I’ve had a number of unique and interesting jobs.

Grade school

In addition to the at-home chores I did for my 75-cent allowance and neighborhood jobs, like snow shoveling, lawn mowing, and babysitting, my best job as a grade schooler was one I discovered in a Boy’s Life Magazine ad. I sold seeds and earned sports equipment. I went door-to-door selling flower seed packets for 10 cents each. I did very well earning footballs, baseball mitts, ice skates, and other fun rewards. My friend Billy wanted a piece of my action, so one day I gave him half my packets and told him to cover the opposite side of the street. I also told him my pitch was to introduce myself, saying I lived in the neighborhood, and I was trying to earn a baseball glove. I sold a minimum of a dollar’s worth of seeds at practically every house. Billy had no sales on his side of the street. “What did you say? I asked.

“Do you want to buy some seeds?” he answered. That’s when I decided I must be the world’s greatest salesman.

High School

In the summer of my 15th year, I worked on my uncle’s Ohio farm where I enjoyed driving farm equipment and the endless variety of work. My dad drove out from Connecticut to pick me up at the end of the summer. After showing off how I could drive tractors and farm trucks, he put me behind the wheel on the Pennsylvania Turnpike and climbed in the back seat to sleep. He didn’t realize I had never driven anything over 15-miles-per-hour.

At sixteen, I joined a friend to maintain the grounds of a wealthy man’s country estate. The man was prominent in the Republican party and on one occasion asked my friend to escort Richard Nixon’s daughter, Julie, to a formal affair.

During my middle teen years, I became a garbage collector hanging off the back of a garage truck emptying garbage cans. Also, during this period, I worked on our town’s road crew paving streets. Some of my fellow workers were ex-sailors. They educated me on the activities of sailors on leave in foreign ports. Wowee!

One summer I worked in a factory punching timecards for production workers doing piece work. It was my responsibility to make sure the workers didn’t screw up the union standards by working too fast or not taking the allowed restroom breaks.

I also had a short-term job as a security guard in an armored car. We delivered payroll to plant sites. All I did was walk along beside the guards carrying the money bags, but I got to wear a holster and gun. I doubt my gun was loaded.


For several years, after school and on weekends I worked at a gas station, lubing cars, mounting tires, pumping gas, and doing minor tune-ups. It took me years to get the grease from under my fingernails.


During college summers I worked as a clerk in an exclusive Westport, Connecticut, men’s store, selling men’s furnishings. I waited on Paul Newman’s wife, Joanne Woodward, the newsman, Eric Sevareid, and other Westport celebrities.

My freshman year of college, I had a job stocking shelves in a supermarket. The market locked us in the store at closing time and let us out the following morning. We were permitted to eat any food we wished. Since we were burning cardboard boxes in an incinerator, we used to wrap steaks in aluminum foil, cooking them in the fire. I gained weight on that job.

During the school year I played football earning my scholarship. I also drove school buses and charter buses. My bus driving routes included morning runs transporting students to high school, driving athletic teams to away competition, taking factory workers home in the evening, and carrying tour groups into Chicago. I learned a big bus in Chicago traffic got priority and cars got out of your way.

Other odd jobs in college included being on-call with a moving company to help load or unload moving vans, working weekends for homeowners washing walls, ceilings, and doing some painting, and working for the college as a custodian in dorms to earn money to drive home for the summer. I also worked for a local farmer installing fencing, selling Watkins Products door-to-door, and working as a busboy at a local country club.

In my junior year of college, I interned at Carson, Pirie, Scott in Chicago as an executive trainee, getting credit at college. I worked in the men’s department as an assistant department manager. A collateral job at Carsons was modeling men’s wear during noontime fashion shows. That led to other modeling jobs on TV and a gig at the International Boat Show in the newly opened McCormack Place. My picture appeared in the Chicago Tribune surrounded by professional women models in bathing suits.

Post College

My best job ever was as a pilot in the U.S. Navy. I was stationed in Maine and deployed to Iceland, Newfoundland, Spain, Sicily, Bermuda, and operated out of Key West during the Cuban Missile Crisis.

After the Navy, I became a life insurance salesman. That’s when I discovered I wasn’t the best salesman in the world. I was too thin skinned and couldn’t handle rejection. “Boo-hoo, why don’t you want to buy my policy?” The best part of that job was working for Jim Longley, the General Agent of our insurance agency. Jim was incredible—the most inspiring, impressive man I even met. Later, Longley became governor of the state of Maine.

I had a thirty-year career in an electrical wholesaling company, Kirby Risk Supply Co. My assignments over those years included warehouse worker, counter salesman, outside salesman, branch manager, district manager, vice-president, member of the board of directors, and became responsible for directing our strategic planning effort and writing and publishing a weekly newsletter. I hired hundreds of employees over the years, one of them, Michele, became my wife.

During those Kirby Risk years, I used my commercial pilot’s license to fly other managers and executives to out-of-town meetings and was once hired by National Geographic to fly one of its photographers over our town to take aerial photos for an article it was writing. I didn’t know when I agreed to that I would be expected to take the side door off my airplane.

I have also written and published magazine articles and three books. One of my favorite activities is public speaking to service clubs, library groups, and military organizations. Although speaking wages usually amounted to nothing more than a gift coffee mug, a framed certificate of appreciation, or a free meal, I did have one engagement in Boston that included airfare, hotel and travel benefits. My presentations have been about genealogy research, motorcycling adventures, sailing experiences, running achievements, and aviation exploits.

The least favorite job during all those years was the factory timekeeper job. Boring! There were several favorites. My service in the Navy tops the list. The 30-year wholesaling career included numerous highlights. And writing and speaking opportunities have brought many post-retirement satisfactions.

I bet a number of my readers have had equally unique and interesting jobs. I’d like to hear about them. That might make an interesting follow-up blog article.

3 thoughts on “Jobs

  1. Jim,
    …..and I thought the highlight of your career was as President of our HOA !!
    Anyone who can pilot a Navy jet and do the Boston Marathon, (in spite of leaving your son at the rest stop) has my admiration and respect.

  2. Jim, I’m exhausted just reading about all of your many jobs. However, I am wondering why you didn’t just work at one or two jobs to completion. You might have been able to accumulate increased retirement benefits so Michele could have stayed home and relaxed.

  3. Great story Jim.
    I can’t compete with that!

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