#8 Why You Feel Stuck at Work and How to Find Meaning w/ Rachel Pacheco

#8 Why You Feel Stuck at Work and How to Find Meaning w/ Rachel Pacheco

As author of "Bringing Up the Boss" and upcoming book "Manage What Matters," Rachel Pacheco has spent her career researching what actually drives meaningful work. And the answer surprised her: 26% of people would keep their job even if they won the lottery. Not because they have perfect jobs. Because they've built meaning intentionally. This episode is for anyone who feels stuck waiting for the "right job" to make their work feel meaningful. We cover: * Why dream jobs (NASA, nonprofits, mission-driven companies) often feel the most meaningless * The perpetual journey vs. the destination trap * How to align your personal values with your daily work * The Wednesday morning test: what are you actually doing moment-to-moment * Operating at the "top of your license"—using your strengths every day * Signal vs. noise: how to optimize what matters and minimize what doesn't * Why genuine friendships at work are one of the primary drivers of meaning Core Values Worksheet: https://stan.store/jjthelen/p/defining-your-core-values [https://stan.store/jjthelen/p/defining-your-core-values] Rachel Pacheco Bringing Up the Boss: https://www.amazon.com/Bringing-Up-Boss-Rachel-Pacheco-ebook/dp/B0936LSFFB/ [https://www.amazon.com/Bringing-Up-Boss-Rachel-Pacheco-ebook/dp/B0936LSFFB/]Upcoming Book: "Manage What Matters" Website: rachelpacheco.com [http://rachelpacheco.com/]Substack: //bringinguptheboss.substack.com [https://bringinguptheboss.substack.com/?utm_source=%2Fsearch%2Fbringing%2520up%2520boss&utm_medium=reader2&utm_campaign=reader2]LinkedIn: https://www.linkedin.com/in/rachel-pacheco/ [https://www.linkedin.com/in/rachel-pacheco/] JJ Thelen Instagram: https://www.instagram.com/jeffthelen TikTok: https://www.tiktok.com/@jjthelen LinkedIn: https://www.linkedin.com/in/jjthelen

#7 How Chelsea Turgeon Quit Medicine and Built a Six-Figure Coaching Business

Chelsea Turgeon spent over a decade on the medical path—psychology undergrad, med school, OBGYN residency—before hitting rock bottom and realizing she was living someone else's dream. She quit mid-residency, sold everything she owned, and bought a one-way ticket to South Korea to teach English. With no savings and no clear plan, she figured it out as she went—first trying travel blogging, then discovering coaching, and eventually building a business helping other healthcare professionals escape the system and find work that actually fits them. In this conversation, we get into: * How to know if you're on the wrong path vs. just going through a rough patch * Look at the people furthest along—are they living a life you actually want? * Why she chose medicine for the wrong reasons (and how to avoid that trap) * The questions that cut through overthinking: "What are you done pretending to care about?" and "If I couldn't mess it up, what would I do?" * Why most people already know what they want—they're just intimidated by their own calling * The concept of a "career bridge" to buy yourself time to figure things out * Why false starts aren't failures—they're part of the path * "Don't look for clarity. Look for aliveness." Chelsea now coaches clinicians and healthcare professionals who want to build their own healing businesses. She's active on LinkedIn and Substack (The 100K Healer). Where to find more information about Chelsea LinkedIn: https://www.linkedin.com/in/coachchelsmd $100k Healer Substack: https://100khealer.substack.com JJ Thelen Instagram: https://www.instagram.com/jeffthelen TikTok: https://www.tiktok.com/@jjthelen LinkedIn: https://www.linkedin.com/in/jjthelen

#6 Lost on a Pathless Path Until Finding Good Work w/ Paul Millerd

Paul Millerd quit his job with no source of other income. He moved to Asia without a plan, without knowing what he was doing, and intentionally gave himself permission to get lost. What followed wasn’t a linear career pivot or a perfectly executed plan. It was a long period of exploration, writing, freelancing to pay the bills, and slowly realizing that the only work he consistently cared about was writing. At first, the writing was just something he loved doing. Then people started asking if it could be turned into a book. That book became The Pathless Path. Today, Paul has built a life centered around what he calls good work—work that energizes him, gives him time, and fits the kind of life he wants to build with his family. Freelancing and consulting fund the journey. Writing is the work he would never give up. In this conversation, we talk about: - Why getting lost can be necessary - How changing your environment changes how you think - The difference between good work, good-enough work, and bad work - Why Paul designs his life around time, not status - How The Pathless Path came from craft, not strategy - What it actually looks like to leave the default path without forcing an outcome This episode is for anyone who feels stuck in “good enough” work and knows there’s something else they’re meant to do—but doesn’t yet know how to get there. Paul Millerd Personal Website: https://pmillerd.com YouTube: https://www.youtube.com/@PaulMillerd Instagram: https://www.instagram.com/pathlesspaul Pathless Path: https://geni.us/HvqKy (Amazon) Pathless Path (new premium hardcover): https://shop.pathlesspath.com/products/pathless-path-hardcover Good Work: https://geni.us/D5D08 (Amazon) JJ Thelen Instagram: https://www.instagram.com/jeffthelen TikTok: https://www.tiktok.com/@jjthelen LinkedIn: https://www.linkedin.com/in/jjthelen

#5 When Your Dream Job Falls Apart w/ Patrick McGinnis

What happens when the “safe” path isn’t safe at all? In 2008, Patrick McGinnis had the dream job—traveling the world, investing in emerging markets, climbing the ladder. Then the financial crisis hit. His company collapsed, his identity cracked, his health broke down, and suddenly the career he built his life around was gone. In this conversation, Patrick shares the moment he realized no one was coming to save him, and how he rebuilt from the ground up—regaining his health, negotiating a more flexible life, redefining leverage, and eventually becoming the creator of the “10% Entrepreneur” and the originator of FOMO. We talk about: * Why “safe” careers can be the most dangerous * How to know when you’re stuck vs. when you’re scared * The role of health in major reinvention * Finding leverage you didn’t know you had * Escaping FOBO (fear of a better option) and decision paralysis * What most people get wrong about quitting vs. creating options * Why optionality—not blind risk—is the real path to freedom If you’ve been stuck in “fine,” waiting for the perfect moment, or telling yourself you’ll change your life “once things calm down”… this episode is a wake-up call. Patrick McGinnis Website: https://patrickmcginnis.com Instagram: https://www.instagram.com/patrickjmcginnis LinkedIn: https://www.linkedin.com/in/patrick-mcginnis YouTube: https://www.youtube.com/@fomosapiens Spotify: https://open.spotify.com/show/7gVsjLCgWggzjUl5GtFUOs The 10% Entrepreneur: https://geni.us/p7Q3 (Amazon) Fear of Missing Out: https://geni.us/JILPp (Amazon) JJ Thelen Instagram: https://www.instagram.com/jeffthelen TikTok: https://www.tiktok.com/@jjthelen LinkedIn: https://www.linkedin.com/in/jjthelen

#4 Building a Life You Don't Need to Escape from w/ Patrick Farrell

Patrick Farrell was living what looked like the perfect life on paper—high-rise apartment in Manhattan, $150,000/year job, girlfriend, the whole package. But he felt stuck in Groundhog Day, repeating the same patterns and getting more frustrated every day. Then one night in a hotel room, he saw an ad for Nomad Cruise on Facebook. He started jumping around the room, felt this expansive energy come through him, and booked it right then and there—without telling his boss or his girlfriend. Six months later, he left everything behind and hasn't looked back. In this conversation, we dig into what it actually takes to break out of a pattern you've been stuck in for years. Patrick shares the moment he realized he needed to change, the questions he asked himself to get clarity, and why waiting for perfect conditions is just another way of staying stuck. We talk about Tony Robbins' framework of the six human needs and why most people default to certainty and significance—the two needs that keep you from taking risks. Patrick explains how shifting your focus to growth and contribution changes everything, and why getting on an airplane (literally changing your environment) is one of the fastest ways to break patterns and gain clarity. Patrick also shares how he built his software business remotely while traveling, how he's using AI to help entrepreneurs automate their businesses, and his vision for creating a resort space where people can gather, learn, and grow. We discuss the pros and cons of the digital nomad lifestyle, why building systems from the start matters, and how to take your first step this weekend—even if you can't get on a plane to Europe. If you're feeling stuck, frustrated, or like you're living Groundhog Day in your career or life, this conversation will give you a different perspective and actionable steps to make a change. Patrick Farrell Website: https://patrickfarrell.life Instagram: https://www.instagram.com/patrickfarrell.life LinkedIn: https://www.linkedin.com/in/pfarrell85 Free ebook:  JJ Thelen Instagram: https://www.instagram.com/jeffthelen TikTok: https://www.tiktok.com/@jjthelen LinkedIn: https://www.linkedin.com/in/jjthelen