How did you get started with remote work?

Interview with Michael about being an entrepreneur and freelancer

I got started with remote work because I was tired of the 9-5 grind. I had a high paying job, but I was miserable. I hated having a boss, working on stuff that didn't interest me and having a schedule.

I wanted to create an online brand, but knew it took time to grow/monetize a website so freelance writing helped in the interim. Last week was my one year anniversary.

I quit my six-figure job with absolutely ZERO money coming in, I made $60 from my blog when I left corporate America. I saved over 12 months of living expenses in a separate account and forced myself to figure it out.

Freelancing was much harder than I anticipated in the beginning.

At the time I left I also just published my first book, Advice for My Younger Self. This added a new income stream along with my blog and random side hustles. It took some time guest posting, learning new skills, and building a portfolio to get recurring clients on projects that I enjoyed working on.

If I'm not building my blog and freelancing business I'm working on my golf game as I'm turning professional in the next six months.

Michael is an online entrepreneur, author, and freelance writer who specializes in self-improvement and personal finance.

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Interview with Steven Wade, a software engineer working on a remote team

I live in an ok-sized metropolitan area but there isn't much opportunity for PHP software engineers outside of marketing agencies and I wanted to write software, not websites.

I started looking for remote jobs so I could stay near friends and family but enjoy working on something I loved.

I applied for a few places that I found on We Work Remotely, Indeed, and LaraJobs, but none of them panned out.

A friend of mine in town had been recruited by my now company, but he was uninterested. He knew I was looking and thought I'd be a good fit so he sent me the job posting. I applied, had an interview a few days later, and an offer a week after that.

Sometimes work finds you. It's good to stay connected in the community.

Learn more about how Steven works remotely, including his work routine, habits and how he found his remote job

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Interview with Patric, a UX designer and usability engineer that works from home

After being a consultant and living in hotels and airports I took the leap to quit my job and double down on freelancing.

I am a UX Designer / Usability-Engineer and specialized in mobile and web applications. I already had a few clients during my studies but it took a while to get high-quality clients after quitting my full-time job.

At the beginning, I took on programming jobs as well as project management jobs. Only after a year or so I could make choices about the kind of work I took on.

Patric works on his own projects while also consulting for medium sized software companies, learn how he works remotely.

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Interview with Tyler, a director of customer success models how to start a remote work career

In early 2019, I had been studying for an educational leadership master's degree. I intended on becoming an assistant principal or a technology coordinator with a school district, but I kept running into roadblocks.

My spouse met someone who was working remotely as a Salesforce administrator, and that sparked my journey from being a technology-oriented educator to becoming an education-oriented technologist. Eventually, I was hired as a customer success manager at Hubstaff.

From networking to land a remote work gig, to building out an exceptional remote work tool stack, Tyler has quickly figured out how to thrive in remote work. See his tips for starting strong.

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Interview with Taylor, a marketing director and intentional digital nomad

In 2015, I had just gone through a painful breakup. The kind of breakup that makes you take a step back and re-think your entire life, not only your love life because you suddenly feel like you're flailing.

In the process of trying to heal, I buried myself in my job... only to realize that I hated everything about it.

I hated the freneticism, the rigidity of office life, the monotony, the feeling like I was wasting my youth on a job that wouldn't love me back.

I'd always associated remote work with menial "telecommuting" jobs until I read an article about digital nomadism featuring people with careers I genuinely admired.

I hadn't realized that I could travel without taking a career break or a de facto demotion. It all clicked for me. That's what I wanted!

I wanted to live on my terms and integrate travel into my life via a remote career and location independence. I started applying for remote jobs that week, gave notice, and landed at my current employer, Tortuga.

The switch was pretty seamless for me logistically. I'm a self-starter by nature and a fiercely independent person, so I found it relatively natural to build my routine around work.

Taylor shares how co-working spaces, digital nomadism, and work flexibility gave her the work environment she always wanted.

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Interview with Leon, a journalist teaching the world to play chess

Working remotely came completely out of the blue for me. I was a journalist working long hours at The Telegraph in London. Then one day I was offered a new job by one of my contacts that combined one of my big passions, choosing my own hours and a complete change in career.

I decided to roll the dice and take it, to give up my solid established job working for a big internationally-recognized newspaper and join a tiny team working on Chessable, a start-up chess learning platform.

One year on and I find myself working from home, seeing lots more of my toddler and having a far better work-life balance. It has made an incredible difference in my life.

Leon James Watson is a former journalist who has found the intrinsic value of remote work while teaching the masses to play chess.

Read full interview from Interview with Leon, a journalist teaching the world to play chess.

Interview with Michelle, an organizer of digital nomad experiences

About two years a year ago, I started traveling as a 30-year old solo backpacker in Australia. Before that time, I had lived for five years in South America, traveled a bit here and there all over the world, but never left for a year on my own without a plan.

I started looking for a job in a local Facebook group and saw an ad for a road trip, 39 days through the outback, something I had for a long time on my bucket list! With super jet lag, I picked up the phone and negotiated myself in a job on that trip: I could be the tour manager!

I got paid and could travel, how cool was that! Soon I found out that only traveling was not satisfying for me. Even though I was the tour manager and had some responsibilities, I was surrounded by mostly young backpackers, some with great stories and deep souls; others never left home before.

I missed the depth, people to connect with, and talk about ideas and visions about life.

Then I met Andreas, my colleague, and cameraman of the business we worked for. We could talk for hours about the same interests, and his head was constantly producing new ideas. I liked this. Sitting around the campfire, discussing business ideas, talking about life, really connecting.

Andreas and I ended up traveling over 20.000 km together as a team for this business, finding out how our skills and passions were the perfect match. At the same time, I started to look into learning digital marketing skills, finding out that this is the way to make money while being on the road.

With Andreas being the greatest videographer when it comes to travel and tourism, our idea started to develop to create the ultimate trips for people like us. And to capture everything on camera.

A solo backpacking trip led to Michelle organizing co-travel experiences for digital nomads—hear how she manages working while traveling.

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Company Interview with Devin, CEO of Animalz

Being a remote company is about more than just location. It’s a lifestyle and culture choice.

You need to implement supportive policies that help your team thrive in the environment you choose.

How do you keep remote teams motivated? Devin, CEO of Animalz, shares her tips for how leaders can avoid demotivation and her hopes for the future of remote work.

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Interview with Celine, a VP of People Ops and remote team member

Remote work is not (yet) common practice in Europe. And it is even less common in my line of work (People Ops).

After two years of experience being remote, I can say that you work very differently whether you are in a fully distributed organization or whether you are one of the very few remote employees and everyone else commuting to an office.

In a fully remote organization, you thrive with the same tools as everyone else. That helps a lot.

You feel much more isolated, and you are not part of the working culture when you are remote with everyone else at the office. So you adopt a project management type of work, and you constantly ask questions to ensure you are not missing an important piece of information.

Celine has experienced the highs and lows of working with remote and hybrid teams—see her tips for thriving as a member of a remote team.

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Interview with Andrew, a freelance writer who works remotely

Funnily enough, I never intended to freelance remotely full-time. At first, I had found the website Upwork, where you could apply for writing jobs that clients were looking for writers. Thinking it would be a good way to get some side cash here and there, I put in for a few jobs.

Upwork has a simple enough system to apply for jobs, making it easy to apply for a bunch of work at once. Since I had no experience and no ratings, I figured I’d put in for a lot of different jobs, throwing the net wide in the hopes of getting one or two bites.

Much to my surprise, I had multiple clients reply to me fairly quickly.

I was working a delivery job at the time and so had some downtime to the point where I could do both jobs, I’d deliver food and while waiting for another delivery to come in, I’d write.

Then, within a month, I was hit with so many clients that I’d actually be losing money if I didn’t quit my day job.

It happened so quickly that I said to myself “okay, I’ll just take a break from delivery work and see how this goes.” I never went back to working full time anywhere else.

One of the cool things behind Upwork was that not only could you easily find clients, but clients could also find you, inviting you to apply for their jobs. This meant that the more success you had on their platform, the higher chances you’d have of getting invited to various new jobs. This made transitioning to working for myself far easier than I would have anticipated.

Switching from working full-time on a set schedule to working on my own schedule wasn’t particularly challenging for me. Before I started freelance writing, I spent my free time writing various different books and stories, so I had the discipline developed to just sit down and write. Perhaps the biggest challenge was learning how to write to please a client.

I enjoyed the change immensely. Going from always having to follow a bunch of company policies, rules and regulations to being able to just kick back and work at my own pace was a pleasant transition. I still enjoy working remotely today. So fewer headaches and you save a bunch on gas, which is a real plus!

Andrew became a full-time freelance writer after experimenting with freelance marketplaces. After the first month, he was already earning more than his full-time job.

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