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).