Michelle Gass shares how four different careers led her to the work she was truly meant for. In this conversation, she reflects on discovering life planning, building a team that genuinely hums, and creating a practice that finally feels like home.
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In this conversation, I had the true pleasure of sitting down with Michelle Underwood Gass—with Paradigm Advisors. Michelle’s path makes you believe in serendipity and the ways life prepares us for the work we’re meant to do.
Michelle didn’t arrive in financial planning quickly or conventionally. Her journey spans four careers: tax accounting, working in a family office, hedge fund management, and finally financial / life planning. Every chapter added something essential. As she says, her work today is “a culmination of everything I’ve ever done and got me to my happy place.”
What stands out most is her deep love of people. Michelle is very curious, non-judgmental, and committed to treating everyone with dignity. It’s no surprise she found her calling in life planning, where the work moves beyond spreadsheets and goes into values, meaning, time, and what really matters.
Michelle has also built something rare: a truly humming team. Each person plays to their strengths, collaborates closely, and shares ownership of the client experience. Her clients don’t refer to themselves as “Michelle’s clients.” They say, “I’m a Paradigm client.” That team-based clarity takes intention and heart—qualities she embodies.
This episode is full of wisdom for anyone building a practice, questioning their next step, or wanting to serve from a place of purpose. Michelle is proof that our careers can evolve beautifully and surprisingly over time—and that when we listen to what lights us up, we find work that feels like home.
Episode Highlights
- How Michelle’s four-decade journey through tax, family office, and a hedge fund unexpectedly led her to her true calling in financial planning.
- Why discovering the Kinder life-planning approach felt like coming home—and how she uses money, time, and values as the foundation of her work.
- The intentional way she built a four-person team where everyone works in their highest and best role.
- What she loves most about planning: “seeing the sense of relief and fulfillment that our clients get once they realize that they’ve got this.”
- Her early belief that she had to “master everything” before moving forward—and how she eventually learned to leap before everything was perfect.
- How she defines the right client: engaged, willing to collaborate, and ready to invest time in their own financial life.
- Why she wants more women in the profession—and how the industry can demystify the math and build confidence in women earlier
- The power of simplicity: why complex strategies aren’t always better, and why helping people live the life they want matters more than any investment product.
- Her reflections on designing a practice that fits her life now—balancing impact, growth, and making time for family and joy.
- The wisdom she hopes younger advisors embrace: don’t wait until everything is perfected. “If you don’t try, you can’t fail. If you can’t fail, you’ve never done anything.”
