4 Life Lessons From the Life of a Wanderer


It’s been three months since I packed up my life in Santa Cruz to wander the Hawaiian islands. Never have I not had a home and a permanent mailing address. It’s an interesting feeling to call where ever I am in that moment home. When people ask where I’m from I tell them I’m wandering and that my goal is to explore all the islands to see if I would want to call one home, one day. My favorite moment so far is when a man asked me where I lived and I pointed to his pet turtle, indicating that I live where I am. During my travels, I have been learning a lot and now appreciate why so many people choose to wander for periods of their life. It’s a unique vantage point to live life from.

Lesson 1: Travel light to go far

This is true in reality and metaphorically. With inspiration from my travel-light friends, I originally packed my belonging into a suitcase and a small duffle bag, weighing about 100 pounds. Trust me it’s not easy to pack your life into 2 bags and 100 pounds. Before my trip, I sat on the floor with stacks of clothing, books, supplies, food, and other essentials. I was sorting through my life and trying to gain clarity on what I needed and wanted with me. Given that I would be creating home where I went, I wanted some creature comforts with me like my pillow, journal and some other treasured pieces. Of course, I needed my laptop, toiletries, clothing and other essentials. When all was said and done, I was proud that I only had 100 pounds. I know I was far from travel-light. After my first flight and hauling 100 pounds around the airport, I knew I had to further reduce what I had. When I recently hopped on my flight to Maui my bags now weight 75 pounds. After wandering for weeks, it’s become very clear what I really need each day.

I’ve always been inspired by simple living and minimalism. Yes, I’m one of those that is also fascinated with tiny homes. I also get very excited when I finish something. I look forward to the day when I finish a tube of toothpaste, a pen, or a lip stick. It makes me happy to think I’ve used something well and its purpose is complete. How often do we really finish something before we throw it away? There is nothing like life on the road when you are literally hauling all your stuff from place to place to help gain clarity on what’s important to you. Every extra thing to pack and coordinate takes time and energy. I think about the two pods of belongings I have in storage and have an ease that if anything was to be lost or damaged I’d be ok.

Lesson 2: Get a new perspective

Being in a new home, city, or island every week shakes things up. It takes me a day or two to get my footing. Which for me means finding the local health grocery store, the best coffee shop, yoga classes, hikes, and restaurants. Then it’s a blank slate, a white terrain of unknown. When I lived in the Bay Area, I had my usual spots that I visited and knew how to get from one to another. I see now how easy it is, and necessary, to become a creature of habit. These habits provide a structure of belonging and ease of life. At the same time, I see how easy it is to live a smaller life stuck in a routine.

I’ve also had the opportunity to hang out with locals and explore life through their eyes. I’ve been on the secret hiking trails, their favorite restaurants, unlisted dance classes, and more. I watched their movies, ate their foods, lived their ways and listened to their music. Each time, I get to see that there is more life going on every day than I really know about. Now it’s up to me to find the balance I need of creature comforts and being open to trying new things.

Lesson 3: Our context shapes us

After living in the Bay Area for almost 20 years, the societal norms have become deeply engrained in me. I’m accustomed to easy access to good coffee, organic foods, great restaurants, all the classes and interests anyone could dream of. I’m also accustomed to standards around dress, cars, acquisition, and ways of working. I’m going to generalize that the Bay Area is built on technology and the norms that come with it. Increasingly over the last 5 years, I’ve felt more and more like I didn’t belong. Traveling in Hawaii has challenged my perspectives on life and has opened my eyes to new ways of living. It has given me an opportunity to throw off mainland ways and embrace island living. I traded in my high heels and leather boots for flip flops, jeans for skirts, and now wear a swim suit under everything. This made packing for the island easy. With the heat and focus on ease, it’s less about how you look and what you are wearing and more about being.

Another huge influence in Hawaii is Ohana and Aloha. These words permeate the culture on the islands. I learned the most about this in Kauai. With 70k people, it’s not surprising when you run into the same people and those people know who so and so is and how so and so are doing. These 70k people become your people, provoking a strong sense of belonging and care. In addition, most people who move to Hawaii full-time are intentional about it. They make clear decisions and sacrifices to move here. Since each island has its own culture and character, it draws similar people which creates a stronger bond and love for their home. All of this makes it easier to live a simpler life. Values and priorities are set. Not until now have I realized how much the Bay Area norms have shaped who I am, what I valued, and what I thought I needed.

Lesson 4: Freedom from responsibility and alone isn’t lonely

Traveling alone offers a new perspective on being alone, home, and belonging. Each day I can do what I want when I want. There is no time and investment in discussion to figure out the routine for the day. I just do what I want moment after moment. If I want to stay in for the day and read I can. If I want to get up early and go for a hike I can. If I’m at a restaurant for dinner I usually sit at the bar to meet people. On hot days in Kauai, I frequented a coffee shop called Java Kai where I bought air conditioning in the form of iced tea. On the hottest afternoons, I would often share my table with others seeking a respite from the heat. One afternoon, I met an English Professor who had just moved from the Big Island. We talked about literature, poetry, and life on Hawaii. To entertain ourselves we played a game. We each picked interesting people in the coffee shop for the other to write a poem about. If the poem was complete and the person still there, we’d share it with them. If I had been in the coffee shop with someone, this moment would have never happened. There is freedom in being alone. If you are open, you’ll see more of life and have a heightened awareness of the life around you.

On the other side, the life of a single wanderer is one of being alone. There is a tenacity required to live out of a suitcase and practice non-attachment every day. Never knowing where you are going to be or what the day will hold. It brings up the question of belonging and what I want to belong to. What I choose to belong to. It brings up a clarity of what it means to be alone versus lonely. A gift of wandering has been the understanding that I enjoy my own company and can be alone. And another gift has been that of appreciation for my friendships and the people I meet every day. I treasure how nice it is to have someone else to share an experience with and talk about the sweet monotony of life with. And I’ve come to realize that I have an opportunity to see and be seen by new people every day.

I continue to wander

Where you go is where you are. It’s up to me to find what makes me happy and go there. I can be in Hawaii and be absolutely miserable or absolutely happy. At the end of the day, I’m in Hawaii, life is good. Really at the end of the day, I’m alive, life is good.


Kim-ElishaPersonal Musings