Do You Have Any Regrets About Selling It All To Hit The Road?

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Do you have any regrets?

We are often asked this question by families thinking about ditching the suburbs.

We understand the angst behind the question.

That house took months to find and buy. You just got the lawn to where the neighbors aren’t frowning at it. The tidy new garage shelves still smell of fresh-cut lumber.

And that’s just the stuff. What about your family?

Your kids?

All that time evaluating and purchasing the best homeschool curriculum. All that worry - making sure your decision to homeschool them won’t hurt their chances of success.

And the socialization. Yea - you are tired of hearing that question, have read 100 blog posts about how well-socialized homeschool kids are, and have ranted to your spouse about how stupid it is that people keep bringing it up. Yet, you do want your kids to be comfortable in different social settings.

The idea of selling it all to hit the road sounds a lot like freedom.  But your head starts doing the what-ifs.

What If:

  • You hate it?
  • You hate it and can’t afford to buy a house again?
  • Your kids can’t find other kids to play with out on the road, on the water, or on a farm?
  • Your kids end up behind where they should be academically or socially?
  • Your kids end up….weird? Unhappy? Resentful?
  • This idea of a big family adventure is just candy-coating around your personal mid-life crisis?

Do you have any regrets?

When I hear that question what I hear instead is:

Please save us from making a decision that will bring us pain.

I scanned back through our first year on the road, looking for the most painful moments. I wanted to ask myself: Because of that pain, do I regret our decision to ditch the suburbs and hit the road?

Here are the two most painful things that happened to us that first year:

Truck Accident/Ice Storm

It was Christmas time. We had dropped the RV at a friends and were driving back to Michigan to be with family. We got into an accident on the freeway.

We got to Michigan and got the truck into a repair shop. We stayed at relatives and at borrowed condos. We lived out of plastic totes. A planned 10-day visit turned into 25 days.

We finally got the call that the truck was done. We picked it up and headed south - straight into an ice storm that paralyzed Atlanta and delayed us again. We spent 10 days in a tiny hotel room. We taught a class twice and got paid once.

Any Regrets?

When we first left Michigan our daughter was a black hole of anger in the back seat of the truck. She was upset over leaving her comfort zone and scared about what life was going to be.

This accident and storm broke through the ice in her spirit.

She went on to become a cactus expert, an equestrienne, a bmx racer, and a friend.

So no, no regrets.

Roof Replacement/Camphosting

Later that year we took the RV in for a brake inspection and drove away with a $7K bill for a roof replacement.

To help recover from that unplanned expense we took a crappy camp-hosting job in Washington. The campground owners lied to us, watched us work through a telescope, monitored our radio conversations, and wanted us to launder their uniforms on our dime.

The aftermath of our truck accident in Kentucky.

The aftermath of our truck accident in Kentucky.

Miranda shows a piece of the ice covering all of Atlanta.

Miranda shows a piece of the ice covering all of Atlanta.

Smiling - so it must have been the first day at the camphosting job from hell.

Smiling - so it must have been the first day at the camphosting job from hell.

Any Regrets?

When we set off on this adventure one of our goals was to break out of our comfortable suburban life and trust God more.

The roof incident was June. By the following May we had paid off our credit card debt before selling our home. We used income from the home sale to instead fulfill a long-term dream of living on a houseboat.

Do I still feel stupid for not getting the RV roof inspected before buying it? Yup. Do I still cringe at the thought of that first camp-hosting job? Oh yea.

Would I undo any of it?


We learned so much. We endured crisis as a family. We learned about crappy jobs together. We saw God’s hand in restoring our finances. We stuck with it and fulfilled a dream.

We have great family stories to tell.

And the sunset photo on this post? Taken at that crappy camp-hosting job.

So no - no regrets.


I do have one regret.

We should have done it all sooner. Years sooner.

But What About The What-ifs?

Look at each one and play it out in your head.

What if you hate it? Then you stop doing it.

What if your kids can’t find friends? Then you move to where they can.

What if you can’t afford the same house after trying something different? Then you rent or buy something smaller. Big deal.

What if your kids end up “behind”? They won’t. But you’ll realize that what is “ahead” or “behind” for any kid at a certain age is defined by you and not some external person or organization. If they need to spend some focused time on learning something, just do that.

You get the idea. Every what-if is just a fear that grows when you feed it in the dark. Bring it out into the light, play it out and you’ll find that there can be happiness and contentment on the other side of any of them.

The best part about ditching the suburbs is how flexible and adaptable you will become. You will flex to catch whatever curve ball life throws at you.

Fellow Non-conformists

Have you made a big transition with your family? Moved into an RV, Boat, or started a farm?

Lend me your comments and speak to those considering a similar move with their own families.

Any Regrets?

18 Comments Do You Have Any Regrets About Selling It All To Hit The Road?

  1. Picture of Meg Meg May 12, 2015

    Great post! I think I worry most about my sanity and not ever getting a break from the kids. What about date night with my husband?! (Not that we have had one in the past 3 months while living in the burbs!)

  2. Picture of Michael Boyink Michael Boyink May 12, 2015

    Hey Meg -

    Thanks for stopping by.  Did you pick out paint yet? ;)

    Our kids are older…but we’ve had “date nights” out by the fire after the kids were in bed.

    Maybe feed them first and then cook a steak to eat together (my parents use to do this in our old Winnebago but we knew Mom would never finish hers so if we stayed awake we’d get it anyway..;)

    Or just be on the lookout for another family where you can tradeoff parenting duties and catch a break.

    There are also baby-sitter-vetting websites you could look at for a night away as well.

  3. Picture of JorDanee JorDanee May 12, 2015

    We have a few regrets and we’re only 1.5 weeks into fulltiming. Our biggest regret? Not doing it sooner. Our second biggest regret? Not getting a more thorough inspection of the Airstream. Granted, we now have a much more intimate relationship with how our Airstream is built. However, those are really our only two regrets, and the first one is the most painful one.

  4. Picture of Michael Boyink Michael Boyink May 12, 2015

    Yea - that’s a bummer about the trailer. But that’s really no different than issues with buying a sticks and bricks home.

    And you guys figured the nomadic life out way sooner than we did!

  5. Picture of Connie Perry Connie Perry May 13, 2015

    I never knew you guys had dreamed of living on a houseboat.  We are headed back east at the end of the summer and hope to start looking at boats.
      Great article as always!

  6. Picture of Michael Boyink Michael Boyink May 13, 2015

    Hah - it was probably more “me” than “us”...but yea -I thought about that houseboat trip for years.

    Having done it, we’re over it. Unless we rented one with friends on Lake Powell or something.

  7. Picture of Heather Gebbia Heather Gebbia May 13, 2015

    I had all the same fears and questions just before we launched in January. Now I’m relieved to say I have no regrets and wish we would have done it sooner. I know it’s only been a few months but so far we’re all loving it. Even my 8 year old that didn’t want to do this at first.

  8. Picture of Michael Boyink Michael Boyink May 13, 2015

    Ah - another reluctant child turned! Hopefully yours didn’t require an accident and ice storm..;)

  9. Picture of Jenni Jenni May 13, 2015

    You’re right on the money with your answers to the “what if” questions.  We had a lot of the same and we had to finally go, “If we hate it we go back.  If someone needs major medical attention, we go back.  Really, what could happen that could leave us penniless that couldn’t (more likely) happen if we stayed put in a house?  Nothing.”  I think my biggest regret is not putting the blog/url decal on our rig sooner in the trip.  We met so many great people because they saw that decal and contacted us.  I wonder who we missed meeting during the 6 months prior…

  10. Picture of Michael Boyink Michael Boyink May 13, 2015

    No one that God had intended you to meet..:)

  11. Picture of Beverly Beverly August 28, 2015

    I love this post!  Reading this was perfect timing and is exactly what I am quietly thinking as we are just a buyer away from selling and getting on the road with two girls (17 & 12).  Our older one is already thinking like your daughter was and planning her exit as soon as she can.  *sigh*  We are trusting Him and in the mean time I keep reading, reading knowing someone has/is traveling before us that can give us clarity and maybe insight that these thoughts are normal. ; )  Thank you!!

  12. Picture of Michael Boyink Michael Boyink August 28, 2015

    Hi Beverly -

    Coincidentally as I write this my wife and oldest (my son) are an hour away back in our home town, where the boy is interviewing for a couple of fulltime manufacturing jobs.  We’ve already secured him a room to rent with a cool family (with one parent who was homeschooled).

    It’ll all work out. She may come to love traveling. Or it may be extra incentive to launch on her own, which isn’t a bad thing either..:)

  13. Picture of Beverly Beverly August 28, 2015

    “She may come to love traveling. Or it may be extra incentive to launch on her own, which isn’t a bad thing either..:)”

    Exactly our thoughts!!  Though it has taken the last few weeks to come to this thinking.  After home schooling for so long (we have two adult children) it is always hard to begin that “launching” out time but you are right…if it is His timing it will not be a bad thing.  Hope all goes well today for your son! 

  14. Picture of Michael Boyink Michael Boyink August 28, 2015

    Thanks - this is our first ‘launching of kid’ so it - along with the fact that we’ll be dropping him off and immediately heading out of state - is especially nerve-wracking.

  15. Picture of Carissa Waggoner Carissa Waggoner December 07, 2017

    I am so glad I found your blogs!

    I am became a single mom recently. I have a 13 year old and a 8 or old both boys.

    In 47 and live in Christiana, Tn.

    For many reasons I am about to embark on the RV life style trail.

    But I can not move my children out of state and I need to have some sort of address due to the parenting plan and TN child custody laws. So I am looking for land as well where I can park and live in the RV, but not travel in it just yet.

    I am still waiting the sell of my house to buy an RV, but before I do, what must I know about heating costs propane vs electric?and hooking it up where it isn’t simple park type hook ups?

  16. Picture of Crissa Boyink Crissa Boyink December 09, 2017

    Carissa -
    I would recommend looking at property that either has electric run to it or that allows you to have electric installed. For us, we preferred to run an electric heater rather than the propane heater when possible. Of course, the electric was included in the cost of a campsite rental, so I’m not sure which would be cheaper for you if you have your own property.

    You are going to want water access and a safe place to dump the black tank. If there is an open nearby campground, you could always go there, pay a nominal fee, and dump your tanks.

    I’m sorry I don’t have any real advice. I wish you well with researching the situation and finding what is right for you and your family.

  17. Picture of Susan Davis Susan Davis December 11, 2017

    GREAT post!  We too have learned that all those things that are thrown at us only give up opportunities to GROW.  I bought our first brand new RV then before making the first payment hit a rock and ripped off two basement doors.  I thought I was going to have a nervous breakdown. Then we got stuck in the Yosemite forest fire and unable to get back to the RV.  BUT…handling all of those things that came up made me stronger and helped my kids see life differently.  Now my 24 year old is on his own adventure in Florida.  Without our travels adventures and MISadventures I don’t think he could be where he is.  He was a professional diver for the last year and now he’s looking at going into the yachting business.  If we had stayed home I doubt he would have ever ventured outside our city. 

  18. Picture of Diane Diane June 02, 2018

    After raising 3 teens alone and the last one moved out I had come to the conclusion that now that I was “free”, it was time to do me. I quit a very good job, sold everything I owned except what fit in my Jeep and I’ve now been living a gypsy life for 2 years. I first left my home in Denver, travelled to the San Juan Islands and spent 7 months there. Afterwards I travelled to Los Angeles and have now been here for 9 months. I live in a van that I’ve turnef into a very comfortable and organized living quarters. I have a Job and I live along the Pacific Coast. The only thing I have questioned is that I feel somewhat concerned that I’ve abandoned my adult children. I have no home base for them to visit, no kitchen to prepare holiday meals and no place for them to land. Should they ever need one. Having said that, I have been able to pursue many dreams and goals that I could not while raising a family. I have accomplished more in the last year, than I have in the last 20 years.  Giving up my corporate status job looks bad to most employers. They wonder why I’m now slinging coffee at the beach, instead of analyzing financial data. My concern is that should I want to go back to the 9-5 grind, will my choice to live this way become a black mark on my background. At this point, I’m darned happy about my decision, and I want to keep it going. I do have the 100% support if my kids, do what anyone else may think about my lifestyle is no concern of mine, except maybe for said future employment. I’m a 52 year old single female. I’m saving to buy a better and more equipped van so that I can start traveling more. My goal is to be able to live off of a small business I started at the beginning of 2018 so I’m working hard every day to reach that.

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