Could you imagine driving 2,000 miles to Disney (NYSE:DIS) World only to find that it's not really that fun? Sure, Space Mountain was thrilling the first five times. But once you know the twist and turns -- and consider the wait -- it's just another trip, bringing you back to where you started.

No, I'm not knocking Mickey. (Hey, I grew up in Florida.) But everyone has a Magic Kingdom in mind -- a destination that looms in the distance, giving us something to work for. The ultimate getaway, of course, is retirement. It's a permanent vacation!

Or is it?

In reality, many retirees report feeling a sense of loss after they've bid adieu to their colleagues and sold their lunch pails on eBay (NASDAQ:EBAY). They've been saving and investing for decades for the Big Day only to ask soon thereafter, "Is this all there is?"

So says Dr. Ron Manheimer, the director of the North Carolina Center for Creative Retirement (NCCCR). "There is kind of a nothingness, a drift to retirement," says Manheimer. "It can be a vacuum. We get our identity from our jobs, from our accomplishments."

Manheimer's job, and the mission of the NCCCR, is to help retirees and near-retirees fill the void formerly occupied by gainful employment. This past Labor Day weekend, the Center hosted its biannual "Paths to a Creative Retirement in Uncertain Times" workshop in the Blue Ridge Mountains of Asheville, N.C. For three days, 39 participants -- a group comprising lawyers, teachers, CFOs, librarians, psychologists, investment bankers, and one Motley Fool (i.e., yours truly) -- mapped out their retirement fantasies and fears.

I know -- many of us who count ourselves among the working stiffs might find this ambivalence about retirement hard to believe. What we wouldn't give for a break from long commutes, tedious meetings, office politics, and daily personal hygiene!

But the angst of the recently retired is real. One workshop attendee said, "Retirement left a greater void in my life than I expected." Another said, "I can fill the time, but at the end of the day, what have I accomplished?"

Think about it for a moment: What would you do with 24/7 free time? By the time you reach your 60s, you have spent decades on your career. You met many, if not most, of your friends through your job. A sizeable chunk of your self-worth and sense of usefulness comes from how you've earned a paycheck. Is it possible that you'd be lost -- at least for a while -- after you've given it all up?

I'm not suggesting that you should work forever. In my Rule Your Retirement newsletter, I profile retirees who have designed self-sustaining portfolios and crafted fulfilling lives, usually through a mixture of travel, family, and challenging ventures (sometimes for pay, sometimes not).

But creating such a retirement doesn't just happen. It takes planning, which is best done long before you kiss the boss good-bye. At the NCCCR retreat, participants began the process through various self-assessments, case studies, and discussions. Will you want to relocate in retirement? How will family -- kids, grandkids, or elderly parents -- figure into your plans? How will you structure your time once you're freed from 9-to-5 requirements? Will you try a new career -- or some other rewarding, new endeavor? (As one participant put it, "I'm looking for a way to contribute, to be productive, to have an impact -- but not a job.")

So how can you start planning the rest of your life? Consider these possibilities:

  • Begin a "rehearsal retirement" by visiting new locations and dabbling in new activities. One workshop attendee explained to me the concept of the "gap year" -- taking time off, especially in between big transitions, to audition a different life.

  • Discuss a "phased retirement" with your employer, allowing a transition time between full-time work and full-time free time.

  • If you think you'll want to continue to work part-time, seek out employers known for valuing older workers, such as Deere (NYSE:DE), Home Depot (NYSE:HD), and Principal Financial Group (NYSE:PFG).

  • Don't wait until retirement to begin your philanthropic pursuits. Start now working with organizations that support the causes you care about.

  • If you're married, don't keep all your dreams and anxieties to yourself. No plan will work until both spouses agree on it.

One of the workshop's participants pointed out that the dictionary says "retire" means "to remove from service." Another attendee said retirement means going from "Who's Who" to "Who's he?" While most of us may not want to be employed full-time forever, I bet most of us want to be of service, of use -- valued, by ourselves and others. Considering how we'll spend our time is as crucial to any retirement plan as calculating how we'll spend our money.

Robert Brokamp is the editor of the Motley Fool Rule Your Retirement newsletter service. Receive a 30-day free trial, and the 8 Ways to Supercharge Your Retirement special report, byclicking here. Brokamp owns shares of Home Depot. The Motley Fool is Fools writing for Fools.