"If I had a million dollars..."
Funny you should post this because I've been thinking of posting the same thing. When I graduated from college, my plan was to save and invest so that once I had a million dollars, I wouldn't have to work again. Or I could choose to do whatever work I wanted.
Now that we have a million dollars (not including home equity), it's not that simple. Kids, community activities, and other commitments have us in a stable situation that would be a shame to screw up. Work is up and down - great boss, great product, great co-workers and team, some drama and difficulty in related groups. Not perfect, but not terrible. Mostly I need an extended break sometime soon, but I have more I want to accomplish there, so I'm not ready to leave permanently.
Right now my plan is that I will work at least three more years, we'll invest $75k a year and accelerate mortgage payments by $25k or more per year, and then think about what's next. By that time, net worth should be closer to $2M, with $1.5M or more in investments. Kids will all still be in grade school, so we could stick with it and enjoy 6 weeks of vacation a year, paid (non-working) holidays, 5 minute commute, somewhat flexible schedules, and a good lifestyle in our hometown. Or, we could shift gears. Travel for a while, perhaps a PhD for my wife, maybe graduate school for me or stumble into something else. Who knows?
The biggest thing a million dollars does for me is it provides options. I'm not ready to retire yet, but it is comforting to know that we can leave our jobs and have options.
If the numbers line up and I decide to retire in three years (or earlier), I'm really curious to see the reactions on people's faces. We have lots of people who retire out of the company in their sixties with 20, 30, or 40 years of service. But it would be fun to see how people react to someone retiring in their forties with 20 years.