TT#026 - 4 lessons I learned running a business on the road for 6-weeks...

Last weekend, my family and I got back from 6 weeks of summer travel. 

In all, our family of 4: 

  • Hopped on 6 flights. ✈️ 

  • Slept in 7 different places. 🏠

  • And saw friends & family in 4 cities. 🌆

(Hey Green Family. 👋🏼)

All while having my best month in sales since starting my business more than 3 years ago. 


That said, I learned a lot about running a business on the road. I’ve been remote for several years, but this is the first time I ran my business without a “home base.” 

As I learned, that home base allows me to control (or significantly influence) a lot of things that I couldn’t as a nomad. For example, my office changed frequently, and I didn’t always get to pick where I worked. Hell, on this trip I worked from… 

  • A room covered in pink polka dots, dollhouses, and Minnie Mouse furniture. (Thanks, Sis. 😉)

  • A patio that would’ve been perfect, except it was in the Texas heat.  

  • A house that had literally 14 people in it, 9 of which were kids. 

Bottom line: Running a business on the road is different than running a business from a home office. 

And this week I’ll share 4 things I learned that, if incorporated on future trips, will make business building easier and the time traveling even better. I hope you find some value in the lessons, too. 

1. Clarify the high leverage priorities and keep them front and center.  


Like any other business owner, I can sometimes let day-to-day demands keep me from making progress on the big, strategic priorities.

I know this can be fatal for a business, so I clarify my “big rocks” each year and break them down by quarter. These are the initiatives that, when completed, will move the business forward the fastest.

The thing is, it gets even easier to let those priorities slip when travel is involved, or there are just more demands on my time. 

By the end of the trip I’d incorporated reminding myself of these every single morning by adding them to my “Weekly Focus” in Asana. The tool I used isn’t as important as the habit I adopted.

Clarify those high leverage priorities, and keep them top of mind. 

2.Define the order of operations for day-to-day tasks.


Keeping the high leverage activities top of mind is critical, but there’s no getting around the fact that you’ll have more day-to-day demands than you can reasonably tackle in a day.

On the trip, I created an order of operations to help me organize what needed to get done first. For me, that was:

First: Client success related tasks
Second: Sales and revenue generating tasks
Third: Content and demand generation related tasks

Everything else, like improvements to our systems, operations, reporting, playbooks, tech, etc. didn’t make the cut. I kept a list of those observations and ideas, logged them, and moved on.

Even with an order of operations, I couldn’t get to everything on the list. But, I knew what needed to get done first and I accepted that every day would end with some tasks not done.

3. Double check the technology. 

I take some of the technology I use to run my remote business for granted. This trip highlighted how important it was to make adjustments and preparations in the absence of my home base.

One of the adjustments will be modifying my automated calendars in advance. I didn’t adjust my automated calendars ahead time, which meant as I was changing time zones my 4:00 pm calls at home were now 6:00 pm calls on the East Coast. Not what I wanted on a working vacation.

One of the preparations will be not assuming I’ll have what I need, like sufficient bandwidth. I mistakenly assumed that being in major cities in the States would supply more than enough bandwidth to do everything I needed to do. As I learned while speaking on a sales practices webinar with 250+ people, that’s not the case.

Note to self: Don’t assume, and plan backups.

4. Don’t break your critical personal routines. 

Remote work isn’t perfect, and nomading makes remote work more uncertain. But, like anything else, you learn from experience. 

I hope these lessons learned help you if you’re working on the road, and when I look at it again, work from anywhere. Prioritizing, planning, preparing, and physical/mental self-care are just good habits, whether you’re working on the road, at home, or in an office.

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