You really need to explain how working for a little while and then "cashing out" was a viable option for these men that they simply chose not to exercise.
You're comment points out very effectively that this is an illusion. I'm sure you're aware that the other 90% of the people in your country are also at least scraping by, even though many of them have an income that is a fraction of yours. Do you suppose they spend all their time missing the conveniences you take for granted? Unless those conveniences are things like access to surgery and adequate food for their children (do you live in Zimbabwe?) probably not.
So consider whether the conveniences that account for the discrepancy between their scraping along and your scraping along are really worth the inconveniences required to buy them.
If you're like 90% of people, you never will consider this seriously — because if it wasn't crazy, everybody would be doing it, right? — until it's time for you to retire.
The point is : in free countries, we all get to choose our destiny, particularly so if born into middle class families. Any of us can choose to work hard for a while, find success and cash out. These men chose to take paid, salaried positions : they sacrificed their time for security of income stream. They (apparently, we have no evidence otherwise) never tried to question this, or try any other way of gaining both money and free time.
My point is they should have investigated other ways to make their money rather than work for someone else their whole life. The Authors conclusion, to me, is that working for money doesn't give you freedom. I agree completely, and say you should be finding ways to make money work for you.
I don't think my explanations are coming through very well, that's a shortcoming in my writing. But I fully understand that many readers won't get what I'm trying to say, because they probably have the same mindset as the Author, his Father and Grandfather.
We can't choose whether we get run over, and we can't choose whether we "find success" or have an opportunity to "cash out." We can try to influence things the way we want, but choosing our actions is not the same as choosing our results.
Actually he doesn't.
They lived far above subsistence. That's a choice. One consequence of that choice is that they weren't saving the difference between subsistence and their chosen lifestyle for investment and/or later use, including early retirement at subsisistence.
I'm also pretty sure that no one forced them into their occupations and that they ignored opportunities that they could have done while pursuing said occupations.
I don't know what they did with their time, but I do know that they had time to do other things that would have had different outcomes. If they're unhappy with the consequences of their choices....
In other words : you can't sell a job, so why spend 40 years working at one?
Whatever you want! Start another job, go trekking, work for a charity, write poetry.
The original article questions whether money can get you freedom, the answer is : yes it can! The ultimate freedom is choosing to do things each day because you want to, not because you have to.
Your life is made up of what you are doing right now, not what you think you're going to do sometime in the future.
What he failed to realise that neither his father or grandfather ever got control over their situation. The continually worked for money by trading their precious time for security. It's that which made them unhappy, not the actual money.
The author, to me, is making the fundamental mistake of thinking that you have to work 40 hours a week for 40 years to have 'money', so the choice is between working like a dog or having nothing, not realising that their is another way. Can money set you free? Of course it can, but not if you're trading your free time for your money.
For most people, it is a choice between security of income and freedom to spend your time as you want. The most secure people on the planet are prisoners, but they don't have the freedom to do what they want. If you're prepared to accept a less-secure income (by being risky, ie, startups) then you're going to gain the benefits of freedom when/if it does work out.
Bottom line : if this guy's Dad had cashed out at a younger age and spent the last 20 years of his life doing things on his own terms, he wouldn't have died an unhappy man in a short retirement.