Ambition, Regret, and College Applications: The Conversation I Wish I’d Had 30 Years Ago

What colleges did you apply to in high school? Did you apply to colleges at all? Do you regret those decisions now? And what would you do differently if you could do it over again? Those are the questions I would have liked to have asked my future middle-aged self when I was a teenager. [read more]

Google President Kirk Perry’s 3 Lessons from Losing a Fight

My guest this week is Google President of Brand Solutions, Kirk Perry. He shares a very personal story about a loss on a high school wrestling mat that has both haunted and blessed him ever since. Kirk is much more interesting (and charming) to listen to than my prose is to read. So I encourage [read more]

Would you rather be the head of a dog or the tail of a lion? Leadership opportunities for kids

The kind of goals people deem worthy can vary over time and across cultures. In the U.S., for example, we often tell our kids to set lofty goals. If we fail, so what. At least we tried. In Asia, on the other hand, setting an aspirational goal and falling short might not be what most [read more]

Best Crash! One cub scout’s life lesson in defining your own success

As many parents find out, we often learn just as much from our kids as they learn from us. This week’s life lesson is an example of that, so I’ve asked my 11-year-old son, Ben, to join me on the podcast. You can listen to that conversation by clicking the play button above, or you [read more]

Ambition: How to become an adult, raised on your childhood dreams

Renaissance artist Michelangelo once observed, “The greater danger for most of us is not that our aim is too high and we miss it, but that it is too low and we reach it.” I’m convinced that’s true, and perhaps best example of what happens to someone when they set high goals, even if they [read more]