Surviving the Side Hustle

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What happens when you leave everything familiar behind to discover who you truly are? Emily Erstad, speech language pathologist turned hospice executive director and author, reveals the transformative power of intentionally embracing discomfort.

Emily's remarkable journey began with a spontaneous move from the Midwest to Montana during the pandemic, followed by randomly selecting Tucson, Arizona on a map and simply showing up. These bold decisions became the foundation for her leadership philosophy and her book "It's Not That Deep," which explores emotional intelligence as a practical leadership tool rather than just a theoretical concept.

"We spend a lot of time talking about what emotional intelligence is, but we never talk about what to do with it," Emily explains, highlighting the gap her work fills. Through personal stories and practical strategies, she guides readers through professional chaos while maintaining authenticity and purpose.

The conversation delves into the critical relationship between vulnerability and leadership, with Emily distinguishing between transparency and true vulnerability. She argues that once you know your core self, showing people who you are becomes natural and opens doors to connection and opportunity. Most importantly, this journey begins with trusting yourself—perhaps the hardest part but essential for effective leadership.

For anyone feeling stuck in a cycle of people-pleasing or running a race with no end, Emily offers this powerful advice: "If it makes you happy and you're inspired, it's worth your time. Do it for you. Don't do it for everyone else, because if you're empty and uninspired, nobody else around you is going to be inspired either."

Ready to step outside your comfort zone and discover the leader within? Listen now and find Emily's book "It's Not That Deep" on Amazon or connect with her on Instagram @its_not_that_deep_author to continue your journey of self-discovery and growth.

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Ever found yourself wearing burnout as a badge of honor? That was me until a conversation with Garrett Wood changed everything. 

Garrett is the founder of Gnosis Therapy, a clinical hypnotherapist and executive coach who helps high achievers transform burnout into sustainable performance. His journey resonates deeply—he wasn't a theorist but someone who lived through managing multiple departments, overseeing 100 staff across seven locations, and working 70+ hours weekly until his body started breaking down with knee pain, back pain, and sleepless nights.

What he discovered revolutionized my thinking: success isn't fueled by grinding harder but by recovery and nervous system regulation. This insight led him to explore non-sleep deep rest states and clinical hypnotherapy—which, contrary to popular belief, isn't some magic trick but focused awareness we all experience naturally when driving, visualizing, or getting absorbed in work.

The conversation revealed three crucial insights that could transform your approach to work and life. First, sustainable success comes through well-being, not at its expense. Second, hypnosis is everyday focus that you're already experiencing—the question is whether you're using it intentionally. Third, burnout has early warning signs, particularly the inability to quiet your mind at night.

Garrett compared stress to weight training—you can handle tension in short sets, but holding the heaviest weight at the hardest point indefinitely will break you. The key is creating sustainable rhythms so you can perform over time without collapsing.

Ready to protect yourself from burnout? Take Garrett's free five-minute burnout assessment on his LinkedIn page. Use it as a mirror now and check in again later this year. Remember, you don't earn more shots at success by emptying the tank—you earn them by taking care of it.

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Ever found yourself grinding away at your side hustle, feeling exhausted but still unable to turn off your racing thoughts at night? You're not alone—and you might be closer to burnout than you realize.

Clinical hypnotherapist Garrett Wood's journey into the world of burnout prevention began with his own crisis. Working 70-80 hour weeks as a corporate leader, he was successful by external measures but failing in his personal life. "I was a jerk to my dog and my partner," he admits candidly. The turning point came when he discovered non-sleep deep rest—a practice that induces a hypnotic state providing profound restoration in just minutes. This single change transformed not just his well-being but his professional performance, relationships, and quality of life.

Contrary to stage performances and Hollywood depictions, hypnosis isn't magical or mysterious—it's a natural state we all experience regularly. "All hypnosis is self-hypnosis," Garrett explains. "You go in and out of hypnosis every time you fall asleep and wake up." Athletes trigger this state with pre-performance rituals, and we sometimes experience it while driving or becoming absorbed in creative work. The power lies in harnessing this state intentionally to reprogram how your nervous system responds to stress.

The most dangerous myth for entrepreneurs? That success comes at the expense of well-being. Garrett's work with executives reveals the opposite truth: sustainable success is built through well-being, not despite it. "The more of it we have, the longer we can work, the healthier we are, the more shots we can take, the more likely we're going to experience success and actually be able to appreciate it." His five-minute assessment not only measures current burnout levels but identifies specific contributing factors and can even predict whether you'll be successful or burned out five years from now.

Ready to transform your relationship with work and success? Take Garrett's free burnout assessment through Gnosis Therapy on LinkedIn and discover what specific factors might be contributing to your burnout risk. Your future self will thank you.

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What happens when professional success leaves you feeling empty inside? For many high-achieving women, the path to external validation often leads away from their authentic selves. In this deeply insightful conversation, self-discovery expert and certified life coach Zerina Derveni shares her transformative journey from corporate success to helping others reconnect with their true identity.

Zerina's story will resonate with anyone who's ever heard that nagging inner voice asking "is this really all there is?" After building an impressive career across multiple industries, she couldn't ignore the persistent feeling that something was missing. This awakening led her through what she now identifies as the three crucial phases of self-discovery: awakening (questioning your path), unlearning (breaking free from old patterns), and exploration (experiencing life with a fresh perspective).

What makes this episode particularly valuable is Zerina's practical definition of authenticity. She cuts through the buzzwords to explain that self-discovery means "getting to a state where you're actually being versus doing." It's about understanding who you are at your core when you remove all external achievements and influences – who you truly are when no one is watching.

For listeners struggling with their own identity questions, Zerina offers powerful insights on why we struggle to be authentic (constant information overload), how our values evolve over time, and why mastering the communication of your needs might be the single most important skill for personal and professional success. Her approach blends compassionate understanding with strategic insight, focusing on building strengths rather than fixating on weaknesses.

Whether you're feeling stuck in your career, questioning your path, or simply curious about living more authentically, this conversation provides both the inspiration and practical guidance to begin your own journey of self-discovery. Ready to stop performing and start being? Listen now, and take the first step toward reconnecting with your authentic self.

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Have you ever achieved everything you thought you wanted, only to find yourself wondering, "Is this it?" That nagging voice isn't a sign you're lost—it's the first whisper of awakening.

In this illuminating conversation with Zerina Derveni, a self-discovery expert and certified health life coach, we explore how high-achieving women can reconnect with their authentic selves and build lives driven by purpose, not just performance. Zerina shares her powerful journey through three successful careers and how she finally stopped ignoring that persistent inner voice questioning whether her achievements were truly fulfilling her.

The heart of our discussion centers around Zerina's transformative three-phase framework: awakening (realizing something is misaligned), unlearning (questioning values and dismantling old patterns), and exploration (trying new things from a place of clarity). Most people rush through or completely skip the unlearning phase—and that's precisely why they find themselves repeating the same unfulfilling cycles despite surface-level changes.

We also dig deep into what authentic living really means beyond buzzwords. Your authentic self isn't found on your resume or curated social media presence—it's who you are when no one's watching, and it naturally evolves throughout your life. The key is developing tools to stay aligned with your core values as you grow. Equally important is mastering how to communicate your needs clearly and with emotional intelligence, whether in your career, relationships, or leadership roles.

This conversation serves as a powerful reminder that doing well and feeling fulfilled aren't synonymous. If you're feeling stuck, misaligned, or ready to explore your next chapter, listen through to the end and then share your biggest takeaway with me. I'm curious to know: where are you in your own awakening, unlearning, or exploration journey?

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Ever wonder why some entrepreneurs can walk away from their businesses with millions while others remain chained to theirs forever? This revealing conversation with Jordan Calderon, two-time exited founder and president of top 100 marketing agency StratDev, challenges everything you think you know about building a sustainable business.

Jordan drops a truth bomb that most entrepreneurs never consider: build your business like you plan to sell it, even if that's not your goal. Clean systems, founder independence, and clear transition plans aren't just exit strategies—they're the foundation of a healthy operation. As Rob reflects, this buyer's mindset fundamentally changes how you approach growth, prompting a crucial question: if someone took over your business tomorrow, would they find clear procedures or chaotic confusion?

The conversation takes a fascinating turn when Jordan shares how, at 20, he pitched clients twice his age while looking 16. After initially trying to fake maturity, he made a breakthrough by embracing his youth as his superpower. "I know how to market to young people better than you do" became his winning differentiator. This authentic approach exemplifies Rob's coaching principle: stop wasting energy pretending to be someone else—real credibility comes from owning your unique perspective.

Perhaps most impressive is StratDev's remarkable achievement of almost zero turnover in five years. Jordan's secret? Small, consistent signals of care—from gift cards and hotel giveaways to a dedicated Slack channel celebrating wins. Most surprising is his daily 30-minute block specifically for showing appreciation to his girlfriend and team members. This intentional culture-building demonstrates that high-performing businesses are built on high-trust relationships cultivated through genuine care.

Ready to transform your approach? As Jordan says: "Just do it, take action, jump off the cliff and figure out how to fly on the way down." Schedule a strategy session at survivingthesidehustle.com/freecall to build sellable systems, develop leadership habits, and create a business that grows while building a life that fulfills.

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Ever wonder what separates the entrepreneurs who actually exit their businesses from those who just dream about it? Jordan Calderon has done it twice already, and he's just getting started.

Jordan's entrepreneurial spark ignited at the tender age of five, selling plums from his father's backyard tree at the community pool. This early venture taught him three pivotal lessons that would shape his future: the joy of making people smile, the thrill of selling, and the satisfaction of providing solutions. Fast forward through high school side hustles to college, where Jordan made the bold decision to reject an Apple internship—much to his father's dismay—to pour his energy into his own ventures.

The gamble paid off. Jordan successfully built and sold College Clout, a college apparel company, while still a student. More significantly, he launched StratDev, now a top-100 ranked marketing firm specializing in explosive growth for B2B startups. One client even skyrocketed from zero to $40 million in just five months under their guidance.

What makes Jordan's approach unique? Rather than disguising his youth, he transformed it into his greatest asset. When pitching to business owners his parents' age, he positioned himself as the expert who understood platforms like TikTok and Instagram—digital landscapes where the next generation of buyers lives.

Perhaps most valuable is Jordan's insight about building "sellable businesses" rather than simply trying to sell businesses. He reveals the critical factors buyers look for: minimal founder dependency, consistent growth, documented processes, competitive advantages, and clear transition plans. By focusing on these elements from day one, entrepreneurs position themselves for successful exits whenever opportunity knocks.

For those juggling multiple priorities, Jordan shares his time-blocking strategy—scheduling everything from lunch breaks to "touch grass" moments—ensuring no aspect of life gets completely sacrificed at the altar of entrepreneurship.

Ready to break free from analysis paralysis? Take Jordan's simple but powerful advice: just do it. Like a baby bird pushed from the nest, you'll figure out how to fly just in time—but only if you take that first leap.

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Ever felt like business is just a series of punches to the face? You're not alone. In this compelling episode, I break down my recent conversation with former UFC fighter Cliff Starks, who perfectly captures the entrepreneurial journey as a fight in the octagon - constantly dodging hits from clients, doubt, and your inner critic.

Cliff dropped some serious truth bombs that apply to every high performer. Most notably: we don't fail from lack of knowledge but from lack of clarity and accountability. Think about it - how many courses have you bought or masterminds have you joined, yet still found yourself stuck? You didn't need more content; you needed coaching to help you ask better questions and take aligned action.

One of the most powerful concepts Cliff shared was the be-do-have framework that transformed him from an overweight kid to an elite fighter. This maps perfectly to resilience and my Rise to the Challenge framework - becoming someone who does hard things and earns the right to big wins. He also emphasized that trust comes before transformation, which aligns with my Team Triangle framework for identifying the coaches, captains, and crowd that supports your journey.

The ultimate currency in entrepreneurship isn't money or connections - it's momentum. Cliff's advice for anyone starting out resonates deeply: "What's a small win that can give you momentum to go after your next win?" Start there. In future solo episodes, I'll be breaking down each of my principles more deeply, from the Pirate's Flag framework to the Resilience Matrix, giving you bite-sized lessons you can actually apply to your side hustle or full-time entrepreneurial journey. Check out my free coaching newsletter at surviveinsidehustle.com for more behind-the-scenes insights and frameworks.

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The arena of business bears a striking resemblance to a UFC octagon, according to former fighter Cliff Starks. Both environments throw punches, demand resilience, and teach harsh lessons in real-time. The difference? With the right coach, those business lessons don't have to leave quite as many bruises.

Cliff's journey from professional fighter to sought-after business coach reveals a powerful truth: success leaves clues across disciplines. When everyone kept calling him "coach" during his entrepreneurial journey, he decided to make it official, getting certified and developing a methodology that targets the blind spots we all have but cannot see from within our own containers.

His approach is refreshingly straightforward—listen four times more than he speaks, identify patterns that either serve or hinder his clients, and help high-achieving entrepreneurs take actions aligned with their ultimate goals. Through his "Training Room" concept, Cliff guides ambitious professionals through five-day challenges that build trust and momentum simultaneously.

What sets Cliff's coaching philosophy apart is his emphasis on asking better questions. As he explains, "The quality of your life comes down to the quality of the questions that you ask." This insight prompted him to create "The Fighter's Formula: Winning the Game of Life," a book designed to transform readers when he can't be physically present.

For entrepreneurs at any stage, Cliff offers differentiated wisdom: beginners should focus on small wins that create momentum, while veterans need the reminder to have fun and listen more carefully to what people are actually telling them. His own daily declarations—"I'm a champion and I am amplified"—demonstrate the power of intentional mindset conditioning.

Whether you're launching a side hustle or scaling an established company, the fighter's formula offers a blueprint for success: identify your blind spots, focus on the next actionable step, and maintain your championship mindset through daily practice. Connect with Cliff on LinkedIn or Facebook to learn how his coaching can help you win your own business battles—with fewer metaphorical bruises.

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The journey from success to burnout and back to purpose is rarely discussed with complete honesty in entrepreneurial circles. Louis Kim breaks that silence, sharing his powerful story of building and selling businesses worth over $50 million, only to discover an emptiness that money couldn't fill.

Born to Korean immigrant parents who instilled a fierce work ethic, Louis achieved financial freedom early and seemed to have it all – wealth, status, relationships – the markers of success that most entrepreneurs chase. Yet there he was, unable to get out of bed, spending days in the bathtub watching Netflix while money sat untouched in his bank account. "What does it all mean?" became the haunting question that no business achievement could answer.

Louis takes us through his raw, unfiltered breakdown and the subsequent rebirth that transformed his approach to business and life. Through plant medicine journeys, somatic breath work, and deep personal growth, he discovered that clarity – knowing exactly who you are and where you're heading – is the entrepreneur's most valuable asset. "When you're clear in your direction, it's like that lighthouse in a dark sea. When you see it, it doesn't matter what's going on around you."

Today, Louis channels his experience into helping others find purpose through ownership. With $64 trillion in wealth transferring from baby boomers and 2.5 million small businesses needing succession plans, he's created "The Owner's Path" apprenticeship program to guide mid-career professionals toward entrepreneurship that aligns with their natural talents and deeper purpose.

Whether you're burning out, feeling lost despite success, or simply searching for more meaning in your entrepreneurial journey, this conversation offers practical wisdom on maintaining mental clarity through positive relationships, meditation, cold plunging, and the transformative power of genuine gratitude. Ready to reclaim your purpose and rebuild from the inside out? This episode shows you how.