I talked to Jordan Carroll, a program consultant at Remote Year and a career and life coach for aspiring digital nomads.

After a corporate job at IBM and co-founding his own event agency, Jordan realized his ultimate calling to travel and see the world. He joined Remote Year: first, as a client; and after a few months — as a program consultant. Jordan continues to work for Remote Year while maintaining his own coaching business. In this interview, he shares his challenging journey to becoming a successful life and career coach and opines on the state and future of remote work. Jordan has recently visited Running Remote, the world’s largest remote work conference which has taken place in Bali this year, and shares his impressions about the event. Soshace is Media Partner of Running Remote.

Hello Jordan, and welcome to the interview with Running Remote! Please, share your story.

I grew up in Fremont, CA in the San Francisco Bay Area.

Growing up I had two particular interests I remember vividly. One was playing sports. Specifically, I played baseball for about 13 years competitively, and I was always good at other sports although I didn’t play them as seriously. I had a high competitive drive.

I also enjoyed creating videos. I used to take my dad’s HI-8 camcorder and film fake commercials with my friends, music videos, or comedy shorts. To this days I still find ways to incorporate video content into my life.

It was always important for me to do well in school, and it seemed somewhat easy for me most of the time. I’ve always had a creative brain — not a scientific or analytical. So I really didn’t like math or science but thrived in my English and writing classes. I would write poetry, stories, and even raps.

I thought I wanted to be a psychologist when I was younger, but over time I realized how much of the psychology field could be applied to sales. I pursued a marketing degree at Chico State, a college about 3 hours north of where I was from. The college was notorious for its parties. In high school, I struggled to fit in with any particular group, and I think part of my motivation for going to Chico was to redefine myself and also have a chance to party. That lifestyle shaped who I am today quite significantly.

At Chico, I was part of 7 different organizations or clubs. I really came out of my shell, became extroverted, and got as involved as possible in developing myself. I knew that I was setting the foundation for my sales or marketing career by doing so.

Please take me through your professional career. From the earliest time possible up to the present day culminating in your current position and role. Why do you think you decided to become a life and career coach?

I started my first job out of Chico State at IBM. I did corporate software sales for 4 years in the company — and spent time living in Boston, California, and Portland, OR. While I’m grateful for the experience, it wasn’t my calling. It taught me a lot to interact with Fortune 50 companies, network within the organization, and gain valuable training.

After IBM I went to a small PR firm in Portland to work as a VP of Customer Engagement. We focused on generating press opportunities for our clients. It was a good learning experience and something very different from what I was used to. I also co-founded an event company that did bi-monthly networking events in the Portland area.

After about 8 or 9 months of being with these companies, and a traumatic break-up, I decided I wanted to travel the world. I shut down my involvement in these other two positions and left on my first Remote Year trip.

Remote Year coordinates 4, 6, and 12-month travel programs for professionals who already have remote jobs. For a monthly fee, they take care of booking the clients’ apartments, workspaces, events, flights, and provide a community to travel with to different countries each month.

This was an amazing experience. During my time on the program, I had to support myself somehow. I took a remote 100% commission sales job as a high ticket sales closer for a women’s dating coach. After a few months of that, I was struggling with the time differences and being in a commission only role. Luckily I was also earning affiliate and partner commissions for some companies I did work with.

Then I decided to just go all in on myself. I started my first coaching business, called Negotiable Reality, and created a 4-week course. After a couple of months of business development and creation, I acquired 7 clients for the first live course. It was an eye-opening experience.

At the end of my time on the 4-month remote year program, I applied to become part of the team as a program consultant.

See, one of the reasons I joined the Remote Year program was to eventually get a job with them. I really enjoyed the culture of the company, the community, and the values they stood by. As I had been very active in the community, multiple employees referred me and I got the job. I continued to refine my coaching business as my side project, and now, today, I specialize in coaching high achievers to transition to remote employment.

I’ve been through the process of finding remote jobs. I’ve worked remotely for 5+ years. I’ve spent countless hours researching remote work topics and amassing a valuable international network in multiple industries. I know how the freedom and flexibility of a remote position can ultimately help someone’s growth — both personally and professionally. I want to contribute to enable others to do that — whether it be to travel, spend more time with their family, or simply have the flexibility to work where they want during the day.

Is Remote Year your own business? What makes your company different from other similar coaching companies?

Remote Year is not my business. I work full time for them selling the programs. My coaching business is separate.

It’s distinct because unlike many coaches who are selling ‘work remote’ programs, I’m not trying to teach them how to become an entrepreneur, freelancer, travel blogger, or influencer. This is purely about finding a legitimate company who will employ you to work fully remote.

I help professionals through the entire process of examining their background, finding the remote jobs for them, applying, interviewing, and following up to improve their chances of landing a remote job.

Who do you think has had the greatest influence on the development of your career interests?


If you had the opportunity to do the last 10 years of your career over again, what would you do differently?

Absolutely nothing.

How successful do you believe you’ve been so far?

While I’ve accomplished some things, I view success simply as a measure of happiness. I am content with myself. I feel successful in some ways, but I still have so much I want to achieve. Right now I have achieved locational independence. At some point, my next levels of success are financial and time independence.

In your career, what negotiation are you most proud of?

Leaving my corporate job. It was my first big step into the world of entrepreneurship, travel, and where I am now.

What’s about your participation in Entrepreneurship TV?

I was a guest on two of the episodes that they created for their pilot. They have been pitching to different networks and streaming services in Los Angeles. I knew Rohan and Josh, who are hosts on the show from previous avenues. They take their production very seriously and I’m happy to be a part of their show.

What is the question you’d like to ask yourself? How would you answer?

I ask myself all the time if I’m happy and if I like what I’m doing. The answer right now is yes.

What are the biggest challenges remote workers face? How do you think they should tackle them?

Isolation: By finding community.

Productivity: By finding a routine.

What do both of these have in common? Self-awareness.

Knowing what’s important to you in a community will help you choose the right one. By choosing the right community you help establish an environment and people around you that can help your success. With more self-awareness, you will understand what kind of routine you need to establish.

What do you think is inherently wrong with the office culture?

I think every culture is different. I think many can be inherently wrong if they are not established intentionally.

What’s your long-term goal?

I have many:

  • 10 streams of income
  • Learn Spanish and salsa dancing
  • Forbes Coaches council
  • Speak at a TEDx
  • Tony Robbins Platinum partnership
  • Own 30 properties
  • Write 5 books
  • Create a documentary
  • Own a Kava Bar near a beach

What’s the future of remote work?

GIG and remote. There will be job marketplaces, many, if not most of us will be independent workers or working part-time remotely for many companies, not one. The companies will pay us for completing small tasks or processes. They will outsource little things and people will bid on them from all over the world. There still will be a hybrid, established teams that create the culture of companies, but many companies will find it more cost-effective to outsource many of the tasks for projects or possibly crowdsource them and decentralize the payment based on contribution.

At the Running Remote conference, Ilyas spoke about this, and Naval Ravakant also did on the Joe Rogan podcast.

Do you have any hobbies?

Yes of course:

  • Running
  • Writing
  • Reading
  • Video production
  • Sport, especially basketball
  • Karaoke
  • Networking

Say what you liked most about Running Remote or what talk you were most impressed with. What are your impressions from the event?

Running Remote was a fantastic event, which I described in this article and in the following video.

The interview was conducted by Marina Vorontsova from Soshace, a hiring platform for web developers.