My dad’s career change, and how to know if it’s time for yours

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My dad just called. He said one of his fifteen-year-old students asked, “Why do we need to know this? How will To Kill a Mockingbird help me in life?” My dad loves questions like that because he has asked them himself.

My dad has always loved school. He was the kid who did the extra credit even though he already had an A. So he had a lot of options at the end of college. He applied to two graduate schools: Yale for history and Harvard for law. He got into them both.

Before I tell you what he chose, I have to tell you about my family. Rich. Mob money. My great-grandfather, my dad’s grandpa, was the lawyer for the Chicago mob: solid work during prohibition and a reliable profession during the depression. Money flowed freely during my dad’s college days, but his grandfather threatened the inheritance if my dad chose history over law. The way my dad tells the story, he always knew he wanted to teach, but he was scared to risk his family “?s wrath, to say nothing of their wealth.

So, after Harvard, my dad went to the top law firm in Chicago (without even having to interview.) My dad hated it, but he wasn’t a risk taker, so he hated it for a long time, thinking the money was worth it. Like the BMW: he drove one of the first cars (when the motorcycle company diversified in desperation) and the cars were so rare that the BMWs would flash each other when they passed. (I’d yell from the back seat, “Hey, there’s one! Flash, Dad, flash!)

There came a point, though when my dad asked himself, “Why do I need to know about all these cases? How is this helping me in life?” His grandpa died, his law firm merged, and the bottom of the BMW fell out.

Finally, after years of thinking his career would get better, it didn’t, and he quit. He went to graduate school to teach high school history. He was older than all the professors. His kids were older than all the students. After thirty years of practicing law, he started over.

I asked him about classes and he’s say, “It’s hard to go back to school. It’s hard to no know what I’m dong after so many years of doing the same thing.” He said his favorite class was the history of civil rights, because when they got to the ’60s he could write papers about his college days.

Upon graduation, everyone in his class got interviews and he didn’t. No one even talked about age discrimination because it was so obviously there and so obviously unavoidable. Finally, though, he got a job. Teaching English. He wanted to teach history, but he’s entry level now. It’s like doing HTML when you’ve got a degree in computer science.

But my dad is thrilled. He took a big career risk and he’s happy. He’s happy to be interacting with the students, but also, I have a feeling that he’s happy he took a risk. Changing careers is so scary, but it’s so empowering-it gives you assurance that you can al ways choose to do what you want most — the hard part is to know yourself well enough to know what that is. So think like a fifteen-year-old and ask yourself, “Why am I doing this?” And then think like a risk taker and jump like my dad when you know your time is right.

6 replies
  1. Andrey
    Andrey says:

    Hi, Penelope,
    good writing, your dad is correct, we should choose what are our Childhood or Youth Dreams, not what we like or dislike, but what we were dreaming about at the period of youth.

    This is the time when we already know much from schools, and still haven’t lost all our bright hopes and clear minds. This is a cure-healing for our souls. And your dad wasn’t just looking for new adventures, he was looking for happiness, and he seems to have found himself now.

    I know you don’t need any praises, but I read your blog not just for taking advices from you, but for networking too, and this is how I’ve detected the writing of around 6 years old.

  2. Charlie
    Charlie says:

    This post is very inspirational to me! Thank you very much for sharing that story.

    I think you are dead on that the hardest part is knowing what you want most! Once you figure that out, all you have to do is make it happen (and since you want it so badly, you WILL do the hard work to make it happen).

  3. Ken Forester
    Ken Forester says:


    Great story. My personal take is that economy is a major issue today and I would know when to change a job or make a career change when I see that my job security score for my present job is decreasing and if the future doesn’t look bright for my type of jobs. With less and less manufacturing now in the US, and dependency on foreign trade, outsourcing, etc, I feel that one should constantly revaluate their Job Security Score and make appropriate career change plans.


  4. Emily
    Emily says:

    Hi, I’m puzzled by something on this site… You claim in other posts that your dad sexually abused you, and in this post you are saying that he is a high school teacher. If he has, in fact, sexually abused you, why is he working with high school students?

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