Home > Remote Workers Q&A > How and why did you start working remotely?

    How and why did you start working remotely?

  • Karen LaGraff

    I am onsite employee with an office, but started taking the option to work remotely about 10 years ago. In this day and age, where we all have laptops and cell phones, adding a couple of apps makes it pretty simple and makes business sense. I have meetings throughout my day with global teams. Some days I start very early; some I go very late to accommodate projects and different time zones. I often feel more productive and engaged if I work remotely because I avoid commutes and have more flexibility in balancing my workday and personal needs.

  • James Clark

    I started out making websites as a side interest/hobby. Eventually I realized it was something I could do as a job so I started planning for that. The digital nomad/remote worker culture wasn’t a thing when I started in 2003 so I didn’t even know I was becoming a remote worker. I just wanted a job I liked and to be able to travel more.

  • Harald Johnsen

    I’ve always loved traveling, and I could never come to terms with only being able to travel 4-5 weeks a year—which was all I was able to do back when I had a “real” job in a “real” office. I basically wanted to explore the world more, not just in terms of traveling and seeing the world, but experiencing what it is like to live in and immerse myself different cultures and so on. Besides that, I’ve always seen myself as a bit of an outsider—not really wanting (or even being able) to really fit in as far as my own culture goes. The thought of living a “normal” 9-5 life always seemed a bit, well, dreadful to me, to be honest. I don’t think I’d be happy living that way. For years I tried to, and it always felt like a bit of a lie.

  • Lauren Antonian

    I requested the option due to difficulties with the commute to the nearest office.

  • Jen Hubley Luckwaldt

    I’d wanted to try freelance life for a while when I was laid off in 2011. I gave myself one year to make it work. Five years later, I’m earning more than I did as a full-time staffer. Plus, my wardrobe is primarily athleisure and my office is in my house.

  • Jonathan Kalan

    After graduating college, I worked at a startup in Los Angeles for a year. It was a grueling yet rewarding experience, and towards the end of it I was convinced that I was not meant to be tied to a desk, an office, and a 9-5 job. I moved to Africa in 2010 to pursue a career as a photographer and journalist, and loved the freedom and mobility I had to create my own schedule and follow my curiosity. I’ve worked remotely or set my own schedule / hours / locations more or less since then.

  • David Daniel

    For the last 15 years, I have been an onsite consultant for major firms. While I always had ‘an office,’ I was rarely if ever there. This work style forces a person to learn to live and adapt to ever changing environments. It also creates a working culture that does not demand face-to-face interaction with your management.

    Rather than fight to get back ‘home’ for the weekends, my wife and I just stayed wherever we were (or went somewhere interesting) and explored the area as a local. My productivity was always better than those who made their mad dashes for the weekend.

    If we liked where the client was located, we just enjoyed the local culture and food. If it was not that interesting, we would fly to Paris, or San Francisco or somewhere else anywhere in the world…for the weekend.  

    At a certain point, we realized that we had not been back to our ‘house’ in Arizona for 6 months! Our concept of ‘home’ was wherever we were together.  

    When we sold it, the benefits were more mental than they were financial. Sure, we liked not making our mortgage payment, but it was so nice not wondering if a pipe broke, or the the roof was damaged in a storm. Gone was the dread of coming home to a house that needed dozens of little repairs during the short time we were there. (You cannot imagine how many light bulbs blow out when they come on for the first time in a few months.) A person doesn’t realize the emotional overhead surrounding a ‘house’ until it is not there.

    In short, we sold everything and went remote. We have never looked back once. It was the best decision my wife and I have ever made. The world is our home, not some country or building where we’ve accumulated ‘stuff.’   

  • Taryn Barnes

    I worked in a corporate setting that required long hours and tons of traveling. It took a lot of time away from being part of the lives of my loved ones. 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.

  • Jenn Leaver

    A few years ago, I found myself in an interesting situation; I was a few months pregnant with my second child and had just been laid off. I worked a few contract jobs at home over the next year and a half and loved the flexibility that it provided. When I decided to go back to work full-time, I knew that I would be happiest working remotely. Even though my kids are in daycare and school, working at home gives me the flexibility to be a more active part of their lives. Rather than commuting four hours a day (like I used to!), I’m able to do things like eat breakfast with them, go to their doctor’s appointments, and in general, be there for them in a way that I wasn’t able to before. I found my current position at GitHub through FlexJobs and am grateful every day for the life I have because of it.

  • Conni Biesalski

    I have lived a pretty nomadic life since I was a teenager. I tried the 9-5 for eight months, but realized very quickly that I need a lot of freedom and that I want to work on my own dream rather than one for someone else. I just couldn’t imagine myself living a static life in one place, going to the same office every day—it literally felt like a man-made prison.

  • Jennifer Bird

    I had at least an hour and a half commute each way to and from work, which left me exhausted before I even started my workday and drained me by the time I got home fighting traffic. I live in a suburb of a bigger city so to find a company with great values, people, culture, and challenging work was tough to come by. Yet, I was able to find it all working from home with the right company that isn’t afraid to break the mold of a typical office environment.

  • Kristen Marano

    My partner and I quit our corporate office jobs in May 2014 to change up our lifestyle and routine. We backpacked through South East Asia, Australia, and New Zealand for one year before making Perth, Australia, a base.

    We wanted to ensure we stayed relevant while on the road so we didn’t have a gap in our experience. We launched a small digital communications firm and worked with a few Canadian clients from the road, and I also started contributing international fashion pieces to Huffington Post Canada.

  • CarouLLou

    Early 90s, even before I started to live abroad, I became location independent… I started a ‘press clipping’ and communication business, going around with my floppy disk between my apartment and a little office I had rented. So all I needed was a computer, a phone, a photocopier, and a fax.

    Then, when I left my home country in 1994, I had set up a little telemarketing organization with 2 people taking phone appointments…and I had arranged to manage everything by fax, providing them with prepaid phone cards so that it wouldn’t cost anything to communicate with me.

    I also started my ‘life potentials’ and ‘business strategies’ consultation business, also all managed by phone and fax. And eventually, word of mouth, I had clients all over the world. At the beginning, It was costing me a fortune in long distance phone calls (like 60 cents/minute from Asia), but I still took my chance as I had the vision that it would cost less and less over time…(and wow, it sure did!)

    Following those experiences that I could deal with my clients from distance…from wherever I was, to wherever they were…I really felt freedom, and the unlimited potential of that way of life! So from that time, I decided that whatever I would do, whichever business I would start, projects I would get involved in, or investment I would make, it would have to be completely mobile and manageable from distance, no matter where I was in the world.

    Then in 1998, when I was living in Bangkok, I had my first email and launched my first websites…

    All and all, I would say freedom and unlimited potential were always my main motivations. In terms of freedom of movement, it’s wonderful to feel that I am wherever I am, always by choice…and for as long as I want (only limitation being each country’s regulations. But even this doesn’t feel oppressive as it’s just part of the things we need to accept). And also being able to leave whenever I feel it’s time to go, whether it is for personal or external reasons.

  • Roxanne M. Tamayo

    I was working in an office when I decided to find a part-time job working online. Eventually I quit my office job due to health problems and decided to work as a freelancer working online full-time.

  • Shannon O'Donnell

    Originally, I began working remotely as a way to facilitate my goals to become an actress in Los Angeles. I took an internship at a film company in college, and one of the producers there offered me remote work for his other company. I lept at the opportunity. I was graduating from university within a few months and I had plans to work as 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. Within two years, however, I realized that my dreams of long-term travel were a larger priority. I made the decision to travel the world by booking a one-way ticket to Australia. Then I made a mad scramble to find additional clients and line up the roughly 25 hours of work that I would need to afford my yearlong trip around the world.

    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.

  • Jay Meistrich

    I burned out from overworking myself while at Microsoft, so I decided to take a break to travel and relax before getting another job. I got bored of just traveling after a couple of weeks, so I started learning web development while freelancing on an iPhone app. After half a year of traveling, I went home to spend a few months with my parents, where I came up with a problem I wanted to solve.

    I did what I thought I was supposed to do when founding a startup and made the move to San Francisco, which turned out to be a huge mistake as I realized it was not the promised land of my dreams. Although I was working huge hours trying to crush it, I felt myself slowing down because I was spending most of my days in front of my computer in my apartment. I went on a few trips to visit friends and felt like I was waking up out of a fog, and my productivity skyrocketed. It’s actually more productive and far cheaper than San Francisco, so I got rid of all of my stuff and fully committed to traveling.

  • Mike & Anne Howard

    After working the 9-to-9 in NYC 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. Half way through the journey our travel site HoneyTrek.com 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 business from the road.

  • Randle Browning

    It was sort of an accident! I had moved to Waco to get married (my husband and I own a restaurant there that we had opened before I moved away to grad school). Long story short, I didn’t really fit into my local economy. I had a graduate degree in English but didn’t want to work as an adjunct teacher or pursue a PhD at the local university; I had worked as a chef but didn’t want to work in a steakhouse (Waco’s a smaller town); and I didn’t want to work in the restaurant with my husband day-to-day. 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. 🙂

    After 2 years of working remotely, I decided to take full advantage of the work flexibility. Now I live on the road full-time in an RV with my husband and dog. We don’t know how long we’ll travel, but at least through the end of 2016.

  • Nicole Fu

    I’ve always loved traveling, and I think location independence has always been the dream. In 2014/2015 I started to have “the itch.” I had been in Montreal for 4-5 years then. Before that I was in Tokyo for a year, and before that Halifax for a year.

    Then it happened. The startup I was working for faced a cash crunch, and had to immediately let a few people go. Myself included. “We can hire you back in 2-3 months,” they said. That was my cue. I already had a one-way ticket to Singapore for my annual trip there; I only had enough miles to claim a one-way and hadn’t bought the return. Within a month, I sold everything I owned, wrapped up my life in Montreal, said my goodbyes, and left.

    I had a rough plan. I’d join a company remotely. One that I love. Whose (SaaS) product I loved. Who’s in “growth mode”/just raised a Series A. (I’ve seen too many seed startups run out of money.) Can’t be that difficult, right?

    As it turns out, finding a company with all 3 ticks was quite the unicorn hunt. So, I turned to freelancing, and dipping my toes into drop shipping and affiliate marketing.

  • Theresa Cramer

    I started at EContent in 2008 and we always had a small, satellite office. As our numbers dwindled, so did the reasons to have an office. First I started working from home on Fridays—then I became the editor of the magazine during a particular bad winter in New England. I was lucky if I could get out of my driveway and to the office once or twice a week. I started to realize I didn’t need to be near the office and started thinking about moving closer to friends and family. Eventually we closed the office—which was down to two people—and just started working from home full time.

  • Scott Hanselman

    I started 9 years ago at Microsoft because I wanted to work there on Open Source but I didn’t want to move to Seattle. I was born in Portland and this is where we’re staying. It wasn’t negotiable. All our people are here.

  • Liz McGrory

    The first time I worked remotely I was working for my previous company and I was at the end of my pregnancy. I couldn’t believe how much work I got done when I was home, plus how good it felt to be *so* pregnant and still being able to work up until I literally left for the hospital.  

    After my third child was born I left my corporate job to focus on my business and a year later I became a freelance writer for About.com as their Working Mom Expert. I am able to support working moms because I’m not deep in the trenches stuck to a schedule! I’m unsure how I could be there for my clients without the flexibility that I have.  

    My writing job has been amazing because I am a one-person show guided solely by the numbers. I have very little interaction and guidance from the company and am free to write about what I want.  

    In my previous corporate job, I worked as a senior technical support engineer. My schedule was done for me each week and was cut up in 30-minute chunks of time on an Excel sheet. I will never again live 40 hours a week by an Excel sheet. Working remotely with such great flexibility is what I had wanted for a very long time.

    Most importantly, I am more present for my family now more than ever. I have three children with some special needs and special dietary needs. I feel like my choice to work remote has made my family a happier one.

  • Christine Bielak

    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.

  • Tom Paronis

    I started in the 1990s because I was living in New York and working for people in Chicago. I also had a customer in NY who I worked for from home (this was at the dawn of the internet era).

  • Andrea Bing

    I was a federal contractor for over 10 years and I wanted to have a flexible work schedule and work at home.

  • Kat Christofer

    I worked as a journalist previous to tech, so reporting offsite and on location was part of the job. News agencies needed spot news, and I was happy to file stories for them by email. I also had private clients for whom I built websites, and no physical presence was needed in an office.

  • Jodi Ettenberg

    By accident. I quit my job as a corporate lawyer to travel for a year, having long wanted to visit Siberia and Mongolia and explore the trans-Siberian trains. That year turned into more when I realized that I had over-budgeted for the trip. At the same time, I had started a website to keep my family and friends updated with my travels, less intrusive than a bulk email. The site grew with my extended travels, and suddenly I found myself receiving pitches for freelance writing work and grappling with the idea that I might not be going back to being a lawyer after all.

  • Jan Lindborg

    I started working remotely because I wanted to live where I liked (in this case, another country altogether) and there wasn’t a corporate office there. Plus, I actually work better in a home environment; it works well for me.

  • Ben Dodson

    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.

  • Kelli Neely

    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.

  • Lisette Sutherland

    About 10 years ago, I lived in California and belonged to a social community interested in the future, technology, and staying healthy. We met up by going hiking together every Sunday. One person in the group was particularly interesting to me because he was working on a peculiar startup idea: he wanted to eradicate death.

    To the outside world, he was building an online project management tool, a very “normal” startup idea. But what most people didn’t know was that he was building the tool so longevity scientists from all over the world could collaborate and solve the problem of aging. He found that the best people needed for the job were not living in the same city. So his vision was to build a tool that they could use to work together remotely.

    It was an “aha experience” for me. If we remove the issue of being geographically dispersed, we can get the best, most enthusiastic people working together to do great things. It’s not necessarily “remote working” that I’m so enthusiastic about. It’s the idea that we can get the best people working together regardless of location that I find so exciting.

  • Audrey Fairbrother

    My husband is in the military. I knew if I wanted a sustainable career, I needed to be location independent.

  • Hillary Heinz

    Life is too short to be sitting in the same office with the same people every day, and I really wanted the option to live more nomadically and experience new things in my day-to-day life. A remote career was just the ticket. This year I’m going on a “winter workcation” to Austin, Texas, for a few months and last year I rented a little beach cottage in North Carolina. Often the cost of a monthly Airbnb rental is only a little more than if you’d stay for a week, so this kind of longer term traveling gives me more bang for my travel buck, which allows me to really get to know a new city. And instead of taking tons of time off, I get to experience the new location in the evenings and on weekends. Bonus!

  • Colin Wright

    In 2008 I started a branding company in Los Angeles, and worked primarily from an at-home studio.