Episode 10: Dream or Drain? The Rise of the Intrapreneur

May 19, 2025•7 min read

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Dream or Drain? Why Intrapreneurship Might Be Your Perfect Path to Career Fulfillment

"Not everyone is made to be an entrepreneur, but that doesn't make you less ambitious." - Kristen Boss

In an era dominated by hustle culture, Instagram business coaches, and "quit your 9-to-5" manifestos, entrepreneurship has been glorified as the ultimate career aspiration. The message is clear: if you're truly ambitious, you'll build your own empire instead of someone else's.

But what if that narrative isn't just oversimplified—what if it's fundamentally flawed?

In a refreshingly honest episode of "The Pursuit of Happywell" podcast, hosts Kristen and Scott Boss challenge this one-size-fits-all approach to career fulfillment, introducing a powerful alternative path that might just be the permission slip you need to pursue work that energizes rather than drains you.

The Great Entrepreneurship Myth: What They Don't Tell You

Before launching their current business venture, Kristen was known for her signature talk: "Quit the 9-to-5, be your own boss, build your dream." She admits, "I was telling people, 'If you don't build your dream, you're going to build someone else's,'" essentially vilifying traditional employment.

But years of watching entrepreneurs struggle—including herself—revealed a more nuanced truth: entrepreneurship can be for anyone, but it doesn't mean it should be.

"Just because you could doesn't mean you should," Kristen emphasizes. "We have this generation of people that have been sold entrepreneurship as the only path to freedom, flexibility, and fulfillment."

The result? Countless driven, talented individuals internalizing shame because they were sold an inaccurate picture of what building a business actually entails.

Debunking the Common Myths That Lead to Burnout

Let's examine the seductive myths that have led so many down the path of entrepreneurial burnout:

Myth #1: "Be Your Own Boss"

Reality: You're accountable to everyone.

"You might not report to somebody directly like a traditional nine-to-five employee-employer relationship, but you are now held accountable to the people you serve," Kristen explains.

Not only are entrepreneurs answerable to customers, but they must also be their own boss—a role that requires self-discipline many don't anticipate. "Without some external cue or external authority to make sure they're showing up, they just don't," Scott adds.

Myth #2: "Time Freedom"

Reality: You often work more, not less.

The distinction between time freedom and free time is critical. "I think people think like, 'I'm gonna have all kinds of free time,' which is different than time freedom," Scott clarifies.

True time freedom means controlling where you allocate your time, not necessarily having more of it. In fact, entrepreneurs often work significantly more hours, especially in the early stages.

"Entrepreneurship, the lights are always on," Kristen shares from experience.

Myth #3: "Do What You Love"

Reality: You'll spend most of your time on everything but that.

The harsh truth? That thing you love doing might represent only 20% of your workload as an entrepreneur.

"For example, me coaching—I love coaching, it fills my cup. That's 20% of what I do. 80% is marketing, vision-casting, leading teams, systems, infrastructure," Kristen reveals.

Myth #4: "Make More Money"

Reality: There's significant financial instability.

Unlike the predictable paychecks of traditional employment, entrepreneurial income fluctuates wildly, especially in the beginning stages.

"It's not like you're getting a regular paycheck where it's like, this is my salary, this is what I get. I clock in, I go out," Scott explains. "There's so many variables. There's so much financial unpredictability."

Myth #5: "Anyone Can Do It"

Reality: Not everyone is wired for it.

This is perhaps the most important revelation: some people are naturally equipped for entrepreneurship, while others simply aren't—and that's perfectly okay.

"Some of us are the Red Bull athletes of business," Kristen compares, "and we live for that adrenaline, whereas most people, you put them on that trail and on that bike, they will collapse under the adrenaline. And entrepreneurship is no different."

The Hidden Stressors of Entrepreneurship

Beyond the myths lie tangible stressors that drain entrepreneurs daily:

Decision Fatigue: Every vision, initiative, and detail requires your decision.
Emotional Isolation: "You're alone in holding the risk, the fear. If this all goes south, it's all on me," Kristen shares.
Identity Fusion: When you over-identify with your business, every rejection feels catastrophic.
Uncertainty Tolerance: Can you handle high levels of uncertainty for extended periods? Most can't.
Over-Responsibility: Everything falls on you—for yourself, your clients, your team.

The Rise of the Intrapreneur: A Powerful Alternative

So what's the solution if entrepreneurship feels like forcing a square peg into a round hole? Enter: intrapreneurship.

"There's actually a middle ground," Kristen explains. "People are realizing entrepreneurship isn't for me. I don't necessarily wanna go back to the nine-to-five, but where can I bring my genius to someone else's vision?"

Signs You Might Be an Intrapreneur (Not an Entrepreneur)

If these resonate with you, you might be an intrapreneur at heart:

You want to lead but not carry it all
You do your best work inside a mission, not building solo
You're brilliant at ideas but overwhelmed by operations
You crave impact but not ownership
You love collaborating and refining
You want creative freedom without full financial risk

When hiring for their current venture, Kristen and Scott discovered many applicants were former entrepreneurs who had realized they preferred contributing to a team. "I just want to be a part of a team," they all said. "We love the vision and I love what I can bring here."

These were individuals who could be entrepreneurs—but found it draining rather than energizing.

10 Exciting Career Paths for Intrapreneurs

If you're thinking, "This sounds like me, but what options do I have?" Here are just a few roles where intrapreneurs can thrive:

Creative Director/Brand Strategist: Dream in colors, fonts, and visuals
Program/Course Developer: Build engaging learning experiences
Director of Operations/COO: Implement systems that eliminate friction
Community Manager: Cultivate culture and engagement
Launch/Marketing Manager: Create strategies that make it "rain"
Podcast/YouTube Producer: Manage content behind the scenes
Client Success Coach: Guide others within an established framework
Ghostwriter/Content Creator: Craft compelling messaging
Chief of Staff: Hire and develop team talent
Virtual/Executive Assistant: Manage schedules, communications, and operations

Finding Your Path: Success Is About Alignment, Not Ownership

"You don't have to be the face of something to change lives," Kristen emphasizes. "You don't have to be the founder. You don't have to be your own boss. You just have to find work that aligns with you."

The ultimate measure of career success isn't ownership or autonomy—it's alignment and fulfillment. Are you doing work that fills you up, or are you playing out of position and taking on roles that secretly drain you?

Your Next Step: Happywell Homework

Ready to explore whether you're more aligned with entrepreneurship or intrapreneurship? Try this exercise:

If you're currently an entrepreneur, list everything you're currently doing
Highlight the tasks that energize you and fill you up
Consider whether these align more with being a "fire starter" or a "fire keeper"

As Kristen concludes, "Don't let your dream be a drain." You deserve to pursue work that feels aligned and fulfilling—whether that's as an entrepreneur or as the equally valuable intrapreneur.

If this episode hit you - take our FREE Adaptive Personality Type Quiz. Discover how your brain has learned to cope with stress, uncertainty, and challenges which could be keeping you stuck.

For more insights on building a fulfilling career and life, join The Pursuit of Happywell Community on Facebook or visit LiveHappywell.com.

Listen to the full episode of The Pursuit of Happywell podcast, "Dream or Drain? The Rise of the Intrapreneur," wherever you get your podcasts.

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Ready to redefine what success and happiness look like for you?

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Remember, you're not just here to exist—you're here to thrive. Keep going, keep growing, and join us next time on The Pursuit of Happywell.

Ready to Build Your Happywell?

Start by discovering your Adaptive Personality Type (APT) with a FREE quiz. Your APT is the way your brain has learned to cope with stress, uncertainty, and challenges. And it could be keeping you stuck.

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.