The Kristen Boss Podcast — Episode 242: The Messy Middle

Release Date: December 8, 2025
Host: Kristen Boss

Episode Overview

In Episode 242, "The Messy Middle," Kristen Boss offers an honest, unfiltered solo deep dive into the often-overlooked and uncomfortable transition phase in any transformation journey: the "messy middle." Speaking candidly from personal experience as both a high-performing entrepreneur and someone navigating major life transitions, Kristen explores why this challenging stretch—between exciting beginnings and celebrated outcomes—is crucial for true growth and sustainable success. She addresses the emotional complexity of enduring long periods without outward reward, how to build resilience and self-trust, and practical strategies for persevering when progress feels slow, invisible, or frustratingly mundane.

Key Discussion Points & Insights

1. Setting the Context: Unpolished Realities

• Kristen records from her parents' basement due to unexpected lack of internet at home, setting a tone of authenticity and embracing imperfection.
  • "If you notice that I sound a little different, that is because I am without my podcast mic... I'm in the basement of my parents house because we have no Internet." (01:00)

2. The Allure of Beginnings and Endings vs. The Messy Middle

• People eagerly buy into the excitement of starting new ventures or pursuing big goals, and they fantasize about the victorious end.
• The "messy middle," however, is emotionally neglected; it's when people most often consider quitting.
  • "We are emotionally bought into two parts of transformation... the beginning is always exciting... and then we of course are excited about the end goal... But the part that we have little to no buy in with... is the messy middle." (01:49)

3. The Reality of Foundation Building

• Kristen compares major life changes to digging the foundation for a skyscraper—the deeper the change, the deeper and longer-lasting the foundational phase.
  • "The higher the skyscraper has to go, the deeper you have to dig the foundation. And I feel like this year has been digging a foundation far longer than I wanted to and feeling like all there is is a hole in the ground." (03:35)

4. Transformation Happens in the Middle

• The messy middle is where character, resilience, and true skill are built—not at the start, nor upon achieving the result.
  • "This is your training ground. This is when your character is built. This is where all your lessons are. We don't learn our lessons in the beginning." (04:25)
• Reflection often brings clarity to this period, seen only in hindsight.

5. Mistakes, Frustration, and Compassion: A Piano Lesson Analogy

• Using her daughter's emotional struggle learning new piano songs as an example, Kristen draws parallels between childhood frustration at learning and adults' discomfort with being new/bad at something.
  • "Sometimes as adults, we don't grow out of that version of ourselves that gets frustrated at the piano when we're making mistakes of our first run through. We get emotional, we get frustrated, we stand up and walk away, and we forget to tell ourselves, like, oh, of course I'm making mistakes. This is my first time trying this." (06:29)

Notable Quotes & Memorable Moments

• On Social Media vs. Reality:
  • "Honestly, this year for me, I just feel like I have nothing. Like, what's the opposite of a highlight reel? Like a downer." (07:40)
• On Transformation:
  • "When you start out, you're not the person who's able to get the results. It's the process that builds you. The middle is the transformative part of the process." (08:30)
• On High Achievers' Fear of Failure:
  • "I also think that's why some successful people are terrified to try new things, because what if they're not successful at the next thing?" (09:29)
• On the Value of Consistency over Intensity:
  • "We are a society that values intensity and not consistency. And so if it's not happening fast enough, fancy enough, sexy enough, you know, we quit." (12:59)
• On Low Frustration Tolerance:
  • "My coach at the time said, Kristen, you have to build your tolerance for fresh—your frustration tolerance. And I, like, hated that." (13:52)
• On Building Habits and Self-Trust:
  • "When you actually stay in the middle, this is about building reps. This is about building your trust with yourself that you're not somebody who gives up when it's boring and hard." (15:49)
• On Boredom as a Necessary Challenge:
  • "If we don't know how to navigate boredom, then we're constantly going to be people that seek stimulus and excitement and dopamine. And I think—we have a real problem with that. I think boredom is actually important for us." (17:21)
• Final Encouragement:
  • "I honestly think the best things in life are not a product of doing really sexy things, but doing the boring, the mundane, over and over again." (19:36)

Practical Guidance: How to Survive (and Thrive in) the Messy Middle

Kristen offers concrete strategies for staying the course:

• Expect Boredom:
  • "If things feel repetitive or ordinary, congratulations, you're in the right place." (16:32)
• Look for Small Wins:
  • "Condition yourself to look for smaller wins instead of big ones." (16:33)
• Downsize Your Work:
  • "Make the work smaller so at least you can be consistent in your follow through instead of bigger... Smaller is about consistency." (16:40)
• Don’t Rely on Motivation Alone:
  • "Motivation is inconsistent. So if you're only working when you're motivated, you're only going to be working some of the time." (16:58)
• Revisit Your ‘Why’:
  • Connecting with your purpose is critical when excitement isn’t available.
  • "When it's painful and thankless and not rewarding and frustrating, you have to remind yourself, this is why I'm doing this." (17:06)

Timestamps for Important Segments

• [01:31] — Kristen sets the scene and introduces the messy middle as the episode’s main focus.
• [03:28] — Using the skyscraper analogy to discuss deep foundational work.
• [04:22] — The messy middle as a training ground for character and skill-building.
• [06:29] — The piano lesson anecdote: learning to embrace mistakes and frustration.
• [07:40] — Social media’s highlight reel vs. real life’s “downer reel.”
• [09:29] — The struggles high-achievers face with being new and risking failure.
• [10:03] — Learning from failure and seeking micro-wins (plant/money tree analogy).
• [12:59] — Society’s bias for intensity over consistency.
• [13:52] — Building a tolerance for frustration.
• [16:33] — Practical strategies for not quitting in the middle.
• [17:21] — Why learning to cope with boredom matters for long-term growth.
• [19:36] — Final encouragement to appreciate the compound effects of consistent, mundane effort.

Episode Takeaways

• The messy middle is an inevitable, essential, and highly transformative phase in any personal or professional journey.
• Progress is often slow and invisible; learning to notice small wins and build frustration tolerance is crucial.
• Sustainable success is the product of mundane, consistent effort—and the willingness to keep going when things are neither exciting nor externally rewarding.
• Learn to value your internal growth, not just external achievements, and revisit your purpose when motivation runs dry.

Kristen’s message: Embrace the messy middle, develop compassion for yourself, and recognize that real change is forged in the ordinary, not the extraordinary.