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

Rachel Pacheco
Bringing Up the Boss: https://www.amazon.com/Bringing-Up-Boss-Rachel-Pacheco-ebook/dp/B0936LSFFB/
Upcoming Book: "Manage What Matters"
Website: rachelpacheco.com
Substack: //bringinguptheboss.substack.com
LinkedIn: 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

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

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

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

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

David Kadavy (author of The Heart to Start, Mind Management Not Time Management, and more) sits down to talk about the real reasons people delay their creative dreams for years and exactly how to break the cycle and finally ship.
We dive deep into why waiting for the “perfect” big idea is a trap (the fortress fallacy), how to start with a dramatically scaled-down version instead of fantasizing forever, and why action on almost any idea beats endless planning. David shares his own story of thinking about podcasting for over a decade before launching in 2015 and instantly regretting not starting sooner.
Key takeaways:

Start before you’re ready, but start small enough that you’ll actually finish and ship
The hidden skill most people lack isn’t talent, it’s knowing how to hit publish when everything feels terrible
Four stages of creativity (preparation → incubation → illumination → verification) and why ideas almost never arrive while grinding at your desk
How to use mental states, environment, routines, and modern tools (AI, walking voice notes, Readwise) to get way more done with less resistance
The difference between inductive creators (innovative but struggle to finish, like Leonardo da Vinci) and deductive creators (reliable finishers, like Raphael)
Why quantity almost always beats obsessive quality in the long run
The counterintuitive truth: sometimes you have to quit more things to finish what truly matters

David also gives a behind-the-scenes look at his upcoming book Finish What Matters and his exact systems for remembering what he reads, managing ideas, and staying consistent for 18+ years as an independent creator.
If you’ve been “meaning to start” a podcast, YouTube channel, book, business, or any creative project for months (or years), this episode is the push you need.
Timestamps and resources → [add your links]
Connect with David:
kdv.co (newsletter + everything)
Free short book How to Write a Book → kadavy.net
How to Sell a Book → shop.kadavy.net
Enjoy! If this helped you finally take that first step, let me know in the comments what you’re starting. 🚀

David Kadavy
Website: https://kadavy.net
YouTube: https://www.youtube.com/@kadavy
Podcast (Spotify): https://open.spotify.com/show/2O09bB3o5zeedomi3CmeBs
How to Write a Book: https://kadavy.net/blog/posts/how-to-write-a-book/
Instagram: https://www.instagram.com/kadavy
TikTok: https://www.tiktok.com/@davidkadavy

Camden David and his wife did something most people only dream about: they quit their corporate jobs in Chicago, sold everything they owned, and started traveling the world one month at a time. Four years later, they've lived in over 40 countries and have no plans to stop.

In this conversation, we dig into the real story behind their decision to leave—the fears, the financial reality (they started with just $15,000), and what actually happened when they took the leap. Camden breaks down how they afford this lifestyle, from negotiating Airbnbs 25-35% below asking price to choosing destinations during off-season when costs are dramatically lower.

But this isn't just another "quit your job and travel" story. Camden talks about the transition from chasing the FIRE (Financial Independence Retire Early) movement to realizing they could build their ideal life right now instead of waiting 15 years. He shares how they find remote work, develop routines in new cities every month, and connect with locals instead of falling into tourist traps.

We also explore the harder parts: dealing with doubt from friends and family, managing the social side of constant movement, and figuring out if they'll ever choose a home base. Camden gives practical advice on everything from walking culture in Europe to why spending a month somewhere gives you a completely different experience than a typical vacation.

If you've been stuck researching instead of taking action, if you're wondering whether it's actually possible to build a location-independent life, or if you're just curious what four years of monthly moves teaches you—this conversation will give you a realistic look at what's possible when you stop waiting for perfect conditions and just start.

Camden's YouTube channel focuses on honest travel guides and "what I wish I knew" videos for destinations around the world. Find him at Camden David on YouTube.

Camden David
YouTube: https://www.youtube.com/@camdendavid
Instagram: https://www.instagram.com/itscamdendavid/
Newsletter: https://bit.ly/TheTuesdayTravelTip

JJ Thelen
Instagram: https://www.instagram.com/jeffthelen
TikTok: https://www.tiktok.com/@jjthelen
LinkedIn: https://www.linkedin.com/in/jjthelen

Arjun Mahadevan (CEO of doola) breaks down why "follow your passion" is backwards, what actually causes founder burnout, and when the right time is to start a business. We dig into the fears that keep people stuck, why you don't need VC funding or years of experience, and how passion grows from solving problems--not the other way around. If you're overthinking whether to take the leap, this conversation will help you cut through the noise.

Arjun Mahadevan
YouTube: https://www.youtube.com/@ceo.arjunmahadevan
Instagram: https://www.instagram.com/ceo.arjunmahadevan/

doola
Website: https://www.doola.com
YouTube: https://www.youtube.com/@doolaHQ


**Takeaways:** • You're not scared of failure--you're scared of what others think • The right time to start is when you'd regret not trying • You don't need VC funding; most successful businesses bootstrap • Work-life balance is a myth--find your flywheel instead • Passion comes from results and impact, not from following your hobbies • You need clear goals, not just a vague direction • Surround yourself with people who are also taking risks • Experience helps, but doing is the best teacher • You can start small while keeping your day job • Climb "Cringe Mountain"--get comfortable being uncomfortable

**Sound Bites:** "Follow your passion is bullshit" "Burnout isn't from overwork--it's from no results" "You need to climb Cringe Mountain" "The right time is when you'd regret not trying"

**Chapters:** 
00:00 - Overcoming Fear of Failure 
03:05 - The Journey to Entrepreneurship 
05:56 - Lessons from Early Ventures 
08:48 - The Right Time to Start a Business 
12:00 - The Role of Experience in Entrepreneurship 
15:12 - Side Hustles vs. Full Commitment 
18:09 - Financial Preparedness for Entrepreneurs 
20:46 - The Importance of Co-Founders 
23:53 - Navigating Y Combinator 
26:49 - The Value of Venture Capital 
29:47 - Work-Life Balance and Intensity 
33:08 - Finding Passion in Business 
36:06 - Knowing When to Pivot or Quit 
39:04 - Climbing Cringe Mountain 
42:06 - Advice for Taking the First Step