Managing Businesses Online While Traveling The World: Highlighting Remote Workers

In this series, we will be highlighting real, successful remote workers working in various industries across the globe. They'll give us an insight into how they got started in their industry, their advice to their younger selves, and tell us why they chose remote work.

Introducing Tayler Gill: Online Business Manager And Digital Nomad!

Tayler Gill is a world traveler, remote work enthusiast, and coffee addict who is always in search of genuine connections. She is passionate about finding the most productive and practical way to live the work and travel life while inspiring others to reach their laptop lifestyle goals. She is also an Online Business Manager that serves solopreneurs and small business professionals in the sports and entertainment industries.

Check out her website at, follow her on YouTube and Instagram, and connect with her on LinkedIn.

How did you start working remotely?

After I graduated from college, I had an internship in London for 6 months. It was during that time that I realized how much I loved working and living overseas and dreamed of being able to do it for an extended period of time. That internship led me to getting a job working for a study abroad company. And for 6 years I talked about all of these amazing locations while I was stuck in a cubicle and never able to go anywhere myself.

It was during my last year at this company that my friend hired a Virtual Assistant for her new coaching business. She showed me how they communicated and what tasks she did for her and I immediately knew this was my way to begin working remotely and travel. I built my business on the side while working full-time before finally quitting about 6 months later and going fully remote as a freelance Virtual Assistant.

What made you choose your current field, and what do you love about it?

I chose it because I could use the skills I already had to get started quickly. The minute I was introduced to the world of virtual assistance I immediately knew it was for me. I really love being able to work with different people, different businesses, and constantly learning new things. I work with a lot of solopreneurs and I know they appreciate the support and knowledge I bring.

I’ve since transitioned into an Online Business Manager which is even more aligned with my skillset and something I never thought I would be able to do remotely.

What has been the highlight of your remote career so far?

Being able to travel to places and live like the locals while visiting. Studying abroad and then interning abroad really showed me that I prefer to travel slow and live as the locals do as much as possible.

I started traveling about 4 months after going fully remote and began in New Zealand on the Holiday Working Visa. The visa allowed me to stay for up to 12 months and get a job there if needed. I figured, if my freelancer career didn’t work out at the very least I could live and work in New Zealand.

Fortunately, my business continued to grow and I was able to travel all over New Zealand via house sitting for a year before spending some time in Asia and Europe. In total, I spent 18 months traveling solo before the pandemic grounded me back at home in the US.

What are some of the challenges you faced?

Of course, balancing work and travel was a new skill I had to learn. House sitting really helped with providing quiet dedicated places I could work and explore my new city from.

I also tried to do too much at the beginning. I felt like I had to know everything about everything online business related to being seen as valuable and so I would say yes to clients and tasks that I knew nothing about and weren’t a great fit for me. This caused me to spend days and evenings slogging through my to-do list instead of curating my skills to my ideal client.

How did you stay motivated when facing these challenges?

I would tell myself that at the end of the day I would have a new skill and that it was worth it. And I did acquire a lot of new skills. But two years later, I’m just now learning to really say “no” to things that I’m not interested in and aren’t worth the energy it takes me to do them, even if I have the know-how.

I also had to make the mental switch in understanding that I bring value by performing in my zone of genius and not trying to do everything for everyone. But I think when you are no longer working in an office and your boss/supervisor/client can’t see you working all the time there is a sense of trying to overcompensate for that. And that was a hard thing for me to unlearn.

What is your opinion of remote work? Benefits vs disadvantages?

Overall, remote work is great! I’m very good at managing my time and being disciplined so having a more flexible schedule really suits me. I also can’t imagine commuting to an office ever again. I really love that I can change my location from a house to a coffee shop or to a coworking space whenever I need to. And being able to travel and continue to do work that I enjoy is a bonus!

The thing I miss most about my office job was the people. I was friends with a lot of my coworkers and I miss the camaraderie. When you only speak with your clients over Slack or Zoom, there are a lot less impromptu chats and definitely no group outings. People who work remotely for a company may miss this less, but as a freelancer working remotely continuing to make meaningful connections with the people I work with has been the hardest part.

If you could advise a younger version of yourself to do something different - what would it be?

Just start. I wish I would’ve taken more time while at my corporate job to start learning about different online jobs I could do and gaining new skills.

For instance, I had considered starting a blog but didn’t think I could do it well. When I finally did start my blog, Traveling Tayler, last year I realized it wasn’t so scary and that I could’ve learned to do it 5 years ago as easily as learning to do it now.

What do you predict for the future of your industry?

The freelance industry will continue to grow. As technology continues to improve the ability to work from anywhere gets easier and so I think a lot of people will jump all in and start their own company or begin working for themselves. As an Online Business Manager, this is great news as these small businesses will need more people like me.

What would you like to achieve professionally in the next five years?

Professionally, I would like to make my blog and youtube channel a larger part of my income. My goal is to diversify my income so that if I lose a client or something happens I can rebound quickly.

Any words of wisdom for people looking to get hired in your industry?

Start with what you know and go from there. It’s good to learn new skills, but most of the time you don’t need to go back to school or have a completely different skill set to be successful. You can start where you are, right now, today.

Any predictions for what will happen to remote work as a whole?

I think it’s here to stay. Right now it’s a bit unbalanced with so many people working from home and once it’s safe to go back to working in offices, many companies and people will choose to do that. So we’ll see a shift back away from remote working for a time before it evens out. But we have already seen many companies realizing employees working remotely is possible and even if not full time, allowing at least part-time remote work. So more people will begin to do it regularly and new inventions and systems will pop up to help with the challenges of the remote work lifestyle.

Final question, what is your go-to recommendation for others to read/listen to/watch right now?

“You Are a Badass” book series by Jen Sincero

Digital Nomad Wannabe website for learning about how to make money from blogging

Small Biz Chat podcast with Melinda Emerson

You can start your own remote journey with Desk To Remote by clicking here.

85 views0 comments
  • Instagram
  • Facebook
  • LinkedIn

©2020 by Desk To Remote.

Proudly Created By Remote Work Enthusiasts ❤️

View Our Privacy Policy