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

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