Reader Questions: JoEllen

We love getting reader questions, and one of us always take the time to answer them, but occasionally I find the questions interesting enough that I think they deserve a blog post.  That was the case when I received some questions from JoEllen a few days ago, and since I thought many of you might have similar questions I decided I would answer them in this format instead of directly to her. The questions themselves are in italics, and my answers are in blue. Lee’s comments are in red. (She’s not the boss of me. My comments are in bold orange italics. – Lee)

Tracy, I have emailed you before several times and learn a lot from you 2. Hopefully in 2-3 years we will hit the road and will need to work also. We have already sold our house and all our goods. 

Thanks!  Always nice to hear people are getting something out of this blog, and congratulations on completing two huge steps towards you new life.  (Yes, congrats from me as well, but in bold orange italics. – Lee)

  1. My BIG question is, “why” did you and Lee (almost) throw in the towel and stay PUT for a full time job that could change the direction of your life only after 4 years of being on the road? 

I don’t know if we got to the point where we were willing to throw in the towel completely, but we were having conversations about what this all looks like going forward.  For those of you who have read the blog for a while, you know I have found work kamping to be very challenging.  I, at least, am constantly evaluating risk versus reward and it is tempting when the jobs are particularly challenging to think about taking a break and finding something stable for awhile.  A huge part of that is fear, some of that is a “grass is greener” mentality, and some of it is just frustration.  There are trade-offs in this lifestyle, just like any other, and I think those trade-offs should be constantly weighed.  I tend to be more introspective than some people and more open about my introspection but I think most people have these thoughts at some point. (Believe it or not, while I understand where Trace is coming from, I don’t feel the same way. We’re very different people. For example, she tends to write in blue, while I tend to write in bold orange italics. But seriously, I generally feel like the idea of taking a break and finding something stable is a trick/trap. I don’t believe there’s any such thing as stable. I would rather experiment and see “what’s next” than sit around thinking I’m safe and secure while someone (without my knowledge) is deciding I make too much money, or I’m too old, or too bold, or italicky. I feel more in control of my own destiny now than I ever have in my entire life. – Lee)

I would like to make one more comment.  You say “only after 4 years of being on the road” and I found that interesting.  In this lifestyle 4 years is a long time.  I say that because it is so packed with experiences and living in the moment that I personally would say 4 years equals 10 in a more traditional life.  That’s my rear view perspective, but I stand by it. (And for me four years seems to have screamed by so fast I actually have to do the math in my head to make sure that 2014 to 2018 was actually four years. It feels more like 2  1/2 years to me. Except for Amazon. That felt like eternity. – Lee)

  1. Is 4 years the turning point to start thinking, “OK we have moved enough” let’s put more grass under our tires instead of asphalt? What I have noticed in keeping up with your age group (and I keep up with a lot of blogs) of starting on the road verses those 62 years old and beyond (who don’t work as much or at all) is that the 62 year old and beyond stay on the road LONGER. I know about Howard and Linda but their situation (not working all the time) is different than most people. I just read the other day about a couple I keep up with at times who are hanging up the keys, but he is 82 and been of the road a little over 10 years.

That’s a great question and opens the door for me to talk about a trend I have been noticing.  My short answer would be “Yes”, for many people four years seems to be a crossroads of sorts.  Many people I know are buying a piece of property and putting down roots at least part of the year. Others are coming off the road completely. Many of us who haven’t found a place we would like to settle are looking for a “route” where we can find a summer and winter “home.”  There are still lots of people I know who are traveling somewhat randomly, but almost everyone has slowed the pace from those first couple of years.  One point I would like to make though is using people who write blogs as the representatives of the lifestyle doesn’t tell the whole story.  I did the same thing by the way, but since we have been out here working we have met TONS of people that have been on the road for many, many years and the lifestyle of the working group is different than those who have lots of money in the bank.  (I also agree that there might seem to be a significant number of people that make some kind of major change to how they do this after four years. I think the reason for that might be that four years of heavy travelling or aimless wandering or racing from place to place can be exhausting for a lot of people. But I also think there’s no trustworthy data so I would have a hard time declaring anything. The scientist in me bristles at all that jumping to conclusions in the absence of verifiable facts. – Lee)

  1. Should “One” consider it safer to “WAIT” till in their 60’s and feel as if “this is now my NEW life?” Verses those in late forties early fifties who may consider the road as a “cool down period” then charge back into a daily grind?

My struggle has been finding work that is satisfying and maintaining a roving lifestyle.  The longer I get away from my old professional life the more of a gap I have in my resume and the harder it is to find that type of work.  I also find that emotionally I am less suited to a traditional 9-5 gig as time goes on and the postings I do see are much less appealing.   If I was 60+ I think I might care less.  At 52 I am looking at 13 more solid earning years and I hate to give up the money and satisfaction I get from working in my field.  If I had a job with a pension or had socked more money away I would probably feel differently, so really it is less about age than financial circumstance.  Simply put since I have to work, I want that work to have some meaning.  From a financial standpoint, I get nervous as our nest egg dwindles over time.  These are prime earning years and because of my lifestyle choice it feels like I am giving that away.  

All that being said I know several people who kept their corporate jobs on the road and even one who lost that job, found another, and is still living a mobile life.  I hear stories about the 30 somethings who work while on the road and they made sure they kept their corporate type jobs from day one.  My journey was a little different.  I wanted to try pure work kamping for a variety of reasons, but wasn’t really aware when I made that decision on how difficult it would be for me to jump back into my profession.  And to be clear I am not even 100% sure that I want to.  That’s the main conflict I am having right now. (I don’t feel the way she feels about career work. The work I did I could go right back to doing, although the last few times I did it as a freelancer I felt “not as young as I once was” for the first time. Show business is hard work. But I say the same thing to everyone I talk to about this; Do it. Don’t wait. People die or become incapable of doing this every day with little or no warning. The money will take care of itself. Be happy. At the end, we all go in the same size hole. – Lee)


  1. Again WHY did you 2 ponder such thoughts?

Lee rarely has these thoughts.  He had a career that required living in one place and he knew he might never work in it again.  For him the trade-off was more than worth it and he made the decision with that in mind.  I kept my job for the first year and knew that I had a skill set that was friendly to working remotely.  Because I have always done this lifestyle in baby steps, it has taken me longer to  come to terms with the sacrifices I might have to make professionally.  This summer and this job brought those things to the foreground and the subsequent job search has really brought those issues home.  I was stuck on the idea that I would have to spend the next 13 years working at jobs I didn’t enjoy because we wouldn’t stay in one place.  Those thoughts were in no way about not liking the lifestyle itself, but about not wanting to make that sacrifice.  I didn’t see why I couldn’t have both, and succinctly put, it was pissing me off. 

Then I had a conversation with my Mom. You know how sometimes your Mom can say the exact right thing at the exact right time? Well this was one of those times. Recently she lost her husband, sold her house and moved to her dream condo on the ocean in Myrtle Beach.  For the last several months she has been very happy, but misses what she gave up, living next door to my brother and one of her grandsons.  My Mom, who is a no-nonsense kind of chick, said “Best not to dwell on things you do not have when your life is so rich with experience.”  After I called her she went on to say that I have a pretty terrific life and better than many people my age.  Then she asked me why I would want to give that up for the possibility of something that I wasn’t even sure I wanted?  My answer, which came from the gut, was “fear”.  And really that’s what it comes down to.  Do I believe that it’s possible to find both meaningful work and continue to live the lifestyle? Yes. Do I think that is a certainty? No. Am I afraid the longer I do this the less likely it will be.? Yes.  

So I have three choices.

  1. I can give up on that and just take what jobs I get and find my peace with that. 
  2. I can continue to try to find jobs that allow me to stay on the road and give me satisfaction, allowing that it will be a ton of work and I will probably be disappointed quite a bit. 
  3. I can find a job, leave the road, and possibly reenter at a later time. 

These are all valid choices, by the way, and I have very close friends who chose one of these three routes in the past year.  For right now, I have decided to go with the middle option.  The downside for both of us is things remain unsettled.  The upside is we don’t have to settle. 

And if I can say one more thing and this is more to the general audience than just you, because I don’t want to assume anything.  When I started this lifestyle I thought it was an “all or nothing” proposition.  I thought the amount of time on the road mattered, and for me at least full timing was something I wanted to conquer and win in some way.  I don’t feel that way anymore.  It is an amazing and wonderful way to live sometimes, but it is not the romantic dream that I thought it would be.  Every year in November, I take stock of the trade-offs the previous year and decide if it was worth it.  I look at what we had to do for work, the mechanical issues we had, and the pictures we took.  The pictures tell the story and every year to date, this year included, the pictures (and the corresponding experiences) have won.  Some year they might not, and that’s OK.  Personally I don’t ever want to be in a place again where I am not living my best possible life.  What that looks like depends on lots of different factors, some of which are outside of my control. So that’s why I ponder these things, and I hope I continue to challenge myself to do so 🙂 (I don’t ponder these things at all, really. For me it’s mostly about practicalities, which I see as broken things to fix, or systems or processes that need tweaking. I already feel like I’m beating the system most of the time in this lifestyle, instead of the system beating me. I sleep better than I have in 30 years, I’m more relaxed, and I just generally feel like a better person most days. I’ll take that over how I used to feel any day of the week and twice on Sunday. – Lee)

Thanks for your time and sharing your life, and family with us.

Your very welcome.  Thanks for the interest and allowing me to share my thoughts with others. 

(Write in whatever color you want. It’s good for the soul. – Lee)


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9 thoughts on “Reader Questions: JoEllen

  1. Thank you JoEllen for the questions! Led to some very insightful feedback. I come to this blog for a number of reasons, especially the parts where you guys are keeping it real. Setting realistic expectations about travel and work is so very important.

    Speaking as someone that went from the corporate world to a dream job; I can tell you that even the dream job turns into a heart attack waiting to happen. I’m trying to move myself into an attitude similar to Lee’s in this post. Hard to do. I’m thinking a person just has to wake up one morning and make the decision to let the fear go. Much easier to do I’d suspect if you have a fearless person by your side.

    It is a blast watching your class of 2014 move through the lifestyle….

  2. As the one who lost the corporate job and found another and have been on the road for a little more than 5 years, all I can say is don’t settle, there’s too much life out there to keep living.

    My new corporate job does not bring me nearly the career satisfaction that the old one did, but this one is much less demanding of my time and guess what that means? More life!! More walks, hikes, bike rides, etc. on week nights, weekends that generally start early on Fridays, etc. It’s a trade off, but as I read about the tremendous hours you both worked this summer, I’m thankful a job that I can continue to find the right work / life balance and continue to build up our retirement funds.

    One comment on career satisfaction, I’m not sure career satisfaction exists quite the way it used to with the continuing, never ending focus on the bottom line and the ongoing outsourcing to overseas for so many professional jobs. The corporate climate has changed dramatically over the last 30 years and in my mind it’s pace of change continues to accelerate leaving many employees wondering how long the merry go round will last. Maybe I’m a bit jaded because as I write this, I’m facing my 5th merger, acquisition, spin-off, corporate consolidation in 10 years. 5 different major corporate restructurings in 10 years can cause a great deal of angst and mental exhaustion.

    Yes, we’re doing this differently than many, we’ve slowed our pace down considerably and we travel a circuit due to Dale’s business schedule, but somehow there’s always somewhere new to explore along the way, a new hike, a different waterfall, a new bike trail, etc. etc. And that keeps us energized and excited to continue this journey.

    Wishing you the best in finding the best way to pursue the middle option, this life we live is just too precious to give up and settle. Compromise? Yes, Settle? No.

    • Ruth thanks so much for taking the time to write this. It’s interesting that you write about mergers because I was facing my fourth one as well when I took the buyout and a major factor was I was feeling I just didn’t have it in me. I find your work life balance something to aspire to 😄.

  3. As always, I applaud your courage in looking inward, and then sharing the good, the bad, and the ugly. As someone who fulltimed for a year, looking back, it was really an extended vacation, and when I realized that the spending would not be sustainable without quickly depleting our resources, as you know, I opted to jump back into the full time work force. I now see that in the future, we will be able to “part time/full time” meaning have our modest home base in the winter where we are, then travel 4-5 mos in the summer…without having to worry about working. Do I wish that I could “hurry up and get to that point”…at times, yes, but I am trying to live in the moment, and enjoy the fact that I can still earn a robust income and feel that the work I do matters, knowing that in a few more years it will all change again. Life….it is always an adventure!

    • Ellen thanks so much for sharing your experience. The fact that you left the work force and reentered it is important! You are certainly not the only people who chose this route. Plus you are living on the ocean which is pretty awesome 😎

  4. An excellent post again. Thanks for your honesty. We have been full timing 5 years now, after taking early retirement because my husband couldn’t physically do his job anymore. I would tell anyone, if you can find a way to do this while you are younger, do it, and try to be debt free going into this. As you get older you don’t know what your physical capabilities or health will be like. Find a way to make it work, and see this fantastic country. Have you considered campground management at a place that closes in winter?

  5. Great questions and love the answers. Lee you always put a smile on my face. I always love your answers. If I could put this in orange I would LOL
    Enjoy your day both of you –

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