Interesting stuff. I think there’s a fairly simple recipe for digital nomad happiness that is borne out of observing people living like me for the last 20 years or so. Yes, nomads existed long before the term “digital nomad” was coined.
There are two types of people who make this “digital nomad” life work in my experience:
The far most common group is the “took an internet business which already worked fine and then started to travel the world.” Some of those jumped straight into a lifetime of travel, others dipped their toes in the water (as you suggest) and slowly worked up to it. The advantage they had was that they had no stress regarding their income stream — they had the time to adjust to traveling because they weren’t desperately seeking clients and revenue. They understand that geo-arbitrage is taking a Western income and using it to leverage a better standard of living in other parts of the world.
The second group, like me, are those who were already somewhere else in the world when they transitioned from expat working to freelance/entrepreneurial life. We had the opposite problem; no issues with travel whatsoever but the insecurities of finding clients and revenue played a big part in the first few months (or even years) of the game. Some people sink during that phase — it’s hard to find clients at home, it’s harder still to find them in Egypt or China. This is doubly so if you want the clients to pay you real money rather than local money. But those that remain pushed through the pain barrier.
Some may want to add those with a remote job to this list. I am yet to meet anyone on the road who has had a remote job for a decade or more — I’m not saying they don’t exist, I am saying that they’re not common or significant in the long-term nomad groupings. This may change a decade or two down the road but somehow, I doubt it.
This bears out your own observations that a single rapid act of transformation is probably a bad idea for people who want to be digital nomads.
I recently challenged a group of nomads on the idea that quitting your job, selling your stuff and moving to Thailand was a good thing. I noted that if it was a good thing — by now there should be endless numbers of success stories coming out of Thailand of people who have done that and gone on to great things. I was downvoted a lot but when asked for examples… nobody managed to supply any. In fact, one guy was so desperate for this to be true that he fabricated examples which completely failed to check out with a cursory Google.
There’s an industry dedicated to telling people that “quitting your job, selling your stuff and moving to Thailand is a good thing” and sadly, it’s an industry that doesn’t deal in truth very often.
And finally, it’s worth noting that the “digital nomad life” isn’t for everyone anyway. Living a life of constant travel means sacrificing the life that most people want (or at least have been raised to want) of 2.4 children, a high flying career, and social and professional climbing. I am now in my mid-40s and it becomes clearer every day that while I love this life, there are other lives I might have loved too.