Dustin - Wadi Rum

9 Lessons Learned From Running a Regular Business From the Road

By Dustin Main Work RemotelyNo Comments

We may earn a commission from purchases you make after clicking links on this site. Learn more.

My story is a bit different to that of your typical digital nomad.

When I left Canada in 2009 for travel, adventure, and a life less ordinary, I was leaving behind a more traditional technology services company that I had started less than five years earlier.

Here’s how I went from working 50 hours a week running my company in Canada, to a few hours a month while on the road.

Laying the Groundwork

Prepping the Company for My Location Independence

Six months before I left, I was already prepping the business for my departure. I spent some time looking at the tasks I would do day-to-day and how I could delegate them properly, as I knew I’d have spotty internet access right from the beginning of my trip.

Dealing with day-to-day tasks was easy, but it was the less-frequent monthly, quarterly, and yearly tasks that took more time to break down and make procedures for.

Giving myself that six month lead time gave me a decent amount of time to write out procedures for these tasks as they came up and were still fresh in my mind.

Lesson: Give yourself some lead time to anticipate the oddball things you may run into when you’re away.

Assembling My “Dream Team”

One of the things I found during this prep time was that I acting as a middle-man between some of the important people we deal with on an infrequent basis.

For example, if the accountant needed a document from the bookkeeper, he would e-mail me. I would then e-mail the bookkeeper, who would send me the document that I’d forward on to the accountant. It didn’t happen all that often, but it was time-consuming and unnecessary.

I solved this by assembling my “Dream Team,” made up of the professionals we dealt with for the company. These are:

  • Accountant
  • Banker
  • Bookkeeper
  • Lawyer
  • and my POA (Power of Attorney)

I introduced them all to each other via email, and had them meet in person when possible. I also gave them the OK to contact each other for the information they needed, instead of going through me.

Lesson: Enable lines of communication between people you work with, so they don’t need you for every little thing.

Assigning a “Power of Attorney”

Some of the biggest issues about not physically being around are signing important documents and making authorizations that need to be done in person. While most things aren’t time-sensitive, if I’m not there to sign something, it can hold up important deals.

So with the help of a lawyer, I set up a trusted family member to have “power of attorney.” This is a written legal document that authorizes another person to act on behalf of me for personal and business affairs.

With this document, for example, this person can go into a bank and sign documents on my behalf, or deal with an auditor.

You can create a power of attorney document through your lawyer, and set out the parameters for what it covers. It’s the sort of thing that should be done before you leave the country.

Lesson: A trusted person on the ground with the right authorization will make your life much easier.

Better than the "office"
My new “office”

Enabling My Staff to Make Decisions

Although this isn’t something that is specifically for location-independent managers (any good manager should be doing this), it’s even more important when you’re rarely in the office.

Those little things you’re called upon for, sometimes numbering in the dozens per day, can be a huge time suck when you’re face-to-face, and completely unmanageable when you’re away.

Whenever a staff member stops what they’re doing to mail me for sign-off on something, time is lost. Sometimes I’m unavailable for weeks, and that’s just not acceptable for holding up simple decisions.

This doesn’t mean the management has free reign to make every decision, but we have an outline of what should go through me and what should just go ahead without requiring my OK.

A few examples:


  • Things that cost less than ~$200
  • Replenishing stock
  • Quoting clients
  • Staff asking for days off

Requires my authorization:

  • Large purchases ie: buying new laptops
  • Negotiating new contracts
  • Changes to payroll
  • Major changes to advertising
  • Extended vacations
  • Hiring & firing of staff

In the first year I was away, this was a fluid process as we learned where the lines were being drawn. I never closed off the lines of communication, but instead moved the bar as required, and reinforced which decisions required me and which didn’t.

Lesson: Empowering your staff to make decisions makes them happier and work better, all while easing your workload.


Dealing With Timezones

Timezones can be a major challenge. With a more traditional business, your customers and staff may be less understanding about timezone differences than a freelancer and their clients might be.

windows clock

In my case, I take this responsibility solely onto my own plate. I set my clocks to show my main locations on my laptop and phone at a glance, and set my Google Calendar to use multiple timezones. With this, I can easily assign appointments for a particular timezone and see when they will fit into my own schedule wherever I happen to be.

Lesson: Use Google Calendar, which makes dealing with multiple timezones a cinch. Mixing them up is embarrassing.

Keeping in the Loop with Google Hangouts

Email is great, but it’s horrible for messaging in a group or taking part in a timely chat. That’s why I love Google Hangouts. Communication is key to keeping the wheels greased and things moving between the staff.

Google Hangouts is built into Gmail (or GSuite if you use it company-wide) making it something that almost everyone has access to right at the start.

There are a few benefits to using Google Hangouts over other chat applications:

  • Almost everyone has a Gmail account
  • All chats are searchable right in your Gmail
  • Easy access on mobile
  • A handy Chrome extension puts it right on your desktop
  • You can make “chat rooms” with several people
  • You can easily mute conversations

This last one is the key for me. We have a few chat rooms for the staff members to communicate with each other on specific projects, and a generic “chat” room for “water cooler” stuff (ie: posting pictures of their lunch).

I like having access to these chats to check in on them once in a while, but I don’t want to see any notifications about them. With just a quick click, notifications for these chats are turned off on all of my devices.

Figuring out the best way to keep in touch with the staff was a major challenge at the start, but over time we’ve figured out the right balance.

Lesson: Enabling easy communication between staff members means less work for you.

Human Resources

Catching Up in Person

Carve your own path
Carve your own path

While I can oversee my company from the road, no amount of video chatting, e-mail, or IM can do what a little face-to-face time can. You see this when it comes to networking all the time, and it’s no different dealing with your staff (and to a lesser degree, clients).

So for the past four years, I’ve come back once a year (usually for a couple of months) to see how things are going. I’m careful to observe for a week or two before I really start working on the issues that need tweaking. What’s worse than someone who you rarely see in person, coming barging in and telling you what to do?

After these first weeks go by, I meet with each of the staff individually and start to implement my changes.

I’m under no illusion that if I was here, things would be exactly the same. The fact is that I can get a whole lot more accomplished when I’m here in the office for a few weeks than I can when I’m away for a couple of months, so I try to make the most of it by bringing things up to a more efficient level, and working out issues with the staff in person.

Lesson: Face-to-face time is invaluable, so make a regular appearance back at the office.

Hiring Virtual Assistants

Recently I’ve dived into the world of virtual assistants to further reduce my workload and that of the on-site manager. These are tasks that aren’t really suited to others in the company, but could be done outside of the office fairly easily on a monthly basis.

I feel as though there has been a race to the bottom in terms of virtual assistants, and I hear many people touting the fact that they’re paying someone $2/hr for some menial task.

The thing is, I’m not willing to take chances on shoddy work, or deal with turnover to save a couple of dollars. I’d rather have someone talented, reliable, and in it for the long haul with me.

My experience with virtual assistants has (so far) been excellent. I’ve only hired people I’ve met in person, and who speak English as a first language. This isn’t to say that someone cheaper won’t work out for you, but I think it’s important to factor in the time of finding, training, and overseeing your assistant into the overall cost.

One off-shoot of this is that in designing the workflows for virtual assistants, it has helped me look deeper at what I’m doing and what I require. Creating these documents forces me to look at tasks from an outsider’s point of view.

Lesson: Virtual assistants can give you access to talented people and their skills on a more casual basis.

Hire Good People

Finally, I’m going to leave you with a no-brainer. Hiring good people on the ground will make your job so much easier. Staff turnover is a huge waste of resources.

Do what you can to hire good people from the start, and rid yourself of problem people as soon as you can. Dealing with these types of issues is much more difficult from the road.

Lesson: Good people are hard to find, so keep the ones you’ve got and always be on the lookout for more.

So there you have it. Overseeing a more traditional business can definitely be done with the right amount of preparation, keeping the lines of communication open, and having the right people supporting you. Just be prepared to make some sacrifices to live your (travel) dreams.

Are you thinking about going location-independent with a business running back home? Have you done so already? Let us know how it’s going in the comments.

This post is part of Digital Nomad Month on Too Many Adapters.

About the Author
Dustin Main

Dustin Main

Twitter Google+

Dustin just can't get enough travel or technology, but when he's not directly feeding one of those insatiable habits, you can probably find him at some far away ice cream shop taking pictures of empty cups. That, or on top of a mountain somewhere shooting photos and finding adventures to share on his website "A Skinny Escape".

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.