How to Start Working Remotely, From 7 Remote Workers Who Did It

How to Start Working Remotely, From 7 Remote Workers Who Did It

Working remotely is a highly desired way to work. With remote work being the fastest-growing commute method, and 80% of survey respondents reporting that working from home full-time is their most wanted form of work flex, it’s no wonder so many workers are seeking out remote jobs.

If you’re wanting to get started working remotely, we’ve explained six ways to get started on your remote work journey, with tips from seven remote workers who have shared their wisdom.

One of the features on is a great Q&A section featuring answers from 36 remote workers. These workers run the gamut on their job types and experiences. We rifled through their answers to the question, “How and why did you start working remotely?” to glean some insights into how to start working remotely.

Here is what they had to say about how to start working remotely:

Start freelancing.

Freelancing can be a great way to ease in—or jump in—to remote work. The freelance lifestyle involves finding yourself short-term or long-term projects and jobs that are typically done from home. If your job could be translated to a freelance business, consider ditching the 9-to-5 job in favor of more flexibility. Here’s the story of a couple of remote workers who switched to freelancing:

“I worked in a corporate setting. …While I was making great money, I missed having a life outside of work. After leaving my job, I took some time off to recalibrate. It was then I found out about freelancing. I was intrigued about working for myself as a writer, so I did some research and then took the plunge.” —Taryn Barnes, freelance writer

“I started working remotely as I quit my job as a development manager for a London agency and decided to work freelance as a PHP developer and then iOS developer. This necessitated working from home (initially) and after a few ‘on-site’ projects I decided I preferred the freedom of remote working.” —Ben Dodson, director

Have a niche skill.

Demonstrating your worth to a company is a major part of landing any job. And if you have a niche skill, that can make you even more valuable. Christine Bielak, a programmer, found that companies far away were willing to work with her remotely to take advantage of her skill set:

“I have an odd/distinct skill set; companies couldn’t find people anywhere near them when they needed someone like me. Knew a project manager from a prior position and when she heard I had changed positions (she was [a] vendor with my old company), she immediately called me to see if I was interested in remote work.”

Ask your current job for flexibility. 

Asking your current job for flexibility is a great way to start working remotely. Suggesting a trial run or a few hours per week can help a reticent employer see that remote work is a productive way to work, and not an excuse to evade work duties. Kelli Neely, an IT program manager, did just that when she became a single parent:

“When I first separated from my husband, I made arrangements with my manager to allow me time to leave mid-afternoon to pick up the kids from school, and then I could log on from home and finish my work. This arrangement worked so well, that I was able to keep this schedule throughout the kids’ school years. Once I was able to demonstrate productivity while working from home, each manager that followed was supportive.”

Start small.

Sometimes starting small can lead to bigger things. Taking on a remote side gig or one-off project can earn you some extra money and get your feet wet in the world of remote work. As Shannon O’Donnell found, trying out a remote job went from a way to earn money to a lifestyle:

“Originally, I began working remotely as a way to facilitate my goals to become an actress in Los Angeles. …The remote work gave me the funds and the location independence to pick up and move to LA, while also attending auditions once I was there. …At the time, I didn’t see the remote work as a career move, but more as a chance to leverage online work to afford a lifestyle that I enjoyed. Over the years, my travel website has also become a part of my work and a portion of my income. My work and life melded as the years wore on. It’s an odd combination of work, travel, life, but I wouldn’t change it for all the world.”

Work while traveling.

Sometimes the itch to travel can encourage workers to take the plunge and start working remotely. The key is finding remote work that will fit with your nomadic lifestyle and that can be done from the locations you plan to visit. In the case of digital nomads Mike and and Anne Howard, a website is what supported their traveling:

“After working the 9-to-9 in New York City for over a decade we decided that the world was too big, and our vacation time was too short. So we quit our traditional jobs and set out on a 500-day honeymoon around the world. Halfway through the journey our travel site had gained a loyal following and enough acclaim (Conde Nast Traveler, Daily Mail, LA Times, etc.) that we were able to continue traveling (today is day 1,703 on the road) and run it as a business from the road.”

Be open to networking anywhere.

Connections can be made anywhere and your remote work opportunity could come from an unlikely place. Be open to networking and talking about your skills and interests with a variety of people. Take Randle Browning’s story, for example:

“I started learning to code online via Skillcrush, really clicked with Adda, the CEO, and a few months later was hired to kick the blog into shape and take over the newsletter. From there I quickly took on more hours and went full-time building the content marketing team.”

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By Rachel Jay | October 29, 2018 | Categories: Work Remotely

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