A Week in the Life of a Nomadic Travel Blogger

By Sherry Ott on April 20th, 2015
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“You have my dream job!” is the most frequent statement I hear every day, week, month, and year.

As a travel blogger and freelance writer/photographer, my work has taken me all over the world for the last 8 years and rendered me nomadic. I’ve set foot on every continent, been to some of the most luxurious hotels in the world, and done some epic adventures criss-crossing the globe that would make most people gasp in excitement or fear.

Yes, it is a dream job, and most people believe in the romantic notion that I gallivant around the world just having fun, because part of my job is to really show the great, beautiful parts of travel.

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But there is some wizardry at work, as I don’t always show people what the “Great Oz” is doing behind the curtain. Like any job, it can be full of stress, sleepless nights, and hardships – not to mention jetlag and wondering where my next payment is going to come from!

I decided to track a typical week in my life in order to give people a peek behind the “curtain” and see the reality of this lifestyle. However, let me be clear, I love what I do and am not ready to give up my dream job anytime soon – so don’t ask me to trade places!

March 18 – Wednesday – Molokai, Hawaii

6AM – the day starts early so that we can pack as much as possible into this press trip. I’m in Molokai, Hawaii as a part of a small press trip with 4 other writers hosted by the Molokai tourist board. I check email, schedule social media, frantically trying to figure out the time difference between Hawaii and NYC, grab a coffee to-go mug, and run out the door of my hotel room with every camera I have packed into my backpack.

I groan as I swing the backpack on to my back always forgetting how heavy the bag is. It normally weighs in at 20 to 25 pounds with my DSLR, 3 lenses, Gopro, and accessories, phone, notebook, and emergency food. Yes, my one travel rule is ALWAYS have emergency Cliff Bars.

We arrive at Kalaupapa Mule rides at 8:30, sign waivers, and before I know it I’m situated on top of my mule, Koa. I’ve placed all of my photo equipment to be within reachable distance on my body as our guide Audrey gives me instructions on how to ride and manage Koa on this 2 hour ride down 1600 feet via the steepest sea cliffs in the world.

Sherry Ott Molokai


The ride down is a series of 30 switchbacks on extremely narrow paths teetering on the ledge – not for the faint of heart. And not for someone carrying a bunch of cameras! Yet somehow I handle it well even with my fear of heights, mainly because I was so pre-occupied by trying to get shots and footage that I hadn’t considered the fact that often we were wobbling on the edge! I do fantasize about what this ride would be like for someone without 3 cameras and not working.

I spend the afternoon touring Kalaupapa, a fascinating national historic park that was home to an infamous leper colony secluded away on the island of Molokai. An afternoon consisted of more photographs, rapid note taking on Evernote, and trying to digest the history. Honestly the digesting part is really lost until I sit down to write the stories. At this part I’m just trying to get as much info as I can and consider how it will all fit together. I do some photography shots for Molokai visitor bureau, as they are looking for new photography to use in their marketing channels and asked me to create a portfolio for them to consider. I go through the motions in the hopes that I can make some photography sales.

After a day on the mules, we make more scenic stops, clean up quickly, race to get sunset photos, and then to dinner with the group. The night ends around 10PM, and I go back to my room to edit photos and answer email emergencies until midnight, when I collapse.

A typical press trip day – a mixture of fun and work.

March 19 – Thursday – Molkai, Hawaii

Up at 6AM to work on gathering all of my tax docs up to mail to my accountant since I knew we were planning on stopping by a post office today as part of touring around the island. Coffee on my lanai as the sun comes up is a lovely way to start my morning before it turns into a whirlwind of photos, sights, and notes. I beg the front desk to make copies for me before I mail my tax paperwork off. It’s never easy conducting day-to-day business and obligations on the road while in a constant state of motion.

We tour around the beaches and little towns of Molokai, and I focus on photography while trying to take notes that I think will be relevant for my future writing. I dipped my toe in the water, but there was no real time to swim. We get back to the hotel at 4PM, when I remember that I have yet to book a hotel room for the next night in LA. I quickly try to find a last minute deal that is super close to LAX.

Next up we had a fun and inspirational jewelry making session with locals and then a hotel reception/dinner to attend. It takes the entire evening, and I’m back to my room at 10PM and slightly tipsy. I’ve made some great new friends on this trip and feel that it’s important that I also try to fit in social time amidst the work that’s piling up. I stay up to edit photos and do logistics for my next 3 days of travel to Australia, trying to get myself somewhat organized on where I’m staying and who I still need to follow up with about schedule. Start to fall in and out of sleep at my computer, shit – where did the time go? Asleep at 12:30AM.

March 20 – Friday – Molokai to Oahu to LA


Sherry Ott Molokai 2 (1)

I am up early at 6AM to meet the Molokai Tourism rep at 6:30AM to head to the east side of the island and do early morning photography before we leave the island. The morning light is always best, but I really hate getting up this early. I’m exhausted and coffee can’t even help the situation at this point.

Get email from the PR rep at South Australia. They have run out of budget for the year and even though they thought they could host me for a week, it appears that they can’t at this point. Easy come, easy go. I grab some oatmeal and run out the door slightly manic. We spend the next 3 hours being driven around the east coast of Molokai meeting people and taking photos. I get back to the hotel and have an hour to pack, shower, and download photos, then off to the airport.

” I had just spent the last 4 days touring around Molokai, and now I had to sit and work at times when most people just relax. But I get to have fun in the middle of the day when everyone is working. I figure it’s a trade off in a way.”

I connect in Oahu for my flight to LAX and take the time to try to catch up with some calls to family and friends while waiting to board. My sister reminds me that the NCAA Basketball tournament is on, and I’m reminded that it’s March. It’s really easy to lose site of what month or time of year it is in my life – and all of a sudden I feel grounded again in a calendar…it’s March…ok…March.

I edit photos on my phone while we wait to take off, and then once at cruising altitude, I look at my big to-do list for the plane and start in on all of the emails I’ve put off for the last 2 weeks. Responding to emails take 3 hours on the plane. I watch 1 hour of TV, and then start to work on writing.

The woman next to me asks me what I do for a living as she said she was amazed that I sat and worked for the whole flight! OK – now I’m a little embarrassed. It’s always hard to explain to family, friends, and strangers that I do work a lot, but that’s because I get to play a lot too. I had just spent the last 4 days touring around Molokai, and now I had to sit and work at times when most people just relax. But I get to have fun in the middle of the day when everyone is working. I figure it’s a trade off in a way. I get to travel the world and do all of these amazing things.

I arrive in LA at midnight, shuttle to airport hotel, and collapse.

March 21 – Saturday – LA to Sydney (Travel day)

Determined to try to stay on my Hawaii time since I only have a day in LA, I got up late and entertained a few ideas of going out and exploring, but my to do list got the better of me, so I asked for a late checkout and opted to sit and work instead. I met my friend Charlie at the airport, and we caught up over wine and then boarded our flight to Sydney at 10PM. We lucked out. The flight was not full and entire rows were empty! This is exactly the kind of news you want when you are about to embark on a 13 hour flight – poor man’s first class! As soon as they allowed us to move. we all dashed to empty roads and claimed our space.

March 23 – Monday – Sydney, Australia

I did a little time travel and skipped a whole day on my way to Sydney. We land on Monday morning at 7AM. It always feels so strange to lose an entire day, even though I was technically only 3 hours earlier from Hawaii time. And since I don’t pay attention to day of the week anyway, I didn’t think this would be a big deal, until it hit noon, and I felt like I was going to pass out into a little sad ball.

“I sort of questioned for a moment if I even remembered how to travel independently any longer.”

This trip was technically not work as I won this trip for two to Australia at a conference I attended last fall. It felt really foreign to arrive in a place and not have someone waiting for me and immediately being wined and dined.

I sort of questioned for a moment if I even remembered how to travel independently any longer. But as soon as I found an ATM and public transport, I realized that independent travel was like riding a bike. We decided the best way to stay awake was to go for a walk, so we picked up brochures from the concierge and started walking around Sydney neighborhoods. It felt nice for once to not have to take pictures – I didn’t even take my big camera with me on the walk – a true vacation! We found a place to have dinner and forced ourselves to stay out late – meaning make it to 8PM before going back to our hotel!

March 24 – Tuesday – Sydney, Australia

It feels weird to be back in Sydney, the last time I was here it was on my initial career break travels in 2006 – the trip that really propelled me into this whole nomadic lifestyle.

I walked around the city thinking about all of the changes that have happened to my life between now and then and how not a single one of them was predictable. Back then I was just starting to think about trying to live a life of travel, but I had no answers or ideas on how to make that happen. There was no Twitter, no one really knew what a blog was, Skype was just getting popular and there were no smart phones!

Now 8 years later here I am, still traveling and working on projects in fields that didn’t even exist 8 years ago. I find trips like this a good time to reflect upon where I’ve been and where I’m going.

“Back then I was just starting to think about trying to live a life of travel, but I had no answers or ideas on how to make that happen. There was no Twitter, no one really knew what a blog was, Skype was just getting popular and there were no smart phones!”

Another blast from the past as I met my friend Natasha for dinner in Sydney. I met Natasha in Italy 8 years ago when we both found ourselves studying Italian in Sorrento for a month while I was traveling on my career break. We attended the same language school for a month and became fast friends. However I hadn’t seen her since Italy, so it was a great reunion over super wine and food.

Sadly, I spent most of the day fighting with the internet, which also seemed like it was from 2006. Good internet access is my lifeline to doing my job, and normally I expect 1st world countries to have great internet – however Australia is an exception. Seriously – Australia – please fix this!

March 25 – Wednesday – Sydney, Australia

Even though this trip wasn’t for a specific project, as a freelancer I am still always looking for unique things to cover regardless – sometimes on my own dime in the hopes of selling a story, and sometimes I get hired to cover one off stories.

One company I work with regularly is Viator Travel in their Ambassador program. I take Viator tours and do reviews of them for the Viator blog, as well as writing them up on my own blog. I try to choose Viator tours that are unusual and was quite excited when I came across a tour in Sydney Harbor racing an America’s Cup class boat. It was a beautiful day to spend out on the water and learn something about racing. I was laden with cameras and sunscreen as I got on the racing boat and met the crew. They race every Wednesday in the harbor and sell crew spots to tourists. So I wasn’t just there to take pictures and enjoy the ride, I was there to be a part of the crew – how the hell was I going to juggle this? I spent my time between winding winches, trimming sails, and taking pictures and video all while trying not to fall in the heeled over boat.

Sherry Ott sydney sailing 1

March 26 – Thursday – Blue Mountains, Australia

You get a bonus day since we completely lost a day to time travel!

We checked out of the hotel in Sydney, and a rep from Blue Mountains tourism picked us up and drove us to our next destination – the beautiful Blue Mountains world heritage site. Only 2 hours from Sydney – this would be my home for the next 4 days.


This was a typical week for me: 4 different beds (counting a night sleeping on a plane), a press trip, a few countries, jetlag, internet struggles, freelance gigs, seeing friends around the world, heart pounding adventures, and any remaining time spent on this computer putting out 2 to 3 blog posts a week plus freelancing work.

This is the life of a nomadic travel blogger.

Read more about the travel blogging and location independence:

Sherry Ott is a long-term traveler, blogger, and photographer. She writes about her nomadic lifestyle and around the world adventures on Otts World. She’s circled the globe numerous times and has visited all 7 continents. She lived in Vietnam, hiked the Annapurna Circuit with her father, finished the Mongol Rally, walked the Camino de Santiago, kayaked in Antarctica, and drove a auto rickshaw across India. She continues to seek out adventurous unique opportunities to inspire people to overcome their fears and reap the benefits of travel. She’s also a co-founder of Meet, Plan, Go!, a website and national travel event teaching you how you can take your very own traveling career break or sabbatical.

Photo credits: All photos courtesy of the author and may not be used without permission.