Many of us hit a point in our career when we’re ready for change. Be that a promotion or raise, industry switch, maybe a leap into entrepreneurship. But we all share the same bottom line — looking for an answer to the difficult question:

“What’s Next For Me?”

For some, working remotely or becoming a freelancer is just the transition he or she needs. With nearly “36 percent of the U.S. workforce” working in remote or freelance roles, it’s no wonder that perceptions of freelancing as a career are becoming more positive (at least, 69 percent agreed to that in a recent study). And yet, the idea of transitioning into a remote role or asking for flexibility is paralyzing. Our fear of the unknown or of being told “no” holds us back from discovering our new potential. I’m sure I’m not the only one who secretly dreams about sitting at a cafe in Italy, cappuccino in hand, while answering emails for a job you love. But how do we get there?

And this is exactly where SB* comes in.

As a Merchandising Marketing Manager for start-up, SB did the seemingly unthinkable: She went from being a full-time, in-office employee to a contractor role working remotely in Europe. Not to mention — while still working for the same company. Which up until SB, had very few employees working remotely outside of headquarters. In this interview, SB shares how she successfully negotiated this new scenario, manages her work schedule and budget, and what it really looks like to live abroad. Her advice will leave you feeling motivated to evaluate your career, and how you can ask for what you truly want.

“The major catalyst for me was watching one of my best friends travel the world while working remotely as a graphic designer. She was on the road for a full year, but after only a few months I decided it was something I needed to do.” SB recalls. “I started looking for remote jobs, with fully remote companies, thinking that [working remotely] wouldn’t even be an option in my current role. So when I approached my boss, nearly a year later, I was shocked she was willing to try it out. I was confident I would figure out a way to make it successful, but the amount of trust that must have taken on the company’s end is enormous.”

The year long build up for SB gave her the courage (and urge) she needed to confidently work with her boss to develop a schedule that would work best for her, the team, and ultimately, the company.

“We had a verbal agreement within a week or two, but it took a while to figure out the major logistics; when I would leave, what hours I would work, how I would be paid, etc. My boss had [worked remotely] in the past and suggested that I transition into a contractor role. This would last for 10 weeks, and I would work 30 hours per week, leaving plenty of time for moped rides and gelato. After that, we officially set a ‘resignation’ date, along with a start date for my new role, and my new life.” SB explains. “The freedom to go anywhere in the world was really exciting, but no matter where I was, I was still expected to work pacific time hours and hit all of my major KPIs. I have a very data driven role, and I was so thankful for that when going through this negotiation process, because we all agreed that with my job it’s very transparent if I’m not performing.”

Living abroad sounds expensive, right? I was curious to know how SB was able to make it work financially, and what preparation she needed to do before jetting off. This transition from full-time employee to contractor did require a significant change to her salary, and the complete loss of benefits. For the first three months, she was able to live off of her salary without touching her savings, a success in-and-of-itself.

“Once I got the approval to go abroad, I ended my month-to-month apartment lease and and turned in my car. What I used to spend on those expenses was then transferred towards paying for Airbnbs and big city metro passes,” SB explains. “I did the math and my hourly contractor rate was what I would have been making had I been paid hourly all along, but I was cutting down by 15-20 hours per week. This resulted in about a $30,000 pay cut at the start. But at that point, I was thinking ‘it’s just three months, I can make this work’ and it turns out I was able to live off of that just fine. I also knew that the pay cut would be worth it in order to live out my dream, and I haven’t regretted it once.”

After her first contract period ended, SB was ready to negotiate. Triple-negotiate, to be exact. She asked to extend her contract, for a raise, and for more hours. As SB remarks, asking to work remotely in the first place completely changed her outlook on negotiation. With practice, the confidence to ask for what she wanted got a lot easier.

“After the initial 10 weeks were up, I was hooked. I had never been happier, in both work and life, and I knew I wanted to continue. So I went back to my boss with a proposal. At that point I’d proven that this could work, and that I could be successful in my role even if I wasn’t at my desk. While I was confident in my ask, I was still a little nervous, and was genuinely surprised at how open they were to all of it. We ended up extending another 10 weeks, increased my hours to 35 per week and raised my hourly rate,” SB explains. “Going back to the beginning, I never would have thought, in a million years, that they would have let me do this. My biggest takeaway is: just ask. If you don’t ask for what you want, you won’t get it, because no one else is going to ask for it for you,” SB says.

So now you may be thinking:

“How Can I Do This, Too”?

While learning how to manage her time and maintain a social life came somewhat naturally to SB, she does believe that it takes a certain type of person to successfully work remotely.

“There is a great amount of self discipline required, because no one is going to be watching over your shoulder to make sure you’re doing all of the things, and working the hours that you need to be. But with that discipline comes an exhilarating sense of freedom,” SB says. “I don’t start work until about 4pm, to coincide with Pacific Time hours, so I have a large part of the day to spend how I please. The work-life balance is beyond anything I’ve ever experienced with a 9-to-5. And then when it does comes time for work, I can work from almost anywhere: the airport in Paris, a pub in London while watching the World Cup, on the rooftop of a riad in Marrakech, or by a pool in Santorini. I’ve done all of them. Don’t get me wrong, it can be really difficult at times, and and it’s definitely not always fun. But I’m so thankful for this opportunity and committed to making it work, that the reward far outweighs the bad.”

Throughout the last few months, SB has began to feel more “confident, invincible.” Her new lifestyle has “made her more adventurous and open to new experiences, more free, and overall happier.” Enough said, right? We can all learn from SB’s story — that if you genuinely believe in something, you can make it your reality. Simply mix a bit of confidence, courage, and commitment together, and your future will become all the more clear.

By: Lily Comba 

By day, Lily works in business development for an online marketplace. By night, Lily lives an entrepreneurial life. After working as a Career Consultant for two years at her alma mater, Scripps College, Lily developed a passion for helping women in their careers. She embodies the mantra, “If not me, who? If not now, when?” in her work as a career advisor to college students, and creative and business strategist for fellow entrepreneurs. Catch her running around Los Angeles or at lilycomba.com.

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