At forty, I realized I could be half way through my life. I’d been married ten years, and eating dinner in front of the TV was considered our “quality time”. While it was comfortable, I had to ask myself if this is how I wanted to spend the second half of my life. I felt like I was looking into a funnel, only I was looking towards the end that narrowed. It didn’t take long to realize I wanted to turn the funnel around and look out the expanding side.

Ending my marriage was one of the hardest things I’ve ever done. I take commitments very seriously, which is why I rarely make them, but this seemed like a necessary change of course. What I can compare it to is living in a wonderful city like Rome. I loved it for 10 years, and I had many wonderful experiences, but now I was ready to live in a new city. My life changed significantly in the following 10 years. I quit my job, I gave away my house, I started a business, I traveled the world.

Quitting the job wasn’t too difficult. It was one of those jobs where you go to work for 40 hours a week but do about 4 hours worth of actual work. I wasn’t stupid; I kept this job for as long as I could, but I began filling my free time with something I was more passionate about: leading tours. With no accountability at work, I was able to offer walking tours downtown during my extended lunch breaks. I even tried to see if I could offer the walks through work, but eventually I realized we were wasting each other’s time.

I went to my boss and confessed how little I was doing. I asked her if she could let me go and then hire me back as an independent contractor to perform work as needed. This would provide me some income while I focused the majority of my energy on my tour business. My boss said that we worked for a conservative company and she couldn’t be sure I’d be working when I was home. I had to remind her that I wasn’t working when I was at work.

The end result was that I quit and traveled to Europe for a couple months before getting homesick and returning early. Working for years in a field that is constantly evolving, I found that I no longer had the skill set demanded in my field. I searched for work for a couple months before realizing I would have to go back to school just to qualify for the job I had left, so I decided to create my own job.

I had been posting tour walks on a web platform called MeetUp. With a little research, to provide more narrative on my walks, I began to charge $5 per walk. It worked. People loved what I was doing, and I had as many as 40 people on some walks. There were also bad days. Oregon gets a lot of rain so I often watched a walk, with several people signed up, dwindle to just the few over the course of a rainy afternoon.

I was barely making it economically and took a retreat to Mexico to think about what I would do next. One day I was sharing my dilemma with my father and asked his advice, something I rarely do since our lifestyles are very different. He said, “Tom, you’ve always made the most money when you’re working for someone else”. It remains one of the best insights he’s ever given me.

I returned to Oregon and applied for jobs with several local tour companies. With my experience and initiative, I was quickly hired and have been working for the same company for four seasons now. I get to pick the days of the week I want to work, and I travel for six months during the off season.

Having found the perfect job, I began the quest for a perfect life. After figuring out how to overcome homesickness, my travels became longer and farther away. I learned how people lived all over the world and learned to travel for months out of nothing more than a backpack.

I met with many people who worked as they were traveling and even received offers to work in exchange for room and board. There are whole web sites dedicated to this lifestyle, but I prefered the more organic approach of offering help to those I met while traveling.

So now I am ready to redefine my life again. My mission: to travel and serve. I will spend this summer saving money and head out into the world. This time, instead of just traveling, I will look for opportunities to help others. In exchange, I hope to find places to sleep and meals to share. With this, I expect I can turn one year of savings into 3 years of travel.

Given the opportunities that each new adventure has provided, there is no reason to expect that I will ever have to stop traveling, but I look forward to determining what new city I’ll be heading to 10 years from now when I’m 60.