
“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

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
So, Where Does My Bucket List Stand Today?
- Drive from San Diego, California to Pavonnes, Costa Rica
- Take Valentina to Disneyland
- Live in the United States again
- Spend a month or more in different locations: San Sebastian, Spain; Lombok, Indonesia; Puerto Escondido, Mexico; Road Tripping in California and Western U.S.
- Surf in South Africa
- 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?