The Goal Digger Podcast

Episode 926: What I Wish You’d Ask Me… And the Answers I’ve Been Holding Back Until Now
Host: Jenna Kutcher
Date: October 29, 2025

Episode Overview

In this deeply personal episode, Jenna Kutcher flips the script and answers the questions she wishes people would ask her—the ones no one has ever actually asked, but that reveal the true shifts happening in her life, business, health, motherhood, and marriage. Drawing from her own experiences, she offers honest, vulnerable reflections on therapy, partnership, privacy, her evolving health journey, work-life balance, creativity, loneliness at the top, how she’s redefining success, and more. Jenna hopes her candor inspires listeners to ask themselves tougher, more meaningful questions and to pursue authenticity over perfection in their own journeys.

Key Discussion Points and Insights

1. Why These Questions? Facing Vulnerability

• Jenna reveals she pushed off recording this episode for months out of fear of “going there” and sharing unfiltered truth.
• She frequently asks her guests, “What is something nobody’s asking you, but you wish they would?” and finally turns this on herself.
• “Maybe if you're just, like, tuning in and you're like, at some point, you become fearless. Nope, that doesn't happen.”—Jenna (03:26)

2. Processing in Therapy

[05:15]

• Therapy has been transformative, helping Jenna untangle the belief that “if I just stay ahead, nothing bad can happen,” a mindset developed from her roots as a gymnast and relentless early achiever.
• She’s now slowly unlearning tying her worth to productivity, and learning the importance of integrating and living lessons outside of therapy sessions.
• “I have a really hard time resting… there’s always more to do and there’s always more to get ahead on.”—Jenna (09:06)
• Insight: “Time out of therapy is just as important as time in therapy.”
  Jenna parallels this to business, encouraging time for integration, not just endless learning or hustle.

3. Keeping Marriage Strong

[13:30]

• Jenna and her husband Drew have intentionally pulled back their family’s online presence, valuing privacy and consent.
• Both are at pivots: Drew’s exploring life post–stay-at-home-dad, Jenna considering new professional directions.
• Couples coaching has led to deeper conversations and a new, shared vision for their next chapter.
• “Staying on the same page and consistently working together on what you want the next chapter to look like—that’s been really beautiful.”—Jenna (19:40)

4. Why She Stopped Showing Her Kids Online

[23:26]

• Jenna describes the shift, kicked off by a moment when a stranger recognized her daughter from IG:
  “She looked at me with this look of confusion—like, who is this person and why did they see that?” (25:02)
• She has no regrets: “I have never second guessed that choice for even a minute.” (23:40)—expressing added relief given the rise of AI and deepfakes.
• She sees herself now as an “oversharer” who “chose again” when new information and intuition arose.
• She still shares motherhood experiences, but not her children’s faces or identities—drawing a respectful boundary.

5. Her Physical & Self-Love Transformation

[32:05]

• After years as a champion for body positivity and plus-size advocacy, Jenna embarked on a health journey focused not on weight, but energy and well-being to keep up with young children and big projects.
• She emphasizes authenticity at every stage:
  “When I said I loved my size 14 body, you better believe I loved that body… And when I say that I love feeling strong and lifting weights, I love that.”—Jenna (36:50)
• She calls out how the body positivity movement can feel exclusionary once someone’s body changes or no longer fits within certain bounds.
• “My motivation to love myself now has changed… but it was never really about my body. It was about how I wanted to feel in my life.”—Jenna (39:00)

6. On Slowing Down & Missing the Old Momentum

[41:47]

• Becoming a mom reframed her sense of urgency and ambition.
• Contrary to her own expectations, she doesn’t want to ramp back up now that her kids are in school; instead, she’s fallen in love with rest, “creating momentum” on her own terms, and making work the least interesting part of her life.
• “I want my work to be the least interesting part of my life. And I feel like I have effectively done that. And that feels so good.”—Jenna (46:44)

7. Navigating Creative Dry Spells

[49:20]

• Jenna challenges the belief that the world expects us to bring constant fresh ideas:
  “We are not as important as we think we are and nobody is watching us as closely as we assume they are... and that’s beautiful.” (49:49)
• Finds creative fuel in non-business pursuits: gardening, rowing, beekeeping, etc.—living “the homestead pipeline, but make it CEO level.”
• Urges: “Time outside of work is just as important as time in work, if you want to stay creative.” (52:25)

8. Friendship, Loneliness, and Depth at the Top

[54:06]

• Addresses a common loneliness among high achievers, but contrasts: she’s never been lonely because she’s invested in deep, diverse friendships—within business and far outside it.
• She and her friend Amy Porterfield, for example, are “truly best friends” and talk daily, blending business and personal life (57:45).
• Encourages listeners not to self-isolate:
  “It’s no one else’s job to understand fully what my business is and how it works... How do you let people in if they’re curious? And how do you also just have things to talk about outside of work?” (55:45)
• Real relationships can exist both on and offline—and both are valuable.

9. Redefining Success

[1:04:15]

• Jenna shares she’s actively unlearning the belief that numbers (revenue, followers) are the only success metric, now favoring a “whole human” definition.
• “My idea of success is being active in our community, making a difference, being rested, being present, being joyful and playful... Success, to me, feels a certain way versus looking a certain way.” (1:05:20)
• Draws on gardening as an example of embodied, non-quantifiable success.

10. Who Is She Outside ‘Jenna Kutcher the Brand’?

[1:09:20]

• Jenna draws boundaries between her brand and private life, finding comfort in the fact that if the “brand” was stripped away, she’d still be whole.
• “If I were to remove the things that, quote, make me important… would I be okay with myself? Absolutely.” (1:10:07)
• She encourages listeners to do the same inner work: find identity, value, and meaning outside of public-facing roles.

11. What She’s Ready to Say Out Loud Now

[1:14:30]

• Jenna closes with an outpouring of gratitude for her audience, expressing that content is crafted for “the one person” on the other end of the earbuds, not for the numbers.
• “The fact that I get to be even a tiny little piece on your journey means more than you will ever know. And my belief in you is so big and so wide. And I’m just really grateful.” (1:15:00)
• She hopes her own willingness to go vulnerable will spark deeper questions and conversations for her listeners.

Notable Quotes

• On fear and vulnerability:
  “At some point, you become fearless. Nope, that doesn’t happen.” —Jenna (03:26)

• On productivity and self-worth:
  “I have a really hard time resting... because there’s always more to do and there’s always more to get ahead on.” (09:06)

• On marriage privacy:
  “Anyone that I’m going to bring into that fold [online], I want to be so conscious of. And I want them to, like, have consent in. And so we just have gotten really private. And I think that’s really good. Like, I’ve really loved it.” (16:44)

• On choosing privacy for her kids:
  “I have never second guessed that choice for even a minute. I am so grateful that I made that decision.” (23:40)

• On changing bodies and self love:
  “I have been authentic every step of the way... And when I say that I love feeling strong and lifting weights, I love that.” (36:50)

• On redefining momentum:
  “I want my work to be the least interesting part of my life. And I feel like I have effectively done that. And that feels so good.” (46:44)

• On creative dry seasons:
  “Nobody is expecting you to reinvent the wheel every single day. You’re not that important. And that is beautiful, too.” (53:00)

• On success:
  “Success, to me, feels a certain way versus looking a certain way.” (1:05:30)

• On audience gratitude:
  “The fact that I get to be even a tiny little piece on your journey means more than you will ever know. And my belief in you is so big and so wide. And I’m just really grateful.” (1:15:00)

Timestamps for Core Segments

• 05:15 – Processing in therapy and unwiring beliefs about productivity
• 13:30 – Keeping marriage strong through life’s pivots
• 23:26 – Why she stopped showing her kids online
• 32:05 – Physical and self-love transformation narrative
• 41:47 – On slowing down and missing (or not missing) old momentum
• 49:20 – Navigating creative dry spells
• 54:06 – Navigating loneliness, building friendships at the top, online and offline
• 1:04:15 – Beliefs about success Jenna is unlearning
• 1:09:20 – Identity outside the “Jenna Kutcher” brand
• 1:14:30 – Secret she’s ready to say out loud: gratitude for listeners

Episode Tone & Final Thoughts

Jenna’s tone is genuine, introspective, and candid—bouncing easily between hard-won wisdom, vulnerability, and encouragement. She delivers soulful reminders that it’s okay to redefine success, to set boundaries, to slow down when life asks you to, and to be at peace with sharing your full, changing self. For anyone feeling the pressure of perfection, stuck in achievement loops, or searching for purpose and balance, this episode provides a comforting and honest North Star.

This summary covers all major themes and memorable moments—giving you the heart and actionable wisdom of an episode designed to help you get real with yourself and your business dreams.