How and why did you start working remotely?

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.’   

What advice would you give someone considering a remote job?

This sounds somewhat trite, but “Just do it.” I seemingly found every excuse not to leave the confines of the office environment, but in the end I was better off when I just jumped in with both feet.

What are the biggest benefits to working remotely?

From a work perspective, my productivity is GREATLY improved as a remote worker. I do not ‘commute’ in any sense of the word, nor do I have any daily preparations. I start working almost immediately upon my first cup of coffee, and generally take my laptop to bed with me.  

Without distractions, I am clear to focus on what I need to accomplish.

What are the greatest challenges to working remotely?

There are two things that a remote worker must be strong in: focus and compromise. These two may at first seem at cross purposes, but they are actually strong complements to each other.

It is easy for a remote worker to lose focus without the structure of an office environment. If you are easily distracted by children, television, the car needing an oil change, the grocery store…the list goes on…then you have to focus on doing the job as you would in an office, but your office is a mental construct, not a physical one.  

One friend of mine actually goes so far as to get dressed ‘for work’ and go to his basement. His wife and children know that this is his office. He needed to make the mental transition to ‘work mode’ every day—in a physical sense.

For me, I make the shift mentally. In fact, my wife has to remind me to get up and walk around more often!

Along with this focus, a person has to compromise often. When I was living in Asia and working with clients in North America, I often had 2 or 3 a.m. calls. I never let on that it annoyed me to be up at that hour. It was the ‘price I paid’ for living the way I wanted to.  

I go to GREAT lengths to ensure that my choices for where I want to live do not impact my clients or coworkers. Without that commitment, remote work is simply not feasible to me! I have to be the one to change and adapt, not them.

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

No. I actually work far more than I ever did while working in an office environment. As I mentioned before, I also adapt to other’s schedules as needed. My choices for living and working should not impact my ability to provide service to my clients and coworkers.

I am much more ‘delivery focused’ than ‘time centric.’ I gauge my benefit in the value my work provides, rather than the hours I put in. Of course, my wife tells me I work too many hours as well!

How do you avoid becoming distracted when working remotely?

For me, it is a constant mental state. That said, in addition to what I have mentioned before, I also don’t worry too much about working ‘correct hours.’ Thus, if i need to take extra time running an errand, I have typically more than made up for it by working until late at night.  

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

Inconsistent internet connectivity is the key pain point to working remotely in the manner that I do. To combat this, I typically have 2-3 other methods to connect at my disposal. In addition to local ‘house’ wifi, I also buy a local telecom ‘hotspot,’ and have my phone ready to tether.  

In the past, I have also gone to the extreme of renting a hotel room for the day to ensure I had a quiet, well-connected space.

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

I have not yet. I don’t typically need to be ‘team focused’ or even be around others when I work. However, I might try one out on my upcoming trip to Thailand.

What gear can't you work remotely without?

Two physical must-haves: cellular “hotspots” and a really good headset for your phone/VoIP. Additionally, I require somewhat easy access to a major airport. I never know when I need to make customer visits, so this is good to have available.

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

Two must-have virtual tools: cloud-based collaboration environments like Google Drive, etc., as well as Airbnb. Airbnb has made finding accommodations anywhere in the world easy and affordable. We use it for almost all of our longer-term stays.

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

No. Then again, I don’t have a ‘dedicated home’!

How do you stay in touch with virtual teammates?

I actively use Skype for quick chats, as well as the Citrix GoToMeeting, as well as Dialpad’s Uber conference (free basic!). I have a T-Mobile plan that allows free calls in 200+ countries!

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

Compromise! I am the one who made the choice to live the life I do, so it behooves me to be the one to ensure that it does not impact my team! If that means taking a 2 a.m. meeting while living on an island in the south Pacific, then it is the price I pay for my living arrangement!

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

I was offered a position making 4x what I was previously earning—but it was an office job. I worked it for 4 months and realized that the money was not worth my freedom and peace of mind.

I would say never, but I always leave room for the outside possibility—however unlikely.

How has working remotely impacted your career plans?

For me, I was in the ‘cruise phase’ of my career. I am never going to be the CEO, so I stopped thinking that was a possibility. When I became comfortable with where I was in my career, I gained a lot of peace of mind in my job. That allows me to do whatever I want without the need to be thinking about my next promotion. It isn’t coming… so I might as well enjoy where I am.  

I make enough money to enjoy the life I want. I don’t need more.

How do you stay connected to your professional community virtually?

LinkedIn is a wonderful resource. Also, I am constantly producing white papers and blog posts, so I keep my name—and my brand—alive and well in the cyber community.

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

Never underestimate who you will meet and where you meet them. I have met venture capitalists on the beach, and CEOs in the restaurant next to me.  

I also produce a LOT of content for numerous virtual platforms that allows my brand to be ‘out there.’

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

Last year, I left Italy for a meeting in Los Angeles. I was struck by how rushed and frantic people were in their daily lives. While I was just as productive—or more so—than they were, I was visibly more relaxed mentally and physically.

I tried to tell them that they don’t HAVE to live like that, but it is an integral part of their persona. I could not understand them as much as they could not understand me.

How has working remotely impacted your family life?

My wife and I have never been more in love. We experience the world—together.

How do you manage work life integration?

Because I am so integrated with work and life, I don’t make a tremendous distinction between the two. I love my work and I love my life. The two compliment each other, rather than be at odds with one another.

How do you stay physically active while working remotely?

Lately, I have been swimming in the Caribbean every day at lunch! Sure beats sweaty gym equipment!

How do you cope with feeling lonely while working remotely?

Never! There is a world of interesting people out there to meet!

What are your favorite cities in which to work remotely?

Florence, Italy—great connectivity, fantastic culture, food, and wonderful people. An Airbnb rental makes it a fantastic place to be for a month or so!

Cancun, Mexico—Caribbean! Food! People!

Kuala Lumpur, Malaysia—urban wondefulness in a tropical climate! Food! People!