What Could Go Right?
By Erik Orton + Emily Orton
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Image by Erik Orton + Emily Orton
Category: Self-Improvement
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Episodes: 163
Description
Living Boldly On and Off the Water
What if the life you want is waiting on the other side of one brave decision? On What Could Go Right? you’ll discover how to face fear, take meaningful risks, and step into deeper connection, adventure, and a more intentional life.
Hosted by lifelong explorers and the founders of The Awesome Factory, we don’t just talk about adventure — we practice it, inviting you into playful, guided sailing experiences around the world, where growth happens through laughter, learning, and shared moments of awe.
Each week, we’ll help you trade 'what could go wrong?' for a far more energizing question: What could go right?
| Episode | Date |
|---|---|
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Ep 163 The Hidden Cost of Playing it Safe
|
Aug 05, 2026 |
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Ep 162 How to Stop Overthinking Your Next Sailing Trip
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Jul 29, 2026 |
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Ep 161 Why Greece Is Perfect for Your First Sailing Trip
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Jul 22, 2026 |
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Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill
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Jul 15, 2026 |
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Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science)
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Jul 14, 2026 |
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Ep 158 He Let a Beginner Sail a 47-Foot Boat – What Great Captains Know with Matt Holt
|
Jul 01, 2026 |
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Ep 157 Field-Tested Gear for Sailing Trips
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Jul 01, 2026 |
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Ep 156 Milestones and New Beginnings
|
Jun 11, 2026 |
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Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us)
|
Jun 04, 2026 |
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Ep 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites)
|
May 28, 2026 |
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Ep 153 Burnout, Productivity, and Why Rest Is the Missing Skill
|
May 21, 2026 |
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Ep 152 The Real Reason Travel Changes You (It’s Not the Destination)
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May 14, 2026 |
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Ep 151 Exhaustion vs. Motivation: How to Know When to Push and When to Rest
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May 07, 2026 |
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Ep 150 New Growth Over Glory Days: Why Your Best Adventures Are Still Ahead
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Apr 23, 2026 |
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Ep 149 New Favorite Boat? Tour the Leopard 4600
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Apr 16, 2026 |
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Ep 148 The Knock That Changed Everything: Overcoming Fear, Burnout, and Starting Over Midlife
|
Apr 09, 2026 |
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Ep 147 How to Rewire Your Brain for Self-Trust, Resilience, and Joy
|
Apr 02, 2026 |
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Ep 146 How to Know When to Persist or Pivot (Overcoming Challenges on Your Personal Growth Journey)
|
Mar 26, 2026 |
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Ep 145 How to Get Clear on What You Want in Life (The Desire List Practice)
|
Mar 19, 2026 |
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Ep 144 Feeling Stuck When You Want Momentum? The Unexpected Gift of Stillness with Ganel-Lyn Condie
|
Mar 12, 2026 |
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Ep 143 From Rural Indiana to Rwanda with Mark Richardson: What Goes Right When You Step Outside Your Comfort Zone
|
Mar 05, 2026 |
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Ep 142 - He Retired. Then the Real Adventure Began – Everest, PTSD & Reinvention
|
Feb 26, 2026 |
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Ep 141 - Sailing, Adventure, Transformation: Matt & Julie’s Story
|
Feb 19, 2026 |
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Ep 140 – Why Celebrating Small Wins Builds Confidence & Lasting Habits
|
Feb 12, 2026 |
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Ep 139 – The Amalfi Coast by Sea: Italy's Most Iconic Islands
|
Feb 05, 2026 |
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Ep 138 – Real Connection is Real Luxury
|
Jan 29, 2026 |
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Ep - 137 Bora Bora – Beyond the Postcard
|
Jan 22, 2026 |
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Ep 136 – How to Pack Light: Your Suitcase and Your Life
|
Jan 15, 2026 |
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Ep 135 – Magical Mexico: Sea of Cortez
|
Jan 08, 2026 |
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Ep 134 – From Stuck to Soaring with Curtis and Irene Hill
|
Jan 01, 2026 |
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Ep 133 – Behind the Scenes: Progress in Real Life
|
Dec 18, 2025 |
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Ep 132 – Best of The Bahamas
|
Dec 10, 2025 |
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Ep 131- When You Can't See Your Progress
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Dec 04, 2025 |
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Ep 130 - Burnt Out From Giving?
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Nov 27, 2025 |
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Ep 129 - If You're NOT Having Fun...
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Nov 20, 2025 |
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Ep 128 - We Talked to 1,000 People: Most Frequently Asked Questions about sailing with us
|
Nov 13, 2025 |
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Ep 127 - Courage to Begin
|
Nov 06, 2025 |
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Ep 126 - Best of the British Virgin Islands
|
Oct 30, 2025 |
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Ep 125 - Life is Short. Legacy is Long.
|
Oct 23, 2025 |
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Ep 124 - Compass vs. Map: Navigating Life Without Perfect Plans
|
Oct 16, 2025 |
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Ep 123 - Anchoring: Stable vs Stuck
|
Oct 09, 2025 |
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Ep 122 - Adventure Right Where You Are
|
Oct 02, 2025 |
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Ep 121 - Planning Your Private Sailing Trip
|
Sep 25, 2025 |
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Ep 120 - 2026 Sailing Schedule
|
Sep 18, 2025 |
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Ep 119 - First Trip To Croatia
|
Sep 11, 2025 |
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Ep 118 - Adventure for Everyone with Paul and Val Osborne
|
Sep 04, 2025 |
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Ep 117 - Travelpreneur Christina McEvoy on Adventure and Growth
|
Aug 28, 2025 |
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Ep 116 - The Readiness Myth
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Aug 21, 2025 |
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Ep 115 - Navigating Disappointment, Lessons in Resilience
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Aug 14, 2025 |
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Ep 114 - Croatia Close Up with Jordan + Christinah Mulder
|
Aug 07, 2025 |
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Ep 113 - Staying Close When Abilities Change
|
Jul 31, 2025 |
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Ep 112 - Catamaran Tour of Leopard 4500
|
Jul 24, 2025 |
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Ep 111 - What if it's Better Than You Imagined?
|
Jul 17, 2025 |
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Ep 110 - This is Your Call to Adventure
|
Jul 10, 2025 |
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Ep 109 - Slow Time, Strong Ties
|
Jul 03, 2025 |
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Ep 108 - Sailing the Spectrum of Routine and Risk
|
Jun 27, 2025 |
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Ep 107 - The Best Sailing Trip You’ve Never Heard Of
|
Jun 19, 2025 |
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Ep 106 - Steady Swiss Pace
|
Jun 12, 2025 |
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Ep 104 - "Garbage is Not My Passion"
|
Jun 06, 2025 |
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Ep 105 - From Cubicle to the Alps - Wild Career Pivot with Nicki Preece
|
Jun 05, 2025 |
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Ep 103 - Our Top 10 Most Popular Episodes
|
May 22, 2025 |
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Ep 102 - Beyond the Booze Cruise
|
May 15, 2025 |
|
Ep 101 - Marriage, Work & Love with Steve & Donna Kuhr
|
May 08, 2025 |
|
Ep 100 - A Time to Mourn
|
May 01, 2025 |
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Ep 99 - Flexibility Over Frustration
|
Apr 24, 2025 |
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Ep 98 - Why Italy Now
|
Apr 17, 2025 |
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Ep 97 - Then vs Now (Our Sailing Journey)
|
Apr 10, 2025 |
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Ep 96 - How to Grow Your Confidence
|
Apr 03, 2025 |
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Ep 95 - Spring Cleaning - How to Reset Yourself
|
Mar 27, 2025 |
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Ep 94 - 3 Sailing Stories (Racing)
|
Mar 20, 2025 |
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Ep 93 - People Can Change (Les Miserables)
|
Mar 13, 2025 |
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Ep 92 - Daily Sailing Life - Wifi, Waste & Water
|
Mar 06, 2025 |
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Ep 91 - Daily Sailing Life - What NOT to Pack: Managing Electricity
|
Feb 27, 2025 |
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Ep 90 - The Language of the Universe
|
Feb 13, 2025 |
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Ep 89 - Boat Tour - Lagoon 52 Catamaran
|
Feb 07, 2025 |
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Ep 88 - Seven at Sea Revisited (Karina's Version)
|
Jan 30, 2025 |
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Ep 87 - Cruise Ship or Custom Sailing Trip – Side by Side Comparison
|
Jan 23, 2025 |
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Ep 86 - Saying Yes: Flying Over the Grand Canyon
|
Jan 16, 2025 |
|
Ep 85 - Reclaiming a Sailing Dream - Mary & Jonathan Young
|
Jan 09, 2025 |
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Ep 84 - When Your Dream Makes You Puke
|
Jan 02, 2025 |
|
Ep 83 - Living Big by Starting Small
|
Dec 26, 2024 |
|
Ep 82 - The Christmas Tree Chronicles
|
Dec 19, 2024 |
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Ep 81 - What Surprised Me in Thailand
|
Dec 12, 2024 |
|
Ep 80 - Solo vs. Group Travel: The Benefits
|
Dec 05, 2024 |
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Ep 79 - Why Be Grateful in Adventure
|
Nov 27, 2024 |
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Ep 78 - Our Top Travel Trips
|
Nov 20, 2024 |
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Ep 77 - The Company You Keep
|
Nov 13, 2024 |
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Ep 76 - Sailing in Sardinia
|
Nov 06, 2024 |
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Ep 75 - From First Click to Casting Off
|
Oct 30, 2024 |
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Ep 74 - T-Minus Friday
|
Oct 24, 2024 |
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Ep 73 - Becoming Grandparents
|
Oct 17, 2024 |
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Ep 72 - Not a Scam
|
Oct 10, 2024 |
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Ep 71 - Treat Yourself Like A Person
|
Oct 03, 2024 |
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Ep 70 - Getting Clarity with Stefanie Gass
|
Sep 26, 2024 |
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Ep 69 - RV, Boat, Van - 7 Years of Travel with the Jackson Family
|
Sep 19, 2024 |
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Ep 68 - Overcoming Fear of the Unknown
|
Sep 12, 2024 |
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Ep 67 - The Mentor Advantage
|
Sep 05, 2024 |
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Ep 66 - Getting Started - The First Big Adventure (FAQ)
|
Aug 29, 2024 |
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Ep 65 - Lessons from Lily
|
Aug 22, 2024 |
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Ep 64 - What We Love About Traveling With Kids
|
Aug 15, 2024 |
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Ep 63 - Decluttering - Make Space For Your Dream Life
|
Aug 07, 2024 |
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Ep 62 - How We Sold Our Sailboat
|
Jul 31, 2024 |
|
Ep 61 - DIY vs Who Not How: Finding Balance
|
Jul 25, 2024 |
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Ep 60 - Collaborating as a Couple - Writing Our Book
|
Jul 18, 2024 |
|
Ep 59 - How to Grow the Size of Your Dreams
|
Jul 11, 2024 |
|
Ep 58 - Declare Your Independence
|
Jul 04, 2024 |
|
Ep 57 - Personal Growth + Sailing
|
Jun 27, 2024 |
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Ep 56 - Our Personal Packing List for Sailing Trips
|
Jun 20, 2024 |
|
Ep 55 - Navigating the Empty Nest Transition
|
Jun 13, 2024 |
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Ep 54 - Your Guide to Letting Go - with Y.E. Young
|
Jun 06, 2024 |
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Ep 53 - Why Loved Ones Inadvertantly Try to Hold Us Back
|
May 30, 2024 |
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Ep 52 - Tortillas to $200M - Lisa Binggeli
|
May 23, 2024 |
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Ep 51 - How to Upgrade Your Identity (Part 2)
|
May 16, 2024 |
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Ep 50 - How to Upgrade Your Identity (Part 1)
|
May 09, 2024 |
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Ep 49 - Darling, Let's Be Adventurers
|
May 02, 2024 |
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Ep 48 - Books, Beauty Pageants and Politics
|
Apr 25, 2024 |
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Ep 47 - We Bought An Eco Resort In Belize
|
Apr 18, 2024 |
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Ep 46 - What's Your Credibility Score and Why Does it Matter?
|
Apr 11, 2024 |
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Ep 45 - Our Top Tips on How to Deal with Change
|
Apr 04, 2024 |
|
Ep 44 - Two Takeaways From Our Forties
|
Mar 28, 2024 |
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Ep 43 - How to Stop Worrying and Start Living
|
Mar 21, 2024 |
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Ep 42 - Our Favorite Excuses and What We Did With Them
|
Mar 14, 2024 |
|
Ep 41 - How to Let Your Dreams Come True
|
Mar 07, 2024 |
|
Ep 40 - How Lily Became a Champion and You Can Too + Bonus Song by Erik
|
Feb 29, 2024 |
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Ep 39 - Going from Dreamers to Doers - Tiffani + Jared Wingert
|
Feb 22, 2024 |
|
Ep 38 - Finding Your Purpose - with Michael & Erin Allen
|
Feb 15, 2024 |
|
Ep 37 - Vulnerable Valentine's Day
|
Feb 08, 2024 |
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Ep 36 - Midlife Crisis vs. Midlife Quest
|
Feb 01, 2024 |
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Ep 35 - How Adventures Help You Create Lasting Connections
|
Jan 25, 2024 |
|
Ep 34 - Shifting Your Mindset About Money and Dreams
|
Jan 18, 2024 |
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Ep 33 - Raising Kids and Chasing Dreams at the Same Time - Dreyson + Shaundi Killpack
|
Jan 11, 2024 |
|
Ep 32 - Pulling Off Their First One Month Family Trip - Brooke + Nathan Schmoe
|
Jan 04, 2024 |
|
Ep 31 - What is a New Year's First?
|
Dec 28, 2023 |
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Ep 30 - 3 Stories About Not Getting What You Want
|
Dec 21, 2023 |
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Ep 29 - Our 3 Favorite Gift Ideas That Are Not "Stuff"
|
Dec 14, 2023 |
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Ep 28 - What Every Kid Wants to Hear From You Their Whole Life
|
Dec 07, 2023 |
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Ep 27 - Why You Shouldn't Have Medium Size Dreams
|
Nov 30, 2023 |
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Ep 26 - Why We Are Grateful For You
|
Nov 23, 2023 |
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Ep 25 - How to Play the "I Like" Game
|
Nov 16, 2023 |
|
Ep 24 - Why to Not Read Someone's Mind
|
Nov 09, 2023 |
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Ep 23 - When You And Your Spouse Don't Share the Same Dream
|
Nov 02, 2023 |
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Ep 22 - The Scary Stories We Tell Ourselves
|
Oct 26, 2023 |
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Ep 21 - 3 Questions to Discover What You Really Want
|
Oct 19, 2023 |
|
Ep 20 - How to Ruin a Marriage
|
Oct 12, 2023 |
|
Ep 19 - Our Favorite Quote on Parenting
|
Oct 05, 2023 |
|
Ep 18 - The 100 Year Grid
|
Sep 28, 2023 |
|
Ep 17 - What is Life Design?
|
Sep 21, 2023 |
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Ep 16 - Family Lessons Being Robbed in Rome - Dan + Natalie Reeves
|
Sep 14, 2023 |
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Ep 15 - How Pursuing Your Dreams Helps Your Kids
|
Sep 07, 2023 |
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Ep 14 - Why Your Kids Should Be in 2nd Place
|
Aug 31, 2023 |
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Ep 13 - Who Pays for What? (with adult kids)
|
Aug 24, 2023 |
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Ep 12 - How to Help Your Kids Move Out (and In)
|
Aug 17, 2023 |
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Ep 11 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 2
|
Aug 10, 2023 |
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Ep 10 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 1
|
Aug 03, 2023 |
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Ep 9 - Marriage, New In-Laws and Family Culture
|
Jul 27, 2023 |
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Ep 8 - Helping Your Kids Get in the Driver's Seat of Their Lives
|
Jul 20, 2023 |
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Ep 7 - 4 Easy Things You Can Do Right Now to Connect Your Family
|
Jul 13, 2023 |
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Ep 6 - Why and How To Make Life Long Friends (+ Double Return Parenting)
|
Jul 06, 2023 |
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Ep 5 - Debunking the Myth of the Perfect Family
|
Jun 29, 2023 |
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Ep 4 - What To Do When Your Kids Are Making Bad Choices
|
Jun 22, 2023 |
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Ep 3 - How to Get Your Kids to Stop Rolling Their Eyes at You
|
Jun 15, 2023 |
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Ep 2 - How to Get Your Kids to Take Your Advice
|
Jun 08, 2023 |
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Ep 1 - 1 Question to Immediately Improve Your Life
|
Jun 01, 2023 |