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7 Lessons from a Year on the Road

Cadillac Mountain

One year ago today we set out on a grand adventure. At the time we had no idea how things would turn out. Whether we’d take to the road or return home with our tails between our legs was a complete mystery. Well, a year later we’re still going and have no plans of stopping anytime soon. But as much as we’re enjoying ourselves, no life altering change can happen without learning a few things along the way. Here is my list of the seven biggest lessons from a year on the road:

7) Less is more. Soon after the alarm clock rang for the first time to wake me for a job I didn’t like I realized that every dollar I spent was a claim on my time. Everything we consume, every monthly payment we make, every gadget we need to repair or replace in the future, is an obligation we need to work to support. In that sense, every purchase is a minute, an hour, or month out of our lives. And although each obligation may be small, they can accumulate into Lilliputian bonds that tether us to a job and a place.

Last year we reduced our living space by two-thirds and needed to get rid of more than two-thirds of our things to do so. Are we two-thirds less happy now? Absolutely not. In fact, we’re far happier with fewer items cluttering our life and more time to devote to the things we truly enjoy. Clearly there is no positive correlation between things, and happiness, at least not for us. So why on earth would we spend an hour working at something we don’t want to do to pay for something that doesn’t ultimately increase our happiness? We wouldn’t. I’m not sure why anyone would.

6) Realistic expectations and flexibility are keys to happy travel.The surest way to spoil a trip is to expect too much from it; or to expect it to be something that it is not. We tend to be pretty good travelers in this regard. We try to take destinations for what they are,

If Boston is so great, why did I have such a lousy time there?

rather than what we think they should be. But nobody is perfect. All of our bad experiences basically boil down to our own bad attitudes. We were frustrated with Naples because it wasn’t the Everglades. I was cranky about Boston because I’d traveled there dozens of times for work and wanted our trip to be completely different from that.

After a year on the road, we’ve yet to encounter a ‘bad’ destination. But we have come across many fellow travelers who ‘hated’ this place and warned us not to go to that place. Whenever we probed deeper, the problem was almost never the destination, but a disconnect between what the destination is, and what the traveler wanted it to be.

To get the most out of our experiences, we really need to be open minded and flexible. If something isn’t to our liking, or exactly how we’re accustomed to it, maybe we need to change our likings and our customs. After all, if we want everything to be the way we’re used to, or how we imagined, why bother leaving home? The whole point of traveling is to see and experience new things. To do that, you have to be open to them and appreciate them for what they are, rather than trying to force them to conform to preconceived notions of what they should be.

5) There is never enough time. Before I left my 7 to 7 job, I thought the 70 or more hours I’d gain each week by not working and commuting would be all the additional time I’d ever need. Some folks even cautioned me that I’d get bored with the wealth of free time I’d soon inherit. Nothing could be further from the truth. In fact, I don’t know how I managed to fit all of those working hours into my life before. Where did they come from? More importantly, where did they go?

Shannon and I have had zero problems filling our days. At times we even feel frantic. We have hobbies, and sightseeing, and trip planning, and yes, chores. When all of that is done, we have a back log of things we’d like to do, but never seem to have enough time. The trick is to accept that we are each responsible for our own happiness. If I’m ever bored, I have nobody to blame but myself. Thus far, that hasn’t been a problem. I don’t expect it ever will be.

4) It’s not a vacation. It’s a lifestyle. The frenetic pace of a typical vacation isn’t sustainable week after week. In our previous life, we often came back from a whirlwind trip more tired and worn out than when we left. On vacation, we felt the need to see and do everything because we didn’t know when, or if, we’d ever return. But as full-time travelers we have to be more discerning, with both our time, and our dollars. We simply don’t have the time, energy or money to live every single day like it’s a vacation.

It is not always a day at the beach. Some days, we prefer the pool.

But more to the point, every day is not a vacation. It’s normal life for us. We don’t have hotel maid service to clean up after us. We rarely dine out. So cooking, cleaning, laundry, paying bills and all the other nuts and bolts activities of living a traditional life are still very much a part of our daily routine. Whereas a vacationer puts all of this stuff on hold and steps out of their normal day-to-day activities to go somewhere else, we’ve simply incorporated the ‘somewhere else’ into our normal day-to-day activities. It’s not uncommon for me to go grocery shopping in the morning, and sightseeing in the afternoon. After all, this is not a vacation. This is our life.

3) Spontaneity is overrated. When we first set out, we thought we’d travel as free spirits, venturing here or there on a whim; staying and going as we please. But it turns out, that isn’t a very practical way to travel. We learned very quickly that scrambling for second-best alternatives after being shutout of our first choice isn’t a particularly desirable aspect of spontaneous travel. There are places we simply had to book far in advance if we had any hope of seeing them. If you think you’re going to roll into Key West in January on a whim and find an empty campsite, you’re going to be disappointed. And it’s a long drive back to the mainland.

This sunset brought to you by significant advance planning

But needing reservations isn’t the only reason we plan ahead, or even the major one. We’ve also found that the seasons are relentless task masters, continually forcing us North or South whether we’re ready to go there or not. If we spend the summer wandering aimlessly and don’t get as far north as we’d like before the weather turns, then we’ll either have to skip that northern destination, or backtrack as much as 1,500 miles the following year. Neither of those options is appealing to us. Far better, in our view, is to plan a logical route that takes us to as many great destinations as the calendar will permit in a single season. That kind of planning is a chore, but there is a whole big world to see and we don’t want to waste our valuable time covering the same ground repeatedly.

2) The path is beaten for a reason: It is possible to take good advice to such an extreme that it becomes counterproductive. I see that happening with the admonishment to ‘get off the beaten path’ when traveling. So much so that a false distinction has become conventional wisdom in some circles: that there is a difference between ‘travelers’ and ‘tourists.’ Supposedly the traveler cuts new trails and finds ‘authentic’ experiences that the guidebook-bound tourist misses. Perhaps. But my experience has been different. While it is certainly good to go your own way at times, it is also important to recognize that the path is well-worn for a reason: because it leads to places that are actually worth going. Our backcountry treks in the Everglades were great, but we saw far more wildlife on the most popular trail. Why would we skip one experience in favor of the other when we can do both?

Going your own way can be fun for its own sake, but often the best sites are found on the most popular trails

You can diminish an enormous swatch of the globe by looking down on popular tourist destinations and attractions. After all, there is very little in this world that hasn’t already been discovered. It’s as foolish, in my mind, for someone to ignore guidebook destinations as it is for someone else to visit them exclusively. Close-mindedness is never a path to wisdom. And that’s true regardless of whether you consider yourself a tourist or a traveler.

1) How easy it is to not follow your dreams. Inertia is an incredibly powerful force. It’s far easier to follow a routine, even a hated one, than it is to do something risky, unfamiliar, and meaningfully different.

We started planning in earnest for our journey at least five years before we disembarked. We talked weekly, if not daily, about ‘the plan.’ We changed our lifestyle to accelerate our savings and basically pulled all the levers at our disposal to get in a position to do what we talked so frequently about. That was the easy part, though. Actually putting ‘the plan’ into practice was terribly hard.

Part of the difficulty arose from the simple logistics of doing everything that needed to be done. We were surprised to learn just how complicated it is to walk away from your life (more here and here). But the greater challenge was simply letting go; to take the risk. So many questions could only be answered in retrospect: Will we like it? Can we afford it? How will so much togetherness affect our relationship? What happens to a career I spent a lifetime building? What happens if we fail? The only way to find out was to do it. The only alternative was to forget about doing it altogether.

Harder still was the fact that there wasn’t a single point of no return in our decision making process. Instead we faced a series of steps that gradually increased our level of commitment. It felt like jumping out of an airplane in stages.

Stage 1: Tell our friends and families about our plan.
Stage 2: Fly to Texas to establish a domicile.
Stage 3: Commit a large sum of money to buying an RV.
Stage 4: Resign from a very good job.

Before each decision, we’d ask ourselves, and each other, ‘are we really doing this?’ After each decision, the consequences of backing out grew more severe.

"Sooner or later you are going to realize, just as I did, that there is a difference between knowing the path and walking the path." - Morpheus

A year later we can confidently say we made the right choice. But that was never a foregone conclusion. We experienced a fair amount of angst and second guessing along the way that needed to be overcome to make our dream a reality. And even after we pulled the trigger, we still worked hard every day to make our experience a good one (see item six above).

So what advice do I have for someone looking to make a major life change? You may be surprised to learn that it’s not ‘Just do It,’ at least not straight away. While that may be a great product slogan, it’s a fairly reckless way to approach life altering decisions. Instead, I advise reverse engineering the process. Ask the question ‘Where do I want to be? or ‘What do I want to achieve’ and then think very hard about all of the steps needed to get from where you are now to where you hope to go; keeping in mind that not all of those steps are necessarily forward, some may take you sideways or even backwards. This is true regardless of whether your objective is to change careers or change continents.

If you’re realistic about this initial process, you’ll develop an appreciation for the kinds of sacrifices you’ll have to make to achieve your goal. And there will be sacrifices. Everything worth doing requires them. Identifying those sacrifices, and accepting them early, is a pretty important determinant of success. But once you’ve done that, then all it takes is the discipline to walk the path you’ve planned for yourself. If you do it consistently, you’ll eventually arrive at a place where you can make the change you want to in a responsible way.

And the great thing about knowing the path, and the destination, is that there won’t really be any question once you’ve arrived. You’ll know. That won’t stop the second guessing entirely, but it should give you the confidence to look past the inevitable fears and uncertainties. After all, you’ve done a lot of hard work to get prepared. Now just do it.

46 Comments leave one →
  1. Jared Phillips permalink
    August 5, 2011 10:19 am

    Great article. I’ve enjoyed reading about your travels.

    • August 5, 2011 10:25 am


      We’re always happy to hear when people enjoy our writing. The best way to keep up todate with our travels is to subscribe to our e-mail distribution list or RSS feed.

      Thanks again,

  2. September 25, 2011 10:05 pm

    great list of seven!!!..thanks for the dose of reality!!

  3. September 30, 2011 11:51 am

    Hi guys! Love this post, you had me hooked from point 7 and “the less is more thing”. Couldn’t agree more myself having only backed one bag full of clothes and a computer for my own cultural immersion experience here in Spain. I’m going to be here a year too!

    • September 30, 2011 12:14 pm

      Hi Will, and thanks for the comments. One bag is all you really need. We just got ourselves a couple of 40 liter backpacks for a two month trip through Central America this winter. We already tried them out on an 11 day jaunt back home to NY and we really, really liked them. Had more than enough room for everything we needed. Who needs a 4,000 square foot house when you can have a 40 liter backpack. LOL!

  4. Mark permalink
    October 6, 2011 12:52 am

    Hey, we’ve been out for 5 months on the Traveling Road in USA in our Motorhome. I like your posts and agree with lots of it. Gotta ask a question. What’s with the hats with lights strapped in them..I read some of your blog trying to figure out what they were about.

    Its great your guys are out here. Retired did you say, look mighty young to be retired.

    From or just google up Land Yacht Ahoy for our travel blog.

    • October 6, 2011 6:19 pm

      Thanks for stopping by and for your comments. The “About Us” photo showing us with miner’s helments is from our spelunking adventure in Mammoth Cave (link to our blog post). What a great trip that was.

      Happy travels,

  5. Mark permalink
    October 6, 2011 6:50 pm

    Oh Ok Spelunking, that makes sense now.

    We were near Mammoth Cave just a couple months ago, pretty cool place.

    Enjoy reading your posts.

  6. October 8, 2011 2:03 am

    Loved the idea, I’m giving a thought myself. just travelling….whow!

  7. October 13, 2011 2:54 am

    Truly enjoyed this. I guess it’s because I can relate a lot. Keep on truckin’!

  8. October 14, 2011 6:52 am

    awesome words! was a pleasure to find your site…am facebooking these words…they are definately worth sharing

  9. October 14, 2011 9:37 am

    Some great tips and advice, now just to put them into practise.

    • October 14, 2011 9:41 am

      Thanks. My favorite line in the entire post isn’t mine at all:

      “Sooner or later you are going to realize, just as I did, that there is a difference between knowing the path and walking the path.” It speaks to the difficulty of doing important things.

  10. October 14, 2011 10:11 am

    What a great posting! I echo Rory’s comments – now to put it into practice. We’re planning to take 6 months out to travel through South America next year. Lots of prep to do but can’t wait! Looking forward to more of your posts.

    • October 14, 2011 10:18 am

      Six months in S.A. is a great trip. We’re doing two months in Central America this winter. All the prep seems daunting initially, but somehow it all gets done. Have a great time, and thanks for following along.

  11. October 15, 2011 10:34 pm

    I love your photos! The sunset one is especially magnificent!

    • October 16, 2011 9:20 am

      Thanks you. The sunset (taken in the Florida Keys) is one of my favorites too.

  12. clarehudson permalink
    October 17, 2011 3:29 am

    Inspiring article- I enjoyed reading it.

  13. October 17, 2011 8:07 am

    What a great list! I especially like number 1. It is so easy to trap yourself into a routine and the more money you have the bigger the trap.

    • October 17, 2011 8:24 am

      It’s certainly true that the stuff you own ends up owning you. I don’t really get the desire to spend precious time acquiring useless stuff, but that is the “American Dream.” Who am I to argue?

  14. October 17, 2011 8:25 pm

    Wow -summed up my thoughts about travel in 7 points! I’ve been on the road on and off for many years and am thinking of trying to do it on a permanent basis. One of my mates has been travelling for 11 years and has many more adventures planned. – he has set a high bar.

    • October 18, 2011 9:12 am

      11 years on the road is a pretty high bar. Although it will take that long and longer to see everything there is to see. One of the things that really surprised me on our trip is how big the world is. At our rate we could spend the rest of our lives doing this and still not cover everything.

  15. October 18, 2011 6:42 pm

    Great blog. I agree with every one of your lessons — and I’ve now been on the road for seven years. My adventures started with getting rid of, or giving to my kinds anything of value they wanted, that wouldn’t fit in my small RV. I couldn’t afford to both maintain a home or travel. I chose the later and except for a comfortable bath tub, I have missed a single thing. Thanks for sharing your wisdom

    • October 18, 2011 9:59 pm

      Seven years, that’s quite an accomplishment! Thanks for your comments.

  16. October 19, 2011 10:56 pm

    This is fantastic! Very informative and inspiring. Good for you.

  17. lapoupeequifaitnon permalink
    October 20, 2011 3:48 am

    Point n°7 is poetry, believe me!

  18. October 20, 2011 6:18 am

    Your lifestyle choice is wonderful and something I can definitely relate to. My daughter left for 5 months in New Zealand and will return, husband in tow, after 2.5 years next summer after trekking New Zealand and Australia. My husband and I are planning for his retirement in 2 years when we will begin our own new life of exploration. While full time exploration may not be everyone’s idea of a good time, there are ways people can make changes, keep their home base, but begin to spend more time off the couch and out in the world.

    • October 20, 2011 9:24 am

      Quite right – fulltime travel isn’t for everyone. For us, it’s the right “balance” (if 100% can ever be balanced ;-)). I also think point 7 is applicable to more than a life of travel. It’s true for anything anyone may want out of life. Often times we make excuses why we can’t pursue our dreams when instead we should be working every day to make them a reality.

  19. October 20, 2011 9:07 am

    I’m from Boston and think it’s pretty lousy myself. Maybe because it’s a little…stuck up?

    You two have already gone to so many places; I can’t wait to catch up! Also, I once had neighbors who did a similar thing and sold their apartment (in Boston) to sail away on their yacht to who knows where, but I’m sure they’re happy. Maybe they left because they thought Boston was lousy, too.

    • October 20, 2011 9:28 am

      Is it just Boston you don’t like, or is it all cities? Some people hate cities and love wide open spaces. Other people just the opposite. I guess we’re fortunate in that we love and appreciate it all.

  20. Kathi permalink
    October 20, 2011 9:16 am

    Love your advice and adventures! Forty years ago my sister and I started on a similar globe trot, but when my mother almost died in a car accident going to my grandmother’s funeral, we came back home. I ended up marrying my childhood sweetheart, survived medical school by his side…38 years later he’s the chief medical officer of a hospital and we’re the delighted parents of 7 kids and 5 (going on 8) grand children. We are happy, but our travel adventures come by the week or two, not two lifetimes! God has a way of arranging and rearranging life, but it’s all good! I’m excited for you and your travels and wish you the very best! How do you continue to support yourselves?

    • October 20, 2011 9:38 am

      Congratulations on what sounds like a lifetime of adventure (7 kids, holy cow) and achievement.

      I’m considering adding a “How To” section to the site. Among the topics covered would be “How do we support ourselves?” The short answer is that we saved like mad, kept our spending in check, rented out our city apartment and work from the road. As my old football coach would say – “Agile, hostile, mobile.” Find the target, pursue it relentlessly, and adapt as needed.

  21. October 21, 2011 10:55 am

    This is great! My husband and I have just started our own plan to get the heck out of dodge, so to speak. And you are right-the conversation has to be continual to keep your focus on the dream. I appreciate this and its just what I needed. I will look forward to seeing more of your blog!

  22. October 21, 2011 3:08 pm

    Nice writing 🙂

  23. xinapray permalink
    October 22, 2011 12:21 am

    Thanks for these 7 great lessons! #1 and #7 really spoke to me, for they address the things that keep so many of us tethered to our current situations.

    I follow a guy who goes by Nomadic Matt. Don’t know if you’ve seen his blog but if you haven’t, it might be interesting (apart from being a follower of his writing, I have no connection to him).

    • October 22, 2011 9:19 am

      Thanks for the great comments. You’ll notice that Nomadic Matt is one of the links in my blog roll. He does good work.

  24. October 22, 2011 12:30 am

    Wow, what a great blog, and a great adventure. Love the advice about making a major life change. I don’t read every single word of very many blogs. This one, I did.

  25. October 22, 2011 8:31 am

    Awesome and so true! Congrats on being true to your convictions and doing it! Everything worth doing is tough – plenty to consider. I did it once before – hope to do it again – and like you, I have the multi-year plan starting to take shape. Thanks for helping me get my thoughts in order. Great lessons.

  26. October 22, 2011 9:35 am

    Hi guys,

    I loved your whole blog! This is the first time I have ever looked at a blog to know what the concept is all about. Blogging is a whole new experience for me and I learned so much from reading about your travels. And you are the first person to stumble upon my site. I have never even told anyone that I was doing a blog yet. It was very exciting to see that you actually looked at my blog and gave it a nod. My husband and I are doing the same sort of trip as you and we are neophytes to R/V travelling as you were when you started out in 2009. It was great to see that your lifesyle choice is sustainable. See you down the road. We leave tomorrow. Yikes!


  27. October 24, 2011 7:39 am

    My husband and I live in Israel and have been traveling in the United States for the past two months. This is not the same as your life-changing project, but we have learned some of the same lessons, and most particularly that less is more. On the road, especially if you’re camping, any excess possessions become an intolerable burden. And you discover, almost effortlessly, that time is indeed your most valued asset. That realization is even more powerful when you are older.
    Best of luck.
    Esther Hecht

  28. October 24, 2011 11:11 am

    I found your post to be thoughtful, intelligent and sophisticated. Much of what you explain is what I had to do to start my business –which is essentially a means of allowing people to feel “as if” they are having the experiences you describe as your life. I see many parallels between leaving the traditional 9-5 job/life to bring a long term dream alive and the experience of leaving that life to travel full time. They require adaptation, cultural sensitivity, thorough planning but last minute flexibility –and most of all, openness. If you’re not open, you really miss the best of what’s out there –both on and off the beaten track. Thanks for describing it so well!


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