How and why did you start working remotely?

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.

What advice would you give someone considering a remote job?

When people first go remote, they usually have some trouble figuring out the right place for the work they’re doing. Being able to work from anywhere gives us the luxury to design workspaces where we are most productive. Whether we are telecommuters, freelancers, or digital nomads, setting up a productive workspace will help us be better remote workers. We each have different needs when it comes to productivity. Some people prefer a quiet space on their own, while others thrive with people around. Some like going to the office, while others prefer to work on the road.

What are the biggest benefits to working remotely?

People mainly go remote for the types of freedom it offers: freedom from the commute, freedom to make our own schedules, freedom to create our own workspaces, and freedom to choose what we work on.

Companies go remote for different reasons. They are usually trying to maximize profits, grow the company, and as a benefit to keep the people they already have and entice new potential employees

What are the greatest challenges to working remotely?

When people go remote, they struggle with discipline, isolation, being “always on,” and finding a productive workspace.

When teams are remote, they struggle with having high-quality conversations, staying aligned, building trust, and maintaining a sense of team.

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

I start my day around 8 a.m. with coffee, some stretching, and a short walk. And then I write for a couple of hours (to finish my book, Stories of Remote Teams Doing Great Things). Around noon, I go running or cycling, and when I get home, I work through my task list for the rest of the day. At 6 p.m., I get on Skype with my online collaboration partner in California and we work together (on our own projects) until 10 p.m. At 10 p.m, I have a martini while I listen to podcasts, clean the house, and get ready for the next day.

How do you avoid becoming distracted when working remotely?

I make a to-do list with my top 5 priority tasks and then use the pomodoro technique to timebox my day. This gives me plenty of focus time and plenty of breaks. I also find that going running or cycling in the middle of the day helps reset my energy levels.

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

A big downside of being able to work from anywhere means that we can, and tend to, work around the clock. For example, freelancers tend to do things that they are good at and passionate about. It’s extra hard to turn off because in reality, we don’t really want to. There’s nothing stopping us except discipline, and sometimes, our own physical and mental limits.

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

I love my home office and have always hated going to co-working spaces. Mainly because I like to work on my own, but also because the chairs in co-working spaces are uncomfortable, the temperature is never quite right, and the coffee is generally bad.

However, I do like to be around other people and have helped create a virtual co-working group that meets regularly in a virtual office called Sococo. With virtual coworking, I can have my comfortable home office and work with other people at the same time.

What gear can't you work remotely without?

• My Bose QC20 noise-cancelling headphones
• My Supercards (virtual meeting cards)

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

• Zoom.us (for video conferencing)
• Toodledo (my to-do list)

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

I have a beautiful home office with an excellent internet connection, a comfortable chair, an electric sit-stand desk, multiple monitors, a great stereo system, excellent coffee, and a neighbor cat who comes to visit.

How do you stay in touch with virtual teammates?

My virtual team has different ways for being in touch. For asynchronous communication we use Slack. We also meet several times a week using my favorite video conferencing tool, Zoom: there are a couple of team meetings, one company meeting, and one meeting just for hanging out together (we call it “kitten talk”). To know what each other are working on, we use a combination of iDoneThis and Trello. For those that become close personal friends, we also connect on WhatsApp and social media.

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

The biggest pain point of working with a team while remote is communication. My advice is to have great internet, minimize background noise, use great equipment, and turn the webcams on.

My next piece of advice is to define normal behavior on the team. We can avoid some of the basic miscommunications through the process of creating a team agreement: a basic set of expectations for how to work together. It outlines what kind of information we share, how we communicate with each other, and how we know what each other are doing.  

My last piece of advice is to take my “Work Together Anywhere” workshop. It’s designed to share experiences and learn how to avoid miscommunications, increase camaraderie, run pain-free meetings where everyone contributes, and giving and receiving feedback on a virtual team.

What does your remote company do?

Collaboration Superpowers is a company that helps people work together from anywhere through online and in-person workshops. The Work Together Anywhere workshop will show you how to avoid miscommunications, increase camaraderie, run problem-free meetings where everyone contributes, and inspire continuous improvement in remote teams.

How do you stay connected to your professional community virtually?

I set aside time every day to scan my social networks to see what others are doing and to respond to requests. I’m a member of several Slack communities, I participate in lots of conferences (online and in person), and I make an effort to meet people in person whenever I can.

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

One of the best ways to develop professional contacts is to help people with their projects. Pay attention to what others are trying to accomplish and help them succeed.

I started a podcast where I interview people and companies who work remotely, and that has, by far, been the best way to meet interesting people in my professional network.

How do you stay physically active while working remotely?

I walk in the morning and go running or cycling in the afternoon. I go climbing with friends every weekend. I stand during my online meetings. And I hired a personal trainer to help me build more muscle. Staying physically active while working remotely takes discipline and constant effort. It’s important to build a routine that works for you.

How does working remotely impact your diet?

Working from anywhere gives me the opportunity to eat exactly what I want and when I want it. I’m healthier now than I ever was working at an office where I was constantly being tempted by unhealthy snacks that colleagues would bring in.

How do you cope with feeling lonely while working remotely?

I have several hours of video meetings per day, my virtual coworking group, and my evening collaboration sessions. Even though I am on my own in my home office, I’m almost never alone. And while I have plenty of virtual interactions with people, I still make an effort to spend time outside with my friends and family.

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

I mainly stay in touch through WhatsApp, Skype, and social media.