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Imagine A Conversation with Simon Sinek and Brene Brown

Most of the time I listen to a podcast in the background while doing other things -- driving, doing the dishes, folding the laundry, etc. But there’s that rare podcast where I’m so enraptured by the content that I stand frozen, with a dirty dish in my hand and the water still running. I get so caught in the ideas and story that I completely forget what I’m doing. This was one of those episodes for me.

Fireworks. In my brain. All over the place.

The podcast in question features a mashup of two of my favorite thought leaders on the planet: Simon Sinek, author of Start With Why and The Infinite Game, and Brené Brown, author of Dare to Lead and The Gifts of Imperfection. I invite you to listen to it in full HERE.

What follows is a work of fan fiction. While I was standing there frozen, I felt like I was in the room with them. Which got me to thinking... what if I could be in the room with them? What would I have said? What would I have asked? Their words are straight up quotes from the podcast, and kept to the 500 word copyright limit. I just added my words to weave my own thread into the conversation.


Irene: OMG I can’t believe I’m actually here in this room with you both. It feels like I’m stepping through the wardrobe door into Narnia. This is truly a magical experience.

Simon, I adore your work. Knowing my “why” has changed my life. And Brené, it says boldly on my website that when I grow up, I want to be Brené Brown. In some ways, I feel like I know you both so well from your work that we’re friends.

Simon: I’m a believer that when you meet someone who shares the same cause… even if you have no history, there’s sort of this unspoken deal that you help each other out because we’re trying to advance the greater good and we’re on the same team.

Brené: I feel the same way... We write alone, we travel alone, we speak alone, and I do feel like part of a team of like-spirited people on the same kind of just and worthy cause mission... Do you not agree, sometimes the work can get lonely?

Irene: So lonely! I was speaking with a friend of mine who is also a school leader about just how lonely it is sometimes. I mean we are sometimes dealing with big conflicts, and the leader has to be the impartial one, the one above the fray to help sort it all out.

Simon: Life is not a solo sport. You’re on a team, but you don’t necessarily know who all the players are. It’s not lonely if you remember some of the teammates you’ve met and then you have faith that there are others out there who you don’t know.

Brené: God, I really love that.

Irene: Which brings me to your book, Simon, The Infinite Game. The three of us, and a whole lot of others, are playing an infinite game here where not all the players are known. But we’re teammates, and that makes it less lonely.

I should back up a little. The original idea of the infinite game came from Dr. James Carse who theorized that there were two types of games in this world.

Finite games have known players; fixed rules; an agreed-upon goal; winners and losers; and a clear beginning, middle, and end. Think basketball, Monopoly, or poker.

Infinite games have a changing cast of players where new people can join and others can drop out; changeable rules so you can play how you want; winning can mean different things to different players so that it’s possible for everyone to win or no one to win; and no clear beginning, middle, and end. Think politics, raising a family, leadership, or the game of life. It’s why I love Dungeons and Dragons more than any other game I know. D&D is just so infinite.

I prefer the infinite game in the real world for similar reasons. There’s collective storytelling, that element of everyone contributing to the unfolding of the story. I love how the sum of all the teammates’ strengths, like players in a D&D adventuring party, are greater together than each individual acting alone. And the strengths of one can make up for the weaknesses of another.

Simon: There’s no such thing as strength and weakness. It’s all contextual.

Irene: You’re right. I should be more careful about my language. For instance, the things I once called my weaknesses -- my tendency towards perfectionism, hyper-achievement, and control -- I’m realizing that they are the dark side of some of my greatest strengths -- my organizational, strategic, problem-solving mind. They’re two sides of the same coin and I wouldn’t be me without them.

Simon: We have to know how we show up and, to try as best we can to put ourselves in the context where that thing is a strength, or mitigate it in the times where it might be a weakness. But it’s not a good or bad or right or wrong. It’s just us.

Irene: Exactly! There’s another pairing I have too. Hopefully this won’t sound arrogant, but I’m a great community builder, yet one of my deepest struggles is my own insecurity about belonging. I can even be kinda needy around appreciation and acknowledgement because deep down I am seeking feedback from the group about whether or not I belong, whether my contribution made a difference. It’s the dark side of my community-building superpower. I am really good at helping others feel like they are valued, integral members of a community because I’ve struggled so much personally with belonging.

Brené: Yeah… I can be controlling and I can be micromanaging if I’m not careful, if I’m in fear. But on the same continuum, I am incredibly dependable. You can trust me 100%. And if you throw the whole thing away, you throw away the best of me, too… My need for control can lead me to my best infinite leading and thinking, because when I get really clenched down, I can think, “Open up... You don’t know the players. You don’t know the rules. Just let it go.” And it can also be the worst of me in my finite thinking.

Irene: So true! And that brings us back to the idea of how we show up, and whether that’s with an infinite or a finite mindset.

Simon: You could tell immediately who had the more finite mindset and who had trained themselves to learn the infinite mindset, because when COVID struck, the finite-minded panicked: “Oh my God, we’re not prepared for this. What are we going to do?” ... The infinite-minded went, ‘OK, how are we going to adapt? This is exciting.’

Irene: Yes! This is exactly what happened when COVD hit my school. Sometimes my job as Administrator of a teacher-powered school feels like I’m herding cats. But when COVID arrived, the team was like a pride of lions on the hunt. Within 48 hours of collectively making the decision to close school to students, teachers had distance learning packets out to every student and were already teaching one another Zoom and Google Classroom. The paraprofessionals provided child care on campus for essential workers and low income families. The office had a system for loaning Chromebooks to all kids who lacked a computer at home. Everyone pulled together to make it happen lightning quick.

In contrast, many schools across the country had a finite mindset, with no good options for students or families for months.

It reminds me of what Michael Stallard says in his book Connection Culture. The best organizations, the ones that most successfully play the infinite game, have three things: vision, value, and voice. Vision means a common mission. Value means that each individual and their contributions matter; people truly care about each other; and their efforts are seen and appreciated. Voice means that people have a say. Together, vision, value and voice build a culture of trust and collaboration that makes for a really successful organization.

Simon: The responsibility of the leadership is to obsess about creating great teams that take care of each other and will use all their ingenuity and creativity to find new ways to advance the cause.

Irene: Yet I must admit that I have a hard time staying in an infinite mindset in the face of uncertainty. Like when the rules of the game change, or the goal changes, or when the team is falling apart, or when there’s real deep fear.

Brené: You’re so right... When I am my best self, I am an infinite thinker, an infinite leader, an infinite parent, and when I am in fear and scarcity and the vulnerability is breaching the levees, I turn toward finite thinking.

Irene: Me too! My dark sides show up most when I’m overwhelmed by uncertainty or fear or just plain having too much on my plate. It’s like you were saying when your need for control makes you clench down or open up.

Lately I’ve been saying a little mantra to myself when my own need for control rears its head. I’m a swing dancer. And one of the rules about social dancing is that whenever someone asks you to dance, you say, “Yes.” No matter what. Doesn’t matter if you hate the music or the person who asked you is a total newbie and will step on your toes. You say, “Yes.” You dance and learn what you can from the experience. So when things get really infinite, and I’m feeling that tingling inside that means my controller is not happy about this at all, I tell myself:

“When the universe asks you to dance, say yes.”

I’m curious, how about you? How do you lean into being a little more infinite each day?

Simon: Carse would say infinite-mindedness is loving the play, enjoying the playing.

Brené: Yes.

Irene: So to become more infinite, fall in love with the playing of the game? Is that all?

Simon: I can see that in my mind’s eye as a vision of the future we do not yet live in, and yet we will set ourselves on a course to advance towards that vision, knowing full well that we will never actually get there, because it’s an ideal, but we will die trying. That’s what vision does. It gives our life and our work meaning.

Irene: Wow. That’s beautiful. It’s what finding your “why” can do for you personally or organizationally. I remember reading something by the astronaut, Chris Hadfield, who said that “Success is feeling good about the work you do throughout the long, unheralded journey that may or may not wind up at the launch pad.” It’s like that: there’s this big, inspiring, impossible vision. You know you may never get there, but if you enjoy the playing of the game, and have great teammates alongside, then that’s a life well lived.

Read More

I invite you to listen to the podcast in full HERE.

In addition to his books, Start With Why and The Infinite Game, if you haven’t watched Simon Sinek’s TED talk, you definitely should.

Same with Brené Brown. Her books are amazing Dare to Lead and The Gifts of Imperfection but there’s just nothing like hearing her speak.

Going Further

Are you a leader thinking the world is just a little too infinite right now? Could it be time to reinvent yourself and your career? During the month of February, sign up for a special, FREE “Career Reinvention Session.” Personally, I’ve successfully navigated four major career shifts and would love to help you do the same.

In this one-hour session you will:

  • Clarify your “why” (a’la Simon Sinek) and reconnect with the parts of your work that bring you joy and flow.

  • Uncover hidden challenges and vulnerabilities (a’la Brené Brown), and reveal how those might be impacting other areas of your life.

  • Learn how to utilize the most impactful tool in a career transitioner’s arsenal.

  • Develop a long term strategy and immediate action plan to either intentionally redesign your current position or land a great new job.

  • Leave this session with a career compass that makes you feel renewed, inspired and reenergized.

Why is this being offered for free? I’m pilot testing a new design for my free initial chat / consultation and perfecting my process for helping clients find their “why”. We both get to benefit. My promise to you: NO high pressure sales pitch at the end.

If you are interested, here’s a direct link to my CALENDAR to sign up for a spot.

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