Working Remotely

This week we’re pumped to share a special, and particularly insightful guest post from our friends at Remote Year, an organization that’s all about helping folks jump without having to quit your job. They do it by taking you out of the office and around the world. We spent time speaking with their team and really like the perspective they bring to the question of when to jump. Enjoy this guest piece from Remote Year—we think it’s right on.

From Conventional to Creative Living: When Is It The Right Time to Jump?

There comes a time in everyone’s life when they realize that they’re ready to take the next step. Those “when to jump” moments tend to fall into one of three buckets:

Bucket #1: When you buy a house, venture down a new career path, or start a family. You want to add something new to your life, not fundamentally change the way that you’re living. This bucket could be considered the most “traditional”.

Bucket #2: When you decide to quit your 9-5 job in order to pursue what you’re passionate about. If you fall into this bucket, you’ve got a bit of an independent side. You march to the beat of your own drum and know that life is only worth living if you are doing what you love.

Bucket #3: When you take a leap out of your comfort zone, and make an intentional decision to leave behind the life you’ve grown so used to over the years. You’re ready to embrace a lifestyle that is predicated on breaking down norms and forgoing convention. You rebel, you.

Those people in Bucket #3?

Those are the people that join a work and travel program like Remote Year.

They know that there is a life filled with opportunity beyond the four walls of their corporate office - and they’re ready to reach out and take it.

But how does one know if it is the right time to make the transition out of a conventional lifestyle and into remote work? What is the tipping point for these creative thinkers and outside-the-box dreamers?

We spoke with four Remote Year participants to hear their stories. First, we asked them the question that so many others have on their minds, “How do you know when it’s the right time to jump?”

“To be honest, I felt selfish and scared and excited at the same time. I have never been one for commitment and committing to spending a year in foreign countries with a bunch of strangers was terrifying AF, “ Melissa Scatena, a member of Remote Year Ikigai said.

Once Melissa made the decision to leave behind a more traditional lifestyle, though, she was all in. However, as is the case with most major life changes, there were many challenges that she had to solve or accept before she could make the full jump.

“Submitting my commitment meant I officially had to begin a string of difficult "break-ups"—work, roommates, long-term boyfriend, family traditions, etc. I knew in my heart it was the right choice, and ultimately everyone would be supportive, but it was definitely bittersweet!”

Carin Skowronsky, a member of Remote Year Kublai, had a more measured and practical reaction to the moment when she decided to move on from her regular life and join a work and travel program.

“After the initial shock passed, I decided it was sink or swim. I already knew I was going to leave my present employer and embark on building a solo venture, my freelance business (which is flourishing), but it didn't come easily. I knew that everything I was about to do was going to be hard and crazy, but at the same time, it would be worth it. I was about to take on some of the biggest challenges of my life, both personally and professionally.”

That decision didn’t come without some internal back and forth. It took a bit of self-convincing for Carin to make a move as big as joining Remote Year.

“After an hour-long game of "should I or shouldn't I?", I closed my eyes and hit the submit button. Immediately after, I walked into my kitchen and poured myself a "polite sipper" of whiskey. Then, I put on one of my favorite songs and had a living room dance party because, after all, I was going to be traveling the damn globe!”

That excitement is prevalent in many Remote Year participants when they literally, and figuratively, hit the button that signals the start of their work and travel journey. As you may expect, that excitement is almost immediately followed by an alarm.

“First I felt excitement, but then panic at the thought of everything I needed to organize before I hit the road! It's a big deal packing up your life, but the trick to surviving it was enlisting the help of friends and family, and starting early,” said Tim Nixon, a member of Remote Year Meraki.

“Honestly, it didn't feel real,” Tim said. “Personally, I had a massively delayed onset of emotion so I didn't feel really overwhelmed or scared until I boarded the flight from Houston to Mexico City. It was only then, surrounded by people that didn't look like me, and didn't speak my language, that I properly freaked out. So if you don't feel scared at the start, don't worry, it's coming for you.”

Everyone has a different experience when they are getting ready to change their lives. Melissa ran the gamut of emotions, while Carin spent a considerable amount of time debating whether or not she was doing the right thing. Tim was apprehensive and even a bit doubtful that his decision would turn out the way that he had hoped.

Michael Constable was oddly calm.

“I was questioning why I was so casual,” Michael said. “It didn't phase me at all. I was wondering if there was something wrong with me for being so nonchalant about it. Looking back on it, I think that I was just extremely confident that Remote Year was going to be worth every penny and that has yet to be proven wrong.”

Michael planned on staying with his company as he worked and traveled around the world, so making the commitment also brought him peace of mind.

“I believe [I was feeling] something along the lines of... ‘FINALLY! It's happening and now I'm too invested for work to change their minds! They can't change their minds at this point...can they?’”

Reader, they did not change their minds. Michael set off on his Remote Year with his company’s approval in hand, ready to live a more flexible, creative lifestyle.

The truth is, there is no “right time” to change your life. There will always be a conflict, something holding you back from putting in the work to get to where you want to go. 

You are unique and  you have a different motivator than anyone else that will help you get across the finish line to a life that you want to live, and to doing work  you want to do. 

No matter your emotions, no matter what you believe is in your way, take a deep breath, think of the four people above who had the guts to go after what they’ve always dreamed of, and say “yes” to your next adventure.