The Goal Digger Podcast – Episode 936

Title: I Thought I Was Building a Business: What I Was Really Building All Along
Host: Jenna Kutcher
Date: December 3, 2025

Episode Overview

In this deeply personal solo episode, Jenna Kutcher reflects on nearly a decade of entrepreneurship, unpacking what she’s truly been building through her business journey: not just a business, but a life that feels wholly her own. Jenna reveals the hidden lessons, tensions, and mindset shifts that underpin her “practical strategy, deeper truth” philosophy. This is her “through line” episode—a culmination of her work and wisdom, intended as the one episode to listen to if you ever only hear one Goal Digger.

Key Discussion Points & Insights

Jenna’s Entrepreneurial Origin Story

• Small beginnings:
  Jenna launched her photography business from a 1,200-person village in Wisconsin, hustling after hours while working a demanding corporate job and planning her wedding.
  (06:45) “I was absolutely, positively burning the candle on every end. And yet I knew underneath the surface that it would all be worth it.”
• Realization about the corporate world:
  A touching moment with her boss, who saw her kids for only an hour each night, pushed Jenna to question the true meaning of life and success.
  (10:29) “Am I okay with just seeing this guy one hour a night?”

The Pursuit of Freedom and the Limits of Hustle

• Motivation for entrepreneurship:
  Freedom—of place, time, choice, and purpose—was always Jenna’s driver.
  (12:47) “Time is your currency…it really became the way that I moved closer towards the life I want now.”
• Early grind and burnout:
  Jenna recounts booking 30 weddings per year in the Midwest’s short wedding season, hitting six figures but feeling emptiness and exhaustion.
  (21:10) “I thought this would feel different…I thought that the angels would be singing.”

Redefining Success & Embracing 'Enough'

• Intentionally scaling back:
  Facing burnout, Jenna mapped a return to $50K/year—choosing joy and presence over revenue.
  (23:20) “Revenue without rest is just another cage. It’s just another ladder climb. Except for this time, it’s one I’ve created.”
• Paradoxical growth:
  The year she scaled back to 15 weddings, she found time for creativity and discovered scalable income streams—leading to her first seven-figure year.
  (28:44) “Every time I’ve made this decision to claim back more time… I have unlocked a new lease on life.”

Taming Shiny Object Syndrome & Setting Boundaries

• Jenna’s ADHD & multi-passion tendencies:
  Masterminds and new opportunities threatened to scatter her focus; instead, she chose to build a business that was “rinse-and-repeat.”
  (32:05) “Yes, I can do all of these things—but should I? And do I want to?”
• Motherhood and radical boundaries:
  On the cusp of motherhood, Jenna blacked out her calendar, delegating declines and prioritizing her values.
  (34:41) “Every yes I was saying to someone else was a no to being present as a mom.”
  • Memorable practice: writing a heartfelt “decline” template for her team to automate saying no.

The Power of Systems, Simplicity, and “The Boring Business”

• Enablement through integration:
  Standalone systems (email, Pinterest, podcasting) combine to form a compounding, freedom-giving flywheel.
  (17:14) “One was built and mastered, and then I moved on to the next. My business is a flywheel.”
• Embracing the boring business:
  Systems yield predictability and genuine life freedom—what some may call boring is, for Jenna, true success.
  (62:18) “If you could have a business that runs so smoothly it almost feels boring, I would argue that that is the opposite of failure. It is freedom.”

The Park Bench Moment: On Presence

• Story analogy:
  Two women save 10 minutes on the subway—one fills it with work, the other sits in the park.
  (51:01) “Time isn’t just a resource that you manage. Time is your life.”
• Lesson:
  The point of saving time is not to do more work—but to live more.

What’s Really Being Built: Identity & Transformation

• Business as a vehicle for becoming:
  The journey is less about outward achievement, more about the person you become and the presence you cultivate.
  (73:05) “Work isn’t just what you build. It’s the person you become while you are building it.”
• Presence as the metric of success:
  Through a quote and a compliment (“You’re the first relaxed woman I’ve ever met”), Jenna reframes her entire metric of success.
  Quoting Nicola Jane Hobbs, The Relaxed Woman (68:21):
  “Growing up, I never knew a relaxed woman. Successful women, yes…But relaxed women, at ease women… I'm not sure I've ever met a woman like that, but I would like to become one.”

Sustainable Entrepreneurship & The Joy Journey

• Beyond 'roles':
  Jenna shares how she intentionally made her work the least interesting thing about her, exploring hobbies, volunteering, and building community presence.
• Sustainability as a way of being:
  (80:21) “Sustainability isn’t just a business strategy. It’s literally a way of being.”

Notable Quotes & Memorable Moments

• On accidental self-imprisonment through business:

  “Entrepreneurship is often pursued for freedom, but we knowingly and unknowingly start to build these cages that don’t allow for true freedom to exist in our lives.” (27:48, Jenna Kutcher)

• On the feeling of ‘making it’:

  “I thought this would feel different. I thought I would be using fancier shampoo… But beyond looking different, I thought it would feel different.” (21:13, Jenna Kutcher)

• On systems and creativity:

  “Structure is not the killer of creativity; it is the foundation that will make room for it.” (61:15, Jenna Kutcher)

• On boundaries:

  “Boundaries don’t keep things and people out. They keep you in your life. They are the walls around what is sacred to you in your life. Boundaries are a gift. They’re not a punishment.” (41:20, Jenna Kutcher)

• On presence:

  “Presence was the ultimate success metric. Not revenue, not reach, not recognition.” (70:44, Jenna Kutcher)

• On 'boring' business as freedom:

  “Having a boring business has given me the greatest joy in my life. If you could have a business that runs so smoothly it almost feels boring, I would argue that that is the opposite of failure. It is freedom.” (62:18, Jenna Kutcher)

• On defining your own enough:

  “The brake pedal isn’t giving up. The brake pedal is choosing. It’s deciding what matters and it’s protecting it fiercely.” (86:24, Jenna Kutcher)

Important Timestamps for Key Sections

| Timestamp | Topic | |-----------|-------| | 03:13 | Jenna’s entrepreneurial origin & “through line” concept | | 10:29 | The corporate ‘golden handcuffs’ and pivotal realization | | 21:10 | First six-figure year—dissonance & exhaustion | | 23:20 | Choosing “enough” over endless hustle | | 28:44 | Paradox: growth through doing less | | 32:05 | The temptation and risks of shiny object syndrome | | 34:41 | Radical boundaries in early motherhood | | 41:20 | Boundaries as sacred protectors | | 51:01 | The park bench story—on the purpose of time | | 62:18 | The gift of a “boring business” | | 68:21 | Quote from Nicola Jane Hobbs’s The Relaxed Woman | | 70:44 | Presence as the true metric for success | | 73:05 | Business as the vehicle for becoming who you are | | 80:21 | Sustainability as a lifestyle, not a tactic | | 86:24 | The brake pedal as a metaphor for intentional living | | 90:12 | The closing ‘through line’ and Jenna’s ultimate hope for listeners |

Jenna’s Closing Message

Jenna wraps up with a heartfelt reminder that what most entrepreneurs are really building isn’t a business, but a life spacious enough to hold everything they love. She urges listeners to recognize the “park bench” moments, to own their definition of enough, and to embrace sustainability, not just as a business strategy, but as a way of living.

“You’re probably not just building a business. You’re trying to build a life that can hold everything you love, and it is an honor and a privilege to get to guide you on that path.” (90:33, Jenna Kutcher)

Final Thoughts

This episode is a masterclass in both reframing the purpose of entrepreneurship and realigning “success” with joy, presence, and personal values. Jenna combines strategy, vulnerable storytelling, and the wisdom that comes with lived experience, making it essential listening for anyone seeking to build a business—and a life—that feels like their own.

For more resources, show notes, and future episodes, visit: goaldiggerpodcast.com