Let the Road Trip Begin

Bandon Pier

On a run in Bandon.

We’re going on a road trip! Our house is rented out, our van build-out is done (the neighbors are still rejoicing), and the wireless hotspot for my work needs is blinking green. In fact, I’m typing this from sunny Bandon, Oregon from the Mobile Office Rig overlooking the ocean.

This post almost was entitled “Boomeranging Millennials at Home.” As Chelsea’s dad (mostly?) jokingly reminded us, 1/3 of our age group is currently living with their parents. Thanks for the hospitality while we finished the van build out, Steve and Linda…and for watching our cat Oliver while we’re rolling about! And for letting us use every single tool in your garage workshop to finish out the van build out. Couldn’t have done it without all 1,323 tools that I left strewn about in my wake.

Heading out from Idaho.

Heading out from Idaho.

Nope, moving home is not the plan! After over a year of talking about it, plus the purchase and build out of a road trip vehicle (a Sprinter), Chelsea and I are hitting the  road for a few months (edit March 24: open-ended timeline) of discovery, visiting friends and family, making new friends, and rolling around the California coast (and beyond) in our van. It isn’t a full-time party, as I’ll be working remotely and checking in with two six (as of May 2014) employees back home via my wireless hotspot, but should be a fun adventure.

What’s coming up? Stories of the fun of living in a 6×12 foot space…and the headaches since that’s often the funny stuff. Update June 2014: we’re parking the van for awhile to ride to Maine, then back to the van. (I suspect some of you are thinking only of the inconveniences of a tiny space like that!) Shots of me hard at work in my remote office locations to prove that I can’t get away with just disappearing entirely.

Finishing up the work week at sunset.

Finishing up the work week at sunset.

The plan? To head south from Portland, sleeping in our van along the way. Soon we head to the redwoods on the border of California and Oregon. Thanksgiving in the Redwoods, then onward we go down the northern coast of California. Straight down the coast via highway 1 and 101 through the Bay Area, stopping many times along the way, eventually ending up in San Diego. From there…we shall see.

Plastic whale

Chelsea in a plastic whale rib cage (made of garbage from the beach) at the WashedAshore.org project in Bandon.

Goals for the trip are few…and yet probably still too many! After a long break, I want to write more and take more photos. Hence, the blog. I want to play my guitar. And run. And ride my bikes (mountain and road versions are with us). And visit friends and family along the way, and talk to random strangers. And I want to enjoy it all with Chelsea while overlooking the ocean while sea lions bark down below, or big redwoods sway in the winter breeze, or waves crash on a sunny (<–key word) beach. Slow down, relax a little, and take it all in.

Looking forward to connecting with you along the way! Drop us a line, we’re around. Just don’t mail us anything :) 



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  • RySny

    Great post! I totally agree. Please write more posts like these!!!1!

    • admin

      Thanks Ryan! I put a LOT of thought into that Hello World post and really appreciate your input. Maybe I’ll do “buenos dias world” next!

  • http://sailingsmitty.com Brandon

    Hey Big D.,

    Congrats on finally getting out on the road! I’m proud of you. I know it was a big step and I have a feeling that it’s just the beginning of something even bigger for you. It’s great to see you making it happen. You two are awesome! Looking forward to hearing about the trip and maybe you’ll inspire me to write more on my travel blog. Can you still call it a travel blog after 3 1/2 years? One of the deeper questions of life…


    • Dakota

      Thanks Brandon! Took some serious effort to get the escape velocity to disentangle from it all. And now here we go!

      I think your blog is now just A Vagabond’s Memoirs. You can have the title for free, my gift to you. I’m SURE it isn’t taken yet.


  • http://www.thestartupsessions.com/ Michael Knouse

    I love it! I look forward to following you and Chelsea along your journey. I’ll do my best to keep all jealous remarks to myself as I hear stories of sunny California beaches in January. You guys are an inspiration and I look forward to many stories of adventure and tips for living in tight quarters. Happy trails!

    • Dakota

      I’ll photoshop the heck outta some pictures to make sure they are gray and nasty. Or maybe you’ll just have to jump in the Chieftain and head south to visit?

  • http://www.millerslastresort.blogspot.com Chris

    Thanks for inviting me along! I loved “traveling the world” with you and now look forward to this adventure!

    • Dakota

      It is going to be fun! Glad you’ll be along for the journey with us.

  • Jana

    What an awesome adventure. Congrats you two for making it happen!

  • http://loganblairsmith.com Logan

    Bon Voyage you two! Can’t wait to read about your new perspective as “rubber tramps!” :)

    Cheers, L & T

    • Dakota

      Rubbertramps.com was taken. This is the 2nd best URL I could think of! Already digging this lifestyle – tiny house living with an engine, right?

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  • AshleyO

    Looks horrible so far you two! Maybe see you in the bay in the near future!

    • Dakota

      It would certainly be tougher with a newborn! If you’re around the Bay during Christmas, drop us a line. We’ll be near Santa Cruz.

  • Sean P


    Looks bloody fantastic man! Well done….. an inspiration for an aspiration of ours…just in a 38′ boat :)

    Happy 2014 and safe travels!