It's Labor Day weekend in the United States, the holiday that traditionally marks the end of summer and the beginning of the new school year. Officially, it's intended as “a day off for the working citizens”.

Because it's Labor Day, I've been recalling all of the jobs I've had in my life. When I was young, I wanted to be a business executive or an astronaut or a writer. I've actually managed to become the latter, but it hasn't been a very direct path.

My first paid work came in junior high. During the summer, my friends and I would pick beans and cucumbers and strawberries at nearby farms. This was piece work, though, and I didn't make a lot of money. I spent most of it at the video arcade. My first job where I drew a paycheck was planting cauliflower.

High school

During the summer of 1984 (between my freshman and sophomore year of high school), my friend Torey and I worked for a local farmer. We earned $3.35/hour (minimum wage!) walking behind a big tractor, planting cauliflower. The work was hard, but it was fun. I spent the money on clothes and cassette tapes. (I remember buying Tears for Fears and U2.) My father encouraged me to save, but I didn't listen.

Also during high school, I worked other typical teenage jobs:

• I flipped hamburgers at Burger King (tedious)
• I sheared Christmas trees (hard work, but paid well)
• I flipped hamburgers at McDonald's (loved it because my managers and co-workers were smart, industrious, and funny as hell)
• I spent a summer as a camp counselor

Most notably, however, I worked in the family box factory. On 31 July 1985, his fortieth birthday, my father quit his job to start his own business. In a dilapidated old building on our property, he built his own machinery and the family began producing custom boxes. I hated it. I wanted to be out with my friends, but dad insisted I spend my evenings making boxes. To show my disdain, I would play angst-ridden teenage music (The Cure, New Order, etc.) at full volume and sulk while I worked. I swore that after high school, I would never work for dad again.

College

During college, I held a variety of work-study jobs:

• Creating posters to hang around campus.
• Hanging posters around campus.
• Delivering A/V equipment.
• Answering telephones.
• Working at the information desk.
• Editing the literary magazine.

These didn't pay well, though. For real money, I had to find work off campus.

For a couple of years, I worked a hotel 45 minutes away. I'd drive up on Saturdays and Sundays to bus tables (and, later, to wait tables) in the coffee shop. I kept this same job for a couple summers. It was my first introduction to the Real World, really. Before, I'd been working with other kids my own age. At the Holiday Inn, I was working with 50-year-old waitresses and grumpy cooks who couldn't find work anywhere else. Still, I had a lot of fun and earned a lot of money. (Which I promptly spent on computers and those new-fangled compact discs.)

During my junior and senior years of college, I took a job as a resident assistant to pay for room and board.

Post-collegiate

During the summer after college, I was aimless. I found work at a Japanese school managing the audio-visual equipment. I was paid in room and board.

For spending money, I waited tables at the new Red Robin in town. The interview for that job was memorable. The manager told me, “Remember: the best way to increase your tips is to sell more food. Ask your customers if they would like a drink from the bar. Encourage them to order appetizers or side orders. Offer them dessert.” This had never occurred to me before.

Soon after this, I took a job selling insurance door-to-door around rural Oregon. This was truly the worst job I ever had. I hated it. People would invite me into their homes, and we would have a pleasant chat, but I could not get anyone to buy anything. I maybe sold ten policies in ten weeks. At $40 a policy, I was going broke quickly!

I quit the job with no prospect of another. I had several thousand dollars in credit card debt, I owed on a new Geo Storm, and I was paying rent on two apartments. It was a nightmare. I took temporary work to staunch the bleeding, but ultimately I did something I'd sworn never to do: I returned to work for my father.

The box factory

In January 1992, dad hired me to be his box salesman. This was better than selling insurance, but I still didn't like it. I stayed at it though, because he was paying me the amazing sum of $20,000 a year. With that money, I could pay off my debt in no time! Only I didn't pay off my debt. I bought comic books. I bought a new computer. Kris and I bought a house. I got hooked on the income and allowed myself to succumb to lifestyle inflation. When I got a raise, I spent it.

During my 16 years selling boxes, I did a variety of things on the side:

• I spent a year as a part-time computer programmer (I always thought I'd love this, but I hated it)
• I started my own computer consulting firm
• I began blogging

That last item is most important, of course. Eventually, my websites were generating enough revenue that I could quit my day job to write full time, something I'd always dreamed of doing. I always imagined I'd write science fiction novels, not articles about personal finance, but it turns out I simply love to write. I'm fortunate to be doing something I love.

Working for myself

In the four years since I first shared this article, I've experienced some big life changes. For example, I sold Get Rich Slowly and realized a large windfall. In theory, I could stop working for a period of time. In theory.

In reality, I'm driven to keep working, even if it's not work in a traditional sense. Yes, I continue to work behind the scenes here (doing interviews, attending conferences, editing articles), but I'm also exploring other types of tasks. I'm learning Spanish. I'm meeting other bloggers, both big and small. I'm reading. I'm writing. There's no doubt that this stuff is work, but it doesn't actually produce any income. Who knows where it will lead?

Moving forward, I have plans to start another blog. Or two. Maybe even another blog about money. I feel called to write. Something moves me to do so, and for some reason people find they can relate to my voice. I can't explain it, but it's true. And so long as it remains true, I think I'm meant to keep writing, to continue sharing what I learn with people like you.

That's enough reminiscing for one day. How about you? How many jobs have you worked in your life? Which was your favorite and why? What do you hope to be doing ten years from now?