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Leave Your Job Or Take It With You? We Did Both

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Jeremy Orozco left his job as a firefighter and Sondra Orozco is an Elance-oDesk product manager. Follow this newly married couple as they transition into life on the road as Digital Nomads and learn more via their blog, Nomad Life.

We’ve been Digital Nomads for just over a month. We’re settled in to our new (temporary) home in Honolulu, HI, and we have our work-life balance down to a routine: work in the early mornings and enjoy the Hawaiian sun and surf in the afternoons. We love Nomad Life.

In the months leading up to our year-long trip, figuring out what to do for work was the biggest decision we faced. We took polar opposite approaches to becoming Digital Nomads:

  • Jeremy quit his job as a firefighter and is now an entrepreneur. He’s writing a book and building a website to help people cure their headaches.
  • Sondra kept her job as an Elance-oDesk product manager and now connects with all of her colleagues remotely.

People question us about our work all the time. Sondra is often asked how she convinced her employer to let her work from anywhere, and people ask Jeremy how he could quit his job to travel. Here are our answers.

Figure your life out before you become a Digital Nomad

Jeremy: If you’re serious about being a Digital Nomad, you need to decide if you love your day job. Do you? What happens if you say “no”?

Sondra: I love my job. Jeremy wasn’t sure about his.

Jeremy: I had to weigh my options. People will tell you to take the leap and quit your job, but you better know where you’re going to land. Quitting the fire service meant losing a fulfilling job, a six-figure salary, a three-day work week, lots of vacation, the ability to save cats from trees, job security, full medical benefits, retirement at age 50, and the privilege of driving on the wrong side of the road.

Jeremy fighting a house fireSondra: His job had some downsides, too: it’s dangerous and he would leave for weeks at a time to fight California’s wildfires. Look at this picture where he’s on top of a roof that almost collapsed (right)!

Jeremy: I was considering quitting my job to pursue my book and website full time. People asked, “Can’t you do both?” I believe the research that I am compiling has the potential to cure headaches for millions of people. The job of a firefighter is equally important and time consuming. It’s not possible to do both well.

I watched a famous speech by author Neil Gaiman and realized that if I continued to be a firefighter I would be moving away from my goal, my “mountain,” so I quit my day job. If you need to weigh your options, it generally means you don’t love your job and it’s time to leave — especially when you are a firefighter and need to have your mind focused on what you’re doing.

So you’re going to quit…what now?

Sondra: Jeremy didn’t quit his job out of the blue. He had already spent years building a website and a few months writing his book. If you’re starting from scratch as an entrepreneur or freelancer, you may want to give yourself more time to get your business off the ground before embarking on a life of travel. Start yesterday.

Jeremy: We also made an eight-month plan to pay off all of our debt, save some money, and severely reduce our monthly spending. It’s easy to live like a bum when you know you are about to travel the world. Oh, and we sold everything we own, too.

How to convince your boss to let you work from Bali

Sondra: My path to becoming a Digital Nomad was very different. I do love my job and wasn’t ready to give up my career, but we desperately wanted to travel. As a product manager, my job requires a lot of hours and a lot of meetings with a lot of people. Taking this job on the road is definitely not easy, but I was up for the challenge.

So I asked my boss if I could work remotely while traveling. I was thrilled that she was open to the idea.

Sondra working from home in CaliforniaJeremy: This definitely wasn’t overnight. Sondra started out working from home one day a week, then two, then three — it quickly became five days a week. I think that people are more likely to trust you if you already work hard for them. Sondra works hard. This is not going to be easy — if it were, we wouldn’t be writing about it! It would just be the way everyone would do it, because traveling is awesome.

Sondra: But no matter how hard you work, not all managers are going to be as open-minded about this. If you find yourself needing to negotiate with your boss for a Digital Nomad lifestyle, check out the book Remote. Written by the founders of 37Signals, they make some compelling arguments in favor of remote work that you may be able to use when making your case.

That’s all, folks

Becoming Digital Nomads wasn’t an overnight decision. We spent months preparing for Jeremy’s career change and for Sondra’s transition to a full-time remote gig. You don’t need to quit your job to travel the world, nor do you need to keep doing something you don’t love. There are endless varieties of Digital Nomad lifestyles, you just need to find what works for you.


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