You’re probably listening to the wrong people
This week’s Pebble in the Pond came from something small: a reach-out and a willingness to listen.
The conversation was with someone whose life looks very different than mine right now. She’s earlier in her career, navigating questions I stopped asking years ago and weighing choices I made a long time ago.
Her level of clarity stood out immediately—there was genuine realism paired with the depth of curiosity. It’s a combination that tends to show up long before success does. The conversation didn't convince me of her potential. It confirmed what I already sensed: she's going to have a strong career, not because she has all the answers, but because she understands what questions matter.
I didn't walk away from that conversation thinking, "I gave great advice." I walked away thinking, "I learned something important." It reminded me what early momentum looks like, and how easy it is to forget once you're past it. The exchange made me better.
That's the value of generational connection. It sharpens both sides, because we need alternative perspectives as we grow.
The Theme
It's easy to surround ourselves with people whose lives mirror our own. Same stage. Same pressures. Same reference points. The familiarity is efficient, but it's also limiting. The people who can see us most clearly are often the ones living differently than we are.
Earlier in their career. Later in their career. Single. Married. Kids. No kids. City. Ocean. Dog. No dog.
Differences are valuable when we're willing to listen and share experiences honestly.
Three Reflections
Start with curiosity, not instruction. The temptation, especially later in a career, is to share wisdom too quickly. The more useful posture is to ask questions that invite reflection rather than performance.
Define the relationship realistically and generously. Not every connection needs to become a deep friendship to matter. Some become listening sessions. Some become periodic check-ins. Many become meaningful in ways that don’t need a label.
Celebrate what matters to the other person. Being an enabler of someone else's passion costs very little. It often means everything. The willingness to take their priorities seriously, on their terms, is often underestimated.
The Ripple
Look at the range of perspectives currently in your circle. Who is earlier than you, later than you, living with different constraints, chasing different outcomes? Where is that range narrow?
Then make one reach-out this week to someone outside that range. Not to mentor, not to advise. Just to listen.
The Question
Who in your circle is living a life different from yours and might be seeing what you’re not?
