Pros and Cons of Being a Digital Nomad vs Having a Home Base, with Sherry Ott

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I was a digital nomad (ie: I traveled the world without a home) for 12 years, before returning to Canada and getting an apartment as a home base. It wasn’t that I had stopped traveling; I simply changed the way I travel. Sherry Ott did something similar; she was a digital nomad for 11 years before getting a home base in Colorado. So she and I sat down and had a lengthy discussion about the pros and cons of being a digital nomad vs. having a home base. Learn more about it here. 

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Here are the pros and cons of being a digital nomad vs having a home base, as discussed between Sherry Ott and Nora Dunn, who collectively have almost 25 years' experience as digital nomads! #DigitalNomad #RemoteWork #LocationIndependent #SherryOtt #Ottsworld #TheProfessionalHobo

Sherry Ott’s travel career started innocently enough as a career break, during which she realized she had too much unfinished business with the world to return to her desk job. So she put her stuff in storage and taught English in Vietnam for a year, before really letting loose and roaming the world as a digital nomad for the next 10 years. 

During this time she financially supported herself with her travel website and photography which she showcases on OttsWorld and various social channels. 

Sherry and I traveled in circles around each other, meeting up occasionally in far flung destinations, but mostly maintaining our friendship online. We even simultaneously did a huge campaign with Club Carlson; I traveled through 8 countries in 3 weeks in Europe, while she covered 7 cities in the Americas during the exact same time period. 

Sherry Ott in Vietnam on her Motorbike

Despite our distance, Sherry and I shared a lot in common. We started our remote careers and digital nomad lifestyles in our 30s; older than many of our compadres. We each lasted as digital nomads for over 10 years; something we both admit is an accomplishment we are proud of (while of course acknowledging that it’s not a competition). And within a year of one another, we both got home bases in our home countries. (Here’s more about my Epic Search for a Home Base)

But there are some differences between how Sherry and I traveled and lived around the world as well. She consistently traveled at a feverish pace through most of her 11 years. I did that for one year and it damn near broke me (I needed six months in a near-comatose state in New Zealand to recover). I subsequently traveled slowly and had a few home bases along the way; places I could temporarily call “home” around the world, from which I could venture and travel without lugging everything I owned with me. 

Sherry’s website also had more of a focus on destinations, and thus she was consistently hosted on press trips by tourism boards and tour providers. I have only done a handful of such trips, largely because my style of travel often meant committing to long-term volunteering or house-sitting gigs from which I couldn’t stray for a press trip. 

Sherry Ott hiking the Annapurna circuit with her dad

While in the throes of a discussion about the pros and cons of digital nomad life vs having a home base, we turned on the camera so we could share 25 years of collective travel experiences and lessons with you. Watch below, or click here to watch it on YouTube

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Life as a Digital Nomad vs Home Base: Discussion with Sherry Ott 

Sherry and I covered a lot of territory in our discussion. Here are some of the themes we discussed. 

Digital Nomad Lifestyle

  • The logistics of doing press trips as nomads and why it’s so much easier with a home base
  • Why it’s difficult for people to wrap their heads around the digital nomad lifestyle and the various challenges this presents, both personally and professionally
  • What romance looks like while traveling full-time (Sherry wrote about it here, and I wrote – a lot – about it here)
  • Advice for aspiring digital nomads
Sherry of Ottsworld doing the Rickshaw Run

Fast Travel vs. Slow Travel 

  • The irony of Sherry setting up a home base and then traveling more than ever!
  • Motion Sickness” on the road when traveling fast, especially as a solo traveler
  • Quirks of living abroad, like the increased time it takes to do “regular” tasks such as buying milk

Working Remotely While Traveling

  • How the pandemic has inspired a remote work revolution, and what this means going forward
  • The advent of one-year remote working visas being offered by many countries, and how this can be used as a stepping stone to becoming a digital nomad
  • Advice for remote workers who aspire to travel while working
  • The difference between working on the road and traveling for vacation
  • Discipline! And how it’s crucial
  • The importance of ergonomics

The Finance of Full-Time Travel

  • How full-time travel is cheaper than having a home base (for a few reasons)
  • The pros and cons of keeping your stuff in a storage unit while you travel

Obstacles/Reasons to NOT Become a Digital Nomad

  • STUFF! The cost of it, the space required for it, the crutch it is (and ultimately the obstacle it becomes), and yet the compulsion to accumulate more of it despite all this
  • Easing into full-time travel, and how being a digital nomad is not for everybody
  • Social pressures that contradict the digital nomad lifestyle, especially while working remotely

Why We Eventually Got Home Bases

  • The factors that drove each of us to eventually get a home base
  • The need for cultural context and familiarity
  • The challenges of returning to our home countries after being away for so long
  • Health, and how getting a home base saved Sherry’s life 
Hiking in the Mountains, not always easy to do as a digital nomad

More About Sherry Ott and Her Digital Nomad Journey

Sherry wrote an ebook (it’s free!) called Where to Go and When, and it’s a fabulous tool to stoke your inner travel bug. 

Where to Go and When

She also wrote quite a bit about her nomadic life, and the transition from digital nomad to having a home base here: 

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4 thoughts on “Pros and Cons of Being a Digital Nomad vs Having a Home Base, with Sherry Ott”

  1. Hi Nora,

    REALLY good chat guys as you and Sherry definitely have some resonance with how my wife and I live. We spent far more time in the US over the past decade of global travel; you both were far more digital nomads than we. But I vibe with your takes on both lifestyles.

    Being a full time digital nomad is fun, freeing, challenging and forces you to face your fears FAST, well outside of your comfort zone. But for me, I never feel more alive embracing the joys and happiness of traveling full time while facing my fears, all while building my blogging business.

    Fab advice!


    • Thanks Ryan! You’ve been at this lifestyle for quite some time as well! I’m sure you’ve got lots of great advice to impart. It’s not easy to blog and travel full-time, but it sure can be rewarding. 🙂

  2. What a fabulous interview. I found myself nodding to many of your points, especially about the desire to find a home after travelling for so long. I remember that being a real pull for me, and why I eventually stopped. I craved having my own space, with printer, writing materials, etc, and a super comfy chair 🙂

    • Thanks Becky!
      It’s a common thread for many if not most full-time travelers to eventually want a place with certain individual creature comforts. I love returning to my place in Toronto after traveling and enjoying my comfy bed, fully-equipped kitchen, and home office setup.


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