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Curated Questions

Celebrating The Power Of Questions

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#65 Mitchell Osmond: Everything Is Hard - Choose Your Hard

"Literally everything in life is hard. The question is, what cost are you willing to pay? And you pay that willingly and happily because you value it." - Mitchell Osmond

"Literally everything in life is hard. The question is, what cost are you willing to pay? And you pay that willingly and happily because you value it." - Mitchell Osmond

In this episode of Curated Questions, Ken Woodward sits down with Mitchell Osmond, founder of Dad Nation Co., and host of the Dad Nation Podcast (Top 5% globally), to explore a hard but liberating truth: everything in life is difficult; the question is which difficulty we choose.

Mitchell shares the moment a single question at a funeral, “Are you living a life worthy of imitation?” forced him to confront his health, marriage, finances, and legacy. From that reckoning emerged a framework for growth rooted in discomfort, integrity, and honest self-inquiry.

Together, Ken and Mitchell examine why confidence is built through keeping promises, how avoiding hard questions quietly shapes our futures, and why legacy is forged at home as much as at work.

The conversation challenges the myth of ease, reframes struggle as a signal of alignment, and invites listeners to define success on their own terms. Ultimately, this episode is a call to stop outsourcing meaning, and to choose the hard that leads to a life worth living.

Mitchell is launching a new group coaching program, the High Performance Husband Accelerator! All the details can be found at https://www.dadnationco.com/accelerator

Mitchell is offering The Connection Code as a gift. 50 questions to spark the fun and get the fire back is available at https://www.dadnationco.com/code 

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

Episode Notes

00:00 Introduction: Life is Hard

01:16 Welcome to Curated Questions

01:58 Meet Mitchell Osmond

02:14 Mitchell's Transformation Journey

03:08 The Power of Questions

03:58 A Life Worthy of Imitation

05:08 Breaking the Generational Curse

08:32 Embracing Mortality

12:17 The Eulogy Exercise

14:12 The Importance of Discomfort

20:16 Raising Resilient Children

28:35 The Turning Point

32:02 The Role of Mentors

33:24 The Six-Month Ultimatum

36:36 Defining Your Legacy

38:41 Living with Integrity

40:54 Nobody is Perfect

42:42 The Relationship with Discomfort

43:31 What Would You Do If You Knew You Couldn't Fail?

44:05 The Fear of the Unknown

46:05 Personal Narrative and Self-Belief

48:33 The Power of Tolerating Less

52:15 Broken Promises and Self-Confidence

59:47 Defining Success for Yourself

01:01:26 Living in the Gain, Not the Gap

01:06:58 The Importance of Asking Questions

01:07:29 Personal Reflections on Time and Loss

01:12:02 The Dad Nation Podcast

01:12:51 Helping the Man I Used to Be

01:13:35 Reclaiming Home, Health, and Happiness

01:18:26 The Spark Starter Kit

01:19:15 The Importance of Emotional Connection

01:21:10 Final Thoughts and Gratitude

01:21:46 Closing Remarks and Call to Action

Resources Mentioned

Dad Nation Co website

The Dad Nation Podcast

Dad Nation Co Instagram

Mitchell Osmond on LinkedIn

Josh Waitzkin

Tim Ferriss

Albert Einstein

Seth Godin

Virginia Satir

The Gap in the Gain by Benjamin Hardy and Dan Sullivan

Ed Mylett

John Gray author of Men Are From Mars, Women Are From Venus

The High Performance Husband

Raymond Coates

Spark Starter Kit

Producer Ben Ford

Beauty Pill

tags: Curated Questions, Ken Woodward, Mitchell Osmond, Dad Nation, choosing your hard, life worthy of imitation, power of questions, personal transformation, legacy and integrity, discomfort and growth, confidence through discipline, keeping promises, men and leadership, marriage and meaning, defining success, emotional responsibility, generational cycles, identity and character, hard questions for growth, modern masculinity, purpose and legacy, accountability and honesty, self-inquiry, high performance living, relationships and integrity, resilience and discipline, coaching through questions, intentional living, values-based life, personal growth podcast
categories: Community, Connection, Leadership, Listening, Mental Wellness, Personal Growth, Coaching, Death, Gratitude, Legacy, Podcast, Relationships
Wednesday 01.07.26
Posted by Kenneth Woodward
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