How did you get started with remote work?

Interview with Melissa, a co-founder and remote work champion

I have worked in the advertising industry for about 15 years. About 10 of those years were spent in NYC where the job market can get pretty competitive, and the expectation is always that your butt was in the seat and the "face time" was what enabled you to move up the ladder.

I'm embarrassed to say how many nights I actually slept at the office. I thought it was the only way...

The more experience I gained, the more I realized that I needed solid chunks of thinking time without distractions. It took me a while to gain the confidence to set precedents with when I was willing to be available to my team and my boss.

Initially, I worked one set day from home, and that was enough to get me hooked on the benefits of flexible working environments. I was more productive, more energized and overall, felt like I had a life outside of work for the first time in... well maybe ever.

So when I moved to Atlanta about four years ago, I made some intentional choices that allowed me more flexibility while still focusing on my career goals:

• One, I negotiated part-time status at the agency I was at.
• Two, I picked up other sources of freelance income that allowed me to be more autonomous like teaching, mentoring, and workshop facilitation.

And, most recently, after meeting my amazing business partner, MaryEllen Stockton, we decided to go in all the way and not only work completely remote but focus on the topic itself in our services. We wanted to help other women like us achieve the type of flexibility they only dream of — without the guilt.

Melissa started Work Well Wherever to help individuals & companies embrace remote work—see how she balances entrepreneurship, parenthood, & self-care.

Read full interview from Interview with Melissa, a co-founder and remote work champion.

Interview with Vivek, an entrepreneur building a virtual office for remote teams

I never really expected to work remotely, to be honest. Out of college, I founded a company called StacksWare after graduating from college and sold it after operating the business for two years. The acquiring company was based in Santa Clara at the time, and we were living in San Francisco.

The daily commute was brutal, taking one and a half hours to commute one way during peak traffic. I viscerally remember my lowest point during that period. I was sitting in my car in bumper-to-bumper traffic on the 101 on a Monday morning, calculating the opportunity cost of all the lost time in traffic and dreading the return journey at 6 PM.

I asked if I could work remotely and never looked back.

The long San Francisco commute sent Vivek into remote work—hear about his three strategies for eliminating distractions & his must-have tools.

Read full interview from Interview with Vivek, an entrepreneur building a virtual office for remote teams.

Interview with Henry, a consultant who found remote work by saying No

A friend of mine, based in the small town of Rockland, Massachusetts, was trying to hire a marketing strategist at his agency. He couldn't attract anyone to work in Rockland (the talent pool was too small), so he asked if I wanted to move from California to Massachusetts to join his company.

He had recently leased space with a conference room and five offices. He had a dream of filling it with a growing company.

I said no. Well, he hired me anyhow and I've been working for him ever since. He gave up the office space after that and we realized there was a lot more talent in the world rather than within driving distance of Rockland. We turned the company fully remote.

Sometimes a "no" can lead to an exceptional opportunity. For Henry, that answer led to an ideal remote work career. In this interview, Henry shares his remote work tool stack, and essential tip for remote employees and managers.

Read full interview from Interview with Henry, a consultant who found remote work by saying No.

Interview with Kristi, a CEO and remote team leader

I began working remotely back in 2013, first as a marketing consultant working with startups and universities, and then in a fulltime communications role with a large higher ed IT association.

I'd already spent six years in traditional brick-and-mortar jobs but was eager to break free from the four walls of an office--knowing full well that I could accomplish anything I was working on from anywhere I could use a laptop.

That was such a freeing feeling. I stayed in that role for two years before striking out on my own with a teammate whom I've known for decades. Now there are six of us.

Kristi is a CEO, remote work author, and speaker. In this interview, she shares the impact of new motherhood and remote team leadership on her work.

Read full interview from Interview with Kristi, a CEO and remote team leader.

Interview with Vaishali, a content marketer and a productivity tool expert

I started working at a multinational company right after I got my engineering degree. The job was bliss with lots of learning and a good pay-scale. After I got married, I continued working at my job. Eventually, I got promoted and also received an opportunity to go to the U. S. to work for a very high-profile client.

Everything was going fine. Then we (I and my husband) decided to leap into parenthood. Moreover, that's when I decided to leave the job which I loved so much.

I was happy and content because our world was complete with the arrival of our daughter, but the habit of working was still around. So I started freelancing by building websites and offering consulting services for local businesses.

This went on for a few years until I was fed up of the low returns and the struggle to get new local clients.

I did a few certifications and also earned a distance MBA degree. Meanwhile, I was applying for remote jobs. I kept trying my luck for over a year and a half, and one day I received a reply from my current employer, Time Doctor.

After some discussions and verification, I received the confirmation. That's when I actually started working remotely full time.

Vaishali persevered until she found the right remote work job for her lifestyle—check out how she uses productivity tools and time management strategies to stay productive.

Read full interview from Interview with Vaishali, a content marketer and a productivity tool expert.

Company Interview with Tammy, CEO of Workplaceless, and a remote work leader

Workplaceless was founded as a 100% remote company, and the primary reasons are two-fold:

As the leader in remote work training, it's critical for us to model best practices in remote work for our clients. Our distributed team members have empathy for challenges that remote workers and teams face every day.

We leverage our own operating structure as a virtual testing ground to ensure our trainings are effective for us as well as our clients.

Like many small businesses in small cities, suburban or rural areas, the talent pool in my immediate area is skilled, but also limited in number. When I started to grow beyond myself as a sole-proprietor, I knew from prior remote experience that I could access the greatest talent pool to meet the wide range of needs my business had in a startup stage.

With Workplaceless, Tammy helps companies start off on the "right remote foot." Hear how her 100% remote team stays in sync, and how she keeps her employees engaged

Read full interview from Company Interview with Tammy, CEO of Workplaceless, and a remote work leader.

Interview with Gino, a founder skilled in building remote teams

I got started with remote work back in early 2015 when I moved to the Bay Area (I’m living in Seattle now and loving the Pacific Northwest). By that time, I had spent around a year working with my team in an office in Lima, Peru.

In 2015, we decided that we would start hiring remote team members based throughout the Americas and not just Lima. That’s what got us started in remote hiring.

We started hiring great people in Argentina, Mexico, Chile, and all of a sudden; we had a company with half remote team members and half in-office team members.

It wasn’t long before many of the team members in our Lima office started requesting to work from home. One of our engineers had to commute for an hour and a half each way (to and from the office).

What’s crazy is that the vast majority of companies throughout Latin America continue to operate this way — basically expecting employees to commute for a couple of hours a day on average. Remote work is growing in Latin America, but more slowly than in other parts of the world.

It’s embarrassing to think that we didn’t think about going remote earlier. Once we did, we noticed a spike in productivity and everyone was citing improved work-life balance.

Soon after, we decided to let go of our office altogether in order to become a 100 percent remote company. Today, we have team members from the U.S., Mexico, Chile, Peru, Argentina, Brazil, and others. We all work from home.

Gino realized how important remote work could be to finding the best talent—see his strategies for building remote teams.

Read full interview from Interview with Gino, a founder skilled in building remote teams.

Interview with Marian, a nomadic social media manager and day trader

I started my remote lifestyle four and a half years ago, and it was by chance. I was looking for a job opportunity, and I found out about stock trading.

I invested $50 on stock trading, and I had a mentor that worked with me every time I traded.

I enjoyed, and loved the idea of working and making money at home.

I was a day-trader for over five years. I still sometimes trade, but nowadays, I am focusing on building my own digital marketing skills.

On June 2019, I discovered the idea of the digital nomad, and I joined a Facebook group for entrepreneurs. Within the group, they focus on hiring each other to help further their businesses.

I discovered that I can help other business owners manage their time, as well as schedule and manage their social media business accounts as a virtual assistant.

My first client was an American entrepreneur, and I learned a lot through the experience, like working with Google Sheets and Docs.

Day trading & virtual assisting has allowed Marian to see the world—in this interview, she lays out her routine and priorities for those thinking of traveling while working.

Read full interview from Interview with Marian, a nomadic social media manager and day trader.

Interview with Saibu, an HR content writer for a remote company

My journey started when I was still a student at the University. That time, I needed a hustle that would make me some cash, and after trying many options, I settled on content writing. That got me started – searching for remote work. I landed a few gigs, both short and long-term.

So after graduating in 2016, I decided to go into remote working full-time. Things weren’t that smooth, so I had to take some on-site jobs from time to time. But I realized at a point that on-site jobs aren’t just for me – and went into remote full-time. And, I’ve been working remotely since 2014.

Hear how Saibu, a thriving HR content writer, navigates the complexities—and perks—of working with a remote team from Ghana.

Read full interview from Interview with Saibu, an HR content writer for a remote company.

Interview with Kay, an independent software consultant who found freedom in remote work

I worked as a employee for about 7 years at a small software company. After a big project with much overtime, I asked what the manager what he had in mind for me in terms of career growth. He wanted to make me his replacement for head of R&D, but the rest of the management team was against it. They said, a manager can't get to work at 11am, after all the other employees, haha.

In hindsight they were right, I wasn't made for the management job, but I was pretty salty and quit. I did a sabbatical in 2014 and tried to find out what I really wanted, since it wasn't working from 9-5 in some job without future and I had the feeling most jobs were about this. In 2015 I started interviewing again, this time with the goal in mind to get a remote job, because if I had to work 9-5 in a futureless job, at least it should be as comfortable as possible.

I also had the impression that my schedule was already pretty full with my private life. I already played guitar, learned bass in 2014, started swimming and biking and after I started living in non-monogamous relationships I had two girlfriends. So sitting in an office for 40h a week with potentially 10h extra commute every week wasn't an option anymore.

Took half a year until I got a job as a developer at a startup in Frankfurt, Germany, which is about 300km away from me. They let me work from home, but as a freelancer. They said they would employ me regularly if they get their investment, which they got a year later, but the terms for the employment weren't what I had in mind.

But this was a good thing, because the terms which I didn't approve of, showed me what I really wanted.

I didn't just want to work from home, I wanted freedom.

I wanted to decide that I will work for like 6-8 month in a year and still have enough money to have a good time in the remaining 4-6. I wanted the option to walk away in a matter of weeks or even days if I didn't like how a company behaved, I wanted to seize opportunities I would have to ask my employer for if I wasn't a freelancer.

And so I kept working for this startup until their investor forbade them to hire me, because I was too expensive, lol.

In 2017 then I went on to do the full self-employment thing. Find multiple projects, do them for a few months, learn many new things and move on to the next. While the process of finding these projects (interesting + remote) isn't that easy, I feel much better than ever before in my life.

Learn how Kay made the jump from full-time employee to full-time remote consultant

Read full interview from Interview with Kay, an independent software consultant who found freedom in remote work.