Legacy, Luck, and Learning to Do Hard Things with Tim Conti episode artwork

EPISODE · May 28, 2025 · 48 MIN

Legacy, Luck, and Learning to Do Hard Things with Tim Conti

from Messy Middlescence

Last holiday season, Tara and Tina found themselves laughing over an ad for one of those quirky “Family Questions” games. One sample question stood out: “Who in your family would you ask for help if you needed to bury a body?” Without hesitation - and independently - we both came up with the same answer – our younger brother, Tim.This may sound like an odd way to introduce Tim and our discussion with him --but it perfectly captures Tim’s unique personality and skill set. He’s the sibling you call in a pinch - resourceful, unflappable, and endlessly loyal.Tim is the 5th of our 7 siblings (and coincidentally the 5th sibling to be interviewed on Messy Middlescence) and he very recently turned 51. Tim is a problem solver, a people person of the highest order, a hilarious storyteller, goal-oriented, and, yes, famously stubborn. In our family he is known for saying “I know a guy…” or “I have a buddy…” always leading into either a wild story or an impressive display of his vast network of friends and colleagues.We are excited to talk with Tim about his middlescence journey and to give our Messy Middlescence audience the opportunity to get to know him.  Some of the topics we delve into with Tim include the following:Tim’s circuitous journey to a rewarding and successful career;The important skills he learned in his non-career jobs which ultimately set him up for success in his career;A lively debate on the importance of luck/chance in any career;His desire to volunteer and devote more time to his many interests when he retires;The key lessons he has learned thus far which made a huge impact on his life including the need to prioritize what is important and learning how to do the hard things we would rather avoid;Pride in his family and their beautiful, messy “differences”.How middle age has shifted his goals to be more about his children and retirementThe difficulties of the physical changes that occur in middle age; he simply can’t athletically do what he did 10 years ago;His thoughts on retirement; how he will likely not stop working completely but transition to a less stressful job.

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Legacy, Luck, and Learning to Do Hard Things with Tim Conti

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This episode was published on May 28, 2025.

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