I am often asked what the impetus was for my sailing journey.

Truth be told, I’ve always been drawn to water, from my youth growing up on Lake Michigan to my travels along the shores of the Atlantic and Pacific Oceans. I started taking sailing lessons in my early adulthood, but something ‘more important’ always diverted my attention away from sailing (e.g. work, more work, relationships, shiny silver things, etc). It wasn’t until the last dream I was living (moving to New York City and establishing a career) had long since become a reality and had left me feeling stuck, that I began craving a new adventure.

I seriously began considering the possibility of a global circumnavigation in 2008. I had been chartering sailboats with a childhood friend, Mary Davenport Cook, who was ‘living her bucket list’ after being diagnosed with terminal breast cancer. Mary taught me to enjoy the moments and pursue a dream while I was able.

I enjoyed traveling and taking in the great outdoors in the comfort of my temporary ‘sailing home’. I welcomed the simplicity of sailing, needing only to take along the essentials, leaving everything superfluous behind. I felt a meditative sense of calm and connectedness while on passage. Time would stop. Life was clarified. Everything seemed to make sense. I wanted more of this experience, and thus my new dream was formed.

At first, I was too fearful to follow my dream

I thought that I would jeopardize the career that I loved and had taken so long to build and that I could not afford to undertake such an adventure. I thought that my friends, colleagues and family would think I was crazy and irresponsible, and that I would fall flat on my face. It was only when the fear of not following my dream became greater than all of my other fears that I decided to ‘lift anchor’.

None of my fears materialized. In fact, quite the opposite occurred.

In 2011, I resigned my position (and was subsequently offered an 8-month leave of absence) to earn my RYA Yachtmaster Offshore certification and cross the Atlantic Ocean as crew in the ARC (Atlantic Rally for Cruisers).

I returned to work in 2012 to successfully deliver the biggest project of my career.

In 2013, I started my second ‘sailbatical’ to cross the Pacific. I am currently in Hawaii having sailed here from Isla Mujeres, Mexico via Florida, The Bahamas, Jamaica, Panama, The Galapagos, and French Polynesia (Gambier, Marquesas, Tuamotus and Society Islands) - over 11,000 nautical miles in ten months.

2014 promises more adventure as I head to New Zealand from Hawaii via the Society Islands, Cook Islands, Niue and Tonga. I will return to New York for work in 2015 unless the ‘wind’ takes me in another direction.

There is much more to this story than I can include here, but to summarize, I am amazed how everything came together once I decided to go for it. Even apparent glitches (failed relationships, health issues) along the way turned out to be blessings in disguise and actually supported me on the journey.

Living my dream is not always unicorns and rainbows – sometimes it can be a real nightmare. However, even at its worst, it is much better than sitting around wishing I was living my dream.

If you want to incorporate sailing into your career break, you may want to take one or more of the steps that I did:

• Network – Get ideas and inspiration from other career breakers through organizations like Meet, Plan, Go!

• Travel with a Pro - Sail one or more paid passages with professional skippers such as John Kretschmer or Valerio Bardi

• Go Back to School - Attend an RYA (Royal Yachting Association) accredited school such as British Offshore Sailing School or Stormforce Coaching. Alternatively, you may wish to enroll in an ASA (American Sailing Association) or US Sailing accredited school in the US or Caribbean.

• Hitch A Ride - Join a boat as crew using site such as Crewseekers, Find-A-Crew, or Latitude38. See my Sailing Links page for additional crew sites I have used on my journey.

Aloha and Bon Voyage

Lisa Dorenfest has an unquenchable passion for sailing and a dream to circumnavigate the globe on a sailboat. She has taken a series of breaks from her career as a Project Manager to realize her dream one ocean at a time. Having now sailed over 20,000 + nautical miles in 14 countries, Lisa has learned to enjoy life’s moments and believe in the possibilities. You can read more about Lisa’s sailing adventures on her website and follow her on Twitter.