My Career Journey: A Long and Winding Route

Picking a career can be intimidating

Given that I talk a lot about careers, people are curious about my own job experience.

This is a long post that recounts my work experiences, as well as the thinking behind my career choices (both wise and unwise). If you're looking for practical advice, I recommend reading a different post. This one is just for those who are curious about my past work.

My journey has been messy, and I’ve made a lot of mistakes. But I’ve also gotten lucky. What I’ve learned from both the good and the bad informs how I counsel others regarding career planning. What follows is an overview of the major decisions I've made and the aftermath of those decisions.

College or Trades?

Like many young people, I didn’t have much a plan going out of high school. I ended up spending two years working full time for the family business, my father’s electrical company. At the time, I was interested in college, but I was worried about taking on debt for tuition. I had interest in specific kinds of work that required a college degree, primarily teaching. I had interest in other careers that didn’t necessarily require a college degree, but which I could still study in college: photography, writing, computer science. For a long time, I agonized over whether college would be worth the money.

Apprenticeship Years

Apprentice and the trades are a great career path, with rapid compensation growth, immediate return on investment, and long-term value in our economy.

In the end, I chose to study a trade. I started the electrical apprenticeship program when I was 20. I did this for two reasons. First, I was attracted to the fact that apprenticeships mean making money while learning a career, instead of paying money. Second, I enjoyed working with my father and brothers. Plus, my dad was willing to take me on as an apprentice, which made it much easier to get started. Choosing apprenticeship after high school ended up being a great decision, even though it wasn't ideal for me.

I didn’t love electrical work. I still don’t. But studying a trade was a smart path. I spent four years in the apprenticeship program. This meant working at least 40 hours per week throughout the year, as well as going to night school for about 4 hours per week during 8 months of the year. I had to front a fee for those classes, but I was paid for full time work. My wage was modest at the beginning, but it went up every six months until I was making 85% of a journeyman’s wage, which is more than enough for most Americans to support a family.

The financial side of electrical work made a lot of sense, but as far as my personality and giftedness were considered, I felt out of place. About halfway through my apprenticeship, I was confident that I didn’t want to be an electrician for most of my life. Part of me wanted to quit the program and try something else, but my risk averse and perfectionist tendencies resulted in my seeing it to the end. I’m glad I did. Still, when I was done with the apprenticeship—having become a licensed journeyman electrician in the state of Oregon—I chose to finally go to college.

The Undergraduate Experience

At this point, I was 24 years old, well past the age of a typical college freshman. I worried that this would make me feel awkward. Instead, I was surprised to find that I was more confident, more focused, and often more appreciated by my professors as a result of my age. Although most of my classmates were 4-6 years younger, I still made plenty of friends and integrated well with my peers. I was able to pay for most of my tuition with money that I had saved during my apprenticeship. And even though I was more financially secure than my peers, given my work experience, I still obtained multiple scholarships and forms of financial aid that helped with the cost of college.

I was able to carve about a year out of my undergraduate program thanks to the associate's degree I'd earned in conjunction with my apprenticeship. I was grateful that a good chunk of my degree credit came at the community college rate, instead of the private university's price. Also, most of the credit for the associate's degree came directly from the apprenticeship classes that I was already required to take for my electrician's license. This was an early experience in a career smartcut, and it's stuck with me.

Transitions

Ironically, I finished my bachelor’s degree in English to find that job offerings making direct use of an English degree are sparse. I was still interested in becoming a teacher, preferably in college. My instructors encouraged my to pursue a graduate degree for this purpose. So I did more college. A lot more.

I did take a year off from school after the bachelor’s degree. During that time, I got married, prepared for graduate school, and returned to electrical work.

At this point in my narrative, an important theme emerges: the return to my trade skill. This has happened many times. In fact, even during my undergraduate experience, I worked as an electrician during academic breaks in the spring, summer, and winter. During this year off, I was able to easily get back into paying work while I figured out married life and my future education. If I'd not had that trade skill, work would have been harder to secure and been less well-paid.

Graduate School Years

I enrolled in a two-year master’s of English program at a state university with the goal of becoming a college instructor. I did this because I had enjoyed my experiences as an undergraduate, because I liked teaching, and because I’d been encouraged to pursue this path by my professors. Halfway through the graduate degree, at age 29, I started doing what I should have done before enrolling: I looked at the job offerings for people with an M.A. in English. The outlook? Not good. Very few people with only a master’s degree were finding full-time teaching work. Oops. I decided to see it through, the same way I had with the apprenticeship, but I also started thinking about other options.

Advanced degrees and trainings are commonly recommended for those seeking secure or high-paying jobs, but the investment of time and money doesn't always balance out.

Another option was to seek a PhD in English, which is what most colleges require for a full-time position by this time. This would mean another 4-6 years, depending on the school. It would also mean a lot of additional debt. Having learned my lesson from not paying enough attention to employment trends with the master’s degree, I did quite a bit of research on jobs for people with doctorates in English. The outlook? Not good. The latest data from the Modern Language Association told me that among recent graduates with a PhD in English, only 40% were finding a job that made use of their degree. Hmm. Was I willing to spend approximately 5 more years of my life and about $40,000 on 4 out of 10 odds? Nope.

I looked into other ways to leverage the M.A. I wasn’t particularly interested in becoming a public high school teacher, but I did notice that a select number of teachers in my state taught college credit English classes to advanced high school students. This sounded attractive, but it would mean another year in graduate school to earn my teaching license. I decided to do it. If nothing else, I figured the licensure would increase my employment options as a teacher. At age 30, after finishing the graduate degree in English, I immediately started a graduate program in education. I spent a year student-teaching in a high school, taking graduate classes, and working as a graduate assistant at my university.

About halfway through the education program, I discovered that most of the dual-credit teaching positions were going away from a lack of funding. My plan to teach college classes to high schoolers probably wasn’t going to happen. I also realized that I was not happy teaching in a public high school. The political climate of the schools, the philosophy of most teachers and administrators, the required modes of teaching and engaging with students—all of it was contrary to how I wanted to operate as a teacher. In addition, the bad economy meant that very few jobs were available to new English teachers. Even finding an interview in my state was difficult. Actually using the teaching licensure and master’s degree in education wasn’t looking like an appealing option.

Back to the Future

Bringing kids into the picture impacts the career journey, as any parent knows.

Meanwhile, my first child was born. I needed to return to full-time work when I was finished with the education program. Teaching full-time in college wasn’t going to happen without a doctorate. Teaching in high school was looking increasingly unlikely. Moving into full-time teaching was my dream at this time, but in order to support my family, I went back to electrical work. I would continue in this line of work for five years, during which time my family grew to a total of three children.

Emotionally, returning to the electrical trade at age 32 was frustrating. It felt like a step backwards because a had spent a total of seven years in college with the intention of becoming a full-time teacher. Now I was going back to the job I’d had before all of that academic work, not to mention the significant amount of college debt that I’d accrued during my time in graduate school. Rationally, going back to the electrical trade made a lot of sense. If I’d taken an entry level teaching job in high school, I would have been making about half what I could earn as a journeyman electrician. (Naturally, this would have gone up over time, but it would have taken many years.)

This was the second time that I’d returned to electrical work after exploring another career path. Having already done it once after earning my bachelor’s degree, I was becoming strongly and practically convinced of the value of having an established career skill, even if I wasn’t using it. Electrical work may not have been my first choice in a career, but having the ability (legally and experientially) to return to this line of work at any point in my life was proving to be highly useful. My family’s financial situation was much less stressful during this time than it would have been if I didn’t have the option to return to the trade.

Career Experiments

During these five years of electrical work, I began to pick up part-time teaching appointments at a few colleges. Teaching in addition to full-time construction work was extremely challenging. (Looking back, I’m a little amazed that I made it work.) On top of 8-12 hour days for 5-6 days a week and an average commute of 2 hours round trip, I somehow managed to teach evening and weekend classes on writing. It was my dream of teaching as a career that helped me keep doing it, even when it was tough. The little bit of extra money was also helpful to cover the ongoing expense of college debt and the mortgage for the house we finally able to buy, after years of renting.

This period of working in the electrical field really underscored the personality traits that made me better suited for teaching than for working in a trade. Being deeply interested in ideas and creative pursuits, the practical, hands on nature of construction was not a natural fit for me. In terms of supporting my family, however, continuing the electrical work was much better. I began to understand more clearly the difficulty most people have in balancing their career dreams with the necessity of practically supporting themselves.

I did a lot of reflecting at this time on how these two factors are difficult to balance. I also thought about how seldom I'd been offered realistic advice about these issues. Some people had told me to give up on my dreams and settle for a good job that provided. Other people had told me to chase my dreams and not worry about making a living. Nobody had suggested a realistic way to do both at the same time. My current experience, however, as I did both the electrical work and the teaching, was beginning to convince me that it was indeed possible.

The Convergence of Differing Paths

When I’d been doing the full-time electrical work for four years, my wife and I began planning a way for me to quit full time electrical work. During this last year or so of the full-time job, I had more opportunities to teach part-time teaching at schools. I’d also been building up small sources of income through other kinds of work: paid writing work, small electrical projects for friends, freelance photography jobs. I’d been studying business and entrepreneurship in my spare time, and having some success in selling things online had increased a confidence in myself that I’d lacked before. I was becoming aware that making a living didn’t necessarily mean being somebody else’s employee my entire life. I could also find a way to work for myself, either full-time or part-time.

So after five years, I left the full-time electrical job to try a combination of teaching, writing, and other work. This was largely possible because my generous and hard-working wife was also interested in doing more paid work. Thankfully, she also had an established skill set and a good relationship with an accommodating employer. Between us, we knew we could share the responsibilities of making money and caring for our kids.

Currently, I’m almost two years into this new way of working. Things aren’t always steady or certain. For many people, the variability and uncertainty would be too challenging, but I’m adapting to it. I’m constantly aware of the need to hone my skills and relationships to keep myself available for work.

One very satisfying thing in particular has happened during this time—several of my disparate skills and knowledge sets have converged, giving me unique opportunities. This has been highly encouraging.

For example, I never thought that my teaching experience and my trade experience could realistically support each other. However, I was offered a job to teach technical writing at a school based on the fact that I had done both of these things. Typically, only teachers who have been specifically trained in technical writing are invited to teach that kind of class, so this was remarkable. In this situation, I was being offered the class because of the overlap between to distinct sets of skills. The words of my boss at that school were, "I figured you'd be a good fit for this class because of all of your construction experience."

Later, because of my experience teaching the technical writing courses, I was offered work in helping to write a textbook about technical communication. As a result of this work, I was able to build experience as a paid technical writer (a form of writing I had minimal experience with) and earn paid contracts from clients as a freelance technical writer. My point here is that the accretion of unique skills can serve a united purpose, if those skills are explored, maintained, and bundled together for a larger goal.

What This Means for You

I don't want any of this to sound like I'm patting myself on the back. Many of these career choices were poorly planned. But I do hope that my experiences can help others think through the exploration of careers.

Along these lines, don't dismiss the wealth of information that's available from other people in established careers. So much can be learned just by asking what people do for work, how they got into it, and what they like and dislike about that work.

In another post, I reflected on a few key lessons that I learned from my career path. You can read my advice based on those lessons here.