May 4, 2026Playing the Game of Life: Events and Experiences That Actually Transform

What if the goal was never to finish the game, but to love playing it? That question sat with me long after my conversation with Jess Ekstrom, the 2x social entrepreneur, Forbes Top Rated speaker, and bestselling author behind Headbands of Hope and Mic Drop Workshop. She has spoken for clients like Netflix, Zappos, Canva, and Harvard, and she has built something most people spend years trying to figure out: a career rooted in purpose, play, and genuine human connection.

What Jess and I talked about went beyond events as a business format. We talked about why events work, why they endure, and why they are becoming more valuable the more we lean on artificial intelligence and digital tools to run our lives. Events are not just content delivery mechanisms. They are collision points. They are slow burns. They are the places where one sentence from a speaker can sit quietly in someone’s mind for three years before surfacing exactly when it is needed.

In this post, I want to unpack what Jess shared about the value of in-person experiences, the entrepreneurial mindset that makes them sustainable, and why the game itself, not the finish line, is what keeps people like her, and people like me, coming back to this work.

🎤 Watch and listen to the full interview about events here

Events as Collision Points That No Digital Platform Can Replace

There is a moment that happens at live events that I cannot explain any other way except to call it a collision. You are filling up coffee at the side station before a morning keynote, and you start talking to the person next to you. Maybe they are another speaker on the same lineup. Maybe they are an attendee who traveled three states to be in that room. You were not scheduled to meet. There was no calendar invite. But something happens, and you walk away changed, even slightly.

Jess put it plainly when we spoke: these are collision points with other people that you simply would not get on a Zoom call. She said, and I believe her completely, that these in-person experiences are becoming increasingly more valuable the more we rely on artificial intelligence and technology. Not because technology is the enemy, but because human connection needs to be counteracted, counterbalanced, and protected.

This is something I have seen play out at every level of events production. The conference that looks modest on paper produces a relationship that becomes a business partnership two years later. The workshop, which nobody expected much from, turns into the catalyst for a career pivot. The things that matter most at events are almost never the things on the agenda.

And that is precisely why in-person experiences resist replacement. You can record a keynote. You can stream a panel. You can host a webinar with a thousand attendees. But you cannot engineer serendipity. You cannot schedule the collision. That is the irreplaceable currency of live events, and it is a currency that is appreciating, not depreciating, as our screens multiply.

The more we communicate through apps, the more a real room full of real people feels rare. Jess knows this intimately. Her career as a keynote speaker is not just about standing on stage and delivering content. It is about being present in a space where human moments can happen, and trusting that those moments will do their own work in ways she may never fully see.

The Slow Burn: Why the Best Feedback Takes Years, Not Days

Jess said something in our conversation that I keep coming back to. When I asked her what her favorite thing about speaking is, she gave me two answers. The first was the one you might expect: the ripple effect, the DMs, the emails. But she was quick to clarify which ones she finds most meaningful.

“My favorite ones are the ones that were like, you spoke three years ago, not you spoke three days ago.”

That distinction matters enormously. A message three days after a talk is often a response to the energy in the room. It is the emotional residue of a good event. It is real, and it is meaningful. But a message three years later? That is something else entirely. That is someone telling you that something you said planted itself quietly and waited. It waited until the moment they needed it. Until the question you answered matched the crisis they were living. Until the mindset shift you modeled was the exact one they had to make to move forward.

This is the slow burn that defines the best work in storytelling and public speaking. The ideas that simmer. The ones that work their way through a person’s life on their own timeline, independent of the speaker’s intentions or expectations.

For anyone building a speaking career, or producing events, or even just creating content with the hope that it serves people, this is worth sitting with. The feedback cycle is not short. The returns are not immediate. If you measure your impact only by what lands in the first week, you are measuring the wrong thing.

I spoke about this with Jess in the context of what we believe at The Keynote Curators: that speeches can genuinely change a life. It can sound like marketing language when you read it on a website. But when you have been in this industry long enough, you understand it as a lived truth. Someone hears something in a room. It simmers. It surfaces. And years later, a speaker gets a message that confirms it. That is the slow burn in action. That is why events matter beyond the metrics.

The implication for event organizers and planners is significant. When you book a speaker, when you design a program, when you choose the conversations you want to spark, you are not just planning a day. You are planting things in people that may not bloom for years. That is not a reason to lower expectations. It is a reason to raise the standard of what you put in the room.

Playing the Game: Why Entrepreneurship and Events Demand the Same Mindset

One of the threads running through my conversation with Jess was the idea of playing versus finishing. She talked about working with a business coach during a difficult stretch in her entrepreneurial life. She was frustrated, dealing with an employee situation and a sponsorship that had not worked out the way she hoped.

Her coach asked her to think of a CEO she admired. Jess named Sarah Blakely. Her coach then asked: do you think she has had to fire someone? Lost money on a campaign? Of course. “These are not signs that you’re not qualified. They’re signs that you’re in the game.”

That reframe is one of the most useful things I have heard in any conversation about entrepreneurship or events. When you are in it, the problems feel like evidence against you. They feel like proof that you do not belong, or that you have made a mistake. But they are actually just the texture of the game. They are what it feels like to be playing, not watching.

The parallel to events is direct. Producing live experiences is hard. Speakers cancel. Venues fall through. AV fails. Attendees who RSVP do not show up, and people who did not register become your best sponsors. The process is unpredictable, imperfect, and demanding. And all of that is just what it means to be in the game.

Jess described it through a different lens too: the inbox that never empties. She talked about wanting to get to the bottom of the pile, to reach inbox zero, to finish the last item on the list. And then hitting refresh and watching everything repopulate. “The game is just the pile. It’s always gonna be there.” The shift for her was not clearing the pile. It was changing how she showed up for it.

That shift is what separates people who sustain long careers in events, in speaking, in business leadership, from those who burn out. It is not a productivity system. It is a relationship with the work itself. If the work is something to be finished, you will always be behind. If it is a game you love to play, the pile becomes proof that you are still in it.

Why Goals Can Limit the Winning Scenarios You Never Knew Existed

Jess made a point about goals that challenged me a little, in the best way. She said she thinks goals are great, but that where they get in the way is by making us feel there is a finite number of options available to us. That there is a win or a loss, a right or a wrong, a done or a not done.

She used the example of someone who starts making sourdough bread after watching a TikTok on a Saturday afternoon, and a few months later is running a pop-up bakery at the school carpool line. That person did not set a goal to become a baker. They just started playing. And a winning scenario appeared that they never knew existed.

This applies to events in ways that are both practical and philosophical. When we design events around fixed outcomes, we often close off the possibilities that would have made them memorable. When we are too attached to the agenda, we miss the conversation in the hallway. When we measure success only by the metrics we set in advance, we miss the evidence of impact that shows up later, quietly, in a message from someone who needed exactly what was in that room.

Jess said she did not even know speaking was an industry when she was growing up. She would not have named it as a goal at six years old. But she found it, and it fit, and now she is among the most recognized voices in a field she discovered by playing, not planning.

There is something worth protecting in that. The best thought leadership does not arrive through rigid strategy. It emerges from genuine curiosity, from following what feels meaningful, from being open to winning scenarios that do not appear on any roadmap. Events, at their best, create the conditions for exactly that kind of discovery.

The Ripple Effect and Why In-Person Speaking Scales Differently

There is a common assumption in the content world that digital scales and live does not. You can post a video and reach a million people. You can write an article and have it read in forty countries. A keynote, by contrast, happens in one room, on one day, for a few hundred people at most.

But Jess’s framing of the ripple effect complicates that assumption in a meaningful way. The reach of a live speech is not measured in the room. It is measured over time, through the choices people make, the conversations they have, the things they try or stop trying because of something they heard. It is measured in the messages that arrive years later. It is measured in the way one person, changed by a single idea, changes the people around them.

This is the argument for investing in events that most analytics dashboards cannot capture. A talk does not just reach the people in the seats. It reaches the teams those people lead, the families they go home to, the decisions they make over the next three years. The downstream impact of a single well-placed idea in a well-chosen room is genuinely incalculable.

For organizations thinking about whether live events are worth the investment, this is the case that rarely gets made clearly enough. The ROI of a great speaker is not just the applause at the end of the session. It is the way an organization moves differently because the people inside it were shifted. That shift starts in person, in a room, in the kind of moment that cannot be manufactured on a screen.

Jess built her career on exactly this understanding. Her work in personal development and empowerment is not about delivering a message and walking off stage. It is about planting something that grows in the people who heard it, in timelines she cannot predict and ways she cannot measure. That is what makes speaking, and events more broadly, a category unto itself.

How Playing Not to Lose Changes Everything About Events

There is a distinction I keep returning to from our conversation, one that Jess and I circled around without fully naming until near the end. There is a difference between playing not to lose and playing to win. When you play not to lose, every setback feels catastrophic. Every mistake is evidence of inadequacy. The goal is survival, and survival is exhausting.

When you play to win, the calculation changes. You are not defending. You are building. The mistakes are still there, but they register differently. They are information, not indictment. They are the cost of participation in a game worth playing.

For event professionals, for speakers, for anyone in the business of creating live experiences, this distinction is everything. The events that endure are almost never the ones produced by people trying not to fail. They are the ones produced by people who love what they are building, who find the problems interesting rather than threatening, who show up for the pile because the pile is the game.

Jess embodies this. She started Headbands of Hope on a $300 grant in college. She built Mic Drop Workshop because she wanted more women to find what she found: a stage, a voice, a way to share something that mattered. She did not know either of those companies would become what they became. She just played, and stayed in the game long enough for the winning scenarios to appear.

That is the orientation that events reward most generously. Not the perfect plan, not the locked-in outcome, not the measurable ROI projected three months out. The orientation that says: I believe in what happens when people are in a room together. I believe in the collision. I believe in the slow burn. And I am willing to keep showing up for it.

Why Women in Speaking and Events Need More Stages

One thing Jess said that I want to give its own space is her commitment to getting more women on stages. She founded Mic Drop Workshop not just to teach public speaking, but to close a gap she had witnessed and lived. The speaking industry, like many industries, has not always been built with women’s voices at the center. Jess decided to change that.

She wants to see the 40 Over 40 and the 50 Over 50 lists, not just the 30 Under 30. She wants to see women who pivoted, who started over, who found their voice in the second or third chapter of their career. Because that is also what women leaders in speaking look like. Not just the prodigies and the early achievers, but the ones who kept playing until they found the game that fit.

This connects directly to what makes events powerful in the first place. Stages are not just platforms for information transfer. They are platforms for representation. When a woman in an audience sees a woman on stage speaking her experience with confidence and humor and authority, something happens that no video, no podcast, no digital content can replicate. Presence changes what is possible in people’s minds.

Events are one of the few places where that kind of visibility happens in real time, in a shared space, with the full weight of a live audience witnessing it together. That is not a small thing. It is one of the most important things events do, and it is worth being intentional about.

Concluding Thoughts on Events, Playing, and Staying in the Game

I started this piece with a question: what if the goal was never to finish the game, but to love playing it?

After spending time in conversation with Jess Ekstrom, I am more convinced than ever that this is the right frame for anyone building something in the world of events. Not because the outcomes do not matter. They do. Not because the metrics are irrelevant. They are not. But because the work itself, the collision points, the slow burns, the messages that arrive three years later, the rooms full of people who needed to be in the same place at the same time, that work is its own reward.

Resilience in this industry is not about toughness. It is about orientation. It is about deciding that you are playing, not just surviving. It is about trusting that the pile is the game, and that showing up for it, again and again, is enough.

The more I do this work, the more I believe that in-person events are not a format in competition with digital. They are a category of human experience that digital cannot replicate. And as we build more of our lives on screens and algorithms, the rooms where real people meet, collide, and change each other will only become more precious.

Jess Ekstrom is a living example of that. She built companies out of frustration. She found an industry she did not know existed. She is now helping other women find their stages because she knows what it meant when she found hers. And she keeps playing, not because she has figured it out, but because she loves the game.

That, ultimately, is the argument for events: not the ROI slide, not the engagement metrics, not the post-event survey scores. The argument is that humans change each other in rooms. That speeches can change a life. That a single idea, planted in the right moment, can simmer for years and surface exactly when someone needs it.

That is the game. And I, for one, love to play.

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📙 Check out Jess Ekstrom’s new book, Making It Without Losing It, out now: https://a.co/d/03fBh5AN

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