My experiences with the challenges of early retirement may be atypical but then again, I am not aware of that many people who escaped employment before they were close to 50, so for what it is worth, I present to you the three biggest challenges following early retirement.
These have, perhaps surprisingly nothing to do with being bored or worrying about running out of money. They have mostly to do with explaining the hows and whys and dealing with other people’s prejudices; yes, I care. If you don’t, power to you!
Not having a job title
This is something I have discussed several times before. It is very easy to be a specialist in a culture of specialization. State your job title and everybody, including oneself, will have a mental image of what this means. It is a convenient sound-byte. Retiree even exists.
My father suggested rentier, which is pretty descriptive although I would put it in other and more flattering terms than the wiki-page, but I doubt many people know what the term means. Maybe I should just use capitalist. Problem solved: It is a job.
Perceived standard of living
Show me one person who is excited about extreme early retirement and I will show you five that thinks it is all about sacrifice and making your own toilet paper, something which they are not particularly excited about and even fairly judgmental about. To avoid this it is prudent to pick up something which is highly visible and desirable to Joe Average. Traveling is a sure hit.
Not contributing to society
There is this collectivist belief shared by many(*) that capable persons should contribute to society (Being a rentier capitalist, see above, I contribute my fortune to productive assets instead of suburban real estate and SUVs). An alternative belief is that as long as one can support oneself, that is good enough: This is the individualistic approach. The antidote would be to reflect on how much more participating in a system that pushes paper around between desks contributes compares to playing football all day(**).
(*) Which obviously does not make it correct.
(**) I understand that playing football is paid better than “paperwork”, so it must be more important, right?