How did you get started with remote work?

Question: How did you get started with remote work? Read answers from remote workers to learn.

Interview with Hannah, a freelance writer that travels the world

It wasn't easy at first. The process might be different depending on what type of remote work you're aiming for, but I can explain my process.

My friend John, knowing I enjoy writing, recommended I write on the platform Medium.

He gave me a challenge to write a piece every week. I took that challenge very seriously and didn't miss a week for an entire year. During this time, I worked standard in-person jobs.

I took that challenge very seriously and didn't miss a week for an entire year.

My writing was performing really well—it was getting significant views, comments, etc. When I moved, rather than find a full-time job, I got a part-time one. Now I had the time to make writing a supplemental income and, when I applied for jobs, I had plenty of samples to show.

No matter what your field, I highly recommend spec work whether it be redesigning a popular website to show design skills, coding your own app, or writing your own articles. But do it for yourself and keep all the rights.

Unless it's for a charity or close friend/family member, don't do anything for free. When you start to do work for others, show them creations you've created for yourself, and that proves your value.

My part-time writing grew until I decided to risk having it as my only gig. It was not easy going from there. However, I was in a point in my life where I was willing to take that risk. I recommend easing into 100% freelance unless you have a significant amount of money saved. It ended up working out for me, but not without some stress along the way.

It also helped when I really started to learn to charge closer to what I'm worth. Think about it: Would you rather work 10 hours for $10/hr or 4 hours for $25/hr? It's the same amount of money, but very different amounts of work. Don't charge barely minimum wage rates (or lower—I've seen it an endless amount of times) just because you are newer to a field. You can take that into account, but in the end, you're likely worth more than you think.

Hannah is a freelancer writer and social media manager that travels the world while working remotely. Read her interview to learn how she works.

Read full interview from Interview with Hannah, a freelance writer that travels the world.


Interview with Bennah, a remote ESL teacher that teaches kids English all over the world

I was working in an office before where they operate on online teaching jobs whose students are from Korea and Europe. I have worked there for three years and I resigned since I passed the Licensure Examination for Teachers.

I worked in a college and after four years I felt that the job I had cannot provide well for my family so I filed a resignation at the school where I was employed and a friend sent me a message that the online company he was working with is hiring an online teacher to teach Chinese Kids online.

With an empty pocket, I asked people for loans and bought a computer and installed internet connection to be qualified for the job. The first week was a struggle because I was only using a pocket wifi for my classes, and I don't have a good work station at home since I was only renting an apartment (an old shack).

After I have bought my camera and headset, I worked on a desktop computer which is better than a laptop. So through computers, I have delivered my teaching to students. We use applications like QQ International and Zoom.

Bennah is an ESL (English as a Second Language) Teacher who teaches students from all around the world while working from home.

Read full interview from Interview with Bennah, a remote ESL teacher that teaches kids English all over the world.


Interview with Shauna, founder and business consultant specializing in remote work

My business is Operate Remote. I work with companies to help them maximise their opportunities and minimise their challenges when it comes to distributed working.

I do this through consulting and coaching in a range of different areas; operations and strategy, leadership, communications and even team culture and engagement. I love helping businesses find their own ways of managing distributed teams.

Remote working isn't smooth, and it's definitely not for everyone, but when companies have the right mindset, strategies, and skill sets in place— they can create something extraordinary and unique.

Shauna is a consultant that guides companies in thriving while remote—see her advice for staying grounded as a remote worker.

Read full interview from Interview with Shauna, founder and business consultant specializing in remote work.


Interview with Elizabeth, a graphic designer and art director

I started working remotely in 2012 after being made redundant from a very comfortable corporate job in investment banking. I’d moved out of London to escape the city during my time there, but that resulted in a pretty intense daily three-hour commute.

I didn’t love it, but it was what worked for me and my family at the time.

I knew it wasn’t sustainable and it really hit home that something needed to change when I took a sick day and my then seven-year-old daughter asked me why I was there when she woke up that morning.

I didn’t have an exit strategy and was actually relieved when they provided me with one.

I took some time off, did a bit of ad hoc work here and there and was on the verge of “I’ll never get a job again” panic when an entrepreneur I’d worked with before called me, looking for remote help with a start-up he was working on. I thought, “I have a computer and a phone, it might work, so why not?” and we gave it a go.

The start-up didn’t work out BUT we knew we were on to something with the whole remote assistance thing. We quickly brought one of my investment banking colleagues on board, and the business took off and eventually grew to include a handful of dedicated employees who further proved that remote work was not only viable but rather exciting.

We accidentally created one of the first companies in the UK to provide virtual ‘office in a box’ services in the UK by simply filling a need we had ourselves. I’m very proud of that.

I exited that business and have since started another business, this time calling on my creative background and strengths. I now work as a freelance graphic designer and art director with a specialism in cohesive small business branding.

Elizabeth provides the ultimate list of tips for aspiring freelancers and remote workers. Check out her game-changing tools, and advice for thriving as a freelancer.

Read full interview from Interview with Elizabeth, a graphic designer and art director.


Interview with Deb, a sales copywriter who transitioned from software development

My background - I am an Indian, with a Computer Science and Engineering background. I started my career 19 years ago in Software Development in a small company, in Kolkata, eastern India. Worked there for a bit more than a year and a half, and then got an opportunity to work in Singapore, where I worked as a developer for 6 months.

My next job was in the UK, where I worked as a developer in a start-up dot-com company for 3.5 years. I didn’t live in London or in a big city. Rather, I worked in a quaint village called Burley-In-Wharfedale (near Leeds, West Yorkshire), that had a population of around 1500 people.

The interesting aspect of this job was that I landed in the UK and the dot-com bust took place. So, just imagine the tumultuous emotions that went through my mind as I grappled with fitting in a completely different culture with no surety whether the company I worked on would still be afloat in a week’s time!

However, I stuck to the grind and we scraped through the initial few months of the cull that was taking place all around the world at that time. During that period, the company I worked for was looking for ways to generate revenue, since advertising revenues were plummeting. So, I suggested that we explore the option of opening a software division of our company to execute IT projects with the help of tie-ups with Software companies in India.

Our directors agreed, and we opened a software division of the company and I was the primary contact person and acted as the business development manager for that division. My responsibilities included liaising between the Indian software companies and the UK principals from whom we procured the IT projects.

I was involved in all sorts of written communication between the parties. Starting from vetting the legal contracts (in conjunction with our companies’ legal team), to co-ordinating the conference calls (This was before the days of Skype, so we used to rely on land lines, which were not very cheap!) between the various parties, and so on.

I came back to India around 14 years ago for family reasons and continued working in business development/IT sales for various Indian companies for 7-8 years. During this time, I travelled to the US for Business trips, specifically Orlando, FL and Boston MA to procure software projects. I also went to Los Angeles, CA, and Las Vegas, NV to attend business conferences.

My last corporate job was back in 2010, wherein I led a team of Inside Sales specialists whose job was to sell a software product to various Fortune 500 companies in the UK and the US. All our selling was over email and the phone.

It was during my tenure here, that I developed a skill of being able to write persuasive emails.

I was laid off in 2015 due to a software paradigm shift and thought of taking this opportunity to reassess where my career was going rather than jump into another job right away. I had heard of remote working/freelancing and was entranced with the idea of working on my own and thought of checking it out.

The next hurdle was deciding which area should I focus on when it came to skill sets. Even though there were a few software sales jobs which were available to be done remotely, at that point in time, they were few and far between.

After much self-analysis, I realized that in most of the companies I worked for, I was given the responsibility of writing sales/marketing collateral, vetting legal contracts, and drafting customer facing emails. Since childhood, my passion was the written word, and I had won a few creative writing competitions during my university days. So, I thought of venturing out there and see if I could find any writing work as a freelancer.

A few web searches led me to the availability of content mills, which paid peanuts. But I thought of applying for a few of them to see if I could make any headway. After a month or two of applying randomly for as many jobs as I could, I got my first content writing job – a 1000 word blog post for a princely sum of $5.

I was happy, yet apprehensive. Plunging into research on the web, I soon came up with reference articles, from where I drafted my blog post. After reading and re-reading it at least four times, I finally submitted the blog post and sat back to wait with bated breath. Less than 24 hours later, the client accepted the article, giving me 5 stars for my work, and immediately commissioned me for 5 other similar pieces.

I was overjoyed, because in the depths of my heart, I’d never actually believed that I’d get paid to write!

Cut to a couple of months later and I was writing my heart out, pouring a lot of time and effort into writing close to 10,000 words in a week. But, soon, I faced burnout and realized that this way of working was not sustainable.

While I was writing for this content mill, I used to read the blogs of established bloggers and freelance writers to get inspiration and some direction on which way to go in my writing career.

During one of these searches, I stumbled upon Upwork and realized that this could potentially be a platform where I could leverage my writing skills to get better paying gigs.

I signed up at Upwork, created a profile, took the skills tests, and started applying for jobs there. It took a lot of struggles, and some time, but finally, I’ve reached a stage now, where I can pay my bills while working full time in a freelance capacity.

Deb made the jump from full-time software developer to freelance sales copywriter—learn how he made the transition.

Read full interview from Interview with Deb, a sales copywriter who transitioned from software development.


Interview with Meryl, a digital marketer and master of home office organization

After having my second child in 1999, I enrolled in an online program at New York University to earn a certificate in internet technologies. At the time, I worked for a communications company.

The plan was to work toward a career in web design. While I loved web design, I had a terrible eye for design. Still, I enjoyed reading a weekly e-newsletter about web design. It had a contest where you can submit an article to win a copy of Photoshop.

I won! That started my writing about web design that led to more writing work. Work kept coming in, morphing from writing to marketing. I did all of this at home outside of work hours. By 2005, I left my corporate job to become a full-time remote freelance digital marketer.

Meryl K. Evans is skilled at creating a home office that leads to remote work flexibility. See her advice for creating a successful workspace, and hear about her journey into freelancing.

Read full interview from Interview with Meryl, a digital marketer and master of home office organization.


Interview with Artur, an engineer who found purpose as an Intrapreneur

At some level, the idea to work remotely was obvious to me. I started my career as a web development freelancer and working from home was the only option at 15 (and a bit illegal in Poland).

After learning hard lessons about what not to do in your own business, I moved to Samsung Poland, which was a radically different experience. I was enamored by beautiful office space, benefits, and the scale. From that experience, I knew that I wanted to work for big companies.

Me being me, I negotiated my salary down (how often do you hear that?) in exchange for being able to work remotely 80% of full time, which allowed me to travel a bit. I never spent a day working full-time office-bound.

What ultimately launched me on a quest to find a new and remote position was the drive to work on more significant problems, having more impact and working on a product that people will recognize. I wanted "in" on the Silicon Valley startup culture (which since has lost much of its luster), and I wanted to work on the "hip" things.

Also, I did not want to leave Poland permanently. My family is here, and I didn't want my grandparents to lose their only relative.

With my prior WordPress experience, Automattic was a perfect fit. I spent a lot of time preparing and leveling up my skills to apply. You can read a detailed account of that process here. It also includes a guide to using sandwiches as a competitive advantage.

I got hired one week before the whole company met in Park City, Utah. It was 3.5 years ago, and it's as exciting now as it was then.

Artur realized entrepreneurship wasn't for him—see how he carves out his creativity and purpose as a remote Intrapreneur at Automattic.

Read full interview from Interview with Artur, an engineer who found purpose as an Intrapreneur.


Interview with Chanell, a freelance writer and social media manager

I was working in communications for an educational nonprofit, and while I loved the work I was doing, I realized the brick and mortar office was not for me.

My commute was over an hour each way, co-worker distractions led to tasks taking a much longer time to be completed, and I wanted more freedom in being able to travel while working.

This realization led me to understand that remote work was better suited to my personality.

I began applying for remote work positions in digital marketing management, social media management, and content creation. The field was so competitive that my efforts were proving fruitless, so I figured that I would set up a profile on Upwork just to see what would happen.

I began marketing work I had already done for my current job, and I began to find my niche as a business management writer. I began to find freelance work while I was still at my full-time job. It was a lot of work, but it paved the way for me to make enough to leave within four months. A few clients took a chance on me and the rest is history.

I would offer up the following advice:

Don’t be afraid to pursue a different work style. It was difficult for me because the 9-to-5 brick and mortar work environment was all I knew. It was a risk to pursue something different. However, it turned out to be for my good in the long-run. You know yourself better than anyone, so feel confident in making the decision to go remote.

Be flexible! I originally had this idea that I was going to be a digital marketing/social media marketing associate for a remote company. Well, I quickly found out this was a very competitive field, and that I didn’t have the connections to pursue this fully. So, I ended up finding out that I could be just as successful writing (which I happened to enjoy even more).

Use social media! I have stumbled onto a lot of opportunities while searching different hashtags on Twitter, joining Facebook remote work groups, and keeping an eye on LinkedIn job postings. Job boards are great, but social media can be an awesome resource in finding the next gig.

I am truly grateful for the opportunity to work where I feel most comfortable. The beginning was a bit scary, but I have no regrets in starting on this journey. Remote work has allowed me to be even more productive than I was at an office. There are always late nights, but I would not have it any other way.

Chanell is a freelance writer working from Atlanta that writes about business management tips and video game entertainment threads.

Read full interview from Interview with Chanell, a freelance writer and social media manager.


Interview with Ascencia, a content marketer, and avid gig economy professional

During college, I was already familiar with the gig economy and the possibility of earning money through the Internet. I had accounts on Gengo (translation service), Fiverr, Zerys (writing service), and Upwork. I did several gigs on Gengo and Zerys, and earned about almost $200 in total.

But making a career out of remote work wasn’t my initial plan. After I finished my bachelors’ degree and a year-long traditional office internship, I was offered a full-time position at that company. But I rejected the offer because I was planning to pursue my masters’ degree.

The exact transition was a blur, but one day I remembered that I had an Upwork profile. It was already approved for two years, and it was just sitting there since I didn’t have time to apply for jobs or do the actual work.

So I decided with the free time I had, I could do one or two projects there. However, I didn’t have any specific experience besides the subjects I learned in college and the internship experience as an IT QC staff. Thankfully, there’s a position called virtual assistant on Upwork.

A virtual assistant, just like its name, does every kind of job you could imagine, virtually. It’s the perfect way to learn new skills while earning money, just like an internship. I started at $4/hour. A meager rate, but a pretty decent one if you convert it to Indonesian Rupiah. With my first two clients, I did English to Indonesian translation and Trello/WordPress content management. I’m still working with them now.

About ten projects later, I realized I was attracted to content marketing. I’ve always loved reading, writing, and languages in general. It’s only logical for me to work in content eventually.

Now, 18 months since my first project on Upwork, I’ve specialized myself in content marketing and quadrupled my hourly rate.

A forgotten two-year-old Upwork account allowed Ascencia to become a content marketer—see how the gig economy has offered her an alternative path to success.

Read full interview from Interview with Ascencia, a content marketer, and avid gig economy professional.


Interview with John, a web developer who works from home

In 2009, I was unhappy with my corporate job. A couple of friends and I decided to start a WordPress development agency.

Since one was in Texas and two were in Vegas, it made no sense to try and have an office. So, we all worked from home. Although I don't run that agency any longer, I have yet to go back to working in an office and will avoid it for as long as possible!

John is a web developer running a mini-agency inside a larger WordPress agency - learn how calendar management and establishing boundaries have helped him boost his productivity.

Read full interview from Interview with John, a web developer who works from home.

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