She left a dream job at peak success — because she finally discovered what true alignment feels like.

In this episode of Fit Happens, Jason Baumgarten sits down with Kara Nortman, managing partner of Monarch Collective — the only investment platform exclusively focused on women's sports. Kara's career spans Morgan Stanley, IAC, Battery Ventures, Upfront Ventures, and co-founding Angel City Football Club alongside Natalie Portman. She talks candidly about what it took to leave a role she was thriving in to pursue a fit she didn't know she needed, the role of coaching and personality frameworks in her growth, and what she's learned about assessing people across decades of investing.

Key Takeaways:

1. True alignment feels different from just being good at your job — and recognizing that gap is a gift.
2. Flow isn't something that arrives; it requires deliberately building the right container of habits and environment.
3. Women often take longer than men to recognize and fully own their natural strengths — and this has real career costs.
4. Using tools like the Enneagram and Human Design can help leaders identify patterns and lead more self-aware teams.
5. The victim, villain, hero framework is a powerful lens for reframing how you respond to difficult circumstances at work.
6. Job crafting works: Kara's decision to write a venture blog in 2004 directly led to her role at IAC.
7. The best hires often have broken resumes and something to prove — perfection on paper can be a red flag.
8. Interviewing is no better than a coin toss even for skilled practitioners — but starts improving when you define what you actually need.
9. Reference calls work best when referencers feel they're helping you succeed with the person, not judging whether to hire them.
10. Partnering well — knowing what you're great at and building complementary teams around it — is the long-term driver of enduring companies.

Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/ 
Email the show here: fithappens.fm

• (00:00) - Introduction

Most people are winging one of the most important decisions of their lives.

What's the difference between someone who springs out of bed Monday morning and someone who drags themselves there? It's not salary. It's not title. It's fit — and it's backed by over a century of science that most of us are ignoring. In this premiere episode of Fit Happens, Jason Baumgarten breaks down the five levels of job fit, the dark side of getting it wrong, and why the most dangerous hiring tool in business might be your own gut. Drawing on research, real case studies, and two decades of executive search experience, this episode makes the case that fit isn't a feeling — it's a framework.

Key Takeaways

1. Fit operates at five distinct levels: vocation, job, organization, group, and supervisor — and ignoring any one of them is costly.
2. Gallup Research links poor job fit and disengagement to over $1 trillion in annual economic losses.
3. People well-fitted to their roles are 2.5x more productive, 3x more creative, and 90% less likely to leave.
4. The "beer test" — hiring based on personal affinity — is a great predictor of homogeneity, not performance.
5. Person-org fit is the most discussed and most abused dimension of fit assessment.
6. Fit is dynamic, not static — it shifts as roles evolve and personal values mature.
7. Job crafting (task, relationship, and cognitive) gives individuals real agency over their fit.
8. Perceived fit — how you experience belonging — is more predictive of outcomes than objective measures.
9. Chronic misfit leads to resolution, relief, or resignation — and resignation is the silent killer.
10. Sometimes the best fit is someone who makes you uncomfortable, not someone who feels familiar.

Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/ 
Email the show here: [email protected]

• (00:00) - Why fit matters more than salary or title