Ever dreamed of running your business from the road? Here’s how I do it…

Ever dreamed of running your business from the road? Here’s how I do it…

Five years ago, my parents sold their business, their house and everything they owned and bought an RV. To date, they’re still traveling around (and they’ve become park rangers)! I was in awe of their lifestyle with how they could just pack up and go wherever but also have the comfort and familiarity of their “home” inside their RV wherever they went. My husband and I decided when we retired, that’s what we’d do too.

Only small problem, being 28 years old, we’re not even close to retirement. 

I’ve been running my business, Headbands of Hope for seven years. When I started traveling a lot for speaking engagements, I built out a strong team and started delegating tasks so I could do more of the creative work I love while also being able to travel for speaking. Little did I know, I was slowly preparing myself and my team for constant travel on the road.

One March morning, my husband and I decided that “one day” doesn’t exist so we started planning how we were going to live in an RV full-time. After 10 months of planning, we leased out our place, put our stuff in storage, and hit the open road.

Being mobile has not only been great for my speaking engagements and Headbands of Hope donations at children’s hospitals, it has been surprisingly easy to run my company from the road. If anything, I believe I’ve become a better leader by instilling responsibility in my team and a better creative by going into airplane mode more often.

Here are some things that have helped me run my business from the road:

  1. Staying Connected

One of the first purchases we made was an installation of Airstream Connected. It basically turns your Airstream into a WIFI hotspot. Because of this, I’ve been able to look outside my window at the Rocky Mountains while also sending a few emails. This WIFI hotspot also allowed us to use our Apple TV when we need a break from the wilderness. 

I’d also suggest getting a cellular plan with unlimited data so you can use your phone as a hotspot when you need it. I also use the app Signaly to test and see if we’ll have service where we’re heading so I can alert my team if I’m heading somewhere where I’ll be unreachable. 

2. Hire a Virtual Assistant

Before I left, I started working with a virtual assistant to manage my inbox and calendar. I can’t tell you what a game-changer it is to have someone in your inbox responding to the things she can, forwarding to appropriate people, and starring anything she needs help with. One of my biggest issues is being addicted to email and hiring a VA really helped me step away from it because I know if there’s something urgent, she’ll tell me.

3. WeWork Global Pass

As I’m sure you’ve seen, WeWork is popping up everywhere. With a global pass, you can pop into any WeWork location to work. This has been great when I’m near a major city and need a full day of strong WIFI (and strong coffee). If you don’t want to commit to a global pass, you can always buy day passes at various coworking spaces across the country. 

4. Be “stingy” with your time

Before I moved into the Airstream, I would say yes to anyone who wanted to “pick my brain” for 15-30 minutes. But when you’re on the road, scheduling meetings can be challenging because you want to make sure you’re within cell service and have WiFi. Not to mention, you might want to go on a hike but if you have a call in the middle of the day, you can’t.

I didn’t realize how much these meetings were time robbers for me. Now, I can get into “work mode” and have a few hours of uninterrupted work and then go exploring. Whereas when I was at home, it would take me an entire day to do that amount of work because I was always stepping away for a call or a meeting. 

So it’s okay to say no or pass on an exploratory call that doesn’t have a set purpose. However, what I’ve found helpful for the meetings you do want to have is try to schedule them back to back in one day. That way, you can head into town and knock them all out instead of having them spread over the week and cut into your days.

5. Have Standing Meetings with your team

Instead of exchanging a ton of emails, try having a Google doc where you can enter things you want to discuss then address it in your standing meeting. My entire team has a monthly standing meeting and then I have a weekly standing with one team member. What might take twenty emails and lots of typing could be discussed in one meeting with your team. But keep a running doc of all your ideas so don’t forget them. 

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I don’t want to wait until I’m retired to start crossing things off my bucket list. One of the great parts about being an entrepreneur is the ability to paint your own life and choose how you want to live it. But oftentimes, we guilt ourselves into going into a pattern that doesn’t suit the way we want to live. Even if living on the road has zero appeal to you, I encourage you to try to structure your life in a way that makes you excited. 


Seb Bunster, AIF, CPFA

Independent Financial Advice - Personal Attention - Holistic Approach | Retirement ? Investments ? 401k

5 年

Fascinating read. I liked your virtual assistant insight. Voicemail and email time vampires are everywhere!

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Ken Mead

Creative Leader, Producer, Storyteller....specializing in immersive, experiential design, including Virtual Production, Mixed Reality and VR content capture. Pioneering the use of AI in all areas of production.

5 年

Hi, Jess. I was really sad that I wasn't able to meet you in person after preparing the way for your talk during the 2017 Leadercast event. I heard you did an amazing job, though. And, your success and influence just continues to grow. Great article! Thanks for challenging us all to reject the fear and embrace the adventure.

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