How Not to Screw Up Your Bucket List
After stepping down from Cheezburger last month, my wife and I decided to spend the next year traveling the world. We started by visiting friends and family to reconnect. We are having a great time reveling in our stories, dreaming of the future, and checking items off our bucket list. I am certainly overjoyed by the fact that I have no need to know the day of the week.
When we tell our friends about our plans to spend the next 12 months visiting dozens of countries, we get wonderful reactions like surprise, a sense of shared joy, and great advice. When we get the occasional tinge of jealousy, it goes straight to inflating my ego. (I really should talk to my therapist about that.) But amidst the happiness, there’s a strange missing reaction: No one asks “Why are you traveling?”
I suppose it’s because we all have our own reasons to want to travel the world. I am very aware that it is a luxury to be able to take a year off work. It’s a super-luxury to be able to do that and traveling around the globe. I feel deeply fortunate to be able to do this, and that comes with a self-imposed pressure to not fuck it up.
But there is another way to see it. Travel is a massive investment in one’s self. I will not be able to become who I can be without this investment in myself.
Why do I travel? I am seeking reinvention.
After spending almost a decade doing one thing, I am lucky to be known for something. Even if it is “the meme dude” or “the Cheezburger guy.” Thankfully, I am not known for our short-lived reality TV series, or many other things that didn’t work. Many an entrepreneur spends their career without ever receiving the attention and recognition I have received.
Running the Cheezburger Network was incredibly fulfilling and satisfied a deep desire in my heart to build, to try, and helped me connect with millions of people. But that chapter of my life is closed and I do not wish to tell the same stories over and over. I want to live a life that produces new stories to tell. It’s true that not all those who wander are lost, but all those who wander and post Instagrams of it may be assholes. I’m going to try to not be one.
If I want to have a next chapter that is as fulfilling as Cheezburger and if I want a life that is filled with purpose that is deeply satisfying, I have to find a new perspective. If I want to spend the next year learning and challenging myself, I cannot change the brisk pace of my life. I must change the context but keep the pace.
This weekend, I spent an intense 36-hours at the Stanford d.school in a workshop where I learned new processes and structures around design thinking, prototyping, and visual storytelling. Speaking with one of the organizers, we tried to define the meaning of innovation. What is it? How do you know when you see it?
My definition of innovation is the application of a fresh perspective on an assumed process. Innovation waggles its finger and says, “No, you don’t” when someone says “We know.” The challenge is that in business, we confuses the value of innovation with the act of innovation. Entrepreneurs should create a lot of innovation, but much of it will be of little value. This is a subset of our failures. But one innovation that is left standing will impact many of us for the better.
Reinvention requires new perspectives.
If I am looking for reinvention, I am signing up for innovation. If I am signing up for innovation, I am signing up for new perspectives. As the writer Henry Miller said, “One’s destination is never a place, but a new way of seeing things.”
Much of the new perspectives I will find in my travels will be just for fun. It will exist only as enjoyment in our memories. Those perspectives will fail to move me in a meaningful way, just as many innovations will fail to improve a product, or move the market. Much of these we will visit are on a travel bucket list my wife and I have curated over the last few years. Checking these cities off will be fun, but sightseeing alone does not make them worthy of having been on my bucket list in the first place.
Here’s a better, more satisfying way: If I push myself far enough, if I travel strangely to stranger places, do things I never considered doing, and arrive unconventionally to a conventional place, I am more likely to find a new perspective.
Finding a new perspective also requires getting a lot of perspectives. My travels will take me to Tokyo, to Stockholm, to Havana, to Bangkok and more on the back of planes, motorcycles, boats, and hopefully elephants. We’ll spend nights in hotels, RVs, tents, and under the stars. I hope to find passionate and curious conversations with strangers and find new, old friends over memorable meals. (I’ll try to avoid Instagramming it.) But I really don’t know what I will find. And that unknown — rather than the vistas and destinations — is what truly excites me, my friends, and you when we imagine ourselves traveling around the world.
However, you don’t need to travel to reinvent yourself.
I didn’t travel the world before I started the Cheezburger Network. Travel is just one method, and my way is just that: my way. What is important is to put ourselves in unfamiliar situations that challenge our existing views of the world regardless of the discomfort. But the most important thing is to keep an open mind. A narrow mind takes a fabulous growth opportunity and turns it into a shitty experience. Then, all you’re left with is an hour wasted writing a 1-star review on Trip Advisor.
As my travel continues, I hope to share with you more of the new perspectives I find. Maybe I’m just justifying a huge vacation. Maybe I’ll find that I am full of bullshit today and that I will find no new perspectives.
But I doubt that.