An Unconventional Journey – Life, Learning and Work

My wife, Glenda, in Newfoundland, October 1973

I recently started reading Disrupted, My Misadventure in the Start-Up Bubble by Dan Lyons. Dan and I have crossed paths a few times. The first time was when he was in full Fake Steve persona. He offered me sanctuary when it appeared Apple might be coming after my Applepeels blog.

In Dan’s book which starts with losing his job at Newsweek and finding a new job as an editor at ReadWrite. The description of his first new job made me smile.

“Suddenly I am the editor-in-chief of a struggling technology news website called RedWrite a tiny blog with three full-time employees and a half-dozen, woefully underpaid freelancers”

Disrupted, My Misadventure in the Start-Up Bubble

I was one of those “woefully underpaid freelancers.” Dan was actually my first real editor. I had already written my first book, The Pomme Company, by then but the editor of that book had been my very patient but comma-obsessed wife with some help from two former colleagues.

I wrote for ReadWrite for a few months at end of the five years it took me to find my four or fifth career. After nearly twenty years at Apple that was a tall order. During the years after Apple, I worked at a couple of VP jobs in technology, including one at a startup which fortunately unlike Dan’s misadventure was actually generating revenue and went on to a successful acquisition. However, there were enough similarities in my experience to Dan’s to bring back some interesting memories.

Though writing is one of the things that I love to do, I have never thought of it as a possible career. I also love photography and fishing but I have never understood how to make a career out of any of my favorite things. I have supplemented our income through writing and photography. Perhaps having been “a woefully underpaid freelancer,” I learned how hard it is to make good money doing something you love. Good money is required to send three young adults off to college and help them get off on the right foot. I also figured out that what you do doesn’t matter nearly as much as doing it with someone you love at your side in a place that you both learn to love.

How you end up in your career is an interesting topic that Dan talks about in his book. My experience has some similarities but is very different. I hope to write about it through a number of blog posts here.

Only a couple people in my youth even mentioned a career to me. Things were very different in the fifties especially if you were the only child of a single mother and no one in your family had even gone to college.

Mother worked long hours as a beautician in the beauty shop that was attached to our house. We lived in the small community of Lewisville, just west of Winston-Salem, North Carolina. My elementary school and church were just a short walk from home. There were deep woods around our homes. As we were growing up, we thought more about building forts in the woods than we did about building careers. There is no question that I enjoyed my childhood in spite of its share of challenges.

A big turn in my life came in 1963 when I got sent off to a military school that was a six-hours drive from home. Being a boarding student in a dorm was not how I envisioned my teenage high school years. At some point after I got over the worst of being homesick, I decided to make the best of it. Getting good grades had never been a problem for me so I focused on that first. Next I figured out how to do well in the military, stick to the rules, shine your shoes, and do what you are told.

McCallie, where I went to military school did have an important impact on my future. It was assumed that every student would be headed to college. I was part of the pack there so college was clearly now part of my future as well.

While the years at McCallie rolled by, I did get to meet a number of adults with careers that were new to me. Whether they were at McCallie or in Mount Airy where I moved after my mom and dad decided to get back together, meeting new adults did give me an opportunity to think about my future. One of the most interesting people who came into my life was RJ Berrier, who was at the time was the editor of the Mount Airy Times, one of two small local newspapers. RJ was something of a local legend and he loved what he did which was getting the paper out the door onto people’s doorsteps in time for them to enjoy it with their morning coffee. The Times was still using lead type and bourbon to make deadlines. People looked forward to RJ’s Mount Airy After Midnight column as much as I look forward to the comics and the morning paper today.

Though I was already showing some talent for writing, RJ gave me no encouragement to go into the newspaper business. He often explained the pay was poor, the hours long, and job security non-existent. Getting a liberal arts degree at Harvard was not much of a push in that direction either especially since it was during the turmoil of the late sixties and early seventies. I did really hit my stride with writing at Harvard. I am not sure whether it was the expository writing class or all the long papers. However, something clicked and I could churn papers that got stellar marks even at Harvard. I also got paid to do some research work, but there were other things on my agenda that created a hard turn away from writing.

Perhaps, the best description of what was pulling at me was the necessity to get away from the cities that threatened to smother me. Like many others, getting my hands dirty seemed more important than a law degree.

In my case, Nova Scotia appeared to be the locus for a cure. My wife, Glenda, seen contemplating Newfoundland at the top of the post also became a big part of the equation. That we spent ten years building a herd of two hundred head of Angus before I went to Apple is just part of the magic that has touched our lives. I will get around to our lives in Atlantic Canada and how Nova Scotia, Newfoundland and New Brunswick became part of the magic.

Author: ocracokewaves

An escapee from the world of selling technology, now living on North Carolina's Southern Outer Banks where life revolves around sun, sand, and water. I work at WideOpen Networks helping communities get fiber to their homes. In my spare time I am a photographer, writer, boater, fisherman, kayaker, swimmer, and walker of the beaches.

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