Interview: Sherry Ott of Ottsworld


I ‘met’ Sherry Ott of Ottsworld through the online world of travel. Her story resonated with me on many fronts. The career break after over a decade in a profession, the teaching, New York City, the event organizing (Meet, Plan, Go), the volunteering and of course, the TRAVEL. Having made a jump from IT to travel nomad, Sherry wanders the world telling stories, sharing experiences, and looking for life’s adventures beyond the traditional ‘office walls’. Here she shares a bit of her knowledge and wandering wisdom with me.

sherry ott 5  - hiking the Lycian Way in Turkey

1.When did you get started traveling? I left my corporate career in September 2006 with the plan of traveling around the world for one year on a career break. And yes – 8 plus years later I’m still traveling. Yes, there’s been lots of changes to that original plan!

2.What made you decide make the jump to a location independent/travel-based existence? My addiction to wanting to experience new things every day. I really loved being on the road every day when I started traveling; experiencing new cultures, new ideas, new scenery. And only 3 months into my initial career break travels I decided that I had to figure out a way to keep this travel going. I didn’t want it to end. I spent the next 12 months trying to figure out how to make it happen – and finally settled on teaching ESL in Vietnam in 2008. However things have really evolved from there into what I do today and my travel is quite different these days. But the majority of the time I’m still experiencing new things and cultures.

sherry ott 3 - teaching at Iolani School in Oahu

3.What benefits do you feel you get from this lifestyle? How do you handle the nay-sayers in your life? Strangely when you’ve been doing this as long as I have the naysayers all give up and go away. I don’t really recall any naysayers at this point. I think I’ve proven that it’s possible to be location independent and to build a life around travel. After all – it’s been more than 8 years of this lifestyle – and that’s longer than I ever stayed in any one job or apartment for that matter! The benefits are plentiful – but mainly it helps me accomplish that desire for newness and learning.

4.How did you save money to be able to afford living ‘on the road’/traveling often? How long did it take you to make the jump to a location independent/travel-based life? I saved money for my initial career break trip – but after that I’ve been now working on the road to support myself. I scrap together a living basically. It took a long time to get to where I am today in my travel blogging/writing/photography career. It’s evolved further each year – which is a good argument for why you need to just persevere and time has a way of helping you along. I started as just a career break traveler and kept my own personal little blog, then started teaching ESL, I also started managing websites for expats, I housesat to save money, I wrote for expat magazines, I started another travel website/business (, I started getting paid to travel and cover destinations or tours, I did other teaching and lectures, I run social media for small companies, I am a contributing writer for a number of online website and travel companies…you name it…I do it. I’ve had to hustle and be scrappy – but it has kept me a float and on the road.

tour, phone, motorbike, saigon

5.How do you choose your destinations and for how long you’ll stay? What type of accommodations do you typically choose? Are there any specific resources you recommend? About 40% of the time I choose my destinations myself and simply go there and 50% of the time my travel writing work decides my destinations. Destinations invite me to come cover them in my writing/social media outlets and they pay my way and make most of the decisions on where I stay (mainly hotels). However when I decide myself and pay my way, then I normally just choose based on what flight is cheap, what new country I want to tick off, or what friend I want to see. I stay in short term apartments or rent a room in someone’s home normally – the thing I use most is Airbnb. However recently I have been choosing destinations by activities or adventures that I want to do. I spent 7 weeks in India because I wanted to do the Rickshaw Run Race, I was in Spain for a month walking the Camino de Santiago trail, etc. I based a lot of my decisions on unique adventures I hear about and they speak to me for some reason so I end up making my way there to do those things. The other 10% of the time my nieces decide my destination. I take each one of them traveling with me after they turn 16 yrs old and they get to choose where they want to go in the world and I take them there. So far they’ve chosen Italy, Vietnam, and Peru.

6.How much money do you traditionally need annually to support this lifestyle? Well – I don’t have a home or a car or anything for that matter…I live out of my suitcase and have a small storage unit in NYC. My only regular bills are insurance, cell phone, and storage unit. I need around $15,000 to $20,000 to support this lifestyle. This comes with the assumption that a lot of my travel is free if a destination has invited me there. The key for me is that I keep my expenses very low – then I don’t have to make much.

sherry ott 2 - playing in Holi in India

7.How do you make money on the road and save for retirement? I do freelance writing and am a contributing writer on a few different sites, sell photography, get hired for social media marketing campaigns, run Meet Plan Go events, do travel consulting, I run a facebook page for a photography company, I do speaking engagements, and I sell advertising on my travel website occasionally. And whatever else comes up! I don’t really save for retirement – however I had a 14 year career in corporate IT and saved during that time – so now those are investments that I don’t touch. I was very diligent about saving for retirement ever since I was 22 years old and had my first corporate job. I’m quite conservative financially – so my goal is to simply break even every year and as long as I still love to travel and this lifestyle then I stay on the road. If I weren’t breaking even – I wouldn’t be doing this.

8.How do you handle visas, vaccinations, legal documents/passports, taxes and healthcare while living without a home base or an ever-changing one? I have an expat healthcare medical insurance plan that covers me when I’m in the US and all around the world (GeoBlue). I have a CPA that I work with to file all taxes electronically. I use Expensify app to help me keep track of all expenses for tax purposes – so everything is electronic. I always ensure I have internet access with my Telecom Square mifi devices. I actually wrote a post on this subject! Basically use a bunch of phone apps for document management – and visas and passport needs are handled when I’m in the US or at embassies of the countries I’m in – it’s all pretty simple. I think most people think it’s much harder than it is.

Rickshaw Run-India (Sherry Ott)

9.If you decide to settle somewhere – where and when do you think it will be? I have no idea.

10.What advice do you have for others trying to make the jump to a location independent/travel-heavy lifestyle? It all sort of depends on what you want to do to make money. Are you a tech person designing websites, a travel writer like me, a yoga instructor, an ESL teacher? For me what worked was to pick a place that is cheap and go there and stay for a while, network, use the time to live cheaply, and explore. The key is to go slow – give yourself time to get settled into a place and find a rhythm – and more importantly network and figure out a business strategy for how you are going to make money. You don’t have to have it all figured out before you go – it presented itself while I was in a place going slow.

sherry ott 8 - hiking in Patagonia

11.In your experience, what have been the two most significant gifts of travel? These aren’t actually gifts of ‘travel’ per se, but they are more gifts of living nomadically for this long: It has taught me how to live a simple lifestyle and hone down what is really important to me and live with basic necessities. And whereas it has separated me in many ways from my old relationships and friends, it has given me new friends all over the world, and has brought me a much tighter bond with my own family.

Check out her website for more details.

2 responses »

  1. Hi Sherry,

    If you remember we walked the Camino for a while, up the hill to O’Cebreiro with Michael. I follow your Facebook page so I know where you are at. A great little article this one. I wish you many more years of it.
    I haven’t managed to repeat the trip on the Camino del Norte as I had hoped, as I am virtually a full time carer for my wife who has had heart problems. I still hope to do it one day but unfortunately time moves on and bits of me are wearing out!
    Have you ever written anything on the older people you have met in your travels? I think this would make an interesting article, and you must have a wealth of stories to tell of this.
    Anyway, safe travelling.

    David Masters

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