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Are there any benefits to working, as opposed to having a free ride for life?

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Yeah. Things like:
. having a schedule,
. an eascape from home life and worries,
. More to talk about
. Diversity of people you interact with
. Responsibilities
. Challenges
. Feeling useful
. and making you value your free time more.

However, its also balance.
If you work too much you spend your free time recovering .
Which is depressing.
And conversely, if its all free time, you can become lax and unmotivated,
which is depressing.

I suppose its about finding a way to give your life meaning, whether it's through working, or some other avenue like volunteering .

A sense of giving back to society in some way can be very fulfilling.