Employee’s Sailing Adventure Yields 13 Life (and Career) Lessons

Extended sailing is often described as “days of boredom punctuated by moments of sheer terror.” As a sailor, I can tell you that those boring times give you a lot of time to think. In fact, if you ever find yourself crossing the Atlantic Ocean in your own 40-foot boat, you will have approximately 25 days of thinking. You’ll even have time to reflect on those moments of terror that took you away from your blissful boredom.

Jennifer and Connected Women

After presenting these tips to the Connected Women group in San Jose – #LoveWhereYouWork!

In 2014 and 2015 I took a 2-year sabbatical from Cisco and sailed 16,000 nautical miles, or about halfway around the world, from San Francisco to Europe, on our sailboat with my husband and young son. And what I discovered in all of that time to think is that life at sea has a lot of lessons for life on land and back at your desk.

Let’s set aside the obvious lessons, such that having washing machine is super awesome and your dermatologist will thank you for using SPF 30. The hard-won lessons I learned from my adventure are things I constantly remind myself about while back to work at Cisco:

  1. The secret to achieving your dreams is through planning (spreadsheets!)

It’s not like my husb and and I have a charmed life or are just lucky. We spent five years planning and preparing for our two-year voyage. We have spreadsheets outlining what medications we needed to take, what spare parts we had on board, our son’s homeschool curriculum and about a dozen other plans. If you want something, make it happen. I recommend Excel.

  1. A sailor’s plans are written in the sand at low tide (a.k.a. things change)

Always keep one eye on the conditions and adjust accordingly. As my husband likes to say, “Keep your head out of the cockpit.” Why not do this in life? Life is not meant to be navigated on auto pilot.

  1. Adapt

Some of my friends were aghast that my “closet” for two years consisted of two small shelves. It turns out I only needed one. Give me just a few fast-drying, water-wicking, sun-shielding, wrinkle-resistant outfits from Athleta and I will wear them over and over again. What I learned is that what you want isn’t always what you actually need.

  1. Don’t always follow the instructions

I had to homeschool my son for 4th and 5th grade. It’s fair to say he may have taught me more than I taught him. One day we sat and played with Legos together. My creation was awful and his was amazing. I used to get angry when I’d buy him a $100 Lego set and he’d build it, then immediately take it apart. What he was actually doing was creating more amazing things, using the catalog of Lego parts in his brain. Ever since, I’ve never given him grief for taking his Legos apart. Being creative takes effort; don’t always do what you’re told.

Massaro presenting

Presenting my learnings.

  1. You can get used to almost anything

You might think that it would be awful to spend days at a time at a 15 degree angle, pitching up and down and always having to hold on to something with one hand lest you hurl across the boat and hurt yourself. And it is. But only for about the first three days. Things become normal after a while, even when they’re not comfortable. You can handle a lot more than you think you can.


  1. Consider the source, trust yourself

We got a lot of “advice” from other sailors. “You can’t sail from Panama to Jamaica at this time of year! The waves in the Caribbean are different from the ones in the Pacific!” What we found is that people like to project their own fears on to you. Do your homework and know what you’re capable of. Don’t let anyone else tell you what you can’t do. (For the record, waves are the same everywhere.)

  1. The only way to expand your comfort zone is to get outside of it

Easier said than done. I know. I get it. The thing I was most afraid of before leaving on our trip was getting into bad weather. There were about a dozen situations that I would have been petrified had I known I was going to encounter them. But guess what? After having gone through some sketchy situations, they are the things I’m most proud of dealing with.

  1. We often worry about the wrong things, so try not to worry

I spent about 493 hours worrying about crossing the Atlantic Ocean. Halfway across the Atlantic I sprouted the first gray hair on my head. True story. Yet our Atlantic crossing was mild and we had some amazing experiences. Now, I try not to worry about all the time I wasted worrying.

  1. Courage is doing it anyway, even when you are scared

My husband would ask our son, “Who’s braver? Daddy who’s not too scared? Or Mommy, who is scared and does it anyway? Mom.” This was nice reassurance when I felt like the biggest scardey-cat in the world. Face your fears. Trust me, you will be proud of yourself. You may not feel brave, but you are.

  1. Understand the difference between dangerous and uncomfortable

50+ mph winds and 15 foot seas? Sound dangerous? Actually, it depends. You need to be logical and evaluate: are we really in danger or does it just seem like we are? There were only a small handful of situations when we were potentially in danger. The rest was just uncomfortable. Don’t let your limbic system rule you, use logic. In some uncomfortable moments I would tell myself that I’d give anything to be sitting in an office and just dealing with politics. After all, I wouldn’t feel like my life was in danger. And then I’d remind myself that it just *seemed* like my life was in danger. Keep your perspective.

  1. You appreciate more what you earn 

    Massaro on the boat

    Learning lessons at sea.

We were crossing the Gulf of Genoa off the coast of Italy, and the forecast called for less than 10 mph of wind. We had 40. Fortunately the crossing was only 12 hours. After, we anchored off of the amazingly beautiful town of Portofino. The glass of wine in the cockpit that evening was delicious. Somehow, I don’t think it would have tasted as good if the wind was less than 10 miles on our crossing.

  1. Humor helps; panic doesn’t

There is a saying that there are “two kinds of sailors, those who have run aground and those who haven’t yet.” In the summer of 2015 we went from the first group to the second. It could have been catastrophic, but instead I’m really proud of the way we handled this emergency because we didn’t panic. I even tossed around a few jokes, even though I was stressed on the inside. We got floating again and we made friends in the process. And I’m not embarrassed about how it all went down. Take a deep breath when you think disaster strikes and let stress bring out the best in you, not the worst.

  1. YOU are never done

I thought I had learned all of these lessons from my trip and that they were part of me forever. It turns out that I need to constantly remind myself about them. It’s so easy to get back into a routine. It’s so easy to stop noticing and appreciating the world around you. It takes work. The minute you go on auto pilot is the minute you stop growing.

I’m still a little gob-smacked that Cisco let me take two years off to take a crazy sailing trip, and then hired me back at the end of my trip. In the end I think Cisco is better off because I get to apply all these lessons I learned at work. Every day.


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  1. Congratulations to finding your adventure and sharing it – do you have any plans for the next one?

    • Well it’s probably too much to ask for Cisco to give me another 2 years off, so we’ll wait until our son is out of college before we make another voyage again – most likely!

  2. What an awesome journey to take! Thank you for sharing your life lessons – very insightful.

  3. Amazing to hear the the brave journey your family took, and great learning during this journey together as a family, the risk you took and lessons you have learn, I admire your decision and also your employer to give you leave and take you Back.


  4. That picture sailing with the volcano behind you, is that the Azores?

  5. I am in love with this blog post and now have a girl crush on you! What an amazing adventure. I keep looking back at your list, trying to find a favorite, but there’s just too many. Don’t be surprised if I corner you at your desk and hold you hostage, forcing you to regale sailing stories and life lessons with me.

  6. Terrific piece – just one thing: re “For the record, waves are the same everywhere.” I highly recommend “Tides” by Jonathan White. He is on a book tour and may well be speaking near you this next two months. You might then reconsider your statement about waves. With very best wishes!

    • Thanks for the book recommendation, Trina – I’ve already ordered it on Amazon. We had some long email discussions with our physicist friend about waves prior to crossing the Caribbean, and our discussion mainly centered around the calculation of breaking waves compared to the length of the boat and the probability of capsize. That calculation does not change. But fetch, wind, duration of wind and depth of ocean can all have an impact on waves – but the physics behind it is constant.

  7. Jen,

    Bummed to have missed this particular session in person but am always excited, entertained and inspired by your spirited sharing of sailor wisdom. I love that you love these reflective exercises and that you care enough to clue us in. You make the effort to make it meaningful and relevant in the context of work. The part many of us tend to miss in these adventure stories is the amount of planning. Thanks for highlighting that. I also liked your note on the only way to expand one’s comfort zone: getting outside of it! And my favorite part of your write-up is this: The minute you go on auto pilot is the minute you stop growing.

  8. Amazing journey, thanks for sharing your experience. the bottom line if you are not living your are not growing. Feel excited and uncomfortable everyday.

  9. Wow! Such an inspiring journey and even more inspiring to really think through all the lessons you took from it.

  10. Jennifer, I could hear about your story for hours – I love it and am so admirative. I bet you a bunch of us wish we had the guts to embark on such a crazy but once-in-a-lifetime adventure.

  11. OMG this is awesome. One of my favorite lines:

    You might think that it would be awful to spend days at a time at a 15 degree angle, pitching up and down and always having to hold on to something with one hand lest you hurl across the boat and hurt yourself. And it is. But only for about the first three days. Things become normal after a while, even when they’re not comfortable. You can handle a lot more than you think you can.

    Thanks for writing this, Jen! 🙂

  12. How courageous! We should all remind ourselves that everything is possible, even the unthinkable.

  13. Lots of great lessons here Jen. I see you bringing these to the wonderful world of communications every day! Thanks for sharing.

  14. Great, great read! Amazing to even do this!! Would love to see more pics of your adventure.

  15. That was a great read! Would have really liked to have seen the presentation live.

  16. Love it, Jen! Humor helps; panic doesn’t – that’s my favorite. Some people have questioned me over the years with things like “How are you always joking around?”or “Are you not worried/stressed out about [insert frustrating situation here]?” Innately, I realized freaking out helps no one. BUT, humor helps everyone. 🙂

  17. Great read, Jen. Loved it, lessons learned and insightful advice. Thanks for sharing.