Sherry Ott’s Day Off

February 18, 2014 10 Comments »

teaching raise hands

This is what a day off from travel looks like. Ms. Ott is in the classroom!

“Hello Ms. Ott.” A group of kids said to me as we passed by each other. As I continued to walk down the path I looked around and saw a group of students on the campus lawn basking in the warm Hawaiian sun, suddenly they started waving at me and yelling “Hello!”. I returned the gesture somewhat dumbfounded but still conscious of having good manners. I turned the corner and was startled. There was my face plastered on the wall – a flyer with my name and photography on it. Kids smiled at me as I walked by my own picture feeling somewhat awkward and surreal. For two weeks I was a high school rock star.

Sherry Ott Photography

One of the many displays of my photography they had around campus.

Which was nothing like my original high school experience – rock star wasn’t really in my vocabulary. In fact I was more of a high school jock and nerd rather than rock star. But that was 26 years ago – and a lot has changed in my life.

Bueller? Bueller?

I kept thinking about the popular movie when I was in high school – Ferris Bueller’s Day Off. Well, in some ways I was doing just the opposite – I was taking a Sherry Ott’s Day Off and playing hooky from my regular blogging job and attending school instead!  I was serving as the Keables Chair for Iolani School in Honolulu.  Coming to spend 2 weeks in a school environment is as foreign to me as traveling to another country. And the hardest part for me was simply having to get up every morning before the sun came up, shower, put on makeup and be somewhere. I don’t think I had realized how far from that type of life I’ve moved in the last 7 years until I had two weeks of getting up at 5:30AM. I don’t miss the office. I may miss the paycheck – but not the office.

However since I was ‘traditionally’ working again for two weeks my type A personality kicked into high gear pretty quickly and as I prepared for being the Keables Chair I decided to jot down some goals for myself to try to stay focused and ensure that I accomplished what I set out to do.


I had actually created goals for the Upper School, the Lower School, and the teachers/faculty, but my overall goal was to introduce a concept that I feel is important in life – “make your own way” – something that I learned while walking the Camino de Santiago trail. 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. Reminding them that you don’t have to live in “should”, you can craft your own world. I find that the most successful people in business/science and in artistic fields are people who are doing their own thing and being innovative. It’s easy to follow, but it takes guts to make your own way.

school locker

Luckily I didn’t have to remember any locker combinations!

After giving this inspirational message to the high school students it was fun to see them put the hashtag to use. In fact, I had a number of teachers who told me they discussed it in class. Plus as I met with students like the ones in Women in Literature we talked about how important it is to make your own way in life. The teacher had them write blog posts after my visit which she passed along to me. I was touched and excited as I read through the posts.

Some of my favorite excerpts:

“Furthermore, she reminded me that every once in a while I have to take a step back to reevaluate what I want and where I want to go with my life.”

“Would you ever look at a “hobo” as your role model or even as a successful individual? Me neither, until a fair, dirty blonde, and confident woman walked into the room.”

“I especially found it interesting when she said she wanted to experience something new every day. I had never looked at my life that way and it encouraged me to start trying new things and taking more risks. “

“In my opinion Sherry Ott is by far the most interesting and unique Keables Chair Holder that Iolani has ever brought to its campus. I personally think her likeability is due to the fact that she has gone against the norm of a 6-figure salary, and has made a career based upon her passion of traveling.” – from the teacher of Women in Literature Class

My time was also covered by the school newspaper – Keables Chairholder, Sherry Ott, Captivates Students (this picture in the article proves that I did get up and shower every day and try to look professional!)

Cultural Studies

Every place has a culture – and I make my living observing cultures and comparing them to my own. And even though I wasn’t traveling, I was still exploring a new culture to me. I found a few things that really stood out to me over the last two weeks of observing the school and culture.

Ying and Yang – I loved witnessing such cutting edge technology in a school – iPads for every student – yet at the same time it’s a school that holds on to old cultural tradition such as hula dancing. Watching the dance team was really moving to me. As I think cultures and traditions are so important to maintain throughout the world.

Hula Dance school

Hula dance is one of the many ‘arts’ the kids study

Taught to Give Back – I was lucky enough to see the Team Service group in action during my stay and was absolutely floored by the kids desire to make the world a better place. It’s not just about throwing money at a problem, it’s about education – and I was so excited to sit and brainstorm with them about ideas for educating the student body and faculty about the water crisis.

Intersection of Art and Business/Science – I was impressed by the science and the art facilities at Iolani – in fact I was drooling over the photo studio! I wanted to stow away there for a few weeks. As someone who has lived the 1st half of their career on the business/science/technology side and has now crossed over into the more artistic endeavors – I understand the importance of having an appreciation and understanding of both. It’s essential to success and the kids at Iolani are getting that well balanced education.

A Few Surprises

There were surprises I experienced every day – and that’s what I love about any project – travel related or not! Some of my favorites from the 2 weeks:

-After talking about the culture of Jordan, one 6th grade boy raised his hand and asked me about how the war in Syria effects Jordan. I was stunned! I didn’t even know where those countries were until I was 38 years old (sad but true). So I introduced the term “refugee” to his big brain.

-I taught photography students about street photography and they had an assignment to try to take pictures of strangers one weekend. Some of the results were absolutely stunning and it definitely got them out of their comfort zone. Many of them even went and took on the hardest subjects possible – homeless people. Bravo for guts.

photographing strangers

Photographing Strangers assignment

photographing strangers

Photographing Strangers assignment

-I ran a 5k race thanks to an invite I received from one of the teachers who heard I enjoyed running. It was on a weekend and I figured what the heck – I might as well practice what I preach and go be local! That was the first race I had run in 6 years and it was a great way to see the sun come up in a different part of the city and feel a bit more connected to Honolulu.

-When teaching the Entrepreneurship class I surprisingly introduced the term SEO (Search Engine Optimization) to them and we talked about the inner workings of the interwebs. I mentioned that when I was in college we didn’t even have Google yet. The kids let out a big gasp! Life without Google – how could that be?

-I spent time talking to the kindergarteners about penguins in Antarctica – who actually knew more about penguins than I did! And wow oh wow is it crazy to be around a class of 5 year olds – what energy and enthusiasm. One of them even took my hand as I was leaving and was starting to drag me to lunch with him. I had to sadly tell him I had to go teach another class.

-Two students came to me to get advice on traveling in Nepal. The two kids were going to take on a volunteering project outside of Kathmandu and then do some hiking. I was floored by the ambitions of these kids. After all – they are only in high school! And on that same note, the Team Service group is considering helping me with my charity: water fundraising efforts which completely surprised and humbled me.

-At the final event of my two week position, the school even gave me gifts. Imagine my surprise when they handed me a wooden, laser cut camera specifically designed for me with my #MYOW hashtag on it. It was created by one of their up and coming teachers/artists – Taylor Wong.

Iolani woodworking and design

#MYOW photography gift

Back to Blogging

My time as Keables Chair is complete, but my immediate goals were most definitely met. I even had parents come and talk to me about their kids coming home and talking about travel and following your dreams. Time will only tell if long term these kids are more likely to consider study abroad or travel opportunities. But I was happy with the work I did there – most importantly I opened some eyes to the new world of digital careers and got people to dream of where they may go in life.

I hope I get to do more of this work in the future – despite the getting up early and having to wear makeup! Whenever I get to share the message of travel, following your passion, and making your own way to people – students or adults – it’s makes it all worth it to me. I know that I’m changing lives and ideas out there and making an impact. More than I ever could have in my old career.

My favorite headline that I came across in a student’s blog…
“Sherry Ott-to stay longer!”

Keables Chair 2014

Mark, myself, and Frank – the teachers who supported my every need for 2 weeks as the Keables Chair

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