All Episodes
What Could Go Right? — 165 episodes
Ep 1 65 Sailing Adventures Build Belonging
Ep 164 Travel Like a Beginner: The Curiosity Advantage - Lessons from Finland
Ep 163 The Hidden Cost of Playing it Safe
Ep 162 How to Stop Overthinking Your Next Sailing Trip
Ep 161 Why Greece Is Perfect for Your First Sailing Trip
Ep 160 From Tourist to Contributor: A New Way to Experience Travel with Christopher Hill
Ep 159 Why Sailing Trips Are the Ultimate Reset (Backed by Science)
Ep 158 He Let a Beginner Sail a 47-Foot Boat – What Great Captains Know with Matt Holt
Ep 157 Field-Tested Gear for Sailing Trips
Ep 156 Milestones and New Beginnings
Ep 155 Sailing the Abacos for the First Time (And Why It Surprised Us)
Ep 154 Hidden Perks on our Sailing Trips (+ Travel Insurance, Learning to Sail, and Gear Favorites)
Ep 153 Burnout, Productivity, and Why Rest Is the Missing Skill
Ep 152 The Real Reason Travel Changes You (It’s Not the Destination)
Ep 151 Exhaustion vs. Motivation: How to Know When to Push and When to Rest
Ep 150 New Growth Over Glory Days: Why Your Best Adventures Are Still Ahead
Ep 149 New Favorite Boat? Tour the Leopard 4600
Ep 148 The Knock That Changed Everything: Overcoming Fear, Burnout, and Starting Over Midlife
Ep 147 How to Rewire Your Brain for Self-Trust, Resilience, and Joy
Ep 146 How to Know When to Persist or Pivot (Overcoming Challenges on Your Personal Growth Journey)
Ep 145 How to Get Clear on What You Want in Life (The Desire List Practice)
Ep 144 Feeling Stuck When You Want Momentum? The Unexpected Gift of Stillness with Ganel-Lyn Condie
Ep 143 From Rural Indiana to Rwanda with Mark Richardson: What Goes Right When You Step Outside Your Comfort Zone
Ep 142 - He Retired. Then the Real Adventure Began – Everest, PTSD & Reinvention
Ep 141 - Sailing, Adventure, Transformation: Matt & Julie’s Story
Ep 140 – Why Celebrating Small Wins Builds Confidence & Lasting Habits
Ep 139 – The Amalfi Coast by Sea: Italy's Most Iconic Islands
Ep 138 – Real Connection is Real Luxury
Ep - 137 Bora Bora – Beyond the Postcard
Ep 136 – How to Pack Light: Your Suitcase and Your Life
Ep 135 – Magical Mexico: Sea of Cortez
Ep 134 – From Stuck to Soaring with Curtis and Irene Hill
Ep 133 – Behind the Scenes: Progress in Real Life
Ep 132 – Best of The Bahamas
Ep 131- When You Can't See Your Progress
Ep 130 - Burnt Out From Giving?
Ep 129 - If You're NOT Having Fun...
Ep 128 - We Talked to 1,000 People: Most Frequently Asked Questions about sailing with us
Ep 127 - Courage to Begin
Ep 126 - Best of the British Virgin Islands
Ep 125 - Life is Short. Legacy is Long.
Ep 124 - Compass vs. Map: Navigating Life Without Perfect Plans
Ep 123 - Anchoring: Stable vs Stuck
Ep 122 - Adventure Right Where You Are
Ep 121 - Planning Your Private Sailing Trip
Ep 120 - 2026 Sailing Schedule
Ep 119 - First Trip To Croatia
Ep 118 - Adventure for Everyone with Paul and Val Osborne
Ep 117 - Travelpreneur Christina McEvoy on Adventure and Growth
Ep 116 - The Readiness Myth
Ep 115 - Navigating Disappointment, Lessons in Resilience
Ep 114 - Croatia Close Up with Jordan + Christinah Mulder
Ep 113 - Staying Close When Abilities Change
Ep 112 - Catamaran Tour of Leopard 4500
Ep 111 - What if it's Better Than You Imagined?
Ep 110 - This is Your Call to Adventure
Ep 109 - Slow Time, Strong Ties
Ep 108 - Sailing the Spectrum of Routine and Risk
Ep 107 - The Best Sailing Trip You’ve Never Heard Of
Ep 106 - Steady Swiss Pace
Ep 104 - "Garbage is Not My Passion"
Ep 105 - From Cubicle to the Alps - Wild Career Pivot with Nicki Preece
Ep 103 - Our Top 10 Most Popular Episodes
Ep 102 - Beyond the Booze Cruise
Ep 101 - Marriage, Work & Love with Steve & Donna Kuhr
Ep 100 - A Time to Mourn
Ep 99 - Flexibility Over Frustration
Ep 98 - Why Italy Now
Ep 97 - Then vs Now (Our Sailing Journey)
Ep 96 - How to Grow Your Confidence
Ep 95 - Spring Cleaning - How to Reset Yourself
Ep 94 - 3 Sailing Stories (Racing)
Ep 93 - People Can Change (Les Miserables)
Ep 92 - Daily Sailing Life - Wifi, Waste & Water
Ep 91 - Daily Sailing Life - What NOT to Pack: Managing Electricity
Ep 90 - The Language of the Universe
Ep 89 - Boat Tour - Lagoon 52 Catamaran
Ep 88 - Seven at Sea Revisited (Karina's Version)
Ep 87 - Cruise Ship or Custom Sailing Trip – Side by Side Comparison
Ep 86 - Saying Yes: Flying Over the Grand Canyon
Ep 85 - Reclaiming a Sailing Dream - Mary & Jonathan Young
Ep 84 - When Your Dream Makes You Puke
Ep 83 - Living Big by Starting Small
Ep 82 - The Christmas Tree Chronicles
Ep 81 - What Surprised Me in Thailand
Ep 80 - Solo vs. Group Travel: The Benefits
Ep 79 - Why Be Grateful in Adventure
Ep 78 - Our Top Travel Trips
Ep 77 - The Company You Keep
Ep 76 - Sailing in Sardinia
Ep 75 - From First Click to Casting Off
Ep 74 - T-Minus Friday
Ep 73 - Becoming Grandparents
Ep 72 - Not a Scam
Ep 71 - Treat Yourself Like A Person
Ep 70 - Getting Clarity with Stefanie Gass
Ep 69 - RV, Boat, Van - 7 Years of Travel with the Jackson Family
Ep 68 - Overcoming Fear of the Unknown
Ep 67 - The Mentor Advantage
Ep 66 - Getting Started - The First Big Adventure (FAQ)
Ep 65 - Lessons from Lily
Ep 64 - What We Love About Traveling With Kids
Ep 63 - Decluttering - Make Space For Your Dream Life
Ep 62 - How We Sold Our Sailboat
Ep 61 - DIY vs Who Not How: Finding Balance
Ep 60 - Collaborating as a Couple - Writing Our Book
Ep 59 - How to Grow the Size of Your Dreams
Ep 58 - Declare Your Independence
Ep 57 - Personal Growth + Sailing
Ep 56 - Our Personal Packing List for Sailing Trips
Ep 55 - Navigating the Empty Nest Transition
Ep 54 - Your Guide to Letting Go - with Y.E. Young
Ep 53 - Why Loved Ones Inadvertantly Try to Hold Us Back
Ep 52 - Tortillas to $200M - Lisa Binggeli
Ep 51 - How to Upgrade Your Identity (Part 2)
Ep 50 - How to Upgrade Your Identity (Part 1)
Ep 49 - Darling, Let's Be Adventurers
Ep 48 - Books, Beauty Pageants and Politics
Ep 47 - We Bought An Eco Resort In Belize
Ep 46 - What's Your Credibility Score and Why Does it Matter?
Ep 45 - Our Top Tips on How to Deal with Change
Ep 44 - Two Takeaways From Our Forties
Ep 43 - How to Stop Worrying and Start Living
Ep 42 - Our Favorite Excuses and What We Did With Them
Ep 41 - How to Let Your Dreams Come True
Ep 40 - How Lily Became a Champion and You Can Too + Bonus Song by Erik
Ep 39 - Going from Dreamers to Doers - Tiffani + Jared Wingert
Ep 38 - Finding Your Purpose - with Michael & Erin Allen
Ep 37 - Vulnerable Valentine's Day
Ep 36 - Midlife Crisis vs. Midlife Quest
Ep 35 - How Adventures Help You Create Lasting Connections
Ep 34 - Shifting Your Mindset About Money and Dreams
Ep 33 - Raising Kids and Chasing Dreams at the Same Time - Dreyson + Shaundi Killpack
Ep 32 - Pulling Off Their First One Month Family Trip - Brooke + Nathan Schmoe
Ep 31 - What is a New Year's First?
Ep 30 - 3 Stories About Not Getting What You Want
Ep 29 - Our 3 Favorite Gift Ideas That Are Not "Stuff"
Ep 28 - What Every Kid Wants to Hear From You Their Whole Life
Ep 27 - Why You Shouldn't Have Medium Size Dreams
Ep 26 - Why We Are Grateful For You
Ep 25 - How to Play the "I Like" Game
Ep 24 - Why to Not Read Someone's Mind
Ep 23 - When You And Your Spouse Don't Share the Same Dream
Ep 22 - The Scary Stories We Tell Ourselves
Ep 21 - 3 Questions to Discover What You Really Want
Ep 20 - How to Ruin a Marriage
Ep 19 - Our Favorite Quote on Parenting
Ep 18 - The 100 Year Grid
Ep 17 - What is Life Design?
Ep 16 - Family Lessons Being Robbed in Rome - Dan + Natalie Reeves
Ep 15 - How Pursuing Your Dreams Helps Your Kids
Ep 14 - Why Your Kids Should Be in 2nd Place
Ep 13 - Who Pays for What? (with adult kids)
Ep 12 - How to Help Your Kids Move Out (and In)
Ep 11 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 2
Ep 10 - Marriage & Midlife Pivots: Y.E. Young + Jayne Young - Part 1
Ep 9 - Marriage, New In-Laws and Family Culture
Ep 8 - Helping Your Kids Get in the Driver's Seat of Their Lives
Ep 7 - 4 Easy Things You Can Do Right Now to Connect Your Family
Ep 6 - Why and How To Make Life Long Friends (+ Double Return Parenting)
Ep 5 - Debunking the Myth of the Perfect Family
Ep 4 - What To Do When Your Kids Are Making Bad Choices
Ep 3 - How to Get Your Kids to Stop Rolling Their Eyes at You
Ep 2 - How to Get Your Kids to Take Your Advice
Ep 1 - 1 Question to Immediately Improve Your Life