When you reach a certain age (which some of you have not), you might have occasion to fill out a retirement planning questionnaire. It is a sobering experience. It asks all the expected questions, but somehow still unsettles you. How much do you make? How much do you owe? How much have you saved? And then the big one: how long will you need the money after you retire? Or, to put it differently, how long do you expect to live? You know, how long before you “kick the bucket,” from whence the phrase “bucket list” comes?

Even if you are very young, you are probably already making an unconscious bet on your future. You are assuming that some things must be done pretty soon and that others can wait. Implicit in this decision is that you will be alive long enough to do those things you choose to delay. If you are relatively young, you probably will. But, of course, there are no guarantees. If you’d like to find out what the Northwestern Mutual Life Insurance Company thinks your life expectancy might be, you can take an easy and free 13 question test that will take less than five minutes and give you an immediate estimate: Lifespan Calculator.

When you get a bit older, however, the probabilities begin to turn. You might not want to think about this, and some of you could be about to search the net for the latest update on Snooki; in other words, a topic that is less weighty and more amusing. Still with me? Good. You are a brave soul.

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All of us take risks, including young people, and we usually avoid disaster in spite of that. The sun rises tomorrow despite drinking too much, having unprotected sex, and eating the wrong things. I don’t advise you to do stuff like that, but I can’t imagine having any kind of life worth living if one were so cautious as to avoid all possible risks, always wear a bullet-proof vest, and never give one’s heart away for fear that it might be broken.

But, time does tend to march on, and the odds don’t improve with its passage; specifically, the chance of having enough time to do all the things you might want to do. I bring this up because I retired in December and have had tons of conversations with people in the last two years about their retirement plans. I wanted to learn as much as I could in order to inform myself about what I might be getting myself into.

I talked with a lot of very smart people, some who weren’t retired and couldn’t imagine it, some who were retired involuntarily, and some who made a choice to do it. I tried to find out the ups and downs of it all and, now that I am retired myself, I’ve been asked questions by people who are hoping to learn from my experience; to find out what things are like on this side of the work force.

What have I learned? First, even though I feel good about my personal choice, I know that it fits only the particular circumstances of my life and personality. I can’t promise you that you would be as pleased with the decision to retire as I have been thus far. It might be absolutely wrong for you.

Second, if you are young it might be useful to run through the list below while you have the time to achieve fulfillment in the first half of your life. The eventual retirement decision will be easier if you make good use of the early years and have little regret over misspent time that can no longer be recovered.

Third, I realize that there are risks on both sides of the choice. You can retire when you are at the top of your game or when you are well-past your prime. You can retire when you are still healthy and active enough to enjoy life or when your body and your brain make that impossible. You can retire with enough money to live comfortably or discover that the days of your life have outpaced your ability to pay for lunch.

What factors, then, do people think about as the try to figure this out? For the sake of this list, I’ve not included those individuals for whom continued work is an absolute necessity because they are without the financial resources to retire even for a short time:

1. Money. Even though some people have enough money to retire for a while, many are afraid to take the risk of retirement for fear of eventual destitution. Others have knocked themselves out to make a high salary and find the idea of walking away from that income to be difficult. This is particularly true for people who have known financial hardship in their lives, those who see their income as a kind of measure of their rank among their peers, or folks who simply put great importance on dollars and cents.

In the absence of financial necessity, the decision to retire pits the value of money vs. the value of time, unless your work itself is engaging enough to be the best possible use of that time. Put differently, ask yourself whether you would continue to do the work you do in the absence of financial compensation. The answer will tell you something about how much you value the job vs. how much you value the money that it provides.

2. Lifestyle Issues. This is certainly correlated with the money concerns I’ve just mentioned. The difference with this item, however, is that some people believe it is essential to live just as they always have, or perhaps even more grandly, in terms of vacations and the other non-essential things that money can buy: fine clothing, expensive dinners, and the like. They plan to continue working so that their level of non-essential expenditures can be maintained.

3. Responsibilities, Obligations, and a Strong Work Ethic. Continued work can be driven by having relatives who are financially dependent or have large medical expenses. But even without such demands, I know individuals who have a strong desire to serve others and believe they have a duty to an organization, a team, or simply their fellow-man or woman. Others, however, have a sense of guilt if they do not “work,” because they were required to do so growing up and evaluated accordingly by their parents. For them, work is driven not so much by its “meaning,” but by some sense of having to do it in order to measure up to an old, internalized standard of what makes them worthy of affection or approval.

4. Hobbies, People, and Interests. If one is to have a decent retirement, it is essential to have interesting things to do. Lying around, watching TV, and observing the grass growing are not weigh-stations on the highway to happiness. For most people, a good retirement requires human contact. Those whose social ties are to be found largely in the office can get pretty lonely after the office is permanently closed to them. For doctors, that can include the absence of social fulfillment derived from seeing patients; for teachers, it can be the sorely missed daily contact with students.

Similarly, productive endeavors are essential. Worry and anxiety are likely to close in without some way of organizing your life and engaging in fulfilling activity, even if that activity is labeling your coke bottle collection. Folks who have developed neither social networks nor hobbies often keep working for fear of what the alternative would be like. The routine of work can be comforting and give you a sense of stability. Without an adequate retirement routine — especially for those prone to worry or anxiety — there is also the risk of reliance on the self-medication of alcohol or recreational drugs. Before you retire, you’d best have an idea of how much you will still need the society that work provided and the routine it required, and how else these might be achieved.

5. Energy. If you still feel enormously energetic most of the time once you reach 65 — well, then you are a better man or woman than I am. Some of us retire, at least in part, because the physical cost is greater than it used to be. Others, because they have less resilience available to deal with the stress of working — the “emotional overhead” of staying in the rat-race. Moreover, if you want to have an active retirement, you do still need to have some gas left in the tank. Wait too long and you will be running on empty. It is one reason why a few of us choose to get off the escalator.

6. The Lure of the “Bucket List.” Most of those who belong to the “mature” or middle-aged set have the idea that they will eventually get to the category of things that I mentioned at the beginning of this essay: those items that have been postponed until there is “enough time” to do them. Thanks to the movie starring Jack Nicholson and Morgan Freeman, the concept of The Bucket List has entered popular consciousness.

The list provides an incentive to flee your day job while you still have the capacity to enjoy the activities you’ve delayed. They don’t have to be elaborate or difficult to achieve. The list can include items as simple as taking a course of study in something you’ve always had an interest in, reading Proust’s magnum opus, or learning how to sail or fly a kite. My friend Ron has a very thoughtful list that is part-way toward completion. He has already done things like working for Habitat For Humanity and going to see a space-shuttle launch. The “great hot dog tour” waits for him. Yours truly will be riding shot-gun alongside of him, hoping that eating our way across the country on a diet of “red-hots” (a kind of sausage on a bun) won’t kill us.

Don’t think, however, that everything can be postponed. Something that sounded good at age 25 might not feel as good if you accomplish it at 65. All work and no play when you are young sets you up to miss the boat on those things that are best done early. Paris in the springtime of the year feels better in the springtime of your life, when you can flirt with a comely young Parisian rather than watch someone else do it and realize that you should have made the trip decades before.

7. The Joy of Work and Making a Contribution. I am pleased to say that I know a number of people who get great joy and fulfillment out of doing the job that they also do to make a living. Why give something up if it is akin to a “calling?” Symphony conductors are well-know to continue their work well into their 80s, so strong is their passion for making music. I also had a legendary pediatrician, Dr. Albert Stein (no relation), who maintained his medical practice into his 90s. For myself, I found my work as a clinical psychologist very satisfying. But was it a “calling?” Probably not.

8. The Desire for Freedom From the Oppression of the Clock and “Responsibility.” The wear and tear of life can erode your soul. The second-hand of the clock slices you a small sliver of your life, like a piece of pie that you can no longer consume. We are a “time driven,” deadline-driven society. The machines and electronic devices task us to keep up with them. E-mail, voice mail, and text messages seem to demand instant responses in a way that letters and a hand-written message taken by your secretary did not a few years back. Workplaces often expect you to surrender your life to the company, putting your family second, your friends third, and any personal time out of the question.

You might know that the origin of the word “deadline” comes from a line that was drawn in a military prison yard during the Civil War to make sure that the prisoners did not get too close to the prison wall. If you did cross the “deadline,” it was assumed that you intended to escape. You were shot simply for violating it. Today’s work deadlines might just be killing us too. In Japan, they even have a word for working yourself to death. It is called karõshi.

9. The Desire to Spend More Time with Your Spouse, Family, Grandchildren, and Friends. This is not exactly a “bucket list” item, but can be very important, nonetheless. First, however, I should point out that some people postpone retirement for fear of spending more time with their spouse! Others are surprised only after they have left the job that there are complications from more proximity to their partner. Best to know whether you are really compatible with the older version of your companion (and she with you) before the decision to quit work. If not, make plans to do lots of things separately. With respect to others, one of the most often cited benefits of retirement is the ability to be with grandchildren and the opportunity to spend more time with old friends or make some new ones.

10. Status and Its Loss. Many of us define ourselves, at least in part, by our work. For those who take particular pride in what they do and the status that it confers, it is especially difficult to surrender their profession. Loss of identity is a risk. In such cases a satisfying post-work life requires that one be flexible enough to re-define oneself and no longer feel the necessity of being “the big guy” who is indispensable to the organization. The truth is that work will go on without us. Put very darkly, “the cemetery is full of indispensable people.” However much your absence might mean on a personal level, there is probably someone who can do your job as well or better than you can, other than raising your children and grandchildren.

11. The Ability to Appreciate and Accept Things. It is useful at any age to feel gratitude for the things you have. It is equally beneficial to enjoy simple pleasures: a beautiful day, laughter, and the excitement of a game of ball — especially if you are playing in it.

If you are aging well there will be some loss of restlessness and driving ambition over time — a sense of being “in the hunt.” Be grateful for that, too. Unless you have tamed the beast that youthful ambition can be, you will feel more like the pursued than the pursuer when that youth is well behind you. Win the games you can win while you have the grace and speed and drive of a young man. A good retirement usually requires a belief in accomplishment that one can look back on — the feeling of a job well done. If retirement age finds you still maniacally trying to beat the competition, you should either stay working or ask yourself why you remain driven.

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I think it is pretty easy to fool yourself about the reasons you continue to work, as well as those that might cause you to retire. But, from a psychological viewpoint, the greatest risks in life are usually those that require change. Even though retirement isn’t the same as walking a tightrope over Niagara Falls, to some people it feels that way.

The decision to stop working requires not only that you establish a new kind of life, but some amount of courage in facing the fact that you won’t live forever; and that even if you do live many more years, you might not be in the shape required for the life you imagine. High achieving individuals are generally good at postponing gratification, perhaps too good. Be careful not to fool yourself into thinking that there will always be more “good” time.

That said, neither work nor its absence in retirement ever produce a perfect state of being. Work or no work, all the same daily indignities are available, from people cutting you off in traffic to dealing with insurance companies over a claim. Few people achieve serenity, but acceptance of things “as they are” can occasionally come close. If and when you decide to retire — assuming that you have planned it well, have enough money in the bank, and have a sustaining curiosity about life and people — you just might find it to be lovely.

Whatever your choice, Star Trek’s Mr. Spock (Leonard Nimoy in both the images below) has the best salutation: “Live long and prosper;” to which a fellow Vulcan would respond “Peace and long life.” These extra-terrestrial, science fiction-based humanoids are said to have lifespans that can extend beyond 200 years. Yet, as the above salutations suggest, even they remain mindful of the preciousness of time.

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The top picture is called Card Games and Game Tokens by victor vic. The second image is called No Death (the grim reaper crossed out) by Benjamin Hauber. It is followed by a Green Bucket by 4028mdk09. All are sourced from Wikimedia Commons. Finally, Leonard Nimoy as Mr. Spock in the 1960s and at the 2011 Star Trek Convention, the latter by Beth Madison, sourced from Wikimedia Commons. In each instance he is giving the sign that goes along with the salutation “Live long and prosper.”