Round the World Family Trip: Living the Dream

For years we’ve described it as our “Dream Trip.”

Lots of people have one. It’s the trip that you’ll take one day, when there’s more time, more money, less stress, less school.  The problem with big dreams is that more often than not they’re never realized.

Goals, we’re taught, are attainable: Work hard and you’ll achieve them.


They’re the wishy-washy, pie-in-the-sky intangibles that hang around for years until they turn into regrets.

It doesn’t start out that way.

Dreaming of jellyfish

Will your dreams soar or float away?

As kids, our dreams seem bright and completely possible (one day you’ll fly to the moon, be a cowboy and drive a firetruck!). It’s only with the passage of time and the realities of mortgages and car loans that the big ones begin to falter.

I’ve been there.

Ten years ago I was a lawyer at a Bay Street law firm. I left that – and the paycheque it came with – behind to pursue a fulltime career as a freelance travel writer.  I’ve never been happier.

It’s a lesson I want my children to learn a lot earlier than I did.

More than a decade ago Ish and I talked about “one day” taking a trip around the world.

When the kids came we immediately began to see the benefits the trip could have on their lives but we didn’t know when or how to make it happen. Five years ago we got an unexpected push. Ish was offered a chance to sign up for a “4 for 5” program at work.

For 4 years his work would withhold a portion of his pay and in the 5th year he’d get it back as pay…but wouldn’t have to come in to work. My decision to become a full-time freelance writer meant that I could work from anywhere.

We wanted to see the world as a family and now we had a date when it could happen – 2011.

nasa fam

Family Fun x 365

For four years we would mention the idea to the kids but there was little real interest.It’s really only over the last year that they’ve begun to get it.

At 6 and 8 the fact that they are about to set out on an adventure that will change all of our lives forever is a hard thing to grasp.

Instead we focused on the little things.

We called it “The Wish List”

On it we all write down our dreams. They can be crazy, wild, tame or lame. They are the things we’ve always thought of doing and the things we never thought we could.

My oldest son wants to learn to surf. My youngest wants to see (okay… hug) a penguin. I want to learn to cook and dance (tango would be awesome!). My husband wants to visit friends he’s made around the world and learn to ride a motorcycle. Dinner conversations revolve around changes to the list. “Will we still get to see the pyramids?” ” Do they have chicken nuggets in Australia?”

Often the answer is “I don’t know” and so far the kids are okay with that.

I love that this trip requires us to leave behind the possessions that really don’t matter, grab a couple of bags and set out to meet our dreams head on in far flung places and with only each other for support and company.

fam san fran

Now that the trip is only a few weeks away. The list is growing longer for the kids and shorter for me.

More than anything I want us to be safe and healthy but I also believe that we will learn by having to overcome adversities and come back from the trip as more compassionate human beings.

When it’s over we’re hoping to have strengthened our relationships with each other, written journals full of stories and filled cameras with memories that celebrate our decision to live our dreams.

With every day that passes our excitement grows, and sharing it with you only fuels that. Thanks for reading and sending us your good vibes.

We can’t wait to get out there and begin to live the dream.

Is there something you dream of doing? On your own or with your kids? What’s holding you back?

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{ 29 comments… add one }

Kirsten May 19, 2011, 7:21 PM

Great article.  I’m so excited for you guys!


Heather May 20, 2011, 11:07 AM

Thanks Kirsten!


Heather Greenwood Davis May 22, 2011, 2:51 PM

Thanks Kirsten. We can’t wait to share it with you.


Valerie May 19, 2011, 10:52 PM

Perhaps not surprisingly considering I’ve subscribed to your site, being a world traveller is my dream. And at this moment of time, it’s money that’s holding me back–which I think for most people, tends to be the biggest dream crusher. The work plan your hubby got sounds amazing.

I’ve also dreamt of going to law school ever since I was a kid, but I have too many academic sins (long, boring personal story) to let that become a reality before I hit 40. Such is life! Guess I’ll have to settle for travel at some point down the road… ;)


Heather Greenwood Davis May 22, 2011, 2:55 PM

Valerie- Whey the age of 40 limit on the law degree? I went to school
with people who were much much older than that. I think it’s never too
late to follow a dream. In my mind it doesn’t even matter if you ever
practice. If it’s a passion, you should pursue it however you can – 1
course at a time for the rest of your life if need be. Taking the first
step will fill you with longing for the next, no?

As for the money issue. I get it. It helps that he has a great plan and
that I’m working as we go but I know a lot of families who are doing
similar things in a lot of different ways – savings, work abroad
programs, real estate investments, etc. I think the key is not to think
of it as a huge trip but one flight at a time.


Mo May 25, 2011, 9:10 PM


Don’t let $ hold you back your dream.  Give somethings up and put those $$’s towards your trip.  Get involved with couch surfing etc.  Don’t know where you are but buy a ticket on sale and go someplace.  I wait for sales to buy tickets to London.


Julie May 19, 2011, 11:35 PM

Lovely explanation, Heather, and I am so excited for you all. We’ve taught our own kids similarly and now that they are young adults I am seeing them following their passions to live rich and interesting lives.

I recently wrote a post at BootsNAll on “How to travel without quitting your day job: 10 tips for the restless desk jockey” that might also be of interest to your readers:

Look forward to reading your tales from the road,



Heather Greenwood Davis May 22, 2011, 2:55 PM

Great post Julie. I can’t wait to look back on this year when their young men to see how it affected them.


Go BIG or Go Home May 20, 2011, 1:36 PM

Kudos to you for raising kids who are as stoked about this adventure as you are! I don’t know if mine would be as “on board” as yours are!


Heather Greenwood Davis May 22, 2011, 2:56 PM

Well they’re stoked now We’ll see how they feel when they’ve been missing their grandparents a few weeks in.;)


The Culture Mom May 21, 2011, 11:03 AM

I can not wait to follow your travels!


Heather May 21, 2011, 10:16 AM

:) Thanks


Heather Greenwood Davis May 22, 2011, 2:56 PM



Mo May 25, 2011, 9:07 PM

I am so happy for you all!  Have your started your itinerary yet?  I did what you will be doing and was out of the US for almost 6 years.  Enjoy!!!


Heather Greenwood Davis May 25, 2011, 10:07 PM

Mo we’re tied to coming back for my husband’s job otherwise I could be very tempted to wander longer! The route (big picture) is here:


Wood-sprite-2 July 10, 2011, 11:55 AM

I served almost 30 years in the Armed Forces. In 1993, a single parent, I was serving with the UN in the Middle East. I made the decision to take my son out of school for three weeks and we backpacked through Europe. It was one of the best things I’ve ever done – for both of us! I watched my son grow in so many ways and as a resulot so did I. And yes, my son’s school supported me in my dedcision.   


Heather Greenwood Davis July 13, 2011, 1:03 AM

Comments like yours get me really excited about the journey ahead of us. It has been less than 2 weeks since we left Toronto and we’ve seen our boys grow already. Thanks for sharing your success.


Sherrie Guthrie October 3, 2011, 1:20 PM

i am a student in mrs.guthries class
and i realy like idea the family trip around the world and i also like all the pretty pictures!!


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