John Ensley chases the sun from the Pacific Northwest in summer to Baja California, Mexico, in winter, as one part professional sailing instructor and one part running a virtual financial planning business. As the founder of Cruise n Learn Sailing International, he loves sharing his knowledge, experience, and passion for sailing. John feels strongly that it isn’t just about sailing skills and certifications; it’s really about designing a fantastic lifestyle and living the life of your dreams.

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Show Notes

John Ensley chases the sun from the Pacific Northwest in summer to Baja California Mexico in winter, as one part professional sailing instructor and one part running a virtual financial planning business. As founder of Cruise and Learn Sailing International and loves sharing his knowledge, experience and passion for sailing. John feels strongly that it isn’t just about sailing skills and certifications, it’s really about designing an amazing lifestyle and living the life of your dreams.

04:27 John went on a trip to Mexico, sailed down the beautiful Pacific coast, and managed to stay connected for work while enjoying the journey.

09:02 Their process: Complete bookwork online and then practice on the boat. Subscription option for affordable monthly payments.

10:41 Variety of courses came from teaching sailing for 8-9 years.

13:14 So that's the second reason that people pursue certifications is so that they can go charter in different places. And then thirdly is insurance

17:28 Select a sailing school that aligns with your specific goals and preferences, ensuring that you have an immersive and educational experience on the water. It's important to have a conversation with the school to understand their philosophy, instructors, boats, and operations. Consider your goals, whether it's day sailing on local lakes, buying a boat, or chartering internationally, and find a school that matches your needs and personality. Remember that the cheapest or most expensive option may not always be the best, so focus on finding the right fit and value for your sailing experience.

22:47 I'm really into blending work, play, and technology. I even came up with a 3G dongle back in 2009, and cellular technology has been a big part of my journey.

24:40 A friend from my sailing class is now teaching in Puerto Rico, living on a boat.

26:45 Sailing requires training for advanced navigation and skills.

28:43 Johns favorite outdoor gear under $100,