There are tons of regular working and middle class and even poorer people bicycling, walking, etc huge trips for months and years. Some are basking, some are working odd jobs, some save money up for half a year (and I'm talking random job money, not FAANG level salaries) and travel the rest, etc. I had a friend who spent his 20s working at supermarkets, retail, or sometimes as a waiter for half year (the hot, demand-wise season) and doing nothing the rest, leaving off the money.
If you don't have a family (or health problem) all it takes is the willingness to do it and to withstand some hardship - that is, not expect to also keep all regular luxuries). If you're worried about how it would look on your resume, or can't fathom leaving your cushy desk job, then that's on you.
Heck, in this day you can even travel, leave abroad, have fun, while keeping a regular remote job. I've done 2-3 large trips abroad while working remotely, and it was covid time too! Yes, I had to work late night shifts to sync, because I was on a totally another timezone to the expected by the customer. But I still had my 8 hours for sleep and 8 hours for play.
Many people sail in sub-100k, or even sub-20k boats. Sure, you might not want to sail the Indian Ocean in something small and/or cheap, but there's a lot of other places to sail.
Plus, it's totally possible to live on a boat full time. If you don't have to pay rent or pay a deposit and pay a mortgage many people could buy a bigger boat and live on it. Not many people do, there's downsides, but some do.
I once thought that most people who owned yachts were in a different wealth strata of society than "regular" people, but that's only partially true, and now myself own a boat too, and I'm not a millionaire.
Peer at some listings if you're curious about the startup costs:
https://www.yachtworld.co.uk/boats-for-sale/condition-used/t...
Check out Wind Hippie Sailing on YouTube for a young woman sailing her boat in the pacific (She's probably spent less than many people do on a car) Or Sam Holmes - sailing the North Atlantic. Yes they have patreon funding - but many others do by saving money from working before or while they're travelling.
https://www.youtube.com/watch?v=2JPc1AxRSWA https://www.youtube.com/c/samholmessailing
Learned to sail last year, and got my RYA Day Skipper (which allows for ICC).
We're not millionares, we both run businesses and make alright money, but no more than most of the HN crowd. If you're prepared to put the work in you can get cheaper, older yachts as well.
It's a decision. Like most things in life, you can prioritize it or not. Wanting desperately to do something and not putting in any effort towards it is a sure way for it never to happen. Note: Whether you're interested in sailing I can't tell from your throw away comment.
Since becoming a digital nomad it's been a real journey of understanding the trade-offs that one makes in life. There are things that are gravity wells in life -- family, kids, friends, jobs, commitments. They all have a pull that complicates things.
But not so much that they can't be overcome. I'm friends with a few people that travel with kids. Travelling with a dog can make things more complicated, but not impossible.
Australia is great, but we both felt a little bored with Australia and with a desire to explore the rest of the world (in a way that holidays had only compounded the desire).
We put everything in storage and started by flying a cheap one way flight from Australia to Greece and from there we went to Romania. Early on, the digital nomad thing was part 'budget', so going to cheap places.
We weren't really sure how sustainable it would be. It felt a little like skipping school. I started splitting my time between working on a startup and remote contracting work, and my partner has a business she can run remotely.
If you come from a place where rent is quite expensive (UK, Australia), then there are plenty of places where a months AirBnB will set you back roughly the same or less than a rental property.
Over time we've calibrated our costs, and we no longer try to travel to cheaper places in the same way, and we don't stay at the bottom end of the accommodation spectrum (hostels, etc). Better to have a desk, kitchen and be productive.
In 2018 and 2019 we did a lot of Europe and Asia. When the pandemic hit we briefly went back to Australia (March -> end of May) but realised we couldn't stay, didn't have long-term accomodation (and didn't really want it) and we were crawling up the wall.
We flew back to London and then spent the summer of 2020 in Europe, ending up on a long-term visa in Estonia for a few months. It hasn't been the same, of course. The whole time we've complied with local restrictions wherever we've been -- it's been interesting seeing the way the pandemic is perceived and responded to in different places.
For example, we caught the train from Denmark to Sweden to visit an embassy and it crossed the bridge into Sweden and the announcer said 'ok you can take off your masks now'.
It's meant much more work than play over the last little while. It's allowed me to be very clear on not putting things off (mostly pre-pandemic). So often we have excuses as to why things can't happen. Sailing, our next adventure, has been on my "life list" since 2009 and never really progressed.
Miles, our English Cocker Spaniel is a new challenge (he just turned 1). Having to balance visa issues, covid travel restrictions and pet travel, is one hell of a dependency tree at times. Worth it though.
The whole digital nomad thing is an overloaded term. It means a lot of different things to different people. But if you can work online remotely (and a large number of white-collar/no-collar employees have discovered they can), then you can do it from anywhere in the world. You can explore places in a different way, less pressured and more just soaking in the way people live. It's a balance.
Sailing cruising is supposed to be an extension of that, and we'll split our time between the sailing seasons and continuing to do digital nomad things (or at least that's the plan so far).
I know a blue collar family who spent six years or so cruising and living entirely on parental leave and child benefits. The catch being that they had to make one baby for each year of cruising, so the boat ended up jam packed with them.
I really admire those people, and can you imagine a more exciting childhood?
For example, I bought my second boat in some dude's backyard, in the middle of some major renovations the guy was too old to finish. I wrapped up all the critical stuff, sailed on it for 2 seasons with my family, and sold it in the water at a marina (meaning it was at least navigable; it wasn't when I bought it). If you only look at purchase price, I almost doubled it, but when you account for everything I spent to make it navigable, I'm probably close to even (especially if you count my labor).
Do some side jobs and you can go longer.