I want to explain that this post is not advocating that people should work while on vacation. After all, vacation is taking a break from work (and the day-to-day grind), so you should do just that.
This post, instead, is for anyone who might be thinking about someday living more of their life on the road – but still needing an income while doing it – and want to see how they may fare.
Let me give some back story here…
My partner and I have been thinking about our future and what living life on the road would be like. Now I don’t know if I’m someone who could do it full-time, but half-time might be doable. So we’ve been testing the waters a bit, so to speak.
For years, we’ve been heading down to Florida to see family and spend some time in the sun and warmth. Back in 2021, after Covid hit (and flights were getting a bit crazy) we decided to try our hand at driving down instead. We rented a van; packed up our suitcases, drinks/snacks (and the kids) for our first on-the-road adventure.
We loved it.
So much so, we’ve done the exact same thing for the two years following. We drive.
To be fair, my partner drives. He ’s used to doing overnights at work so on our way down we drive until the next day and stop a hotel wherever we want. Doing it this way I’ve been able to see parts of the country I’ve never seen before. I’ve been to St. Augustine, FL (beautiful), Savannah, GA (gorgeous), Williamsburg, VA (quaint) and a lot more. And I want to see more of the country while I still can. I’ve been around the world…but America-the-Beautiful deserves my attention now.
So these yearly on-the-road trips are giving us a small taste of what spending time on the road is like. More importantly, it gives us a fairly realistic view. Because while traveling is nice, you do always want a place to hang your hat…a place to call home. Not to mention, doing the day-to-day things (like work) require more thought if you’re gonna do it from the road.
So, how DO people run a business while living on the road?
I can’t say I have a full experience of that as I’m only gone for a few weeks and after all, I am on vacation. However, there are some business things that do need my attention while I’m traveling. In those instances, I use my T-Mobile hotspot while in the van. It doesn’t work flawlessly but when you have kids and tablets, it’s very much needed.
I find that doing a little work during the drive actually helps with the boredom that sometimes occurs. I’m able to respond to all my emails (on time), work on new projects and even make updates to my website. If I were traveling more, I’d definitely invest in a better service such as Starlink or WeBoost – which would definitely speed things up and make running a business on-the-road easier.
What I love about traveling on the road is the change of scenery and meeting people from all over. I like being mobile but still being able to be on top of the things I need to, just in case. So these little road trips give me some insight of what things I’d need to better manage my business when we finally decide to go on-the-road for longer periods of time.
Also, you have to be prepared. For example, I always bring my ‘portable office’. Basically, it’s a huge tote bag that holds my cell phone (of course), iPad, MacBook, small laptop table, headphones, battery pack and plenty of chargers (most vehicles have multiple charging units for your electronics). All of that and any notebooks I need (as well as a neck rest) all go in that one big tote that sits right next to me. If I travel in an RV some day – I’ll have a place for these things – but for now, this is how I do it.
So yes, you can do work from on-the-road, even on shorter trips. You just need to prepare and…try not to have high expectations. Your hotspot may not always work right, the roads may be too bumpy to do any typing or maybe the kids are just being too noisy for you to get anything done. That’s actually a good thing because it forces you to stop and smell the roses.
Running a business from the road can not only offer flexibility, it also encourages us to slow down a little to relax and refresh. It teaches us patience and opens us up to accepting change. It’s an adventure into a new way of doing things.
I’m not saying this is for everyone. I understand that most people like having one place to call their home, in a community they are familiar with. I’m saying that if you’ve ever thought about a future living a little more on-the-road (or doing more road travel) a good way to give yourself a test is to…actually take a road trip.
So the next time you have the opportunity for some time off – consider taking a domestic trip and driving to your destination. Plan your route ahead and practice safety at all times. Rent a larger vehicle (if you need to and can afford it ) and pack plenty of water and snacks. Be sure to bring your portable office and keep it handy. Not only will you be able to be productive but you’ll have some great views at the same time.
Oh, and don’t forget to enjoy the ride…
Until next time…
