.” An interview with Lauren Juliff.

    by Amine Rahal
    Impact Photography / Shutterstock

    We Quit our Corporate Jobs to Start a Full-Time Coaching Business on the Road. Here are 4 Unexpected Ways Travel has been Crucial to our Success.

    by Alexandra Davis, Ryan Gleason
    Michael Gardiner

    Meet Michael Gardiner: Digital Nomad

    by Ryan White
    We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.