What if your biggest regret at the end of your life was never truly living as yourself?

In this episode, Sarah and Stef crack open the #1 regret of the dying—wishing they’d had the courage to live authentically, not just follow the script written by others.

With raw honesty and a dash of humor, the hosts swap stories about breaking free from expectations—whether it’s skipping university, ditching a “dream job,” or proudly embracing cat-lady status.

They dig into why it’s so hard to know what you really want, how people-pleasing and cultural “shoulds” sneak into our choices, and why sometimes it’s not about courage, but capacity.

• 0:37 – The Origin: Regrets of the Dying: Introducing Bronnie Ware’s “Top 5 Regrets” and the #1 regret: not living true to yourself.

• 1:33 – The Terry Crews Story: Sarah shares Terry Crews’ realization that he never wanted the life he was living, despite outward success.

• 2:40 – Personal Expectations & Breaking the Mold: Sarah’s story: questioning university, career in the police, and resisting the pressure to always “grow” her business.

• 7:52 – Stef’s Career Pivots & Meaning: Stef’s journey: journalism, therapy, and the struggle to find satisfaction and meaning beyond external validation.

• 12:11 – Is It Courage or Capacity: The hosts debate whether it’s really about courage, or if sometimes we just lack the capacity to change. Because Stef always makes it an issue.

• 14:39 – Social Judgment & Authentic Choices: How fear of judgment and people-pleasing can keep us from living authentically; Sarah’s choice to be single.

• 16:56 – The Conveyor Belt of Life: Waking up to the “automation” of life, questioning mainstream beliefs, and the challenge of knowing what you truly want.

• 25:15 – Mainstream, Subcultures & Critical Thinking: How even “anti-mainstream” ideas can become dogma; the importance of questioning what you subscribe to.

• 38:00 – Listener Challenge: Going Against the Grain: The hosts ask: What’s the last thing you did that was truly for yourself, even if it went against the grain? They share their own recent examples.

More About Stefanie Michele:

• Instagram
• Substack
• Website: Work With Me
• Wednesday Emails

More About Sarah Dosanjh:

• YouTube
• Instagram
• Website
• Book: I Can't Stop Eating