There’s a different type of travel blossoming. Instead of packing the bags for a short weekend trip to discover all the top gems, more people are choosing to travel slower and stay longer.

In the last 4 years, I traveled to 20 countries, staying 1-3 months in each country to truly experience life there as a local. This helps me experience culture at a greater depth, learn from others how to live in a different way, make the most unexpected discoveries, and stay as long as the place brings me joy.

A month-long stay in Nairobi surprised me with the best Chinese food outside of China and the best mobile payment system outside of Wechat. Living in Mexico City blessed me with the time to learn salsa, in Honolulu to surf, and in Madrid to relax at the pace of Spanish life.

A question that I get often from strangers on the internet, and my grandma, is how I can afford to live a nomadic lifestyle.

I’ve done a lot of different things. So depending on your skills, your current bank account, and the trade-offs between money and freedom you’re willing to make, here are all the ways I’ve supported myself while traveling.

Work for a remote company

Already work from your computer in a cubicle or an open floor plan? Great! You can do the same thing from a ski lodge or even a treehouse with good wifi.
You can start by asking your current manager about remote opportunities. If that’s a no-go, then there are plenty of companies hiring for remote roles.

In 2022, 32% of all employees worldwide are remote, up from 17% in 2019, pre-pandemic. 16% of the companies in the world are fully remote.* That’s a low percentage but do you know how many companies there are in the world?!

My husband works for a fully remote startup based in NYC. He found the job on remote-specific job boards like Remote.co and Remoteok.com.

If you find trying to filter through a job board overwhelming because it has a slew of roles or companies in industries that you are not looking for, I’m with you. My preferred way is to build a list of remote companies that I like and then look at all the roles that the company has open.

A final hack is to use Linkedin. Search the keywords “I’m hiring remote [insert role you want]” and all the hiring managers who have those keywords in their Linkedin bios will show up!

See it at work here:

And voila, the first hit, Matt is hiring from a remote company!

You can also see how the hits are connected to you so you can ask for warm intros!

Want more hacks like this on how to get a job in tech, especially if this remote job you’re looking for is your first job in tech? I wrote a guide about everything I know on getting a job in tech!

Working for a local company

One of my favorite nomadic memories was working on a boysenberry farm in rural New Zealand. Every day we would get up to hand-pick berries and sell them on a roadside stall.

Yes, this is very different from my average laptop worker job but that’s exactly why I did it! Traveling is all about gaining new experiences and life is about trying new things! Many of my friends have spent time working at wineries harvesting grapes, in hospitality as a line cook, and in the industrial containers of a fishing transport boat tossing iced blocks of 50lb fish onto a pulley transport for 12 hours a day.

When I first started traveling, I got a working holiday visa for Australia, New Zealand, and Japan. A working holiday visa is a residence permit for 1-2 years that allows young travelers 18-30, or up to 35 in some countries, to work and live in a foreign country. Because I’m Canadian, I can get this visa for 33 countries! You can see which countries you’re eligible for here based on your citizenship.

There’s nothing restricting you to hard labor on a farm or winery. Seasonal work tends to be short term allowing you to save up quickly and spend more time traveling. My friend David traveled across Japan on a motorcycle, stopping to work only to make enough money to keep going. But even the stopping was fun - he worked in a non-profit restaurant that served the community.

There are people who use it as a chance to live and stay put in one city and try out a completely new career. An American we met ended up immigrating to Australia after trying out a new marketing job and falling in love with Melbourne!

There are other ways to work for local companies while exploring a new country other than a working holiday visa. You can become an expat on a regular working visa or find a job that requires traveling, e.g. travel medicine!

Working for yourself

Being your own boss allows you to do whatever you want, like travel the world! In the last few years, I’ve tried starting up multiple different ventures, some succeeding, some epically failing, and some remaining a domain name that never even got a chance to see the light of day.

Most people I meet on the road start as freelancers, doing what they know or coaches, teaching what they know online. These freelancers and coaches may eventually work towards trading less time for money once they have enough clients by starting agencies where they hire other freelancers to do the work or starting an online course.

Others might start e-commerce stores and manage all inventory and logistics online, media brands creating content and working with sponsors, or digital product companies creating software for either consumers or businesses.

I have worked for myself by doing consulting for e-commerce businesses, career coaching for non-tech professionals who want to break into tech, and launched an online school in entrepreneurship for teens.

What didn’t work out was a course-hosting platform for dance teachers that no one signed up for, a boba bomb product that just didn’t taste good, and a sustainable packaging business that took too long to build that I gave up. But that’s all a part of the entrepreneurship journey!

If you are ready for some highs and lows of entrepreneurship, I created a youtube video on how to find business ideas here.

Don’t work

What? How will I make money then?

Hear me out.

I met someone in Bali who runs a waffle cooking class in Brussels that targets bachelor and bachelorette parties. He started the business but has since hired a GM while he chills mimosa in hand, at the beach club.

I’m not here yet, but this is something that I’m working towards. The goal here is to become an investor and generate cash flow without trading any, or very little, time for money.

The way to do this is to invest in cash flowing assets or to turn your existing assets to be cash flowing without you. And I’m talking about consistent, monthly cash flow which can’t be generated from long term investments like the stock market or angel investments.

In my portfolio, this is only rental income from a purchased property and a bit of cash from liquidity farming in defi. I am working on hiring a General Manager for one of my businesses so that I can get cash flow without being the operator. The next goal is to purchase cash flowing businesses with operators in place.

Turns out, you don’t need millions to buy a business either. People I look up to who teach about buying businesses with $0 down (but then you have to operate it for a while) are Codie Sanchez and Ryan Kulp. 

Ivy has been traveling the world since 2018. She spends 1-3 months in each location in order to immerse in its culture, make new friends, and live a completely different life.

In Ivy’s years as a digital nomad who has worked remote jobs, done WOOFing, invested in cash-flowing assets, and started her own company, Prequel, which teaches teens how to build projects online. In this article, she shares how she can afford to travel for years on end.

Check out Ivy’s blog, her traveling newsletter with her husband, and her IG for more AWW vibes!