Jeff Scott Olson

Gentle, amiable and articulate, Jeff Scott Olson likes so many things:  food, wine, gin, daiquiris, audiobooks, playing the banjo, going to the movies, conversation and storytelling.  He's been practicing as a civil rights attorney in Madison, Wisconsin for 40 years. One cold, snowy evening over drinks in Delmonico's dimly lit bar, he answered the Proust Questionnaire. 


What is your idea of perfect happiness? Being able to do something useful every day and go home and relax at night. 

What is your greatest fear? Death.

What is the trait that you most deplore in yourself? My proclivity toward vice and sloth.

What is the trait that you most deplore in others? Chickenheartedness.

Which living person do you most admire? Barack Obama.

What is your greatest extravagance? My boat.

What is your current state of mind? I’m pretty darn happy.  I’m out with a beautiful woman.

What is the most overrated virtue? Ambition.

On what occasion do you lie? If absolutely necessary to preserve someone’s feelings in a small manner.

What do you most dislike about your appearance? 100 pounds.

Which living person do you most despise? I don’t really despise anybody.  I don’t feel I’m qualified to judge.

What is the quality you most like in a man? Courage.

What is the quality you most like in a woman? Emotional intelligence.

Which words or phrases do you most overuse? Emotional intelligence!

What or who is the greatest love of your life? A few different women.

When and where were you happiest? I don’t think I’ve ever been happier than I am right now.

Which talent would you most like to have? If I would have been born with a good singing voice, my life would have been totally different.

If you could change one thing about yourself, what would it be? I’d make myself 50 years younger!


What do you consider your greatest achievement? Keeping a civil rights law firm that represents penniless and destitute individuals open for as long as I have.

If you were to die and come back as a person or thing what would it be? I’d like to come back as a lion.

Where would you most like to live? Just north of Key West.

What is your most treasured possession? My 5-string banjo.

What do you regard as the lowest depth of misery? People who are terminally ill and who are so powerless that they cannot even kill themselves.

What is your favorite occupation? Astronaut.

What is your most marked characteristic? Not losing my cool.

What do you most value in your friends? Honesty.

Who are your favorite writers? Jim Harrison and Ernest Hemingway.

Who is your hero of fiction? Jack Reacher.

Which historical figure do you most identify with? Clarence Darrow, a lawyer in the early 1900s.

Who are your heroes in real life? Clarence Darrow, Abraham Lincoln, Thurgood Marshall, and Percy Julian (my first boss as a lawyer).

What are your favorite names? I feel pretty lucky to have been named Jeffrey Scott.  I like both of those names.

What is it that you most dislike? Delay.

What is your greatest regret? Walking away from a fight and leaving my friend Mike Vinopal to continue it when I was in 2nd grade.  But it made me a fearless person today.

How would you like to die? I’d like to be shot by a jealous husband!

What is your motto? I don’t have a motto.  If I had a motto, it might be Winston Churchill’s: “Success is never final, failure is never fatal, it is courage that counts.”




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