Making Money Working for Myself — What’s Worked

A world traveler with a backpack looking out at the horizon

When I first started this blog in April of 2016 my goal was to explore ways that one could make money on the road. The idea was to start with a long list, and then gradually go through them and write honest, as un-biased as possible reviews on what’s worked and what hasn’t.

It’s been over a year and a half now and I’ve written about everything from mock trials to Craigslist gigs. I’ve committed to honesty so I have to tell you, it’s not easy to make money on the road! That is to say, it’s not easy to make enough money on the road to travel indefinitely. It’s possible, but not easy.

There are many blogs out there that sell the dream and make it sound easier than it is. They have a vested interest in over simplifying what it takes. This blog is a side hustle for me, so I have no problem being up front about the challenges.

Anyway, down to business: after a year and a half, what would I recommend?

Hands down the most viable path to an indefinite nomadic life style seems to be learning a skill, such as computer programming, that can be done remotely. It can take some time and effort to hone your chosen skill, and put together a solid portfolio, but if you do you can make a pretty solid ongoing income from anywhere in the world with an internet connection.

If you’re not into that, the second path that seems most viable is blogging/building websites. This takes even more work and is even more competitive than doing freelance with your chosen skill. Most blogs make very little money, if any at all, and there’re really only a handful of top tier bloggers that make a “good” income by Western standards. That said, if you put in the work and have a solid concept being a pro blogger can be great. You get more freedom and flexibility than normal freelance or work-remote positions and you get to be your own boss, all by writing about something that (hopefully) interests you.

I would consider writing books to be related since, in practice, many digital nomad types use blogs to promote books and books to monetize blogs.

Finally, I have to mention Amazon FBA/retail arbitrage. This, too, is very competitive, but I did it for several years and did make some money at it.

I’m planning to write more in depth on each of these, but I wanted to give a little overview of the information I’ve gained after a year and a half of hands on research.

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