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My Bucket List Revisited

By September 1, 2017 No Comments

“Trading the best decades of your life to compress work into it so you can live in retired leisure afterwards is a mistaken pursuit. Life isn’t meant to be conquered.”

—David “DHH” Heinemeier Hansson

Are dreams meant to be conquered and checked off? Is our society’s obsession with making a Bucket List healthy or conducive to living a fulfilling life?

Ever since Jack Nicholson and Morgan Freeman graced the silver screen as a couple of terminally ill old men who go on a road trip to fulfill their last wishes, people have been making Bucket Lists. The Internet abounds with personal lists of things that must be done before we die.  One blogger even wrote a book about her experience seeking out the adventures she put on her list (https://bucketlistjourney.net/about/) that is wildly popular.   

It should be no surprise that 5 Years ago my younger self, known then as the Life Pirate, created a Bucket List (https://lifepirate.wordpress.com/buckets-list/buckets-dream-trips/) of the places I wanted to go back then.   Of the nine items I listed, I have only checked off one (and have plans to check off #2 at the end of 2017).  Two of nine! Am I a complete and utter failure as a traveler (much less a travel blogger)? Maybe, but as I revisit what I have accomplished since then in terms of travel and life and look to my future adventures, I question the point of such Bucket Lists entirely.  Am I worse off from not meeting my goals as a traveler? Do you actually need goals as a traveler?


Not on my Bucket List, but some of my favorite places are in Australia.

In Support of the Bucket List

A Bucket List is basically a form of goal setting.  You put a name and a description on something you want and you go out there and get it!  I do believe in the positive impact of being able to specifically visualize what you want to do and formulate steps to get there. You want to hike Machu Pichu, you write it down, you think about it, you plan and save and then, one day, you’re climbing Machu Pichu.  It feels damn good.  Would you have arrived there without making it your goal? Hard to say.
I also know that a Bucket List gets people travelling, which is always a good thing.  You’ve heard me sing the accolades of international travel plenty – tolerance, adaptability, creativity and compassion – are a few of the benefits experienced by travelers from 1 month to 100 years.  So if you need a list to get your passport renewed by all means make that list.
These travel experiences, especially ones that have been planned for over long periods of time, mark the happiest times of our lives for some.   Psychologist’s Daniel Kahnerman’s peak-end theory suggests we remember the “peaks” of life, those positive experiences that made us happiest, in order to find fulfillment and meaning. Bucket Lists give us the chance to have those “peaks” and focus on them for long periods of time in order to create positive, lasting memories.



Surfing with my entire family off the Osa Peninsula, Southern Costa Rica

Is the World a Checklist?

You make a list, you check things off, you move on.  This process works great for groceries but what about experiences?  Can you just list ’em, do ’em and move on?  How do you account for spontaneity, changes in plans, and life actually happening as happens? Is it not worth going to Rome if you miss the Colosseum? 

The benefits and impression of travelling is often lost on those who arm themselves with a guidebook and set off to see the sights.  I remember travelling through Europe cursing our Rick Steves’ Guidebook for constantly pointing out the obvious.  Being narrowly focused on seeing a certain monument or beach or even trying to fit too many places into one trip can cause you miss the little details that make international travel so rewarding.  The food.  The customs. The people.  

The list itself can be discouraging.  What if you can’t get to all these places or do all these things?  I mean in 5 years, I’ve only done 2 of 9 on my list!!!  Does your bucket overflow with items that you’ll never actually do?  Or has your bucket sprung a leak and things that once mattered now splash onto the floor?

If we move away from lists and must-sees, we are more likely to connect with other people and be present in the moment.  If I had adhered to my list religiously, I would have visited places like Sri Lanka and Lord Howe Island but I would have missed becoming close friends with a local family in Lombok, surfing with my dad and little brother in Costa Rica and accidentally taking my partner to his first ever Spring Break Wet T-Shirt contest in Mexico.

I was able to take travel opportunities as they came rather than being focused on locations on my list.  In a world of curated experiences, retreats for any interest possible and hype fuelled by social media posts, authenticity is hard to find.  You spend time and money to go to a place because of the pictures you saw on Instagram or you can let an adventure happen to you everywhere you go.  Maybe we should filter our Bucket Lists.  If you weren’t allowed to talk to anyone or post anything about your Bucket List items, would you still go?  


A New Travel Paradigm

My dream is to truly shift the way we travel and make everyday an adventure. Some may call it a disease, but I undoubtedly was born with a gypsy heart.  My mother was an original traveler who lived in Mexico for years on end and was one of the first few surfers to arrive in El Salvador years before the civil war.  When I traveled to that country some 25 years later, people in La Libertad, El Salvador, still remembered my mother.  Oddly enough, my mom stifled her vagabond dreams when she had children.  My sisters and I rarely traveled with our parents (although my grandmother took us everywhere she could).  But as soon as I was old enough to travel alone, I was off to spend a summer in Spain.  After that, my nomadic tendencies took control and I traveled as much as possible and continue to do so as I’ve started my own family in Australia.
Since I turned 18, I’ve lived in New Orleans, Santa Barbara, Mendocino County, Venice Beach and Sydney.  I’m not sure I am meant to stay in one place for the rest of my life.  I am looking forward to the next adventure and an eventual shift in our travel style.  The shift would be moving from short, frenetic bursts overseas to spending longer periods in different places working and just living.  Living, the antipode of checking things off on your Bucket List.


So, Where Does My Bucket List Stand Today?  

I guess this list isn’t a checklist.  I hate to sound to hippy-dippy but I am dream-lining, setting intentions and letting them fly into the universe.
Let it be known that these are some experiences I plan on having:
  1. Drive from San Diego, California to Pavonnes, Costa Rica
  2. Take Valentina to Disneyland
  3. Live in the United States again
  4. Spend a month or more in different locations: San Sebastian, Spain; Lombok, Indonesia; Puerto Escondido, Mexico; Road Tripping in California and Western U.S.
  5. Surf in South Africa
  6. Snowboard in Japan

Becoming really close with a family in Lombok is an experience I wouldn’t trade for a few Bucket List items.


I hope that in five years I can revisit this list and feel no regrets.  If I check off none or all six, I hope that I continue to pursue adventure and not let plans or expectations get in the way of living, real living.  I think I’ll be ok as long as I prioritize real connections to people and places.

I agree with Ayn Rand’s statement:

The world you desire can be won. It exists.. it is real.. it is possible.. it’s yours.

What are your experiences with making a Bucket List? Inspiring and motivating or deflating and limiting?




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