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Scratching the Itch (Tim O'Brien '81)

Writer's picture: John Whelchel '15John Whelchel '15

I’m sure all of us have stayed connected to music since we left the Nassoons, even if just by singing in the shower. When I graduated, I had a vague but pleasant image of myself as a songwriter, based on nothing but a love of good songs and modest success writing tunes for the Triangle Club my senior year. So, with nothing else to guide my steps, I moved back in with my parents in St. Paul, found myself a piano teacher, and began to educate myself in the craft of songwriting.


Two years later, I had very little to show for it. I had improved my skills at the piano (though hardly to the professional level) and had written a few songs, but I couldn't see any clear path to getting what I wanted. I was living in someone else’s nice house and playing someone else’s nice piano, when what I wanted was to live in my own nice house and to play my own nice piano.


So I went to law school, and that turned out to be a good thing. In the first place, I had learned enough by then to be sure that I was not depriving the world of a great songwriter by going into the law. In the second place, my legal career took me to California, where I met and married Francine, and where we had three fabulous daughters. It turns out, in case you didn’t know, that if you are a good-but-not-great commercial lawyer, you can make a very nice living and raise a family in comfort, whereas, if you are a good-but-not-great songwriter, you will starve.



Still, the itch remained. Before going to law school, I wrote a musical for middle school students, and then I wrote another one during law school. Even as I started my legal career out in California, a handful of schools in Minnesota began performing my musicals, and inquired whether there were any more. Between that encouragement, and the disillusionment that almost every big law attorney feels a few years out of law school, I decided to take a year off and go back to writing music. I’m glad I did, but the consequences were the same as before; I managed to write another kids’ musical, but I made no money, and could see no path forward. This time, though, I had a two-year-old daughter underfoot with another on the way.


So I went back to the law firm, and from there to a series of in-house legal positions that led to a very satisfying career. I even found time to write one more middle school musical, bringing the tally to four. By the time I hit forty, though, the well had run dry. I was working flat out lawyering and raising kids. I had a nice house. I had a nice piano. I just didn’t have time to write music.


If you’re really lucky, though, it all comes back around. The kids grew up, and in 2019 I retired from my legal career. My father-in-law died, and I wrote a tribute song to his life as a Korean War vet, which a local country radio station played on Memorial Day. A nearby school recently performed one of my old musicals and asked about another one.



Where will it lead? Who knows? It doesn’t actually have to lead anywhere. I can now play piano to my heart’s content (still not very well), and write whatever songs come to me. When I write something I think is good, I cut a demo with some local musicians. If I like the demo, I play it for people and post it on my website. (You can find my songs at www.timothywobrien.com. Give a listen and let me know what you think. And see if you can find the one with Bob Peskin ’78 singing back-up.) Maybe I’ll write another musical. The point is, I can scratch my itch, and I’ve earned the right to do it. May the same be said of all of us.


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Og Dog
Feb 07, 2021

Thanks for sharing OB! I am glad you persisted. I really like "Ain't doing what you said." You could make some money off that one!

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