How and why did you start working remotely?

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!

How did you convince your company to let you work remotely?

I knew my current gig couldn’t support remote working but my field (marketing + technology) is definitely one that does. I took a leap of faith on the transition and the pieces fell into place. I started as a freelancer and now I’m working full-time for a totally remote startup called Skillcrush!

What are the biggest benefits to working remotely?

I adore my dog Emma and I couldn’t stand the idea of her spending the majority of her life waiting for me to get home from work. Or me spending way too much money on doggie daycare! She’d be so energetic at night when I just wanted to go to bed after a long day of work. Now I get to spend SO much time with her and go on lots of walks to clear my head. She’s a lucky pup!

How do you avoid becoming distracted when working remotely?

I am so much more productive in my remote job than I was at my traditional job. Our team’s scrum project management methodologies certainly help with that and I’d gamble to say that companies and teams with remote workers generally have tighter processes because it simply becomes more of a necessity.

More personally speaking, I don’t switch up my work environment TOO much and if I do, I try to plan ahead and give myself time to adjust. A change of scenery is nice but definitely affects productivity. For example, it would be crazy stressful to work in a new space/place every day!

What is a remote work pain point, and how do you address it?

You’ll discover HOW IMPORTANT THE INTERNET IS! I mean, I knew it was. But now it’s an insanely important portal to my career success and basically the world (OK, I’m being a little dramatic). But really, important decisions will be based on Internet connection and speed, and you’d be surprised at how many places have really bad Internet. I’ve learned to explicitly ask the landlord/renter to show me speedtest.net results and I always test on my computer before placing any lunch or coffee orders. I also always bring my mobile phone hotspot and Jetpack as backups.

What gear can't you work remotely without?

• Something to make my desk a standing desk
• A device that props my phone up for video calls

What apps or websites can't you work remotely without?

• Speedtest.net – Internet speed testing
• Yelp – gotta go to the good spots!
• HipChat – the epicenter of our team’s communication
• Google Hangouts – video calls are a must!

How do you stay in touch with virtual teammates?

I’ve learned how important it is to be able to convey your personality digitally and be an excellent chat communicator. You basically have to rediscover your personality in the form of shorthand expressive chat, emoticons, and video calls! It’s different, but can be just as fun as IRL.

Do you have tips for saving money while working remotely?

I use to order lots of takeout at my non-remote jobs because I was in a rush and never prioritized packing a lunch (or grocery shopping for that matter!). Now I am saving lots of money by eating breakfast and lunch at home most days. The time I got back from my commute and general office shenanigans went into organizing my life—including finding time to cook!

What’s the best way to find a remote job?

Dive headfirst into freelancing. And JUST DO IT. Plan, but don’t overthink it. You’ll learn and adjust as you go.

Would you consider returning to a traditional office job, or are you remote for life?

I was lucky to experience more progressive office environments with lots of great perks and it still doesn’t compare to the customization and flexibility of remote work. Let’s just say it would take a very special job to get me back into any kind of office setting.

How do you stay connected to your professional community virtually?

Aren’t we all connecting virtually already? Working remotely simply makes my IRL connections even more intentional and worth the time!

What's the best way to develop professional contacts while working remotely?

I’m making more connections now than I ever had. People that I haven’t talked to in a while are reaching out and asking for advice because they’re interested in a remote career lifestyle, too. It’s not surprising that we’re drawn to interesting people and ideas and and my remote lifestyle gives me a unique story to tell and helps me connect with new people.

How has your remote job impacted your life outside of work?

My remote work transition was tied closely to a greater lifestyle change so it feels like everything’s different! I feel a much greater sense of freedom and control over my life. While I’m learning that things always take more time than planned, it’s so exciting to map out big new adventures and know that my career can remain stable.

How has working remotely impacted your family life?

My partner also works remotely so I spend LOTS of time with him. We were together for several years before working remotely and suddenly I knew so much more about him just from the sheer amount of time we’re spending together. It’s funny how we suddenly realized how similar our jobs are, too! In general, we feel much more like a team, both at work and outside of work.

How does working remotely impact your diet?

My partner and I always hated how we used to eat dinner so late (9 p.m.) and we’re so proud (and shocked) when we’re often eating dinner at 6 p.m.! No commutes or surprise happy hours certainly help.

How do you cope with feeling lonely while working remotely?

Yes, but then I remember that close friends are literally a text message or phone call away. While it does get lonely (even when you’re in a super exciting new place!), I’ve really enjoyed these “boring” times that allow for deeper self reflection and I prefer that over the craziness that my life used to be sometimes.

How do you stay in touch with friends and family while traveling?

We invite them to visit us at our new location and show them around! Win, win.

What are your tips for making friends while working as a digital nomad?

We’ve worked remotely while camping—campgrounds are FULL of friendly people with interesting lives.

What are your favorite cities in which to work remotely?

I love small, undiscovered towns that no one knows about. Last winter we situated ourselves in a sleepy beachside town during their tourist off season and never experienced a dull moment! We got to know our local bartenders and learn about the town’s inside scoop.