18. Creating a Life You Actually Love with Dr. Wendy O’Connor

The Great Detour

If you’ve been feeling stuck, burnt out, or like you’re just going through the motions, this one’s for you.

In this episode, Jess is joined by Dr. Wendy O’Connor—a Stanford-trained clinical psychologist who now coaches women on how to create lives they truly love. After building a successful private practice and navigating life as a mother of three young children, Dr. Wendy realized she was running on autopilot. That turning point led her to positive psychology—the science of happiness—and a whole new chapter centered around alignment, self-trust, and purpose.

Together, they talk about what it really means to thrive—not just survive—and the small, intentional shifts that can help you reconnect with yourself.

They explore:

• What to do when your life looks “successful” but doesn’t feel fulfilling
• How to tell when you’re out of alignment—and how to get back on track
• The daily habits and mindset shifts that support long-term well-being
• How to stop outsourcing happiness and start building it from the inside out
• Finding “glimmers” in hard seasons—and why they matter
• Setting boundaries without guilt, and why they’re actually an act of love
• The three-part framework Wendy uses to help women design lives they love

This episode is full of grounded wisdom and practical tools—especially if you’re in the middle of a transition or figuring out what’s next. Dr. Wendy reminds us that creating a life you love isn’t about having it all together—it’s about knowing yourself, honoring what you need, and giving yourself permission to shift.

About Dr. Wendy O'Connor:

Dr. Wendy O'Connor is a Stanford-trained clinical psychologist and positive psychology expert who helps women move from burnout and autopilot to living intentional, joy-filled lives. After running a successful private practice and becoming a mother to three daughters in just over a year, she experienced a profound personal shift that led her to embrace the science of happiness. Today, Dr. Wendy blends cognitive behavioral therapy with positive psychology to help women design lives they love—rooted in self-trust, purpose, and aligned action. Dr. Wendy offers virtual coaching and mentorship programs for women ready to thrive beyond the checklist.

Dr. Wendy O'Connnor's Website: https://www.drwendyoconnor.com/

Dr. Wendy O'Connor's Instagram: https://www.instagram.com/drwendyoconnor/

Learn more about The Great Detour™
Website: www.thegreatdetour.com
Instagram: @thegreatdetour

Chapters

1. Introduction and Episode Overview (00:00:00)

2. Navigating Life's Challenges with Positivity (00:01:46)

3. Trusting Yourself and Embracing Change (00:02:51)

4. Personal Stories of Courage and Change (00:04:46)

5. The Journey to Positive Psychology (00:08:35)

6. Creating a Life by Design (00:13:39)

7. Misconceptions About Happiness (00:23:07)

8. Understanding Alignment and the North Star (00:25:53)

9. The Struggle with People Pleasing (00:27:37)

10. The Importance of Setting Boundaries (00:29:51)

11. Navigating Life Transitions (00:35:49)

12. The GRAPES Framework for Well-being (00:38:41)

13. Final Thoughts on Love and Health (00:44:11)