“Don’t fear failure so much that you refuse to try new things. The saddest summary of life contains three descriptions: could have, might have, and should have.”
Louise E. Boone
Our family is leaping into a massive change of pace this year. The end of October, we will say goodbye to our jobs, home, friends and family and begin our search for a live aboard sailboat in Barcelona.
Some old photos of Diego backflipping off a rock in Ibiza, before we were married. I always knew life with him would be improvised!
Why would we want to make such a drastic move?
Because time was slipping away from us. Because in an effort to meet everyone else’s expectations, we lost sight of what made life worth living for us. Because the cost of childcare was insane, and other people were raising our children. Because the cage we had constructed for ourselves was tearing our family apart. Because if we didn’t pursue this dream, we would always regret that we didn’t try.
A Quick Rundown of Our Plans (and a brief history of when it started)
March 2012: Juggling a newborn and toddler and hospitality jobs was exhausting and unfulfilling.
May 2012: We moved back to Quincy, CA (Tiffiney’s hometown) where we had a great community of friends and family.
March 2013: Though life was easier in our hometown, it wasn’t the silver bullet. Life still felt like a joyless struggle, with moments of fun. We knew there was more to life than this. We still blamed each other for our unhappiness, and contemplated divorce. This was our lowest point and I’ve written about it here.
January 2014: Tiffiney broke her wrist and had to stay off the ski slopes and surf the internet instead. Though the injury was challenging, it actually improved our marriage (so did the months of marriage counseling!), as Tiffiney realized she did need help and her husband is actually kind of awesome. She discovered Christine Gilbert’s blog Almost Fearless, and a travel blogging workshop in Barcelona. She dreamed of attending, but shook off the urge to unrealistic fantasy.
March 2014: Tiffiney checked her airline reward points, and realized she had free ticket to anywhere. If she stayed with a friend in Barcelona, she could make the trip for around $600. On a whim and a cheap wine buzz, Tiffiney booked the workshop with Almost Fearless! Wheels are in motion!
March – May 2014: We both worked our jobs, but became more and more disillusioned with the pace of life required of respectable North Americans. BUT, we felt united as team. At night we browsed yacht world like porn addicts surf XXX sites. We strategized funding options for our dream. FINALLY! We had a shared dream again–not just a to-do list of chores to be endured!
May 2014: Diego’s mother came to California and played Mom, while Tiffiney ran away to play with other writers and learn how one could actually make a living on the road. Thanks to an incredible group of inspiring individuals, she came back on fire with ideas on how to make our dream life a reality.
June 2014: Mad dash to spruce up our house and put it on the market. We tell the universe we want to leave this September, then realize it’s next to impossible. Our house would need to sell in the same month we list it. We put an ad on Facebook in our local classified group. We hope and pray. (You can see the ad here)
End of June 2014: Four interested parties come to walk through our home. We get two offers, and the promise of a third. It’s a little less money than we want, but we decide it’s enough and a September departure would be possible! Thank you universe! Could it really be that easy?
July 2014: We formally accept the offer and enter escrow. Life is crazy hectic, and we start selling everything we own. The dream starts to gain momentum.
August 2014: Escrow closes. Life is ridiculously stressful as we figure out where to live while we finish up work and other commitments. The generosity and kindness of community is overwhelming. People are excited for us, and cheering us on. We feel like we’re in the flow carried by the love of our tribe.
September 2014: A blur of logistical details, to move our life overseas. I don’t remember much. I did notice a shift in our children though. Already spending more time away from their friends, their bond seems to grow.
October 2014: Contract with work lags out, as we try to finish respective projects and make our exit to Barcelona. We fly out of Oakland on Monday, October 27th.
November 2014: Boat search begins on the coast of Spain/France. Once found, it will become our new home.
2015: Stay relatively stationary in a Spanish port and build Tiffiney’s coaching business (A Desire Map Facilitator!) and Diego’s film services. Small trips in the Mediterranean will grow Tiffiney into a capable sailor and kids will focus on learning Spanish.
2016: Full-time cruising begins. January is a good time to catch the trade winds from the Canary Islands across the Atlantic. From there we’ll hit the Virgin Islands and wait for the next window to start down the coast of South America. Honestly, we have a lot of study time between now and then to plan these routes! Leave your advice in the comments 🙂