S&S ABROAD with Diana O’Gilvie ~ Filmmaker, Writer, Teacher

This month’s expat profile features a talented woman who wears up to different hats every day. if not more. She’s a Jamaican-born and raised, award-winning freelance filmmaker who recently left the airline industry to pursue her dream of living abroad or rather, outside the US.

Keeping up with Diana is an adventure in itself – when she’s not busy flying off to Jamaica to film her documentary on jerk cuisine (now in its editing stages – can’t wait), she’s teaching her students English in Indonesia, while exploring the country, travel blogging and writing.

Diana’s leap of faith to pack up, sell her stuff and move to Asia is inspiring and shows that any of you dreaming to live and work abroad can do it, too. And as she tells us, it doesn’t have to take that long or cost that much to move.


NAME:  Diana O’Gilvie

Diana in Bali

PATRIA:  Jamaica

OCCUPATION:  Filmmaker, Writer, Blogger, Teacher

CURRENT LOCATION:  Jakarta, Indonesia


Tell me about yourself in one sentence.

I am finally taking care of me.

Love that! You’re originally from Jamaica – where on the island did you grow up and how old were you when you left?

I grew up in Kingston and St. Andrew. I migrated to the US when I was the tender age of 17 years old.

And from the US you moved to Indonesia. How long were you living in the US and what brought about your decision to move abroad?

After living and working in America for 15 years I decided that I wanted to live an international life. I was burnt out from working just to pay the bills – rent for a nice apartment that I hardly ever saw and a cool car I hardly I ever drove. I knew there was more to life than the proverbial rat race and  I earnestly sought that out.

Did you consider other countries or were you sure you wanted to be there? 

The fun part was choosing  a country. I went out and bought a globe, sat in my living room as I spun it and fantasized about where >> I would live.

(HELLO! I thought of doing that very same thing. I just couldn’t find my NatGeo globe.)

I knew I was done with winters so that narrowed my search to the Caribbean, South America and South East Asia. Then came the process of elimination. The Caribbean is all to familiar for me. I wanted something different. I visited Indonesia before and fell in love the natural beauty of the country. I just couldn’t stop thinking about Indonesia, so the decision was clear for me.

How long did it take you from the moment you made the decision to move to finding a job and securing a contract? Is there anything you would have planned differently?

It happened so fast! I made the decision, sent out my resume in late October. A few days later I received a correspondence from the Director of Studies of English First in Indonesia. We set up a Skype interview for 1 a.m. my time  the following week and I was hired immediately on that call. So my life was changed in a matter of two weeks.

Were you nervous the night before your flight out bout the new job and the big move? 

I didn’t sleep for days before my flight, out of sheer excitement. I wasn’t nervous, just anxious and impatient to start this new chapter.

How has life in Jakarta been so far – what has been the best and worst thing about living there? 

I work and live and Jakarta and it can be overwhelming with the dizzying traffic. The best thing about it though is the delicious and cheap street food. I can have a full meal for less than US$1.00.

(Um, that wasn’t a typo: ONE US DOLLAR for a meal.)

The other issue I have is a double sided coin. Indonesians don’t see a lot of Black people. So I get stared at A LOT. Sometimes I get asked to take a photo and for the most part I oblige. But it’s those days when I’m in a hurry or just not feeling very social that this can turn into an annoyance. There have been a few occurrences when I’ve politely declined but my photo is still taken. I’ve had strangers come up to me and rub my skin as if they are expecting the black to rub off. Once a taxi driver shook my hand, then sniffed it. Don’t know what he expected to smell.

How is the cost of living besides food – is your rent reasonable, utilities and transport?

Good schools pay for a teacher’s housing and utilities. I live in a large three bedroom house with two other teachers. The only things I pay for are transport and internet. My share of the internet bill is 89.000Rpi (about US$9.00) per month. I take the minibus to school everyday for 2,000Rpi (about US $0.20) each way.

Do you like your new profession of being a TEFL teacher?

I really like my new profession. I get to teach children and adults daily. Each class and level brings on a different challenge that makes me a better teacher.  I especially like working through cultural exchanges in class which allow me to see things differently. For instance, girls and boys do not sit together. They sit at polar opposites in the classroom. When I’m organizing group activities this poses a challenge for me if the class is an uneven number. So I have to find a workaround.

What’s the one thing you wish you had packed and taken with you?

I wish I bought Walkerswoods jerk sauce. The  food flavors here in Indonesia are nothing like in Jamaica. Sometimes I just crave some jerk chicken!

(Yes, man! What I wouldn’t do for a quarter jerk, dark please.)

Favorite find so far in Indonesia – whether restaurant or place or food?

I like the chill and relaxed vibe of Maroko Cafe, a few minutes walk from my house. It’s operated by three teenaged brothers. They are always smiling, happy and makes me feel welcome every time I go there. We are all Facebook friends and if they haven’t seen me in while I get a message, “When you come to here Diana? We miss you.”

How cute is that. So the one thing I love about your story is that you wear and have worn many hats – very much like myself. In addition to now being a teacher, you’re also a documentary filmmaker, blogger and writer. How do you balance your time between all of these?

I seek balance every minute of every day. It really is a constant struggle. Whatever I am most excited at any time gets precedence.  So if I am writing a juicy travel guide on Jakarta and writing pitches to different publications, then the Jakarta guide will get more time.

Sticking to a schedule is so important.  My teaching day starts at 3pm, so I have the morning and early afternoon to write, edit and do a blog post. I try to blog three times a week. Those days are normally Wednesdays, Fridays and Sundays.  I do about two hours of editing on Mondays, Tuesdays and Thursdays. In between these times I’m pitching stories to publications and developing my photograph skills.  If you or any of your readers have any suggestions for me on time management I’m all ears.

Me too! Are you currently working on any projects besides the teaching?

I am editing my film, “The Jamaican Jerk Tour“. It’s a culinary exploration of Jamaican jerk cuisine from the street food in Jamaica to high brow restaurants in New York.

I can’t wait for it to be done. Do you miss the world of being a flight attendant?

Heck no!

If you could only pick one passion, which would come first – teaching, film making or writing?

That’s like asking which limb I want to cut off! I am more passionate about writing and film making because they fulfill me. Teaching is the means that supports these passions financially.

Do you think you will keep teaching and traveling to different countries?

Oh absolutely! I’m toying with the idea of South Korea as my  next teaching post.

Which other countries have you visited and which were your favorites?

I’ve visited and fallen in love with Helsinki, Amsterdam, San Juan and London.

Do you think you will one day move back to Jamaica?

I honestly don’t know where I want to live. The world’s too big for me to settle in one spot. Ideally, I’d like homes in a few countries worldwide. Jamaica being one of them.

What’s your advice to those who want to leave the US and want to teach abroad?

I know it may seem like a huge step to leave your nest. But once you’ve made the decision, everything falls in to place so quickly and effortlessly. Be certain that this is what you really want to do. Make a plan and follow throughout with it. How much money will you need? When do you plan on leaving? What are you going to pack?

Have fun scouring the globe and deciding what country you will start your adventure. There will be naysayers around, but listen to your gut, it never lies. Some of the those naysayers are just too chicken to pursue their own dreams. Be brave and don’t let fear shackle you.

Can you recommend resources that can help them find a job as quickly as you did?

I went directly to the school’s webpage.  Another good resource is Dave’s ESL Cafe.


Thank you, Diana – for sharing your inspiring story, the second to appear on the new S&S ABROAD Series.

For more on Diana’s travels and projects, follow her blog or check out her Facebook Page.  And as always, feel free to use all the space you need below if you have questions or just want to gush.

The very first S&S ABROAD profile, featuring travel blogger and photographer Brendan Van Son, can be found here.

You can also subscribe to get news on the next S&S ABROAD profile and more inside info!

Lebawit Lily Girma

Lebawit Lily Girma is an award-winning travel journalist, photographer, and guidebook author specializing in the Caribbean region. Her work has been published in major travel publications, including CNN, AFAR, Delta Sky, Lonely Planet, Shermans Travel, and BBC, among others. A self-professed "culture-holic," Lily left her native Ethiopia at age one, fast developing a passion for the expat Caribbean life. In 2008, she ditched her US corporate law career for the road and created Sunshine and Stilettos—a travel photography blog showcasing authentic ways to experience the Caribbean, through culture and nature. Lily has since partnered with Caribbean tourism boards and travel brands on major content projects. She also authors print guidebooks on three destinations, including Belize, the Dominican Republic, and Jamaica. Read more on her site, LebawitGirma.com

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  1. Ashlea P. 31 May, 2012 at 8:11 PM #

    Love this article! Both of you ladies inspire me sooo much!

  2. Lebawit Lily Girma 31 May, 2012 at 8:25 PM #

    Thanks so much Ashlea! Diana’s move really inspired me as well, she left just as I was thinking about my own move abroad next year. I’m glad you loved this piece, thanks for taking the time to read & comment!

  3. Fleur 1 June, 2012 at 10:04 AM #

    Love it! Diana, you globe trotter!

  4. Diana 1 June, 2012 at 10:33 AM #

    Thank you for the opportunity Lily. It’s truly humbling.

  5. Lebawit Lily Girma 1 June, 2012 at 11:31 AM #

    You are so welcome, Diana! I am SO proud to know you. Thank you for being a part of my series.

  6. Lebawit Lily Girma 1 June, 2012 at 1:05 PM #

    Thanks for reading, Fleur!

  7. Andrea 1 June, 2012 at 2:22 PM #

    What a great article about great ladies! I enjoy the reading so much and my wanderlust is burning!

    PS: Forgive me for little mistakes in my english, I am a German Lady LOL

  8. Lebawit Lily Girma 1 June, 2012 at 2:39 PM #

    Your English is just great, Andrea!! I don’t even speak more than two words of German. Ha!

    Thank you for sharing and reading, I’m really glad you enjoyed it. There’s lots more stories to come.

  9. Jubril 1 June, 2012 at 8:17 PM #

    I loved this interview.. I can’t wait to doc. I will def get it.

    The taxi part just made me laugh. I have have a lot that stuff happen to me before but not that.

    I miss asia for their cheap priced food and great food too. I loved this article so much.

  10. Lebawit Lily Girma 1 June, 2012 at 8:20 PM #

    Thanks, Jubril! I’m glad you enjoyed this piece. I know you’ve traveled to Asia quite a bit. I’ve only been to Taiwan so far.

  11. Joan Kleinhans Baker 2 June, 2012 at 2:29 AM #

    Reading the article on Diana was like looking in the mirror and seeing myself. I am retired military (served 26 years) and was stationed in Germany for 13 years where I traveled Europe during my spare time. That really fueled my desire to see the world and experience different cultures. I am now working as a contractor in Iraq and I am having so much fun traveling Asia. People ask if I am not afraid to do it alone and I reply that if i waited on someone to accompany me it would never happen, you have to step out on faith. There is so much world out there to discover and enjoy, don’t be afraid, go for it and not have regrets. Life is too short and tomorrow is not promised. Happy travels.

  12. Mark 2 June, 2012 at 7:28 AM #

    Respect Diana! Was wondering wha happen to you. Looking forward to seeing the documentary. Peace!

  13. lovenia 2 June, 2012 at 12:14 PM #

    I love this post! I am also a writer, and hoping that teaching English abroad will give me a lifestyle that is more conducive to it as well as fulfill my desire to see more of the world and travel. And like Andrea, reading about Diana made my wanderlust burn even more!!

  14. Lebawit Lily Girma 2 June, 2012 at 12:37 PM #

    Hi Joan, thanks for reading and sharing your experiences. Iraq, amazing! Do you get a lot of time off, then? I completely agree on waiting on others – I never would have started my own journey to Jamaica (which started it all), had I not stopped waiting for others to travel. We each have a life to live, and only one – who knows if at 50 you will be healthy enough to travel? We’re on the same page there. Happy travels to you also, cheers for sharing!

  15. Lebawit Lily Girma 2 June, 2012 at 12:39 PM #

    Hi Lovenia, thanks for stopping by and sharing! I know you’ve been looking into teaching abroad also. I’m glad this inspired you! To be honest I can’t wait to get going myself. I’ll be spinning my map this weekend. Ha!

  16. Lynn Denese 2 June, 2012 at 1:33 PM #

    I am inspired by every article I read by Tribe Members. You ladies are making me rethink my future plans. Keep up the good work.

  17. Judine simpson 2 June, 2012 at 10:29 PM #

    I am so inspiried and moved by Diana’s story. I’m very proud of my Jamaican sister doing her thing.

  18. Lebawit Lily Girma 3 June, 2012 at 1:40 PM #

    Thanks for sharing Judine and Lynn! Very inspiring indeed.

  19. Cha Jones 3 June, 2012 at 5:21 PM #

    I love it! I am so excited to women of color living abroad all over the world and following their passion! Makes me think, “I need to go get me a GLOBE and spin it.”

  20. Lebawit Lily Girma 3 June, 2012 at 5:26 PM #

    Same here, Cha! Heck I love seeing anyone doing it – just the courage of doing what you love. It has such a ripple effect.

    Get that globe! I had a beautiful one from National Geographic but I think I remember giving it away now…!

  21. kahleel 4 June, 2012 at 7:28 PM #

    As a fellow Jamaican about to embark on a life changing journey to teach in Abu Dhabi, I am inspired by Diana.
    Prior to accepting the job I never imagined that there were so many women of color traveling the world and living the life I had always dreamed of.
    Thanks Lily for your inspirational life as well.
    You both rock!!!

  22. Lebawit Lily Girma 4 June, 2012 at 7:38 PM #

    Hi Kahleel, thank you for sharing and for the kind words. I am super excited for you – congratulations and you rock too for sure! We’ll be checking you out on your adventures.

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