After 30 years working for big name media brands including Martha Stewart and Fast Company, leading sales and marketing teams, I now help leaders achieve more than they think possible. Sunday Sunshine is my weekly newsletter that's about you, your future, and your success. Getting out of our default habits with insights on mindful productivity and lifelong learning, actionable ideas and exercises to have you hitting the week full of energy and enthusiasm. It's the best way to beat the Sunday Scaries.
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You Can’t Learn Everything Yourself
Published about 20 hours ago • 4 min read
Reader,
I almost said no to one of the best dinners I've had all year because I wasn't sure I belonged at the table.
I was at the National Speakers Association annual conference - a newbie, my first time. I had a conversation with someone who recognized me from a virtual event in 2020, and he asked me if I’d like to join him for dinner with a few others.
I was attending the event with a few other speakers and waffled on the decision. Questioning whether I should hang with my speaker friends or have dinner with people I’ve never met. The man who gave me the invite, who I admired very much, is considered one of the geniuses behind Simon Sinek’s Why.
I asked myself: What would my future self tell me to do? GO!
So ten of us walked over to a local Chinese restaurant a few blocks from the hotel. Suddenly, I felt like one thing didn’t look like the others.
I was surrounded by a sea of greatness.
Around the table were reinvention expert Dr. Nadya Zhexembayeva, differentiation strategist Mark Levy, MMA champion-turned-humanitarian Justin Wren, communication expert Richard Newman, musician Peter Katz, astrophotographer Jon Carmichael, and leadership speaker Bronkar Lee.
I thought, what am I doing here!?
One of the hosts explained this would be a Jeffersonian dinner. One rule: when anybody speaks, everybody listens. No side conversations. He would pose a question, and every person around the table would answer in turn.
The first question was simple. Introduce yourself and tell us what brought you here. From the first intro, you could feel the group's collective presence.
I panicked about what I’d say. My inner monologue said, ‘You’ve worked for Martha, Fast Company, so what?’ These people are changing the world. They’ve actually done first-of-its-kind things. They’ve changed economies of countries. They’ve turned challenges into life-altering dedication to the forgotten.
Feeling like I don't belong is my kryptonite. Inside, I was melting down while seated in the middle of the table with no way to escape, duck out, or excuse myself.
So, I pulled myself out of the drowning thought spiral and decided I could judge myself against these amazing humans, or I could add to the dinner, bring some value to the conversation, ask really good questions, and not try to prove why I earned an invite.
My voice shook when I started talking. Not my best, but I got through.
The second question changed the whole night.
‘Tell us about a moment in your life you are proud of.’
Each person went deeper than the one before. It was like every story gave the next person permission to open the door a little further. Ten professional speakers, and no one was on stage performing.
Real, vulnerable, raw stories. I felt so grateful to be there. I felt like there was a reason I was meant to be there, even if I didn’t know what it was in the moment.
The dinner was more than three hours long, but it didn’t feel like it.
Just two questions.
By the end, I knew those nine people in a way that felt real, meaningful, and memorable—not as contacts or LinkedIn connections, but as people. This was not networking.
Each of us grew through each other. Everyone belonged. A no-judgment zone.
We don't have enough years to learn everything through our own experience.
We need other people's.
Their mistakes and perspectives. The things they've survived, built, lost, learned, and figured out.
And they need ours.
That's one reason the rooms we choose matter so much.
The right room doesn't just introduce you to more people. It gives you access to more life.
I had almost let the feeling that I didn't belong keep me from a room that expanded me. Maybe that's one of the things our inner imposter gets wrong.
It interprets discomfort as evidence that we don't belong, when sometimes discomfort is simply evidence that we're growing.
I went into that dinner worried about whether I measured up. I left thinking much less about myself and much more about what I had learned from everyone else.
I've since met with several of the people around that table one-on-one. This newsletter was inspired by Richard Newman's post about the dinner.
My world feels bigger because of them. Not because they're impressive, although they certainly are, but because I've been able to learn from lives and experiences different from my own.
Maybe that's something we should all be more intentional about.
Put yourself in rooms where people stretch what you know. Where their experience expands yours. Where wisdom is shared, curiosity is expected, and what you've lived has value to someone else, too.
If you don’t know where to find these rooms, why not host your own Jeffersonian dinner? Two questions as the main course.
Lorne Michaels once said: “If you're the smartest person in the room, you're in the wrong room.”
Here's my take:
The right room isn't where you're the smartest. It's where everyone brings something that makes everyone else smarter.
Instead of asking if I belong, I’m asking what I can learn because I said yes to being here.
Me and former MMA fighter, Justin Wren. He's changing the world with water and healthcare for the Forgotten People
P.S. I'm booking Strategic Breakthrough Sessions for people who want an extra set of eyes on what's possible for their 2027 strategies. Email me to book a session, or book time with me here. P.P.S. Know someone who would love this newsletter? Forward this to them so they can subscribe here.
After 30 years working for big name media brands including Martha Stewart and Fast Company, leading sales and marketing teams, I now help leaders achieve more than they think possible. Sunday Sunshine is my weekly newsletter that's about you, your future, and your success. Getting out of our default habits with insights on mindful productivity and lifelong learning, actionable ideas and exercises to have you hitting the week full of energy and enthusiasm. It's the best way to beat the Sunday Scaries.
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