When you ask people what they’re most proud of, people usually mention about the same types of things: their kids, a career accomplishment, or how they lived their life.
But it’s an unfair question that totally catches people off guard and they usually blurt out the first thing that comes to mind. It’s like when you see somebody blindsided on a talk show by being asked, “What’s the funniest, most hilarious thing that ever happened to you?” or “What’s the most amazing, incredible, phenomenal experience you’ve ever had?” You’re just not going to get the real answer with 1.2 seconds of thought. But what’s interesting is when people voluntarily say what they’re proud of or what their most amazing, incredible, phenomenal experience was. When they volunteer this out of the blue, it means they’ve given it a lot of thought. There’s an famous man at the University of Chicago and who’s a legend in academia in the area of how people make decisions. Let’s call him Adam. We became friends and during a late dinner Chicago a couple years ago, our conversation turned to parents. Although Adam’s parents had passed away long ago, he said – out of the blue – “What I’m most proud of in all my life, is how I was there for my parents in their later years.” What? That’s what he’s most proud of? I don’t even know what that means. Here’s a guy who’s published libraries of stuff, whose work has changed at least one industry, who has two successful kids, and what he’s most proud of is “how I was there for my parents in their later years”? This wasn’t a “tell me the funniest thing that ever happened to you” kind of answer. He had clearly thought about this a lot. Taking care of aging parents is particularly very emotionally hard. It’s good if you can see it as a blessing, but even a saint can’t see it as a blessing day after day while they are trying to juggle the rest of their life. Having both a wife and brother who do this daily, I can see the grinding burden it can have even on very strong people. What’s interesting about Adam’s perspective is that it is very forward looking. It says “Regardless of how I feel today, how will I look back on this moment in the future?” If the answer is “With great pride in how I handled it,” that’s powerful to keep in mind. It even goes beyond “no regrets” thinking. Right now it’s 4:08 AM, and for the next week, I’m sleeping here on the couch in my 92-year old Dad’s room in the retirement home (or trying to). Although I’d rather be staying and eating with my brother, I think it means more to my Dad that I’m staying here. If someone asked you today what you’re most proud of, what’s a nonobvious answer you might answer? It's useful to also think about how this looks down the road. If you think about what going to do today, or this month or this year, what will you be most proud of having done in five years? It’s a great set of farsighted glasses to try on.
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