Dream Life

Welcome to Wandering Workers. We are Jordan and Michelle Hollenbeck. I, Michelle, am the author behind the blog and the voice behind the podcast but we are both wandering workers who, after years of traveling on our own, finally collided. We combined storage units in 2010 and started telecommuting together.


For the first few years we hopped around—spending 3 to 6 months in various places around the U.S. and abroad, including…






And Mexico

President's Club

More recently we slowed our travels a bit, bought a house, and added a third wanderer to the mix.


While we love to travel, what we love more is the freedom that comes from designing our own lifestyle. Instead of sitting in traffic on our way to a less-than-rewarding office job, we get to drink coffee together, slowly, every morning, before starting our day. It’s this time together that’s the real reward for living life on our own terms.

In fact, just the other day we took a short break from work to sit outside in the sun with our daughter. This is what we were doing when she took her first steps. It was the middle of the day on a Wednesday, and we got to experience it as a family.

How We Fund Our Dream Life

Jordan works for Teesnap selling what is seriously the best golf software on the planet. He works remotely (of course) but is part of a sales team that’s based in Las Vegas.

I freelance. I am currently doing content strategy for Classy.org, a company that I feel incredibly lucky to be a part of. They empower nonprofits and social impact organizations to do what they do best—make the world a better place.

My Story

It’s not the office, the cubicle, or even the commute that I was trying to get away from. There are antidotes for those: When I worked in San Diego, I biked to avoid traffic. I also had co-workers who inspired me, made me laugh, and challenged me to be better at work and in life.

Routine is what scared me—the sameness of things. I have always loved to move, to try new hobbies, to meet new people and see new things. It’s not that I hop from place to place. I like to stay for a while; I like the challenge of settling into a new city and finding my favorite reading trees. But after a while the local routines become too familiar. I pack the same lunch and drive the same roads. I get antsy and want to shake things up and move on.

In my younger days I was much more careless about when I quit jobs in exchange for the promise of adventure. In my mind I was “living the dream.” But the reality is that I was naive, broke, and not building any kind of skill set or career path. I was jumping from one temporary job to the next and not acquiring any marketable skills.

I’ve since learned that you don’t have to make impulsive decisions in order to live life on your own terms. Now I make more calculated decisions and plan my moves more deliberately.

It started in 2007. I finally had a job in a field that I’d always wanted to be in. I wanted to grow professionally but I also wanted to keep moving. Instead of quitting, I eased into remote work with an arrangement that let me live in San Diego, where the office was, and San Francisco, where I wanted to be at the time. As the time between office visits grew, so did the distance I would travel.

Over the seven years I was with this company, I worked remotely for five of them. I also got three promotions during that time. (Note: I worked from the office for a year after the most significant one before heading back out on the road.)

The most important thing that experience taught me was that you don’t have to choose between an adventure-filled life and a career. You can have both. You can build your skills and advance your career all by making the right choices for you. I talk more about that in a post titled, “5 Lessons From a Corporate Buyout.”

What Wandering Workers Can Do for You

The concept of remote work isn’t such a hard pill for employers to swallow anymore. And that’s the first step—creating more space in your life to dream and plan. This post about how to ask permission to work remotely might help you take that first step toward your dream life.

Whether you create a remote work situation with your current job, build your own online business, or find new opportunities around the world, you can continue to build your personal and professional skills in such a way that also allows you more flexibility in your life. Some people travel, other people simply want to spend more time with their families. The thing that I want most is to continue drinking coffee slowly and savoring my mornings with Jordan.

The point is that you can make calculated decisions that not only give you more flexibility in life but also allow you to advance your career in whatever direction you most want it to go.

Wandering Workers is here to help.

On the blog I share information about how we’ve been able to grow in our careers while living life on our terms, and I provide tips to help you do the same.

On the podcast I interview other people who have built mobile careers. Their stories are evidence that there are endless ways to create the life you want. For example, Robert Isenberg and his wife Kylan created opportunities for themselves in Costa Rica that launched them into new realms of both their careers. And Johnny figured out how to run a location-based business from abroad.

If there’s one thing I want you to get from this blog, it’s the inspiration to look at work—in any profession—with a fresh perspective.

If you’re ready to live your dream life, I want to help you thrive.

Start by joining the wandering workers email list below to get inspiring stories, helpful tips, and more.