How and why did you start working remotely?

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

What advice would you give someone considering a remote job?

Make sure you’re good with deadlines and self-motivation. It’s incredibly easy to become distracted if you rely too much on outside guidance and management to get things done.

What are the biggest benefits to working remotely?

You can focus on your life outside of work while also working. It allows you to customize your space and how you use your time to get the most out of your day, and do your best work.

What are the greatest challenges to working remotely?

You lose a lot of the community you otherwise have by default. That said, this can also be a benefit, as it incentivizes you to spend more time with the people you choose to have in your life, rather than just people who happen to sit in the cubicle next door.

Do you keep a regular remote work schedule? What is it?

I don’t normally keep a fixed schedule. When I’m staying in one place for a long period of time, I do get a little more organized with my schedule, working out at around the same time every night, reading and drinking coffee until late-morning, working hard for a few hours and then taking a walk.

When I’m on the road, though, which is most of the time, I don’t have a consistent enough environment to predict what I’ll have access to, resource- and infrastructure-wise. I roll with the punches, instead.

How do you avoid becoming distracted when working remotely?

I make sure I’m doing work I’m really excited about, and allow myself to feel good about closing loops. That keeps me ever- moving toward the next complete project, rather than dilly-dallying.

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

Ensuring that you have all the resources you need to do your work, which might otherwise be provided by an employer. You have to be a lot more self-sufficient, which is something you learn, but not something everyone is from the beginning.

Do you use coworking spaces? What are the best ones?

Sometimes I use coworking spaces, but usually to network more than work on anything serious. The work I do typically requires a great deal of focus, and there are too many interesting things and people at such spaces a lot of the time.

What gear can't you work remotely without?

• Passport

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

• WordPress
• MailChimp

Do you work from a home office? How is it organized?

Generally I do, but it really depends on where I’m living. When I was renting a place in Mayoyao, in the Philippines, in the middle of nowhere amongst rice terraces, I sat at the kitchen table in the home where I was staying. Here in Wichita, where I’m staying at the moment, I have my entire space set up for work: the living room has a studio, complete with lighting and tripods and a blank white wall, while the back room has podcasting equipment and a sturdy desk.

How do you stay in touch with virtual teammates?

I co-founded a publishing company with some friends, but a lot of the time we’re all dealing with our own facets of the business, and as such don’t have to be in contact all that much. We chat via email and text sometimes, but we don’t speak to each other every day, or even every week. That would be majorly distracting, I think.

Do you have tips for saving money while working remotely?

Focus on what’s most vital and get really nice versions of those things, but eschew the superfluous. So if a laptop and phone are two really important things for doing your work well, get a great laptop and a great phone. But maybe don’t invest in a great big TV or expensive couch. Spend your money where it does the most good and where it will fulfill you the most.

What’s the hardest part about working with a traditional team while you’re remote?

Aligning my schedule with other people has been an issue in the past, and the best way I’ve found to deal with it is by setting up one’s business and lifestyle so that you don’t have to touch base live so often. If you can do more work via email and empower other people to make more decisions for themselves, then you’ll spend less time with pointless meetings (or e-meetings ) and more time focused on what you actually want to get done.

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

It would have to be for a very good reason, and a really important project. And likely a whole lot of money on top of that. Working according to my own schedule, in my own space, is just too valuable to me.

How has working remotely impacted your career plans?

It’s allowed my career to go in a lot of really wonderful, unpredictable directions. So absolutely it has.

How do you stay connected with your local community?

I make ample use of social media tools, while also making sure to take frequent walks and to go on adventures around the area.

How do you stay connected to your professional community virtually?

Social media, and personal relationships that are maintained online and offline.

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

Build something remarkable so that people come to you.

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

It’s really helped shape my entire lifestyle, because working remotely allows me to travel full-time.

How has working remotely impacted your family life?

It allows me to see my family a lot more often, despite the fact that I live far away from them a lot of the time. That I have the opportunity to go see them when I want, and for important events, without asking anyone else’s permissions, is so wonderful.

How do you manage work life integration?

They kind of blend together. I love what I do, and I get to do it while also living life. There’s no hard division, nor do I think there needs to be.

How do you stay physically active while working remotely?

I stand up and work out a bit every half-hour or so. I also make sure to have a regular workout routine, and a good diet, by default. This is easier to do when you work from home than when you work from elsewhere, not necessarily having access to decent food or wanting to stand up and do jumping jacks in front of a crowded office full of people.

How does working remotely impact your diet?

I can eat well, if I choose to (and I do). It’s not that easy, even if you want to, when working from an office, perhaps in a part of town with limited (or expensive) options.

How do you cope with feeling lonely while working remotely?

Not really. If I do, I typically think of it as a valuable moment, where I can focus on me and me alone, rather than everyone else.

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

I make use of the full array of tools we have available these days. I find Facebook is an except touchpoint with people who aren’t super tech-savvy, while other friends I stay in touch with using Snapchat or Instagram or whatever other network pops up that allows us to communicate easily.

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

Be brazen and open, and humble. Don’t be afraid of looking like an idiot. Leave people and places better than you found them.

Did you have to address concerns from family when starting out as a digital nomad?

They had some, but they kept it to themselves, mostly. I primarily made sure to stave off any potential worries by showing that I knew what I was doing, and keeping them abreast of where I was and how things were going.

What are your favorite cities in which to work remotely?

I really enjoyed living and working in Prague, at least partially because of the local culture and history you can see everywhere you walk. I also dig Missoula, Montana, as it’s a generally pleasant place where people are (on average) quite healthy and friendly, and nature blends really well with the low-population, high-density downtown.