Dear Uncle Calvin – With Love, Jack & Jill

It is time once again to address Dear Uncle Cal, in our series of fellow traveler interviews attempting to convince our beloved uncle that long term travel is indeed a very good thing.

And that we’re not really crazy (well, at least not because of this)!

(If you missed Part One of this series, you can find our interview with Dyanne here.)

Meet our friends Jack and Jill – married college sweethearts from California who are, as you read this, in the final hours before embarking on their own round the world adventure!  Yes, they have given it all up – the home, the car, the good jobs – and are heading out into the big scary world with nothing but their backpacks and each other. Sound familiar? Given that they are just starting their adventures, you can bet that they’ve had their share of Uncle Calvin’s questioning their sanity…

1. Thanks for doing this guys!  Please kindly introduce yourselves to our fine readers.

We’re Jack and Jill, a recently homeless and (gainly) unemployed couple from California.

A long time ago we marked 2011 on our Google calendar as ‘the’ year we’re going to travel the world.  Well, it’s 2011 now — so, hmmm, gotta follow the schedule (seriously, if we hadn’t marked the calendar I think we would’ve kept postponing the trip. It’s amazing what the simple act of putting it down on a calendar did to our subconscious).

Our last of employment was March 18th and tonight we are leaving for Colombia.  Finally!

2. What are your current plans?

Photo by: Flickr user

Currently the plan is to travel in South America for a bit and slowly making our way  through Africa, Middle East, Eastern Europe, Asia and… back to the US?

How long and where exactly we’re going — we don’t really know.  We might be able to find jobs on the road and keep on going, or we might get sick of each other 3 months from now and decide to go back, or we might end up never leaving South America.


In general though, the plan is to be open to any opportunity that presents itself… and not to kill each other.

3. Why do you believe travel is important?

Jill: Travel is important to me because I believe it brings out the best of me as a person.  I’m constantly humbled and amazed by experiences that travel brings – it challenges my perceptions on how things should work, it breaks stereotypes I didn’t even know I harbor.

Whenever you take yourself out of your comfort zone, you inevitably learn things about yourself (sometimes things you don’t want to know) and I think learning more about yourself is always a good thing, no?

Photo by: Flickr user Rishi Menon

4. How has travel changed you or, what do you expect to gain from your upcoming travels?

Jack: It has made me more tolerant, more patient, and more accepting of things that I can’t change (such as, yes, people will come up to me out of nowhere to try to sell stuff — I’m learning to be okay with that). At the same time, it has made me aware that I can always do more to help out others than I originally thought I could.

Jill: Traveling as a couple has taught us to laugh at each other’s mistakes and not to take little inconveniences too seriously. We’re hoping that our upcoming travel will show us what living a nomadic lifestyle will be like and whether or not it’s for us.

5. Tell us about your “Uncle Calvin”.

Jack: What a tough question. Let’s just say that our Uncle Calvin is made up of pieces of personality of my parents, Jill’s parents, and some of our friends. They know us well enough not to be surprised at our desire to travel long-term, but still yet managed to be surprised that we’re actually making it happen (tsk, you’d think they know us better than that!)

6. Help us draft a letter to our Uncle Calvin.  What do you say to someone who believes you are crazy for your decision to be a perpetual traveler?

Follow Jack and Jill as they begin their worldwide travels!

Their blog:

On facebook:

On twitter: @jacknjilltravel


31 Comments... Read them below or add one of your own
  • April 18 2011

    “We choose not to be most people.”
    Great answers! Good luck to Jack & Jill on your travels, and I hope you love being nomads too!
    Dalene & Peter – do we get to know your Uncle’s response to this? 🙂
    Kit Whelan recently posted..Tax Day- How do digital nomads handle taxes

  • April 18 2011

    I love this interview. Unique, fun and creative. Well done!
    Michael Hodson recently posted..Friday is the new Saturday

  • April 18 2011

    Awesome interview! I love hearing about people who want to “risk being happy” too 😀
    Roy | cruisesurfingz recently posted..Another Shit Day In Paradise

  • April 18 2011

    Fab interview and so excited for you guys – you’re about to have the time of your lives!
    Nicole @ WomanSeeksWorld recently posted..The Best Smartphone Apps For Travellers

  • April 18 2011

    Ah this makes me so hungry to do the same!! We leave in June for Europe but we have a September end date. I can’t wait to one day have no end in sight.

  • April 19 2011

    It’s so good to see the homeless have a venue for their voice to be heard. 😉

    Just kidding — great interview!
    Raymond recently posted..Life and Death in Peru — The Plight of the Humble Guinea Pig

  • Love that letter to Uncle Calvin – perfectly articulated! Happiness is always worth the risk. 🙂
    Christy @ Technosyncratic recently posted..Confessions of a Dog Who Hates the RV Lifestyle

    • April 19 2011

      I agree! They did pose it quite perfectly!

  • Jeremy B
    April 18 2011

    Good interview and great to get to know some fellow northern California travelers!

  • April 19 2011

    Great couple, great answers!! Have a rockin’ good time you guys =)
    Andrea recently posted..Tired of Being Tired

  • April 19 2011

    I really love the way you’ve chosen to draft this series. I certainly have more than a few “Uncle Cal” figures in my own life. Still, pursuing one’s dreams is worth being different and misunderstood sometimes. And, when there is such a great community of fellow travelers around the world … all the Uncle Cals that you can shove in a house couldn’t persuade me against traveling full time or part time!

    I love how Jill said travel brings out the best in her as a person, I’ve felt that it does the same for me.
    Kirsten recently posted..Dead Apple Tour of NYC

    • April 20 2011

      Thanks Kirsten! And you’re right, it is worth being different and misunderstood. Unfortunately it sometimes also leads to the loss of a relationship, but for as much as that hurts at the time, chances are it never had the legs anyways. I’m thankful for my Uncle Cal that is still supportive (while shaking his head at us!) but there are others that we have lost along the way…

  • April 20 2011

    Nice interview. Have a great time guys, looking forward to tales from the road.
    Mike Lenzen recently posted..Our Itinerary Released

  • April 20 2011

    I can’t wait to be a homeless bum on the beach in St. Lucia! My Uncle Calvin is my mom and aunt. I guess everyone who has a passion for travel has an Uncle Calvin!
    Tai@TraveltoStLucia recently posted..Planning your flights to St Lucia Find out which St Lucia airport to choose!

    • April 20 2011

      You’re right, I’m sure we all do! At least one… 🙂

  • Jack and Jill are going to have a wonderful time – what an inspiration!

    I’m totally jealous. For now we need to stay home, but to make up for it I’m cooking one meal for every country in the world. It’s my best compromise for satisfying my wanderlust. We explore one new country per week and the whole thing will take nearly 4 years 🙂

    Good luck on your Adventures 🙂
    Sasha (Global Table Adventure) recently posted..Menu- Georgia

  • April 21 2011

    Most people would rather be miserable than risk being happy. We chose not to be “most people”

    LOVE IT.

    • April 21 2011

      That is a pretty awesome quote. That is what I love about this series…other people can put into words what I am feeling. 🙂

  • April 24 2011

    As others have said “We choose not to be most people.”

    LOVE, LOVE, LOVE this!

    Always be a first-rate version of yourself, instead of a second-rate version of somebody else. ~Judy Garland

    • April 24 2011

      Awesome Jillian – WONDERFUL quote by Judy! 🙂

  • Kim
    April 26 2011

    Great interview. I especially love that letter to Uncle Calvin!

    • Peter
      April 26 2011

      Thanks Kim. I actually wonder if our Uncle Cal is reading this, hmmmm…

Leave a Comment

CommentLuv badge