In this episode of the JOY² – Live With Joy Podcast, Greg De Koker sits down with Happiness and Life Transition Expert, author, speaker, coach and Founder of Wiser & Free, Dana Hilmer, for a joy-filled conversation about freedom, reinvention, intentional living and giving yourself permission to choose a life that truly feels like your own.
Somewhere along the way, many of us traded "I choose" for "I should." We stay busy. We chase the next milestone. We convince ourselves that joy can wait until everything else gets done.
Dana offers a different path.
With warmth, wisdom and plenty of laughter, she reminds us that joy isn't something we stumble upon someday. It's something we create through the choices we make every single day, even in life's hardest seasons.
Together, Greg and Dana explore how our thoughts, expectations and stories quietly shape our lives, why creating space is often more powerful than doing more, and how a few simple mindset shifts can open the door to greater freedom, gratitude and joy.
In this episode, discover:
• Why "I should" may be stealing more joy than you realize
• How to create peace and gratitude during life's most difficult seasons
• How the stories you tell yourself become your reality
• How to let go of what no longer aligns with who you're becoming
• Dana's unforgettable "Compass Point" question for navigating life's biggest decisions
One of the most powerful moments of the conversation comes when Dana shares the question she uses as her personal compass:
"How do I want to feel about myself and my life on my very last day?"
It's a beautifully simple question that has the power to reshape everyday choices, major life transitions and everything in between.
This episode is full of practical wisdom, joyful perspective and those unexpected little "aha!" moments that stay with you long after the conversation ends.
Because sometimes the biggest transformation begins with replacing just one word...
"I should."
...with...
"I choose."
🎁 Exclusive Offer for JOY² Podcast Listeners:
Dana Hilmer is offering a FREE copy of her workbook:
https://www.wiserandfree.com/happier
No e-mail required either. Just download it and enjoy.
Chapters:
00:00:00 Welcome to Joy Squared
00:02:15 Meet Dana Hilmer
00:07:06 Choosing Joy During Difficult Seasons
00:13:37 Letting Go of Control & Creating Space
00:18:48 Creating Small Moments to Look Forward To
00:25:33 Moving From “I Should” to “I Choose”
00:31:53 How You Begin Your Day Shapes Your Day
00:48:01 Using Feelings as a Filter for Decisions
00:57:52 Turning Insight Into Action
Connect with Greg De Koker
Website: www.joy2.ca
LinkedIn: www.linkedin.com/in/gregdekoker/
Instagram: www.instagram.com/greg_de_koker/
Facebook: www.facebook.com/greg.koker.5/
Connect with Dana Hilmer:
Website - https://www.wiserandfree.com/
Substack - Living Never Gets Old - https://danahilmer.substack.com/
LinkedIn - https://www.linkedin.com/in/danahilmer/
Facebook Group - Happy After 50 - https://www.facebook.com/groups/happyafter50
Instagram - https://www.instagram.com/dana.hilmer/
Listen and Subscribe to JOY²:
Apple Podcast: https://podcasts.apple.com/us/podcast/joy-live-with-joy-podcast/id1886910363
Spotify: creators.spotify.com/pod/show/joy-squared-podcast
YouTube: www.youtube.com/@JOY2LiveWithJoyPodcast
Stay Connected to JOY²:
Instagram: www.instagram.com/joysquaredofficial/
Facebook: www.facebook.com/joysquaredofficial/
Take Action
Ask yourself:
- What am I waiting for before allowing myself to experience more joy?
- Where am I still living from "I should" instead of "I choose"?
- What am I ready to let go of?
- How do I want to feel about my life?
Action Tip
This week, pause before making one decision. Create a little space. Replace one "I should" with "I choose." Notice one moment of joy you might normally rush past.
Sometimes a single intentional choice becomes the beginning of a completely different life.
