I Used to Be Somebody: (Un)Retirement Lessons Learned

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Bob Wolfe Interview: The Pinot Guy now Pickleball Guy

Diana Landau | November 02, 2023

Bob WolfeCarl interviews Bob Wolfe this month, just as Bob "The Pinot Guy" embarks on a new career in his 60's. Timing, hard work, patience and the willingness to deep dive are the hallmarks of having a successful second (or third) career and Bob has been doing just that for decades. A wine expert who owns his own wine business, he has written over a thousand articles for magazines like The Wine Spectator, Wine & Spirits, The Northwest Palate and more. He has also been a long-time judge for wine competitions all over the world. Most people know Carl loves Pinot Noir, but Bob's second act as a pickleball instructor has Carl super-psyched!

Bob grew up in a very small rural town in Monroe, Oregon, (pop. 450.) His family lived on 22 acres with cows, chickens and lots of wood for Bob to chop into firewood. Eager to get out into the world after high school, Bob was intrigued by nuclear submarines and international travel and he joined the U.S. Navy.

In the 1980's, Bob started work on two of his interests at the time, natural pesticides and beer, (but not together.) You'll have to tune in to the episode to hear Bob's story about a 4:30am business phone call with Donald Trump way back then. (Some things don't change.) Bob's passions eventually led him to wine and he was one of the first in the U.S. to publish an e-newsletter devoted to wine. He enjoyed the perks of being a wine reviewer. "Wine writing is a wonderful gig!" he tells us.

He took some of the money from his other ventures and in 1991 he started The Oregon Pinot Noir Wine Club out of his garage. That very first day he had orders. In just a couple of years, he grew the club to a $2 million business. He started judging internationally and his wine biz career as a retailer and expert grew steadily.

Fast forward a couple of decades, Bob says he turned 60 and started thinking about what he wanted to do next. " I knew I wanted to wind down my time in the wine biz. I looked for something to belong to, something more social." Bob joined a pickleball club, took some lessons and loved it. "'I'm meeting new people and having fun. I find it satisfying on so many levels."

Now Bob has found someone to run his wine biz and is planning trips to Mazatlan, Mexico and Da Nang, Vietnam where you guessed it...he's planning to play and teach pickleball. He's even training to be a competition judge. Bob says, "I always ask myself, What's driving me and my passion now? I'm jumping in!"
Bob Wolfe's (un)retirement tips:
  • "No sitting on the sidelines, just thinking about what you want to do. Do it."
  • "Get enough friends to do things with--I'm determined to escape the dreaded senior lonely years."
  • "Give up on owning a lot of stuff. You just don't need it. Unburden yourself from taking care of things you don't use. It will free your mind too."Unretirement
• More about Bob Wolfe
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Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the "I Used to be Somebody" blog.
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