The Courage to Choose More When Life Is Already Full | Lisa Woodruff, Founder & CEO of Organize365

Episode 32  ·  August 5, 2026

The Courage to Choose More When Life Is Already Full | Lisa Woodruff, Founder & CEO of Organize365

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Description

What do you do when your life is already full—but you still have a dream worth pursuing?

In this episode of the Create the Future Podcast, Rick Williams sits down with Lisa Woodruff, Founder and CEO of Organize 365, author, speaker, and business leader, to explore the courage it takes to make a life-changing decision when you already have a career, a business, and a family to care for.

Lisa shares the story behind her decision to pursue a PhD while continuing to lead her business and manage the many responsibilities of family life. The conversation goes beyond time management and organization—it explores ambition, priorities, personal growth, and the difficult choices we have to make when something truly matters to us.

In this episode, you’ll learn:

• How to make difficult life-changing decisions

• Why you sometimes have to create space for what matters most

• How to pursue meaningful goals when life is already busy

• The importance of choosing your priorities intentionally

• How leaders balance ambition, responsibility, and personal growth

• Why courage often means choosing the harder path

• How a major life decision can change your perspective and your future

Whether you’re an entrepreneur, executive, parent, business owner, or simply at a crossroads in life, this conversation offers valuable insights into making courageous decisions, finding purpose, and creating room for the things that matter most.

Guest: Lisa Woodruff

Founder & CEO of Organize 365

Author | Speaker | Business Leader

Learn more about Lisa:

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Learn more about Organize 365:

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Subscribe to the Create the Future Podcast for inspiring conversations with entrepreneurs, executives, founders, and leaders who share the decisions, challenges, and experiences that shape their future.

About Create the Future with Rick Williams Podcast

Rick Williams in his officeRick Williams, host

Create the Future with Rick Williams is a leadership podcast focused on real-world decisions that determine the future of companies, non-profits, and public agencies and the careers of the individuals making the decisions.

Hosted by Rick Williams, the podcast gives leaders an opportunity to share the stories behind the difficult decisions and tough calls they have made — for their companies, their organizations and sometimes for themselves.

Rick wrote Create the Future — your essential leadership guidebook for making difficult decisions. In this best-selling handbook, Rick gives the principles and leadership team exercises leaders use when faced with major choices for their organization and themselves.

Rick’s goal with the Create the Future Podcast is simple: to share practical leadership lessons from real life experiences so that today’s leaders can become better decision-makers and more effective leaders.

Rick Williams is a deeply experienced corporate leader, management consultant, company founder, board member, and author. He works with leaders through his speaking, newsletter, and board service, with a particular focus on helping leaders make difficult decisions.

“You create the future for the organization you lead by the decisions you make today.”Rick Williams

Learn more about Rick Williams and his leadership guidebook Create the Future.
Go to: RickWilliamsLeadership.com