"I am so thrilled to be where I am," says Gary Wenstrup, a former advertising sales executive who reinvented himself as a music historian and educator.  “It was not easy, but to do the things I love to do is a blessing,” In this conversation, Wenstrup shares his journey from the fast-paced world of advertising to teaching courses on legendary artists like The Beatles and Simon & Garfunkel. He emphasizes the importance of starting your reinvention early and keeping an open mind, even when the path feels uncertain. “You have to go very, very wide even if it’s stupid or silly, whatever’s in your head,” he advises. With practical tips like creating a ‘selfie list’ of skills and interests, Wenstruop illustrates how curiosity and exploration can guide you toward a fulfilling next chapter. Tune in to hear how he turned his passion into purpose—and why taking the leap is always worth it.

About Gary Wenstrup:

After a rewarding career in advertising sales, Gary Wenstrup retired and developed courses on the Beatles, Simon & Garfunkel and Motown Records for the Continuing Education Department of College of DuPage. Gary has lectured at over 100 libraries across the country. Gary is also a reoccurring guest on the popular podcast “Something About The Beatles.”

Connect with Gary:

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Time Stamps:

02:32 - Gary Wenstrup's background in advertising and corporate

07:45 - What is a "Selfie List"?

09:47 - How he coped with the false starts

14:49 - Gary started presenting at libraries to grow his lectures

17:47 - Why it's not always important to monetize your passions

20:05 - Scaling as a lecturer

21:29 - "Prepare early"

23:15 - Wenstrup's essential tips for reinvention

Connect with Lesley Jane Seymour:

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