Episode 8: The Grit Behind Entrepreneurship
Have you ever taken a big leap, reinvented yourself, or found yourself asking, "What did I just sign up for?" Whether you're launching a business, changing careers, or simply entering a new chapter in life, the experience of starting over brings both exhilaration and uncertainty. In the latest episode of The Pursuit of Happywell podcast, Scott and Kristen pull back the curtain on what it's really like to build something from scratch – the highs, the lows, and everything in between.
Starting Fresh: More Than Just Entrepreneurship
While Scott and Kristen share their personal experience of closing one successful business and launching a brand new venture, their insights apply to anyone facing significant change. As they emphasize throughout the episode, "You might not be an entrepreneur or have a startup, but you might know what it's like to start a new chapter, take a big risk, decide to reinvent yourself, or outgrow old versions of yourself."
This universal experience of uncertainty and renewal connects us all, whether we're:
Changing careers in midlife
Moving to a new city
Ending a long-term relationship
Starting a family
Reinventing ourselves after a major life event
Let's dive into the key insights from their candid conversation that can help anyone navigating significant change.
The Reality vs. Expectations Gap
One of the first things Scott and Kristen discuss is the difference between what they thought building a startup would be like and the reality they encountered. For Kristen, who describes herself as "the visionary, the creative," the process has required far more meticulous planning than expected.
"I think I thought, I've done this before, no problem," Kristen admits. "There was a little bit of delusion with the lift it would take because the last business I grew with it." She contrasts her previous experience of building a personal brand (where you can start with just "a PayPal link and social media") with creating a company that's "absent of your face," which requires a "massive, very detailed lift."
Scott adds an insightful analogy: their previous business felt like "building the plane as it was in the air," whereas this time they're "building the plane on the ground" – a more methodical but ultimately more sustainable approach.
This gap between expectations and reality exists in virtually any new beginning. It's easy to oversimplify or romanticize a change when we're in the dreaming phase, only to discover the complex reality once we're in it.
The "Uh-Oh" Moment: When It Gets Real
Every new venture has that pivotal moment when the abstract becomes concrete – when you realize, "We're really doing this!" For Scott and Kristen, those moments included filing for trademarks, meeting with lawyers, and most significantly, bringing on team members.
"It moved beyond just you and I," Kristen reflects. "Because it was like, we're gonna put this out, if it doesn't work, we'll be okay. But then when we started hiring..."
Scott adds, "When we were doing all those Zoom interviews, I'm like, 'Crap, this is real. People are signing up to our thing. They believe in this.'"
This transition from idea to reality often brings both affirmation and heightened responsibility. When others begin investing their time, talents, and trust in your vision, the stakes feel different. The same is true whether you're launching a business, leading a project, or making a personal life change that affects your loved ones.
Identity Shifts: From "Me" to "We"
One of the most profound insights from the episode centers on the identity shift Kristen experienced moving from a personal brand to a company-focused venture.
"I did have to grieve the old Kristen," she shares, "the one who got the applause and the affirmation and the accolades from that last business." She describes the challenge of "untangling myself from who I am and what I do in the world," noting how easy it is with a personal brand to "dehumanize yourself and turn yourself into a commodity."
The shift from "me" to "we" represents a fundamental growth edge for many high-achievers. Kristen admits that her "old survival mechanism was being strong and hyper-independent and not needing anything." Learning to partner fully, to ask for help, and to "stay soft" while doing big things has been transformative.
Scott reinforces this idea: "In business, whether we are entrepreneurs and business owners or whether we're in management, sometimes we think 'if it's meant to be, it's up to me.' That is a very 'me' versus 'we' way of doing business, life, community, family."
This shift applies beyond business to anyone learning to collaborate, delegate, or simply allow themselves to be supported through a time of change.
Managing Imposter Syndrome
When venturing into new territory, almost everyone encounters imposter syndrome – that nagging feeling that you don't belong or aren't qualified for what you're attempting. Scott and Kristen talk openly about their experiences with this universal challenge.
Scott shares that he most often feels like an imposter when in rooms with other business owners, observing how they operate and thinking, "I've never even thought about that. Do I need to think about that? Does that mean we don't have a real business?"
Kristen reveals that before launching their new venture, she wrestled with questions like "Do I need to go back to school? Do I need to get my doctorate?" She worked with her therapist and other professionals to address this insecurity.
Her advice for others feeling imposter syndrome is powerful: "What if it's not about your expertise? What if it's about your experience, and you don't elevate yourself as an expert, you just say, 'hey, this is where I am, this is what I'm learning, and maybe you could take something from it too.'"
This perspective shift from "I must be the expert" to "I'm sharing my experience" can liberate anyone feeling paralyzed by perfectionism or inadequacy when stepping into new territory.
Values-Based Decision Making: Feeling Your Way Forward
Perhaps the most actionable insight from the episode is Scott and Kristen's approach to designing their new venture based on how they want it to feel, rather than just what they want it to achieve.
They describe sitting down months ago to reflect on their previous business experience and intentionally design a different experience this time. Instead of just focusing on what the business would do or offer, they asked deeper questions:
How do we want our family rhythms to look?
How do we want to feel in this next season?
How do we want our time to be blocked?
How much free time do we want?
Scott emphasizes that these "value questions that align right here, the soul questions, things that fill you" are crucial whether you're launching a business or making any significant life change.
Kristen adds that it can sometimes be easier to start by identifying what you don't want: "Let me tell you all the things I don't want... Sometimes knowing what you want, it helps to start with what you don't want because that becomes a very firm guardrail."
For their new company, Kristen shares that they want it to feel "meaningful, purposeful, very mission-driven" and for others, she wants it to feel "like coming home... where they can breathe for the first time... put down the mask... don't have to try so damn hard."
This values-first approach can transform any transition from merely changing external circumstances to creating a life that truly resonates at a soul level.
Navigating Uncertainty While "Life Keeps Lifeing"
One of the most relatable challenges discussed is how to build something new while simultaneously managing everyday life demands. As Scott puts it, "Life is always happening. There's never a perfect season. Ever."
For those with limited time and resources, Kristen offers this perspective: "You have to understand that you actually are a human being, you are not a robot. You have limited capacity and bandwidth... based on your season, maybe your current health, maybe what's going on in your family."
She shares a powerful metaphor of different "buckets" in life (career, kids, marriage, health) and acknowledges that during intense building phases, you might need to be okay with some buckets being at a "five" temporarily while others require more energy.
"In this season, what buckets do I need to be okay with being at a five, knowing that I have to put so much energy into this other bucket of building? It allows for some grace for yourself and some compassion."
Scott adds that if you truly only have "nooks and crannies" of time available, you might need to ask, "Is it still the time to build? Maybe this isn't a building season. Maybe this is a healing season, an integrating season."
This permission to align your ambitions with your current life reality is refreshing in a culture that often pushes "hustle at all costs."
The Emotional Reality: Excitement and Terror Coexisting
When asked what they wish someone had warned them about startups, Kristen offers perhaps the most comforting insight of the episode: "It's normal to hold a very big vision and feel very excited about it and also feel deeply terrified at the same time... That both can be true. That you can deeply, deeply believe in your vision while also thinking no one's gonna buy it, it's gonna be a terrible failure."
This acknowledgment of the emotional complexity of new beginnings validates what many feel but few discuss openly. Scott relates this to his experience moving across the country early in their marriage: "I remember driving across and thinking, 'Man, what happens if this doesn't work?'"
Kristen normalizes this further: "That's such a normal question to ask, and I feel like I ask myself it once a week. And I'm like, it's gonna be fine."
Supporting Each Other Through Spirals
The episode concludes with a discussion of how Scott and Kristen handle moments when one is spiraling while the other remains calm. Their insights offer valuable guidance for partnerships of all kinds navigating change together.
Kristen shares that she's learned to "voice my feelings sooner" rather than bottling them up and powering through. Scott notes that in their previous business dynamic, he felt pressure to always remain "calm, cool, and collected," but now they've both "become better at just kind of having that conversation sooner and allowing the human emotions to be a part of it."
Interestingly, Kristen mentions that seeing Scott occasionally struggle actually reassures her: "When I see you feeling the load, I'm like, this is evidence that I'm not carrying it alone this time."
This mutual vulnerability and support creates a healthier dynamic for navigating the inevitable challenges of any new venture.
The Invitation of Uncertainty
At its core, this episode illuminates the universal truth that beginning something new – whether a business, relationship, career, or creative project – inherently involves both risk and possibility. As Scott puts it: "You signed up for growth, period. Anytime we say, 'I'm gonna try this new thing,' you're signing up for growth. And unfortunately, with growth comes discomfort or resistance."
The beauty of the conversation is that it doesn't sugar-coat this reality but instead humanizes it. Scott and Kristen's willingness to share their doubts, spirals, and imposter moments alongside their excitement and vision creates a more complete picture of what transformation really entails.
For anyone standing at the threshold of change, their message offers both challenge and comfort: Yes, it will be harder than you think. Yes, you will question yourself. And yes, it's totally normal to feel simultaneously terrified and exhilarated. That's not a sign something's wrong – it's the natural terrain of growth.
If you're navigating a new beginning and resonated with the insights from this episode, Scott and Kristen invite you to join their upcoming Breakthrough Live Summit. While the in-person event is sold out, virtual tickets are available for the May 16th intensive, where they'll guide participants through exercises designed to create breakthrough, clarity, and forward momentum. Find out more and grab your ticket here.
To hear the full behind-the-scenes conversation about building something new, listen to Episode 8 of The Pursuit of Happywell podcast wherever you get your podcasts.
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About Your Hosts
Scott and Kristen built a $20+ million business before realizing that traditional success metrics weren't telling the whole story. They've coached thousands through both business and life transformations, learning firsthand that the path to fulfillment isn't what social media portrays. Based in Colorado with their two kids and two dogs, they bring authentic conversations about what actually creates a well-lived life in today's complex world.
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