She left Big Tech, coached girls’ basketball, launched a nonprofit, and then built a bootstrapped brand that made it onto Barnes & Noble shelves. This is Sarah Habib’s reinvention and the scrappy, values-first playbook behind Calm Caterpillar.

Sarah started on a prestige path (Nielsen leadership program, product in Big Tech) before choosing purpose over pedigree. Coaching showed her what kids actually need; Mission to Move proved the model; Calm Caterpillar turned it into a product and a company. From pallets and tariffs to turning off ads and growing through community, she breaks down the unglamorous moves that actually work.

Why watch

• Decide when it’s time to leave a “safe” career
• Turn hands-on service into product-market fit
• The realities of working with a national retail chain
• Grow on mission and still make money
• Build a small, resilient team you love

Links:

• The Calm Caterpillar: https://thecalmcaterpillar.com/?srsltid=AfmBOorI0VdLPCsjz4Gx5lRyi_U-DKMjX8-NETAYjjfieWOsS1x6q9QK
• The Calm Caterpillar on Instagram: https://www.instagram.com/thecalmcaterpillar/?hl=en
• Mission to Move: https://www.mission2move.org/
• Sarah Habib: https://www.linkedin.com/in/sarahfhabib/
• The Best Job I've Ever Had: bestjobever.org

Dave Cameron helped build analytics at Merkle (years before the $1.5B Dentsu acquisition), led Data Science as a Global VP at Nielsen, and now runs an independent consultancy while teaching business analytics at universities like the University of Chicago. Dave’s through-line: make data understandable, lead people to find work that fits them, and choose work that aligns your strengths—even if that means leaving a rocket ship to be present for your kids.

In this episode, you’ll learn:

• What 3× growth changes: How Dave helped Merkle go from $25M → $75M and how that changed his career.
• How to build analytics that matter: Start with the decision, not the dashboard.
• Incentives drive teams: How variable comp/profit-sharing changes who works for a company
• Fit is greater than title: A quick filter—energy × ability × values—to choose roles you’ll thrive in.
• Quit Fast (protect your time): If it doesn’t fit your strengths, cut your losses—then move on.

Guest:

• Dave Cameron — Data & Marketing Analytics leader; former Global VP of Data Science (Nielsen); consultant & lecturer.
• LinkedIn: https://www.linkedin.com/in/dfcameron/

From Navy flight school to Facebook, Susan “Spark” Park has chased the most interesting story—then built teams to deliver it. In this episode, Spark shares why identity isn’t the role (stewardship over status), how trust—not just output—drives promotions, and the “trifecta” behind her best job: scope, people, and executive sponsorship.

We talk about designing for time wealth, asking “why” five times, and leading with a simple rule: be a good friend—and ship great work. If you’re navigating big career moves, building PMM teams, or trying to make your work feel like yours (without losing in high-stakes rooms), this one’s for you.

You’ll learn more about how to:

• Identify your Best Job Trifecta (scope • team • sponsors)
• Apply a mission rotation mindset to pick your next role
• Learn how to “get to know yourself” and why you really want that next promotion
• Make mentorship real: block time so it actually happens

Follow Spark: https://www.linkedin.com/in/sparkindustries/

For more on The Best Job I've Ever Had visit: bestjobever.org

What’s it really like to make a living in jazz? 🎸

In this episode, I sit down with Chicago Jazz guitarist Andy Brown to talk about the reality behind the Green Mill stage — the late nights, the mentors who shaped him, the mistakes that taught him, and the gamble that brought him from Cincinnati to Chicago.

We explore:

• Why moving to Chicago was the pivotal decision of Andy’s career
• The grind and joys of being a working jazz musician today
• How mentors, community, and mistakes shaped his unique sound
• What jazz teaches us about work, growth, and resilience

Whether you’re a musician, a fan of Chicago’s jazz scene, or someone curious about turning passion into a career, Andy’s story will inspire and challenge the way you think about work and art.

Links from the show:

• Andy's Website: https://andybrownguitar.com/
• The Green Mill: https://greenmilljazz.com/
• The Jazz showcase: https://www.jazzshowcase.com/
• Andy's Club: https://andysjazzclub.com/
• The Best Job I've Ever Had: bestjobever.org

Michelle Bess left a high-pay HR exec job to build a portfolio career—and got happier earning far less. Today her work spans real estate, yoga, university teaching, and nonprofit advising—more autonomy, more energy, more life.

We talk about:

• How Michelle got a job she wasn't “qualified” for
• What is the job of Diversity, Equity, and Inclusion
• The role of relationships and sponsorship in unlocking career opportunities
• What she’s learned from moving between nonprofits, tech, and entrepreneurship
• Why money and status aren’t the true drivers of career happiness If you’re weighing money vs. meaning, this is your roadmap.

Links from the show: -

• Michelle Y. Bess LinkedIn: https://www.linkedin.com/in/michelleybess/
• LinkedIn Study on Gender Differences in Job Applications: https://www.linkedin.com/business/talent/blog/talent-acquisition/how-women-find-jobs-gender-report

Fact Checks:

1. Jim Carry, not Jerry Seinfeld, said: “I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it's not the answer.”

2. The suggestion that women only apply for jobs they are 100% qualified for, yet men apply for jobs they are 60% qualified for, is hard to source. While found in HBR and McKinsey Quarterly, I can't find a credible source. There may be some truth to this, given that a LinkedIn Study found that women are more selective with job applications. However, the magnitude is likely overstated (i.e., it's not a 40% gap).

Deb Stambaugh has done it all — from scaling Samsung Ads into a $500M+ business to serving as Chief Marketing Officer of Quantcast, and now running her own consultancy, Brave New World. In this conversation, she shares why she left the C-suite to build something on her own, what she’s learned about the “myth of job security,” and why she believes every job is just a stepping stone in your larger career. We talk about:

• The reality of being a CMO (and why it’s not what most people think)
• How Deb built Brave New World into a thriving business
• Why she believes independence is safer than corporate loyalty
• The importance of mentors, sponsors, and investing in women leaders
• Her best career advice: stop putting up your own barriers and just go for it

Whether you’re a marketer, entrepreneur, or simply rethinking your career path, Deb’s story is full of practical wisdom and inspiration. Show Links:

• Brave New World: https://www.bravenewworldinc.com/
• Deb's LinkedIn: https://www.linkedin.com/in/debstambaugh/
• Meet with Deb on Intro.co: https://intro.co/DebStambaugh
• For more on the Best Job I've Ever Had visit our website: https://bestjobever.org/

Can one day a week of meaningful work change your perspective on your job?

In this episode, Alex explores what defines meaningful work. Drawing from Daniel Pink's research and the Harvard Study of Adult Development,

Alex identifies four critical factors: purpose, relationships, autonomy, and mastery. He also discusses strategies for incorporating more meaningful work into your week and shares insights on how to enhance job satisfaction. Relevant for anyone aiming to find more fulfillment in their career.

Show Links:

• The 20% Rule: One Day of Meaningful Work Can Transform Your Career: https://alex-t-lobert.medium.com/the-20-rule-one-day-of-meaningful-work-can-transform-your-career-a1b12a6c80c9
• Drive by Daniel Pink: https://www.danpink.com/books/drive/
• Harvard Study of Adult Development: https://www.adultdevelopmentstudy.org/
• Interpersonal sensemaking and the meaning of work: https://positiveorgs.bus.umich.edu/articles/interpersonal-sensemaking-and-the-meaning-of-work/?utm_source=chatgpt.com
• Mayo Clinic Research on Doctor Burnout: https://www.mayo.edu/research/centers-programs/program-physician-well-being/mayo-clinic-approach/commitment-physician-well-being

Graham Douglas has navigated a fascinating career path—from managing snow cone stands in Texas to founding the creative strategy company, Gus. In this episode, Graham shares with Alex how his unconventional journey has shaped his approach to business and life.

Learn why Graham believes that having a great co-founder and working with a friend can be a game-changer in building a successful business. And discover how Graham's experiences, from working at big agencies to launching impactful campaigns, reveal the power of merging creativity and strategic thinking.

Show Links:

- Gus: gus.biz/

- Graham's Website: www.graham-douglas.com/

- Graham's LinkedIn: www.linkedin.com/in/grahamd/

- Best Job Ever Podcast Website: bestjobever.org

Michelle Bonner Techel has ticked some of the biggest boxes on any résumé—White House advance team, McKinsey consultant, Wells Fargo exec, Meta product leader—but today she tells Alex why none of those “dream jobs” were the finish line. In this episode, Michelle blows up the myth of the one-perfect-career and shows how embracing fresh chapters keeps your ambition (and happiness) alive.

Carlos Cabrera, EVP @ Wild Alaskan Company, swapped breaking news for building tech that ships wild-caught seafood to U.S. doorsteps.

Carlos's Career Journey:

• Passed on a safe consulting offer to chase documentary journalism.

• Cold-emailed a fellow Northwestern Wildcat, joined a media startup Storyhunter (now called Glimmer), and fell into product management.

• Quit a comfy PM role, went contractor-mode, and helped launch Wild Alaskan Company.

Show Links:

Carlos' LinkedIn: https://www.linkedin.com/in/%F0%9F%90%9F%F0%9F%91%8D-carlos-cabrera-9b40b813/

Wild Alaskan Company: https://wildalaskancompany.com/