August 21, 2025
Every day, I share a Thought of the Day and Question of the Day to spark reflection, humor, and maybe a little honesty about how we live. Today’s thought reminds me that sometimes success is less about brilliance and more about timing. And today’s question pushes us into territory many of us avoid, starting conversations with strangers.
Thought of the Day: Sometimes the last person to mess up wins based on that alone
Life isn’t always about flawless execution. In fact, a lot of times it feels like it comes down to who’s still standing after everyone else has slipped up. Think about poker, sports, business, or even parenting, half the time it’s not about being perfect, it’s about not being the first to fold under pressure.
I’ve seen this in my own life. When things get competitive, the people who hang around the longest, even after making their share of mistakes, often find themselves in the winner’s seat. Sometimes the world rewards persistence disguised as “waiting for the other guy to trip.”
It’s a reminder to keep showing up, even if you’re not at your best. Sometimes simply being the last one still trying is enough.
If you like this, here’s some more you may like: Why quitting is harder the more you try and What would you write on a billboard for the whole world to see?
Question of the Day: When was the last time you struck up a conversation with a perfect stranger?
Beyond saying hello to the cashier, I honestly can’t remember the last time I struck up a real conversation with a stranger. And yet, some of the best stories and most surprising moments in life start with those random chats.
I can remember years ago striking up a conversation in a bar with a woman about her tattoo. She told me the Chinese characters said “I love tacos.” Being the trusting soul that I am, I said that’s wonderful and went back to my friends. In retrospect, that conversation could have gone in a completely different direction if I had my wits about me.
Anyhow, today we carry around little supercomputers in our pockets, always “connected,” but the thought of leaning over and talking to the person next to us on a bench or in line feels… unusual.
The truth is, a single conversation can change your day, or even your life. Maybe the point of today’s question isn’t to recall the last time, but to remind ourselves to make the next time happen sooner.
(Related read: What’s the most interesting public conversation you’ve overheard? and What do you think people misunderstand most about you?)
Your Turn
When was the last time you talked to a stranger—and did it lead anywhere interesting? Leave a comment below or better yet, join the free daily email and get the Thought of the Day and Question of the Day delivered to you.