7 Tips to Run Your Business On the Road

Dylan Ogline
6 min readSep 22, 2021
Photo by Airstream Inc. on Unsplash

It seems like the whole world has caught the travel bug. Nearly every one of my Agency 2.0 students wants to build a business that enables them to travel the world or detach from one location and live that Airstream life on the road.

Yes, they want to build a business profitable enough that they can afford it.

They also want a business durable enough that they can disappear into the mountains or the jungle for a month, and emerge back into the world after recovering from frostbite or malaria to discover that their business is still clipping along nicely.

But there’s another level to this nomadic ambition, a “God Mode” if you will — the laptop lifestyle. The ability to travel the world, without neglecting your business. The ability to run their business while on the road, and still enjoy the romance and excitement of travel.

Yes, it is possible. I have been to that mountaintop and seen the plains of milk and honey below. The Laptop Lifestyle is real.

But travel is inherently disruptive. It’s about adventure, the unexpected. If you wanted routine, you would have stayed at home.

So how do you keep a business moving in the midst of all that disruption?

Here are seven basic tips I use to help me run Ogline Digital from anywhere in the world…

1. Automate, Automate, Automate

Automation is a digital nomad’s best friend. It’s how we build lean, mean, and scrappy businesses that make big profits with minimal expenses. Digital automation tools are far less expensive than employees — even remote employees.

Everything you do throughout the day, ask yourself the question — can I automate this task? Then do Google searches to see if an automation tool exists to take that task off your to-do list.

Maybe you could automate your sales funnel — bring in prospects with Facebook or Google ads, entice them with a high-impact sales letter or video, and get them to purchase or book an appointment without taking up any of your time.

Automated tools like Calendly can link to your personal calendar to automate the scheduling process. It’s incredible the amount of people I run in to who still send emails back and forth “How does next Tuesday at 10am sound to you?”. That’s such a waste!

Automated tools can be armed to generate proposals and invoices with the click of a button.

That’s just the tip of the iceberg.

All of this takes work up front. It may even take trial and error. But the freedom they enable is worth it. Your business will be more profitable and scalable even when you’re not on the road.

2. Delegate, Delegate, Delegate

Anything you can’t automate, delegate. Maybe your product or service is so high-ticket, no one is going to enter their credit card into a website after watching a sales video — they have to talk to someone before they purchase.

Can you arm a remote employee with a sales script so that they can close the sales instead of you? What about day-to-day tasks like bookkeeping, proposal generation, invoicing, troubleshooting, and answering client or customer inquiries? Could an employee — even a remote employee in a far-away country — be trained to do all of this?

Even before you have employees, start documenting your processes into Standard Operating Procedures (SOP) or make training videos using apps like Loom. These can become training materials for your first employees to start taking low-level tasks off your plate, freeing up your time to enjoy life on the road.

3. Update Your Scheduling App

This was mentioned before but deserves it’s own spot on this list for this reminder.

A great scheduling web app like Calendly automatically adjusts for the users’ time zones. If you live in California and someone in London wants to book a meeting with you, they see your available times in Greenwich Mean Time, not Pacific Standard Time.

But what if you leave California? You may have to update your schedule app, as well as your calendar app, to adjust for the new time zone.

If it can’t be automated, this is a great task to delegate to your assistants. Build a process for them to follow so when you give them the task “I’m going to Japan on Friday. Please update my scheduler,” they know exactly what to do.

4. Make a Plan For Internet Access

The “digital” in “digital nomad” is there for a reason. You can’t run your business from the road if you find yourself on a road with no internet access.

If you want to stay plugged into your business while you travel, scouting internet access becomes part of the planning phase. Here are some things to consider:

  • Do your flights offer in-flight WiFi? Is it worth the cost? If you want to make productive use of flying time, maybe you would be better off stocking up some offline tasks you can do.
  • Does your hotel or Airbnb have WiFi? Does it cost extra? This is rarely an issue but if you are spending a month somewhere and find out there is no WiFi that could become a big issue.
  • What are the average download and upload speeds in your destination country, for both wired and mobile data? Will it be fast enough? Again, rarely an issue but worth messaging your host about.
  • Are there co-working spaces or WiFi cafes nearby? I personally love this. You get the chance to meet interesting people while still getting out and exploring.

If all else fails, roaming data on your cell phone may be a lifeline. Yes, it could be expensive, but who said running a business was free? You might look into phone plans that offer global mobile solutions. Google Fi and T-Mobile currently have interesting solutions.

You might also look into a portable mobile WiFI hotspot or local SIM card to access the best local data speeds available.

5. Activate Offline Modes for your Apps

Depending on where you travel, internet access may be unreliable at best. It’s good to know which of your critical apps have offline modes.

Google Drive, for example, has an offline mode. You have to activate it, but when activated you can access items stored in your cloud drive even when you have no internet access. When your device regains internet access, changes will sync.

Check for offline modes on every app you use daily, activate them if necessary, and get acquainted with their strengths and weaknesses.

6. Train Your Clients

My clients know that if they email me, it’s not unusual to wait 12–36 before they hear back from me. Don’t build the expectation that you are always available.

Make sure there is someone else on your team that clients can reach out to you if they need faster assistance, and that that first point of contact can make a judgement about whether or not you need to be bothered with the issue.

Even if you are available, don’t set the precedent that you are always immediately available. Train them to be patient. Most “emergencies” aren’t, and your team can be trained to recognize actual emergencies.

Also, fire bad clients that can’t accept this. That’s a topic for another time…

7. Be Flexible

Remember, travel is all about excitement and the unexpected. Don’t get bogged down in your usual routine. Travel exists to break your routine, to surround yourself with foreign sights, sounds, flavors, and experiences.

Don’t put yourself in a position where you have to say “no” to a spontaneous hike or road trip with a newfound travel buddy you meet at a backpacker’s hotel. Build some flexibility into your schedule. Have backup plans to reschedule meetings and deal with technical difficulties.

Most of all, don’t treat every little hiccup like an emergency. Again, most “emergencies” aren’t. If you have built your systems and processes right, your business will survive and prosper, even if there’s a short-term setback.

Running your business from the road is not only possible, it’s extremely rewarding. Not only do you safeguard your income and legacy while checking items off your travel bucket list, there’s the sense of accomplishment that comes from stepping outside of the Matrix and discovering a wider world at your feet.

--

--