Financial Case Study: Layne, AI Operations Director

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Layne is a writer, a remote product operations executive, and a proper vagabond—travelling a lot of the time since 2000, most of the time since 2014, and full time since the end of 2015. So far she has lived on all seven continents in 57 countries and counting! Her online home is Wanderluxed, where you can learn more about her travels, as well as some new projects she is developing (which you’ll read  more about below).

This Financial Case Study features details of Layne’s lifestyle and avant-garde career, so you can learn more about the long-term travel lifestyle and its many forms. Enjoy! 

Financial Case Studies

How long have you been living/working on the road, and where have you traveled to?

I first discovered The Professional Hobo in 2013 and realised I didn’t have to be sedentary and miserable for the rest of my life (imagine!). I think I got fed up and googled something like, “how to travel free,” thinking that a helpful result was about as likely to come up as if I’d googled “what is the meaning of life.” Instead, there was Nora.

I was stunned by what she was doing and jumped on the bandwagon as soon as I could manage it! I took a nine-month practice run in 2014—teaching English in China, volunteering at a backpacker’s lodge in Addo Elephant National Park (South Africa), renting an apartment in Kathmandu, and house-sitting in Doha and London. 

After that, I was (obviously) never the same, and I gave up my last apartment in Seattle at the end of 2015 to travel full time. My most life-changing travel experiences since then have included island-hopping in the Maldives, visiting Antarctica, and road-tripping Madagascar (beaches and baobabs and lemurs, oh my!). 

Please describe what you do for income. 

At first, I did something I don’t necessarily recommend and that was moving into my suitcase and letting my lease expire before I had landed a remote job or started a location independent business. Not the most responsible move I ever made. But sometimes you leap and the net appears! 

Within a month I had found (on the jobs page of the DFW Craigslist) a remote job ghost-writing for a tech startup. As the company grew, I ended up leading a team of writers, and then the whole writing department, and finally I inherited two more departments. 

There is a lot of upward mobility (and remote opportunity) for hard workers in the startup world. Seven years later, I am an AI operations director, specializing in building globally distributed teams of 50+ people for tech companies who need “humans-in-the-loop” on the backend of their AI or SaaS applications. The tech industry’s big secret is that AI is often half-human. 

How many hours per week do you work on average? 

I’m currently working with a completely remote legal tech company called Index Solutions and the workload varies quite a bit. Things are slow at the moment and I don’t often have more than a couple of hours of work to do per weekday (Monday-Friday). During times of rapid expansion, I do work up to 35-40 hours/week. 

How much money do you make? 


Do you make enough money to support your lifestyle? 

Yes, even with a weakness for fancy hotels! I tend to spend about $3k per month (there is a hard-core theatre habit going on, I admit it) and save about $3k per month. 

Most of the year, I’m house sitting all over the world and working remotely. Then, once or twice a year, I take a big blowout trip and spend most of my savings. 

The goal I’m working on at the moment is to save up a down payment to get into real estate investing, so that I can have a home base for a few months a year and also start saving to save, instead of just saving to spend. 

What do you like most about your career and lifestyle? 

I love working completely remotely, coaching others and empowering them to work completely remotely, and being able to change my location at will. I was very, very unhappy as a sedentary person. It still makes me feel a bit panicked if I think too hard about how much of the world I’ll never see, despite my best efforts! 

What are some of the challenges you have with this career and lifestyle?

Constantly moving (and searching for the next roof over my head) does get exhausting. Applying for house sits, having zoom calls with prospective sits, and constant house handoffs are time-consuming.

 I am nowhere near finished with travelling, but I’ve been feeling the need to nest pretty deeply in recent years. After seven years of total homelessness, I’m ready to work toward having a sanctuary that I can return to for a few months each year (and where I can keep The Perfect Pillows, and stash the other seasons’ clothes, and own a favourite mug and one of those scratch-off maps). 

Nora’s Note: I laughed out loud when I read this, because when I got an apartment in Toronto after 12 years of full-time travel, the some of the first items I got included a pillow and a scratch-off map. I’m only there periodically but I always enjoy a few good nights’ sleep and scratching off a few more countries.)

I plan to rent the place out on Airbnb when I’m not there. Another substantial challenge is relationships. I love my solitude but it can get lonely out there, and it does tax my closest relationships that we’re only together a few months a year. 

See also: My Sordid Attempts at Love on the Road 

What is your vision for the future of your lifestyle on the road?

I’m super inspired by Robuilt’s Airbnb empire at the moment and want to create my own portfolio of unique places that I can (a) stay in when I’m around and (b) rent out when I’m not.

I’d like to buy old buildings that were not originally designed for residential use (e.g. a boot factory in Texas, an old firehouse in the Pacific Northwest, a church in North London) and partner with my friend Elizabeth (an artist and architect) to turn them into homes. 

I think that ultimately, I would like to continue travelling to new places 30-60% of the time, while nesting in one of my home bases for the remainder. 

Of course, all of this is expensive! So I’m investing in founding an online travel training business to share all the knowledge I’ve built around air mile hacking, house-sitting, and working remotely. I’m excited about it because it combines the expertise in remote training strategy that I’ve built in seven years of doing my “day job” with the all-consuming and one true love of my life: travel. 

Any advice for the aspiring traveler about living and working on the road and managing finances?

Take my Travel Hacking Masterclass! It’ll teach you everything I know about travelling rich on a backpacker’s budget.

I spent ten years piecing this stuff together and you’ll learn it in 30 days flat, including how to fly (in business class) and stay (in beautiful homes) all over the world for nearly free, how to protect the environments and communities you visit, how to get up to 50% off on luxury hotels and resorts, how to get free car and RV rentals, and so much more. 

You should enrol through the above link specifically in order to share the wealth with the one and only Professional Hobo (she was the first light at the end of my long, dark tunnel of sedentary life, after all!). 

My Nomad Academy bundle has also been released and covers working remotely. I wish you a lifetime of adventure! Please know it’s more possible than it feels at first. 

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