One of the great life benefits of doing a long journey on your own without the assistance friends or family, is that you learn to improvise and build resourcefulness that will cross over to your entire life. Living like a hobo (which requires work while traveling to a destination) is what happens when you go on an unsupported journey with the least amount of resources available (hopefully minus the begging!)

“Living as a hobo means cutting your possessions down to the essentials. Even a few pounds can make all the difference when you are forced to carry everything on your back. Remember, you can buy most anything you really need in any town along your route. You do not need to stock up with two packs of toothpaste. If you are starting out in the summer, wait till late fall to buy winter clothes on the road. Assume that everything you will take will be ruined or lost.’ Marguerite Happe.

Stretching your comfort zone by living like a hobo makes you realize that all the “stuff” you have is not that important in the entire scope of life. Food, water and potentially shelter are the main ingredients to survival and as we move toward more sedentary lifestyles we often forget that all the “stuff” we possess does not guarantee overall happiness. We have an abundance of everything to make us comfortable and when you step into the unknown of living with one’s on resourcefulness and create a personal journey for a short period, you may appreciate more of what you have.

Dream about a journey trip destination that you would like to learn the culture. Even within one country there are many cultures (ex: hiking or cycling across the United States will expose one to many cultural differences). Alternatively hiking a big trail like the Appalachian Trail or Pacific Coast Trail will use all hobo skills to the max.

When you embrace a self-supported journey, you will become obsessed with the planning and thinking of all the challenges and hurdles that may occur over a multi week trip. One absolute truth is that an extended trip will have many unknowns.

Most may discourage you with the typical, how will you get time away from the family, work/job, responsibilities, the cost, etc. This in many cases is the toughest part of the journey, preparation from moving off the grid for an extended period of time.

My personal preference is to find an event that will require 21-30 days and sketch out a summary plan to explore the possibilities and specific action plans to deal with the naysayers and personal responsibilities that need to be covered. Don’t overthink it and overanalyze it ore you want move forward. The most important item is to just sign up or mark down the date you will begin the event our journey. It’s like anything else in life, just start something. This might be a once in a lifetime experience and it’s not for everyone, but if you really want to disrupt your daily life, then become a short-term hobo with an exploration journey!