A Career Break to Take A Sailing Adventure: Judy Lin (Ep. 8)



At age 32, Judy Lin took a career break to go on a sailing adventure, despite having no previous experience. She joined the crew of a French sailboat departing from the Caribbean.

in the lock panama canal.jpg

Judy, pictured here in the lock of the Panama Canal. She enjoyed the experience of sailing and discovering new places so much she extended her initial 3-month break to 12 months.


Judy now lives in the Bay Area with her family: her husband Dave and their two sons, Ryan and Ben.



By all appearances, Judy Lin’s life and career were going just fine. A business-school graduate, she was quickly building a successful career in strategic planning at Turner Broadcasting in Atlanta. Yet she couldn’t shake the sense that she was on a corporate conveyor belt, and needed to be re-inspired.

One night, watching a re-run of Dawson’s Creek after a stressful day at work, an image of a boat sailing off into the sunset sparked her imagination. There was something in that idea that she wanted too. Despite having no sailing experience, she made a plan to leave her career to join the crew of a sailboat departing on a journey from the Caribbean.

Her adventure eventually lasted 12 months, taking her all the way to the South Pacific.

At the end of her sabbatical, Judy decided to go back to her previous career in strategic planning. She was surprised how easy it was – and began working again re-energized and with greater confidence. The most important difference this time was that she felt like she was choosing the life she wanted, rather than simply going along with the life that had chosen her.

Lisa’s interview with Judy, whose sabbatical took place 15 years ago, offers perspective into the way that an adventurous break to learn a whole new set of skills can enhance all aspects of your life and career, far into the future.

Today, Judy lives in the Bay Area with her husband and two young sons, and is the Chief Operating Officer of NatureBridge.


memorable insights

  • What goes into planning a sailing sabbatical -- especially without previous experience.

  • What it's like to plan a sabbatical when nothing is majorly wrong in life, but nothing feels quite right either.

  • Initially it was a 3-month break from life, to do something very different.

  • How each planning step helped Judy to feel more comfortable with such a dramatic idea.

  • How she planned her finances for each month.

  • What it was like to choose a boat to crew on – deciding on the type of people she wanted to join, and taking certain precautions to feel more safe.

  • Having about 50-60 percent of her plan clear before she started to tell her sister and friends – and then the parents.

  • What actually happened to her plan after she started her sabbatical.

  • How she had to quickly learn how to be decisive about what she wanted, and to get out of unsafe situations.

  • What she learned about sailing: That it could be difficult and grueling, and required intense teamwork in sometimes life or death situations.

  • How sailing gave her a unique appreciation for nature, and some of her most amazing moments being in the middle of the ocean.

  • Feeling a very clear endpoint to the trip – that she’d arrived at the end of this chapter and that there was a new one awaiting.

  • Experiencing more confidence and self-accountability on her return.

  • How ultimately taking this break led her back to the same career, but this time with the empowering sense that she was choosing it for herself.



1. What do you wish you had known before you took your leap?

2. What was the most unexpected thing that came of your leap?

3. For someone who is thinking of doing something similar, what one piece of advice would you offer? 


Judy’s recommended RESOURCES

I met Janna on the dock in Tahiti and she is now a dear lifelong friend. She wrote a book about her sailing adventure: The Motion of the Ocean: 1 Small Boat, 2 Average Lovers, and a Woman's Search for the Meaning of Wife. It documents their BHAG (Big, Hairy, Audacious Goal) but also as it relates to being married. This was their honeymoon. I make a direct appearance in the questions for the author at the end and it includes some of the content from the podcast.

Tess Vigeland is a sorority sister from college who recently took a big leap. She wrote a book about it called, Leap: Leaving a Job with No Plan B to Find the Career and Life You Really Want. I read it after the fact but thought it would have been inspirational to have read it beforehand.




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