Encore: Jenna Kutcher on Taking Your Dreams Off the Shelf and Embracing the “What Ifs”

Description:

Jenna Kutcher was a few years into a corporate career at Target when her boss slid a five-year plan across the desk. A promotion, more money, more responsibility, all mapped out by somebody else, and every step of it was something she did not want. She did not know yet what she wanted instead, but she knew exactly what she no longer wanted. So she bought a camera off Craigslist for $300.

We’re in the middle of our Courage to Change: Do It Scared series, and I’m bringing back this conversation from January 2023, when it opened our For the Love of What If series. Jenna walks us through how that camera became a photography business, then the Goal Digger podcast, then the New York Times bestseller How Are You, Really?, and why she built the next thing quietly on the side while the paycheck was still coming in. We talk about what happens when more money doesn’t buy the life you’re longing for, why time became her real currency, and the question she asked me that I could not shake: not how does it look, but how does it feel.

Stay for the end, because something happened after this tape. On the last day of 2025, after 968 episodes, Jenna paused Goal Digger while it was still going strong. She meant every word she said here.

Thought-provoking Quotes:

• Her question is yours now. Not how does it look. How does it feel. (Jen Hatmaker)
• That is what courage to change actually looks like most of the time. Not a blaze of glory. Not a resignation letter thrown in the air. (Jen Hatmaker)
• A woman asking an honest question, hearing an answer she did not love, and then doing something about it anyway. (Jen Hatmaker)
• You are not in prison. You made that rule up, and you are allowed to change it. (Jen Hatmaker)

Resources Mentioned in This Episode:

• How Are You, Really? by Jenna Kutcher - https://bookshop.org/book/9780063221949
• A New Chapter for Goal Digger - https://jennakutcherblog.com/a-new-chapter-for-goal-digger: Jenna on why she paused the podcast
• Leave us a voicemail - https://jenhatmaker.com/podcast: Tell us about the safe thing you walked away from, or the one you’re thinking about leaving.

Guest’s Links:

Website - https://jennakutcher.com

Instagram - https://instagram.com/jennakutcher

Facebook - https://facebook.com/jenna.kutcher

Connect with Jen!
Jen’s Website - https://jenhatmaker.com/

Jen’s Instagram - https://instagram.com/jenhatmaker
Jen’s Twitter -