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Jenna Kutcher, New York Times bestselling author and host of the Goal Digger podcast joins John O’Leary 0n the Live Inspired Podcast.

Jenna Kutcher is a born-and-raised Minnesota wife, mother, and entrepreneur who aims for two things daily: helping others wake up to life and staying in comfy pants.

Creator and host of the top-rated Goal Digger Podcast, she’s helped thousands redefine success and chase bold dreams through her decade-long work as a leading online personality and educator. And just a few weeks ago, Jenna’s debut book How Are You Really? became a New York Times bestseller.

Today, Jenna shares how she learned to value experiences over “things”, the ongoing journey of self-love and how she protects her most valuable asset: time.

If you’re looking to truly enjoy being alive and not merely suffering through it, this episode is for you.

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  • Experiences > Things: Instead of purchasing a bagger for the lawn mower, Jenna family decided on a trip to Wisconsin Dells, which changed the trajectory of her life.
  • Post-college while working at Target, Jenna was compelled to take control of her life and became a first-generation entrepreneur.
  • After hitting her goal of earning six figures, Jenna felt unfulfilled and realigned to more meaningful, purposeful goals.
  • “Time is currency. Time is a non-renewable resource we have to covet and spend so carefully.”
  • In learning to love herself, Jenna has become a “thought shepherd”, meaning being gentle, yet aware of her thoughts and the narratives in her brain.
  • “Every dream will cost you something. But remember, you aren’t the risk. You are the investment.”
  • Are you feeling unworthy? Jenna encourages you to ask someone you love, “what do you see in me” to be reminded of your worthiness.
  • Get a copy of Jenna Kutcher’s How Are You Really?.

Did you enjoy today’s episode?

You’ll love my conversation with Judith Shulevitz. As a society, we’ve put such an emphasis on work and being busy. In our conversation, Judith reminds us of the importance of Sabbath, what “Sabbath” is and what it means in all of our lives – regardless of our faith background – and the challenge to build pause into your week, nourish your community and be reminded that you are so much more than what you do. Listen to Judith Shulevitz on ep. 140.


About our sponsor: Keeley Companies wholeheartedly believes that if you get the people right -the results will follow. They set themselves apart with a forward-thinking culture that empowers their people and fosters loyal partnerships. Keeley Companies are a proud sponsor, partner, and super fan of the Live Inspired Podcast. Learn more about Keeley Companies.



  1. Q. What is the best book you’ve ever read?
    A. Big Magic by Elizabeth Gilbert.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Confidence.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. My memory cards with all my photos.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. My grandma.
  5. Q. What is the best advice you’ve ever received?
    A. “Don’t take crap from anyone.”
  6. Q. What advice would you give your 20-year-old self?
    A. Trust the path and let it unfold.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. She lived fully and made a difference.