I've thought about this a lot too. After college I worked for a while at a big company and saved up a decent amount of money, and then decided I wanted to take a break. At first I was pretty stressed because I left a good job and had no real plan, but as soon as I packed up the car and left on my first road trip all my doubts were gone.

I realized that life isn't about working hard for 30+ years and then finally getting to enjoy your life once you retire. There are many different dimensions to life and there is no reason to get stuck on a single path. As long as you are smart and/or you work hard, you can make it happen... whatever you choose to do.

After I quit and took a break, I spent about 2 years in "retirement" just catching up with friends and working a few short term temporary/consultant jobs here and there, some were just fun jobs and some were more high-level. Eventually I found a full time position that I really liked which is what I'm doing right now.

In terms of financials, I grew up on a low-income budget so I have always been extremely frugal. I max out my IRA / 401k, and the rest of my investments are just in S&P 500 index funds (by far the most reliable investment). I don't really have a plan for retirement, I just live very modestly and continue saving as much as I can.

I think my best advise from what I have learned is to work hard until you reach the point where you are somewhat financially secure, and then you have the choice whether to continue working hard and saving up or take a break or work a lower paying but "fun" job.

The capital's dialectic is at work. Thx Karl Marx.