How did you get started with remote work?

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.

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Interview with Nathan and Connor, owners of Freeeup

It was back in 2012 or so when we were building our first eCommerce business. We had just graduated from college, and we were reaching a point in the business where we needed to start bringing on more people to help grow the company. We already had a core team of full-time and part-time team members, and we were looking to expand that team without breaking the bank.

It was around this time that we were introduced to the idea of hiring remotely from another entrepreneur that we had met. He tipped us off to a site called Odesk (now Upwork).

We started posting jobs on the platform and began interviewing. Eventually, we quickly became addicted to building up a team of remote talent from all over the world to help as we continued to scale the business.

After years of hiring remotely with our first business and running into many frustrations, we decided there must be a better way, and we started FreeeUp.

Thinking of creating your own remote startup? See how Nathan and Connor built a successful and effective remote team from scratch.

Read full interview from Interview with Nathan and Connor, owners of Freeeup.

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 Erin, a virtual assistant with a successful approach to freelancing

My road to remote work was actually quite long and winding. I had been working in film in Louisiana for over 5 years and was already nearing burnout with the demanding hours. In 2013, I took a leap of faith and launched my own business - an on-demand concierge business to assist other crew members.

While on paper it made sense to market concierge services to busy film production crews, I quickly discovered that not many were willing to pay for those services. So, I turned to remote assistance instead.

Initially, I joined a service called Zirtual that matched virtual assistants with clients. While the formal training and support I received from Zirtual were fantastic at the start of my VA career, I eventually left the company to lead my own VA business.

Having greater autonomy over my working hours, the services that I offer, and pricing have been incredibly rewarding, and I haven't looked back since.

Erin has found freelancing success as a virtual assistant—see her organizational tips & insights into how she picks clients that suit her business.

Read full interview from Interview with Erin, a virtual assistant with a successful approach to freelancing.

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 Maggie, a senior product manager at HubSpot

My husband and I were over in Canada for almost ten years, and when I was pregnant with my second son, we decided to move back home to Ireland.

I was lucky to work for a fantastic team at Expedia, where my manager at the time didn’t blink an eye at allowing me to move home and work full time remotely.

Remote work allows Maggie to live in a small town and excel in her career. Hear about how she stays professionally connected, and her essential career advice for remote workers.

Read full interview from Interview with Maggie, a senior product manager at HubSpot.

Interview with Ben, a web developer who freelances from home

I've always been interested in web development. When I was younger, I applied for a job advertised on a local version of Craigslist. The guy didn't have an office, and was only a small company, so I ended up working from home because of that. Eventually the money ran out, and I got an office job (which I hated).

A little more than a year after that, I found myself downsized, and with more than a month of severance and vacation paid out, with a little time on my hands. I did piecemeal work as a freelancer, and was lucky enough that the work kept coming.

Learn the tips and tricks Ben uses to stay productive while working remotely on a hybrid team

Read full interview from Interview with Ben, a web developer who freelances from home.

Interview with Jake, a customer success manager for Atlassian

I was working with Atlassian/Statuspage for a few years and was getting burnt out on the San Francisco lifestyle.

I wanted to keep my job, but I didn't want to live in San Francisco anymore.

So I started looking into the possibility of working remotely. I'm thankful to have a remote-friendly boss and to work for Atlassian—they've been taking a lot of steps to be more remote focused.

Jake was burned out on the San Francisco lifestyle—see how he transitioned from working in-office to working remotely for a remote-friendly company.

Read full interview from Interview with Jake, a customer success manager for Atlassian.

Company Interview with Tricia, CEO of BELAY

If your team is new to remote work, one of the first ways to get your team up to speed is to start with leadership.

Leadership must be on board with promoting and utilizing the tools your team will need to complete their task while away from the physical office.

When it comes to tangible tools, aligning with your IT team and introducing your employees to chat communication tools such as Slack, video conferencing such as Zoom and project management platforms like Asana will become important to help your team stay connected.

For 10 years, BELAY has been a 100% remote work company. CEO, Tricia, shares the tools that keep them thriving and how boundaries & expectations contribute to their success.

Read full interview from Company Interview with Tricia, CEO of BELAY.

Interview with Jenna, a freelance writer who works remotely to help manage her health

To be honest, I feel like I was sort of pushed into working remotely as a freelancer because of my health problems. I was getting these stress-induced migraines frequently that made it dangerous to drive and impossible to get work done. And I wasn’t sleeping much either which of course wasn’t helping.

The office was full of migraine triggers like fluorescent lights, perfumes being sprayed indoors, a lot of noise, blue light, and the stress of the job. I got yelled at a lot because one of my main responsibilities was to diffuse difficult situations with customers. I tried to go outside, take frequent breaks, meditate in my car, just anything to get rid of that stress, but it wasn’t enough.

The attendance policy was really strict, and I had no FMLA protection left after a medical leave I’d taken earlier in the year. I was not at all willing to force myself to drive with a migraine – not only was the pain bad, but I get aura, which is severe brain fogginess and problems seeing, or hallucinations that are zigzags of light that go across my vision. Public transportation wasn’t an option and I wasn’t allowed to work from home. So, I kept missing work.

So then I was placed on a warning for missing too much work. I’d been trying to move into a lateral position that would allow me to work remotely – some of the available jobs involved work I’d already been doing in my current position so it should’ve been a no-brainer. But this company took months to fill any openings, and once I was placed on this verbal warning I was no longer allowed to move into other positions. For 6 months, or a year, I forget which, I was totally stuck. And if I’d missed 2 more days of work in that timeframe I’d lose my job.

It was really frustrating at the time because I’d been there for 3 years at this point, and they weren’t wiling to work with me at all or try to keep me employed. I felt disposable and realized that the stress of not having a steady paycheck was not as bad as the stress this job was causing me.

I considered trying to find a new job that was 100% remote but those jobs are few and far between and I know there is a ton of competition for them.

Plus I really wanted to control my hours so that I could rest as much as I needed to recover my health. I’d always wanted to be a writer and I’d been studying marketing for months at that point in the hopes of trying to freelance, and I also really didn’t want to get fired – I wanted to leave while it was still my choice even if it didn’t feel like much of a choice. So after a few attempts to quit and chickening out, I finally gave my notice and took the leap.

It was pretty scary to do that but I’m lucky to have a very supportive partner. And after a few months of rest, my migraines went from 3-4x weekly to 1x monthly or even less! I definitely feel like I made the right choice, and now that I’ve experienced the freedom that comes with working from home as a freelancer I don’t think I’ll ever be able to go back to a traditional job. I’m still recovering from the burnout I experienced from my old job, but I’m really looking forward to being able to travel and work from anywhere in the world.

I know a lot of employers are resistant to allowing remote work, but I think those types of companies are going to eventually be perceived as old-fashioned.

There’s so many people out there like me who have a hard time being in a regular office whether it’s because they’re introverted or have health problems (or both). Personally, I get way more work done when I’m at home than I ever would in a typical office environment.

Freelancing is hard and definitely not right for everyone, and remote jobs would create a lot of opportunities. I believe a lot of companies would benefit from allowing employees to work from home.

Jenna started working remotely after realizing her office job was causing health problems—now she works as a freelance writer and writes about self-improvement

Read full interview from Interview with Jenna, a freelance writer who works remotely to help manage her health.