Take a practice retirement. One way to tell if you will enjoy retirement is to test it out by taking an extended vacation or leave of absence from your job. "Very often, people who are used to working really hard are just lost when they don't have some place to go," says Ward. "Their value in their own mind is being part of the workforce and going in and solving problems for people every day." Find out if you will enjoy hours of free time and lingering lunches or if you'll crave work to structure your days. "We encourage people to take a leave as an alternative to retirement as a chance to sample it," says Ward. "Consider what you want to do next and what you are going to give up."