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Sherry Teaches Travel at the Iolani School in Hawaii…

The Iolani School, in Honolulu, is a prestigious private school for grades K to 12.

With over 1,800 students, the Iolani School is one of the largest independent schools in the United States.

But the best part…

They take a different approach to education by inviting guest teachers to expose the students to different professions and views on life.

In 2014, Sherry Ott had the honor of becoming the first ever travel blogger and digital media professional to teach the students about how to travel, being flexible with their future, living in the present moment, and how they can make their own way in life.

Learn how Sherry made a HUGE impact on the students at the Iolani School and how teachers (and parents) can incorporate travel in education anywhere in the world…

What is the Keables chair?

The Keables Chair is an endowed teaching position that annually brings outstanding teachers, writers, and artists to the Iolani School.

The goal is to bring more outside, creative exposure to the kids of Hawaii as island life can be isolating at times.

Iolani School

How did get involved with the Iolani School?

Iolani School is located on the island of Oahu in Honolulu.  I had a friend who was familiar with the chair position  and he suggested that I apply. I thought he was crazy when he suggested it.  I’m not a teacher after all.

He felt my story and message of going from corporate cube dweller to world traveler and freelance writer/photographer would be inspirational to the kids.

I was intrigued with the idea and it didn’t take long for me to give in and say yes.

What did your role entail?

I  taught various classes including photography, geography, earth science, entrepreneurship, creative non-fiction writing, and religion.

I even visited a few kindergarten classes and talked about penguins in Antarctica.

I gave the morning school addresses for grades 5 – 12 which were inspirational messages that included ideas about following your passion and showing them some exciting parts of the world.

I also gave a public presentation one evening in Honolulu on behalf of the school.

What were your goals at the Iolani School?

My overall goal was to introduce a concept that I feel is important in life: make your own way.

This is something that I learned while walking the Camino de Santiago.  I even made it ‘kid-friendly’ and gave it a hashtag, #MYOW, and challenged the students and faculty to take different paths, find the unique things in life, and be innovative.

My goal for the high schoolers was to teach them that you don’t have to have all of the answers – including knowing what you want to do with the rest of your life. They can change paths (and they will change paths). Ask adults what they studied in school and what they do now – very few had a planned path that they stuck to. Instead, they had to be willing to change.

My goal for students in grades 5 – 8 was to get their head out of their phones and look around them. I wanted them to strive to live in the present and to look around, talk to people, and see things. The reality that is in front of you can be exciting as you want.  If you could go anywhere in the world where would you go?

My goals for the teachers was to take advantage of their summers and sabbaticals and see the world. The world is a gift and we should use it.

Iolani School

You say children “should” travel. Why?

First of all, traveling is education.

Reading about a volcano or a desert is a lot less meaningful than seeing the volcano or riding a camel into the desert.

It also starts to teach kids how to form heir own opinions of places they they learn about or hear about in the news or main stream media. Traveling widens their perspective more than any book will ever do.

Finally, it’s important to have a world view in a world that is ever reliant on international interaction and peace.

What advice can you give for parents to encourage travel?

Learn what your kids are studying in school and consider incorporating those places into a family vacation.  Get them armed with a passport as you never know when an opportunity to travel out of the country may come up!

You live a non-traditional life. How important is it to teach children to “make their own way in life”?

I think we are programmed to go with the flow.

Following the pack and social norms is just easier.  We are stealthily bombarded by social pressures such as get a good job, get married, have kids, and wait until we are 60+ to retire and do the things we want – and that’s what most of us do.

Making your own way is hard because you’re going against the norm. But I find that those who choose to be innovative and creative in their life choices and business are generally more successful.

For me, I never want to do what everyone else is doing.  I yearn to be different and try different things which is what led me on this journey for the last 7 ½ years.

I make my own way by taking the road less traveled – whether that’s going to different places, being nomadic, choosing not to have kids, or traveling with my nieces.

Iolani School

What did the children teach you?

They taught me how to live life by a bell (again) and be on time!  I forgot what it was like to have your day split up into periods that you couldn’t be late for or run long.

The bell system was fun and stressful at the same time for me.

How do you see the internet changing travel for our youth?

Kids growing up today will be more plugged in when they travel.  They’ll have everything at their fingertips – which also means they will never really be alone.  They won’t be able to do that European backpacking trip where they are really on their own and remote.

I’m not sure if this is good or bad!

What was your favorite travel lesson?

Say “yes” and be open to things when you travel. Don’t plan, just let things happen.  The people you meet and the things you learn will take you down wonderful paths if you just let it.

Iolani School

How did the experience change you?

It gave me a burst of confidence and purpose again.  When you work as a digital nomad blogger, you work hard to publish articles but  you don’t get a lot of feedback (verbal or non-verbal).

You hope people like it and react to it but, it’s really kind of a one way street.

For my two weeks at the Iolani School, I was able to interact with my audience and how they reacted to my stories, thoughts, and lessons.

It rebuilt my confidence.

What one piece of advice would you give for women travelers?

Don’t be afraid to travel alone and do what you want. Traveling solo is the best way to meet other people.

My second piece of advice is to ALWAYS dress in a non-provocative way when in conservative countries.  Be respectful of local customs and help all solo female travelers by setting a good example that women should be treated with respect.

What are you most proud of about yourself?

I’m most proud when I meet someone or hear a story from someone who has been inspired to travel due to one of my stories or my MeetPlanGo events.  There is nothing more rewarding when I hear a story about how someone took the leap thanks to some guidance or inspiration I provided.

I hope in a few years I’ll be hearing this from the kids of Iolani School too!

What did you think about this interview?

Join the discussion and leave your comments, tips, and personal experiences in the comments below.


Thank you Sherry for participating in this interview.  For more info on Sherry and her travels, please visit Otts World and read her experience as the Keables Chair.

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