In this conversation, Ariella Coleman sits down with attorney and entrepreneur Dave Strousberg for an honest, thoughtful discussion about fear, failure, and what it really means to build a sustainable career in law.

Dave shares his journey through law school, the bar exam, and the financial and emotional pressure that followed. He talks openly about the moments when fear might lead to inaction, and how taking imperfect action ultimately helped him make clearer, more aligned decisions about his career.

They explore how health challenges and burnout can quietly create misalignment, often long before we are willing to admit it.

Ariella and Dave also talk about vulnerability and storytelling, and why community matters so much in a profession that often expects people to push through at any cost. They discuss how well-being practices and technology can support lawyers when used intentionally, and how the legal field can move toward healthier, more human ways of working.

This episode is for lawyers who are questioning their path, feeling stretched thin, or simply looking for permission to evolve. Because you are not married to your decisions—and changing course can be an act of clarity, not failure.

Visit Dave Strousberg's website: https://www.willssimplified.com/

Check out The Wellness Esquire on Linkedin: https://www.linkedin.com/company/the-wellness-esquire/

About The Wellness Esquire
The Wellness Esquire is a podcast and Substack by Ariella Coleman exploring well-being, identity, and sustainability in the legal profession. Through honest conversations with lawyers and other professionals, the show examines how we work, why we burn out, and what it looks like to build careers that are both meaningful and humane.

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