Kristin, Denise, and Tim close out the month with a Kenny Rogers classic that becomes the perfect metaphor for March: you’ve got to know when to hold ’em, know when to fold ’em, know when to walk away, and know when to run. What starts as a nostalgic exchange about childhood music rooms, shag carpet, and dads who loved Kenny Rogers quickly shifts into a deeper conversation about projects, perseverance, and the moment you realize something has to change.

The trio revisits the story of the Chicago Spire; once imagined as the tallest building in the Western Hemisphere, later abandoned as nothing more than a massive, disappointing hole in the ground. But now, years later, that hole has hope. It’s a powerful reminder that sometimes the original dream collapses, but the ground can still be used for something new.

Kristin, Tim, and Denise walk listeners through three grounding questions for anyone stuck in the murky middle of a project:
• Is your foundation strong?
• Is the mission still aligned?
• Is the stall external or internal?

Together, they explore the difference between a dip that requires grit and a dead end that requires a pivot. Support systems, timing, vulnerability, and courage: what it takes to either push through or walk away. And they set the stage for next month’s theme: reframing “failure” as something far more nuanced — and sometimes far more beneficial — than we tend to believe.

It’s reflective, warm, and full of the grounded encouragement that makes this show feel like a conversation with friends who want to see you finish strong.

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Kristin, Tim, and Denise returned to the story of the Chicago Spire, the grand dream that became nothing more than a massive hole in the ground. It becomes the perfect backdrop for a deeper look at the danger zone of any project, the moment when you are 90 percent finished and suddenly everything feels harder instead of easier. Kristin explains how that last stretch can be the most treacherous, the place where fatigue sets in, decisions pile up, and the finish line feels both close and impossibly far. The group laughs about grades and odds, but underneath the humor is a truth anyone who has ever tried to finish something meaningful will recognize.

The three explore why the final push can feel so overwhelming. Denise shares her own story of home renovations, and the moment she hit decision fatigue so hard she refused to add a storm door she now wishes she had. Tim introduces the goal gradient effect: people speed up when the finish line is attainable, but stall when it feels out of reach. Kristin brings in Seth Godin’s idea of the quit dip, that predictable slump where motivation drops, and doubt rises. Together, they name the emotional weight of the almost, the place where people abandon projects not because they lack ability but because they are tired, uncertain, or simply worn down.

Here’s the reminder: the dip is not a sign to quit, but a signal to pay attention. Kristin and Denise talk about how support, encouragement, and the right people around you can make all the difference when you are tempted to stop digging. The Chicago metaphor lingers in the background as they wonder aloud whether the next step is to push through or to walk away. It becomes an invitation to look honestly at your own projects, your own dips, and the people who help you climb out of them. The finish line may not always be visible, but the right company can make the path feel possible.

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The hosts delve further into the ambitious yet troubled story of the Chicago Spire, a skyscraper that aimed to redefine Chicago’s skyline at a staggering 2,000 feet. Amid playful banter and musical references, the discussion shifts between nostalgia for the band Chicago’s music and the bubbling excitement surrounding this architectural dream. However, the hosts are quick to point out that this grand vision ultimately faced a harsh reality: the project fell victim to the 2008 financial crisis, leaving behind little more than a deep hole in the ground.

The conversation intertwines the concept of dreams with the often unglamorous reality of execution. There is a reflection on the challenges faced by entrepreneurs and dreamers alike, emphasizing the importance of not only having a vision but also the structure to bring it to life. They draw parallels between the lofty aspirations of the Chicago Spire and the everyday struggles of small business owners, illustrating how excitement can often overshadow the tedious but essential groundwork that lays the foundation for success. As they navigate the pitfalls of ambition, listeners are invited to consider their own dreams and whether they are building excitement or taking the necessary steps to create a solid framework.

A critical gut check emerges: Are we truly prepared to chase our dreams, or are we merely caught up in the thrill of the idea? The hosts challenge listeners to reflect on their personal goals, urging them to balance excitement with practicality. They hint at the next episode’s exploration of the dangers of stalling at the 90% completion mark, leaving the audience on the edge of their seats, eager to learn more about the complexities of ambition, timing, and the often unpredictable nature of pursuing our dreams. This episode serves as a thought-provoking reminder that, while dreams may soar high, the realities of structure and timing are what ultimately determine their success.

Like, rate, review, whatever your podcatcher platform allows. But, above all, subscribe.
Follow Kristin Johnson on her website, KristinJohnsonSpeaks.com