The Ego Is the Thing in the Way

Insights and Activities from September's Joyful Connection Masterclass

September's masterclass opened on celebration, which was fitting, because the host was in the middle of his birthday week and the room was full of people who, by their own admission, are not very good at celebrating themselves. Kids back in school. Trips coming up. A nearly complete team heading to a conference. The updates came in warm and easy before anyone was asked to do anything harder.

Most introductions stay shallow, not because of a lack of time. It is the ego. When we are being asked to describe ourselves, we reach for the version worth showing, the title, the achievement, the polished line. The performance goes up, and it's exactly what keeps two people at arm's length.

This session was built to get underneath it.

None of the four activities asked anyone to be impressive. One started from a competition. One asked what has quietly served you rather than what makes you exceptional. One allowed a single word of reply, repeated, until the polished answer ran out and something true was left. The design across all of them pointed the same way. You reach the real person faster by removing the performance than by asking for depth. Here is a closer look at the activities that shaped the experience.

Celebrating Yourself with Hansen Hunt

Opening on the one kind of praise most people deflect

Hansen Hunt, who hosts the masterclass and leads the Connection Crew at Covve, opened with a prompt borrowed from one of the day's panelists during their planning session. What is a memorable celebration of you?

He was honest that the question is a hard one, for him as much as anyone. He does not celebrate himself easily, and he asked the room who else felt the same. Plenty of hands went up. The discomfort was the point, and naming it out loud made the prompt safe to answer.

Hansen modeled it with his sobriety birthday from the year before. Rather than mark it quietly, as he usually had, he threw a party at a bar where every drink was non-alcoholic and invited his men's group and the friends who had walked his sobriety journey with him. They did not only celebrate him. They celebrated everyone in the room who was sober, and shared a few gratitudes along the way. He named the whole thing plainly, that celebrating himself took real intention and that the effort was worth it.

Opening on a celebration of the self does quiet work. It signals from the first minute that this room is not for the highlight reel, and that the honest answer, the one that admits how hard self-celebration is, is the one that belongs here.

How to Practice It:

• Open a gathering by asking people to name a celebration of themselves, since the prompt most of us deflect is also the one that gets past the polished answer
• Name the discomfort out loud and ask who shares it, so people know the honest answer is the one that belongs
• Model your own with something that mattered, since the weight of your example sets the weight others will feel free to bring

Competing Your Way Into Connection with Luca Oake

Finding the spark before the words

Panelist Luca Oake, co-founder of Moneystep, a step challenge app built around the reward of competition, opened with a defense of a thing that usually needs one. Competition gets a bad rap, she said, especially in professional spaces where so much feels zero-sum. But a game can create an immediate reason to interact, to laugh, to loosen up. For awkward adults meeting for the first time, finding your spark can be far more rewarding than finding your words.

The activity is simple and deliberately silly. Pair up, invent a thirty-second competition on the spot, and the more ridiculous the better. Fastest chair spinning. Toughest tongue twister. Lamest pun. The winning is almost beside the point. The point is what competing together makes possible that talking never would.

Luca modeled her own competitive streak with a story about her step tracker. Years ago she sold her car and built her life around walking, long before anyone counted steps. When trackers arrived they woke a competitive spirit she had not known she had. The story peaked on a travel day in London, where she found herself at eight in the evening sitting on eighteen thousand steps and decided she was not done. She spent an hour hoofing laps around an oval coffee table like it was an Olympic track and she was Usain Bolt, and at twenty-two thousand she threw her hands in the air and declared victory for Team Twenty-Two Step.

Emily Weiner modeled the live version with her. Neither could find a competition that worked, a shared step obsession and a shared couponing streak both went nowhere, until they landed on worst pun, judged by the biggest groan in the chat. What followed was a genuine battle. A pirate's favorite letter, which is not the R you expect but the C. A sad cup of coffee named Morning Joe, whose friends suggested therapy until he became Depreso. Emily closed it out with a bad joke that becomes a dad joke the moment it is apparent, and the groan sealed her win.

The thing the game unlocked was not the jokes. It was that two people who had never competed before were laughing together inside ninety seconds, which is a place a conversation rarely reaches that fast. Competition, done for fun, is a doorway.

How to Practice It:

• Start with a shared action rather than a conversation, since a game gives awkward strangers a reason to engage before they have found their words
• Make the competition ridiculous and low-stakes, so nobody's ego is on the line and the laughing comes easily
• Notice what the game made possible, since the winning matters far less than the connection it opened

Asking Why Until You Reach the Root with Brad Steckart

Stripping a conversation down to its single honest question

Panelist Brad Steckart, the founder and CEO of Sit By Me, an app that helps people connect in real life and real time in cafes and co-working spaces, ran a game called Just Why, sometimes known as Five Whys. The rules are almost nothing. One person finishes the sentence I am, with something like I am a mother or I am a builder. The other person's only job, every single turn, is to ask why. No other questions, no comments, just why, again and again.

Brad was upfront that it gets deep fast, and he handled that with care. He framed it like a yoga class, only go as far as feels comfortable, and gave everyone an exit before they began. If a question reaches too far, you say I am complete, or simply that you would rather stop, and that is entirely fine.

He modeled it on himself to show the speed. I am a connector. Why? Because I believe most people are one conversation away from feeling less alone. Why? Because I have felt that alone before, and one conversation changed it. Why? Because when he was working two jobs, in grad school, in a bad relationship and having a hard time, someone noticed him at a coffee shop and talked to him, and that is the reason he is here. Three whys, and he was at the root of who he is.

Luca Oake modeled the live version. Asked to finish the sentence, she said I am a partner, and the whys pulled the rest into view. Although she works well alone as an only child, she becomes more when connected to someone she cares about who cares back. The reason is a saying she keeps, that safety is the presence of connection, and that being safe is what lets her feel complete. Brad stopped there, because they had already arrived somewhere real.

The design lesson is in the constraint. By forbidding every response except why, the game removes the small talk, the comparing of notes, the polishing, and leaves only the next honest answer. A first conversation almost never asks why more than once. This one asked it until the performance ran out and the root was showing.

How to Practice It:

• Reduce a getting-to-know-you exchange to a single repeated question, since the constraint removes the small talk and leaves only what is true
• Build in a clear exit before you start, so people can go deep by choice rather than by pressure
• Keep asking past the first answer, since the polished version comes first and the real one comes a few whys later

Naming What Has Served You with Emily Weiner

Trading the superpower question for one that leaves the ego out

Panelist Emily Weiner, a systems-thinking entrepreneur and the founder of The Connectors, closed with an activity about the qualities that make a person who they are. Some feel innate, she noted, and some are behaviors cultivated over years, which means they can still be grown. She asked the room to name one quality that has served them well, in any part of their life, and if there was time, one they would like to cultivate more of.

The phrasing was the whole design, and it drew the sharpest reaction of the session. Emily deliberately avoided asking what is your superpower. As several people named afterward, the superpower question invites the ego in, turns the answer into look at me. Asking instead what has served you well quietly removes the ego and turns the answer toward how a person actually shows up for others. One participant said the reframe was refreshing precisely because it lets people go as deep as they want and no deeper, offering the connection without prying anyone open.

Emily modeled it with the empathetic connecting she has done since kindergarten, built out of moving constantly as a child, six schools in nine years across three states, learning to read a playground and fold herself into a new group fast. The quality she is still cultivating is comfort with ambiguity. She has always been the calm in the storm, but she used to treat ambiguity as a problem to solve, and only over the last fifteen years has she learned that sitting with it rather than fixing it can open doors she would otherwise have closed.

Brad Steckart modeled it with her, and named resilience as the quality he has grown. Two years ago, he said, you would not have looked at him and seen it, but building a company has taught him to wake up after a hard day and get an inch further, or a centimeter if that is all there is. The quality he wants to cultivate is planning, admitting that if a thing is not on his calendar he might simply not be there. Emily closed on that gap with a useful point. You cannot embody every quality, and the ones you lack are a reason to seek out and connect with the people who have them. She happens to know Brad's wife is an excellent planner.

How to Practice It:

• Ask what quality has served someone well rather than what their superpower is, since the reframe leaves the ego out and points the answer toward how they show up for others
• Let the question hold both a strength and a quality still being grown, so it invites honesty rather than a performance of confidence
• Treat the qualities you lack as a map of who to connect with, since no one embodies them all and partnership fills the gaps

Thank You

Thank you to Luca Oake, Brad Steckart and Emily Weiner for designing and leading these activities, and to Hansen Hunt for hosting. The three panelists built their activities separately and found, when they came together, that the pieces fit like Lego blocks, each one opening the door a little wider than the last. Thank you also to everyone in the room who set down the polished version and let a stranger meet the real one.

The session made a case worth carrying out. Connection does not arrive because we ask for it or perform our way toward it. It arrives when the ego steps aside, whether a silly game gets it out of the way, or a reframed question quietly sets it down, or a single repeated why wears it through. What is left underneath was always the more interesting thing.

We look forward to continuing this work and to helping more people feel genuinely connected, one conversation at a time.