I plan to follow Justin and Jacob into extreme early retirement and then do whatever startup project is fun from there, no matter the monetary perspectives.
The key is to build up passive income (from businesses and investment) and keep expenses in check. Personally I found passive business income much easier to build than investment income. A server or web app can easily beat every stock market index, but it’s harder to scale it up.
The concept of retirement will drastically change in the next decades. As baby boomers in the West retire, it will be hard to keep everyone’s living standard during classical retirement. There will be many “retired” people still working to make ends meet financially
On the other hand we will have a number of very old people working, simply because they love their jobs. I personally know a number of them. None of them will even consider retiring, while they still stand.
As nomads we have the big advantage of global arbitrage and the flexibility to follow booming regions and industries. This makes it easy to quickly declare retirement (in the new sense) and do whatever is fun from there. It’s just important to stay active, learn new things and adapt to the world.
For anyone, who retired in the classic sense and now gets a pension from a state or company, I recommend to move to a country you like and start a second career there. Charity, resort manager, bar owner, etc. Don’t make the mistake of disconnecting in a closed retirement home.