Sailing Doodles Podcast

Most people have a dream. Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, moving overseas, or just walking away from a life that looks successful on paper but doesn’t actually make you happy. But most people never do it. Not because the dream is impossible, but because they keep waiting until they’re ready. In this episode, I talk about why I believe you have to set a date, prepare as best you can, and then go. My dream was sailing around the world on a yacht, but this isn’t just about sailing. It’s about risk, freedom, time, work, and the trap of waiting for the perfect moment. I also talk about leaving a good career, the idea of “no risk, no reward,” why doing nothing is also a risk, and why chasing the dream might not work out exactly how you planned — but that doesn’t mean it wasn’t worth doing. You can always get another job. You can’t always get another life. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

After a big health scare, I’ve had to ask myself some hard questions about the future of Sailing Doodles. I just bought my dream yacht, but now I’m dealing with blood clots and thrombosis in major abdominal veins, and I still don’t have all the answers about what caused it or what the long-term prognosis looks like. For a while, there was even concern it could be cancer, which thankfully seems to have been ruled out. In this episode, I talk honestly about what this could mean for my future: whether I can keep sailing long term, what happens to the new yacht if my health changes, whether I’d sell the boat, hire crew, slow down, or pivot the channel completely. I also talk about what retirement might actually look like, whether I regret buying the boat right before this happened, and what happens to the dogs, the crew, the travel plans, and Sailing Doodles as a whole. This one is personal. I don’t have all the answers yet, but this scare has definitely changed how I think about life, health, travel, and the future of the channel. Thanks for watching and for all the support. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

This one feels surreal to say out loud — the new boat is getting very close to completion. In this update, I share where the build is at, what’s left to finish, and why this moment feels different than anything before. After months (and years) of planning, I’ll be flying to Thailand next month to finally step onboard and start the next chapter. I know a lot of you have been following this journey from the beginning, and I can honestly say… I’m just as excited (and nervous) as you are. Thanks for sticking with me — things are about to get really interesting. Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

In this podcast, I answer one of the biggest questions I’ve been getting lately: who’s coming with me to Thailand on the new boat? We talk about the new boat timeline, potential crew lineup, and what this next chapter of Sailing Doodles is really going to look—both on and off camera. I also address questions about Chloe, future appearances, and how I handle bringing new people into the videos while balancing privacy, reality, and the internet’s opinions. We also dive into: Who may be joining the boat in February How crew decisions actually get made Viewer questions about drones, sailing, and life on the water What changes (and what stays the same) with the new boat Big changes ahead—this episode gives you the real story.

In this episode, I share my personal thoughts on the tragic aviation accident involving Greg Biffle and his family. I had the opportunity to meet Greg and his wife Kristina about a year and a half ago at Spanish Cay Yacht Club, and they were incredibly kind, welcoming people. This is not an episode about speculation or assigning blame, but rather about acknowledging the human loss, explaining what is currently known, and offering perspective on how unforgiving aviation emergencies can be—especially shortly after takeoff and in marginal weather conditions. Investigations by the Federal Aviation Administration and the National Transportation Safety Board are ongoing, and it will be many months before definitive answers are available. My thoughts and condolences are with everyone affected by this heartbreaking tragedy.

Ever wondered what sailing is really like? After years living aboard, crossing oceans, rescuing boats, breaking boats, and teaching new crews how to sail, I’ve heard every sailing myth in the book… and today we’re busting the big ones. In this episode, we break down the 12 most common (and most misleading!) sailing myths that stop people from getting on the water — including the truth about boat costs, storms, sharks, catamaran safety, anchoring, YouTube crew life, and whether you actually need experience before buying a boat. Whether you’re dreaming of cruising, already sailing, or just love the lifestyle, this podcast will give you a real-world look at what sailing is actually like… the good, the bad, and the hilarious. To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. cruise@sailingdoodles.com Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

Ever wonder where everyday expressions like “three sheets to the wind,” “overboard,” “the bitter end,” or even “windfall” actually came from? Turns out, tons of common words in English were invented by sailors, pirates, and old-school sea captains, and today we still use them without even thinking about it. In this episode of the Sailing Doodles Podcast, I break down over 80 everyday words and sayings that all started on ships — from naval terms, pirate slang, emergency commands, rigging language, and old maritime traditions. Some of these are obvious… but most of them will absolutely blow your mind! If you enjoy sailing, history, language, or just fun trivia, this is a super entertaining deep dive into how much of modern English came from life at sea. Fair winds and following seas — and thanks for listening! If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles