Often on tour, I am asked how I came upon this career. I usually start the story by sharing that I got my degree in architecture so naturally it just followed I became a tour guide, at which point everyone laughs. The reality is not far from the truth and, at times, equally comical.
Like most high school seniors, I had no idea what I wanted to do for a career so when it came time to apply for college, I had to roll the dice and make a decision. Being interested in quite a few things, I first considered the liberal arts. I was also creative so I considered art school. As you can imagine, neither of those sat well with my parents who would be financing my education.
My dad was clear that he would only pay for something with a professional application so I began to look for a practical degree that included my interest in art, people, and history. Fairly quickly architecture began to surface as a career possibility. The problem is that I had no interest in actually producing houses or buildings. In came my imagination.
Not just in choosing a major, but the part of my imagination that had me doodling on blank sheets of binder paper as I sat bored in class. I used to love drawing highway intersections at various stages of development. I’d start with a simple two lane road. Then I’d intersect it with another two lane road, then one road would become four lanes and then the other until, eventually, my sheet of paper was an overhead view of an intersection of two freeways littered with pieces of the eraser I had used while pencilling my highway evolution.
It didn’t stop with roads. I loved to create different types of landscapes around the intersections and highways using a combination of slash marks, dots, and squiggly lines. Off of these roads, I would draw houses, business parks, and shopping centers.
It hindsight, I probably should have pursued urban design, but at the time I was not aware of that major. I had stumbled across landscape architecture in my research, however, a field that would allow me to turn my slash marks to grass, dots to flowers, and squiggly lines to hedges or trees. My dad was initially concerned that this was the field of a glorified gardener, but after talking to one of his friends, he was reassured that it was indeed a professional vocation.
My first mistake came in accepting admission to the landscape architecture program at Virginia Tech without having first visited the campus, a realization that came as we passed a sign that said, “Virginia Tech 2 miles”, while all I could see out the car window were cow pastures. Fortunately, adding a population of 35,000 students to a farm town did bring it to life just a few weeks later.
The orientation was the same for all the disciplines of architecture so I sat together with 150 other people as we learned about the various programs. After the basic introduction, they divided us into our individual disciplines, and I joined 6 other freshman in the dean’s office for the school of landscape architecture. He began to talk about horticulture and plant biology, and I realized that in addition to not having first visited the campus, I hadn’t really researched what it meant to be a landscape architect. My eyes glazed over, and I began to panic over the implication of my under considered degree choice.
When the dean finished his presentation, he asked us if there were any questions. I raised my hand and said, “if I wanted to change majors, would now be a good time?” I laugh now as I try to imagine the dean going home that night wondering if it was his presentation that needed improvement. To be honest, I am not one to confront a problem directly, and this was probably the first time I realized the consequences of not doing so, but I also learned that day that “fortune favors the bold”.
The dean walked me down to the architecture school, and after the dean of that school spent a couple minutes trying to dissuade me from the miserable life I would endure for the next five years, she signed the papers, and I joined the school of architecture as simply as that.
You should understand what a big deal that was. I was nowhere near having the grades that would have gotten me into the architecture program at Virginia Tech had I applied directly. Additionally, had I waited just one more day, I would have had to apply to change majors, which included a mandatory summer session to see if I even qualified to enter the program. Through my momentary bravery, I was able to bypass all the normal channels and slip into the program.
The truth is, I probably shouldn’t have pursued architecture either. Having a short attention span, I still chose the wrong career path, but what do you know at 18 about how you want to spend your life? Upon graduation, something I barely pulled off, I headed west to my hometown of San Francisco.
I spent the first summer driving young people around the western US on camping trips but realized if I wanted to have a life with my girlfriend, who was a teacher, I should probably not focus on a career that had me working during her time off. I enrolled in a graphic design program at the University of Art college in San Francisco. This seemed like a better career choice for someone with a short attention span, but only a year later, something even better appeared: the internet.
Web design was a field that changed quickly and frequently so I developed my programming skills over the next few years before landing a job with Cnet, a company that had already established itself as the go to place for electronic device research.
I continued in my web design career as I moved to Oregon, but working at a conservative insurance company, I found myself easily bored. Nothing moves quickly in insurance, and I easily responded to requests long before decision makers could process what I’d done.
I’d spend my long lunch breaks exploring downtown Portland and learning about the history that made up the surrounding neighborhoods. Eventually, I had friends who wanted to join me on these walks so I created a walking group, and when people I didn’t know asked to join, I decided I had a business model.
Since no one really knew what I did at work, it was easy to extend my lunch break to one and a half hours, during which I’d lead narrated walks downtown under a group I named Uniquely Portland Tours. The walks became so popular, I extended them to different neighborhoods around town, but this meant that I could no longer pull them off during my lunch hour.
I decided to meet with my boss to negotiate a solution. I confessed to her that during any given week I was only doing about four hours of work. I suggested it would be of mutual benefit if they terminated me and hired me back as a contractor when they needed work done. It would be a better use of her money and my time.
She replied that it wasn’t possible due to the conservative nature of the company. They were concerned that they couldn’t be sure that I was working when I was at home. I replied that I wasn’t working, and I was right here under their noses. Unfortunately we couldn’t come to an agreement so I quit my job and devoted myself full time to my walking tours.
Because most of my clientele were locals, and I wanted continuous participation, I priced my tours cheaply, and if you simply divided the amount of money I made by the number of hours I led tours, it appeared that I was making a fortune, but the reality is that there was much planning for each of the tours including research, writing, and reservations. As anyone who’s run their own business knows, once you break down your revenue over the true number of hours actually worked, you don’t come away with a lot of money, and I was barely scraping by each month.
I called my dad for some input and he shared with me that he noticed I always made the most money when working for someone else. While there wasn’t much my dad and I understood about each other, on this he was was right on, and I began to apply for work with local tour companies.
Only three months later, I was hired and I have been working for the same company for the past six years. I really don’t feel that I’ve departed too far from the professions I invested in. Both architecture and web design are concerned with creating a good user experience as we interact with our world. That is how I see my role as a tour guide.
There came a time recently, however, when I thought it was appropriate to apologize to my parents for not having followed through on the architecture education they’d invested so much in. My dad’s reply was this, “Tom, you’ve never been in jail, you’ve never been on drugs, and you’ve never asked me for money. We’re good. A father can wish no more for his children than their happiness at who they’ve become.”