Living by the Odds - Dilbert Blog

Living by the Odds

I like to live my life by the odds. 

For example, I don’t often ride a bicycle because the risk of injury is high while the enjoyment can be matched by safer activities. For most of my sporting life I played tennis because it offers a good exercise-to-injury ratio. Even distance running is less safe.

As a result of my safety bias, and luck too, I have never had a sporting injury of any major consequence. Today, I really, really want to own a motorcycle. But I don’t like the odds. So I don’t.

When I was young, my mother brainwashed me on the importance of education for escaping my low-income life. I was taught that paying attention in class and doing all of my homework would be enough to make my life better, and I’m sure it did. Authority figures told me what I needed to do to improve my odds, and in nearly every case I did exactly that.

I also follow the odds with diet and fitness. That was problematic in my youth because a lot of what I learned about diet and exercise as a kid was completely wrong. I followed all the good advice of the time and found it challenging to keep weight off. Today I follow the scientific guidelines for diet and exercise – which are probably a lot better than in the past – and my results are shocking. I’m in the best shape of my life, by far, as I cruise into my senior citizen years, and I use nothing like “willpower” to get it done. I did not see that coming.

Career-wise, I also pursued the odds as I saw them. But here things get complicated with my “white male privilege” which clearly helped as well. So I won’t compare my situation to anyone else’s except to say that whatever your starting point is, playing the odds probably helps.

For my career, I consciously played the odds in the following simple ways:

1. Upon graduating college I moved from Windham NY, population 2,000, to San Francisco to improve my career odds. An ex-girlfriend lived in San Francisco but I had no other ties there.

2. I took an entry-level job (teller) at Crocker Bank because at the time they were the technology leader in banking and a big deal in California. I went where the energy and money was. I figured I could work my way up from the bottom and learn along the way.

3. I was agnostic about what types of jobs I did so long as they taught me something that improved my odds for something better, no matter what that better thing was. I saw my corporate days as a practical education for whatever I would later do on my own.

4. I took advantage of every free educational offering from my company. When my employer offered to pay for any kind of useful class, I signed up. The bank even paid for most of my MBA classes at Berkeley while I went to school at night. And they paid for me to take the Dale Carnegie course to become an accomplished speaker. The learning opportunities were incredible.

I was not only becoming smarter and more capable in a general way, but many of the skill combinations made me unique in a financially valuable way. For example, I worked in the bank during the dawn of the personal computing era, and I was among the first to learn how to use an IBM PC (on my own time). As quaint as this sounds in retrospect, few bankers were technologically savvy, and since I was, I stood out. It helped on a few promotions for sure.

5. I stayed single and child-free, intentionally, to keep my mobility high during my important early career days. Staying out of jail helped too.

6. I took LOTS of risks with side projects that I hoped would grow into something good. But in each case the risk was one of embarrassment, lost sleep, and wasted time. If one thing did not work out, I would simply move to the next. Dilbert was my first side project that worked.

Most of you would see the success of Dilbert as good luck. And it was. But financially it was probably bad luck because I was a young, ambitious, white, highly-educated man with an entrepreneurial personality living on the edge of Silicon Valley. My best guess is that if cartooning had not worked out, I would have cashed out of a few start-ups by now and would be far richer.

There is little about my story that could be directly applied to a young person today. For example, I doubt you could become a bank teller today and afford to rent a windowless bedroom in San Francisco, as I did. My story is about following the odds, not creating a template that anyone else can follow.

My question to you today is simple. Do you know anyone who played the odds the way I did (with their own variations, in their own time) and found that life did not work out well?

Obviously people have health issues and tragedies that are beyond their control. But I can’t think of anyone in my experience who followed the odds and got a bad result unless they got hit by a car or some other random tragedy visited.

Is there anyone reading this blog who was as dedicated to following the odds as I was and yet things did not work out for you? 


Bonus Thought: My sister told me a story the other day. She graduated high school as Valedictorian and planned to become a scientist until an authority figure in her life informed her that “science isn’t a job.” So she got a major in art and became a teacher. Because science isn’t a fucking job? (The authority figure did not say “for a woman” but I think it was implied.)

This brings us to the question of why more girls do not pursue science and technology jobs. The solution probably involves a thousand small steps, but one of those steps might include the games kids play. See Tamra Teig’s sportlight on a start-up called Build and Imagine and how they plan to make better games for girls. I don’t know if this will make a difference, but it can’t hurt.

Note: I am not an investor in the start-up mentioned but I like to put a spotlight on Berkeley-related start-ups that are doing something good.