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31 questions to ask yourself before you retire


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Face it: Retirement’s not easy. First, there’s the money. Once you get the finances worked out, then the hard part begins.

You may think that you’ll spend your days in happy leisure, playing golf, fishing, traveling and so on. You’ll spend some of your days that way, to be sure, but life is about more than money and recreation.

You got to retirement by doing things and probably doing them well, but retirement is also about more than doing. It is about being; it is about creating a whole different life. It requires discipline, focus and hard work, not to mention a large dose of honest introspection.

Introspection is not just something you one day decide to have. You can’t develop it overnight, and some people never get it. They never examine their own lives, and they never see themselves as others see them. Socrates’ observation that “the life which is unexamined is not worth living” is probably too harsh, but it is true that the unexamined life is likely to be one without significant personal or spiritual growth.

There are no formulas for introspection and reflection, but in helping you begin to look inside yourself, to examine your attitudes and preconceptions, and to take the next steps in preparing yourself for retirement, I offer 31 questions. They are in two somewhat arbitrary categories that I’ll call the “thinking/doing questions” and the “feeling/being questions.”

In both categories there are questions for those of you who are contemplating and planning retirement as well as for those of you who are already retired but who still feel there are aspects to retirement life you’d like to re-examine and, perhaps, adjust or change.

The answers to all these questions will require – in addition to discipline, focus and hard work – considerable time for reflection as well as complete honesty with yourself. Plus one other thing: imagination. The good news is that you already have most of the answers deep within you.

The “thinking/doing” questions:

1. When you think of the word retirement, what image comes to your mind? Is it an old or aging person? If so, what is he or she doing? Puttering around the house? Playing golf or fishing? How then do you think you will fit that image? Do you see yourself differently? Why?

2. Are you looking forward to retirement? If so, why? What is it about retirement you are positively anticipating? Make a list.

3. How do you describe yourself, by who you are or by what you do? A good test is to observe how you most often introduce yourself. Do you feel compelled, within the first few minutes, to tell what your position or job is?

4. When you meet other people, are you more interested in what they do or in who they are? Do you distinguish between the two?

5. When you think of yourself in retirement, do you think of it in terms of what you are going to DO next? If so, you first need to identify and accept that you’re not going to do the same things you’ve been doing.

6. What are you dreading about retirement, if anything? Make a list.

7. Ask yourself how much you love just being at the workplace. Put aside all the cliches of how you’re supposed to feel, or think you’re supposed to feel, and ask yourself the honest question: “How much will I miss just being there?”

In answering this question, don’t discount the everyday stuff such as lunches in the cafeteria or at the corner deli with your friends, or that coffee on your birthday when your colleagues gather briefly to give you funny cards and to joke about your age. You may miss picking your sports teams and putting a dollar in the office pool. It is these kinds of activities and social concourse that help create the rich texture of your work life, and you must face the fact that you’ll miss some of it.

8. List the things you like about the job itself that are going to go away. For me, I knew I’d miss being a leader in an industry and being respected for my accomplishments in that industry. I knew all that would be gone, because I had seen industry leaders retire and knew that they were out of sight, out of mind.

9. Now list the things you don’t like and that you’ll be happy to leave behind. I was sick of the incessant pressure of earnings, the endless meetings, the constant travel and simply having a boss.

10. List the personal – not work – things that your job allows you to do such as travel to nice resorts for conferences, maintain a circle of professional friends and contacts, perhaps be a member of a nice club, eat in good restaurants and so on. Or your organization might be one of those that provides computers or other equipment for personal use. In some cities, there’s simple personal prestige in working for certain companies, and often employees of those companies receive courtesy discounts on everything from clothing to automotive supplies, or even discounts at restaurants and movies. There can be many purely personal advantages to your job; be sure to include them all.

11. Now list the personal things the job keeps you from doing, such as spending more time with your family, or time with hobbies and interests. And don’t forget about not having enough time for intellectual growth through learning new things, reading, taking courses and so on. Not to mention the fact that you have only so much vacation time, and that your travel must fit into an overall vacation schedule. The “feeling/being” questions:

These answers will require thought, but the goal is to identify your honest emotional response. Don’t come up with the answer you think you ought to give but the one that is closest to your feelings.

1. Make a list answering this question: What do I really value most in my life? Job, family, friends, activities? Then put them in priority order according to how you really feel about them. If the job is near the top of the list, then at retirement, you’ll be needing a major values shift.

2. How do you think you are going to feel (or how do you feel) about being replaced in your job, about not being considered relevant to the organization anymore, about not having your opinion valued, about no longer being asked to make “important” decisions, about being “out of the loop” forever?

3. If no one knew what you had done in your professional life and knew you only for who you are, would that bother you? Would it be satisfying enough? Do you think they would like you or respect you to the same degree? Less? More?

4. If you would not be satisfied by people knowing you only for who you are, rather than for what you do or what position you hold, does that mean your sense of self is derived from what others think of you more than from what you think of yourself? Your answer to this question might lead to a need for counseling or therapy.

5. Who would you like to be, and how would you like to be thought of, 10 years from now? Try to describe your ideal self 10 years from now.

6. What do you think you’ll miss, or what do you already miss, about being younger? What do you miss from your earlier life, perhaps even from childhood?

7. Whom would you want to see again, perhaps family or old friends, if you had the chance?

8. What have you always wanted to do but never had the chance?

9. Whom do you really love?

10. With whom do you truly desire to spend more time?

11. Whom would you really like to help?

12. Whom do you really trust?

13. Why don’t you trust more people?

14. Do you have true and abiding friendships or just acquaintances?

15. Do you have the emotional capacity to be alone or do you always need people around you? Being alone does not include watching TV or surfing the Internet alone.

16. List your talents, not your skills.

17. How good are you at doing nothing?

18. Describe yourself in spiritual or, if you prefer, religious terms. How important is this to you?

19. Do you think of yourself as having a spiritual quest? Of being spiritually curious?

20. Do you pray or meditate? Are those things important to you or marginal in your life?

The process of developing honest and deeply felt answers to all these questions may take weeks or even months of work. In addition, you’ll find that your answers provoke other questions that need to be answered. For instance, if in the list of thinking/doing questions you are giving answers that indicate you’re really going to miss being at the workplace more than you’re looking forward to retirement, this is a danger signal and raises the question of what you’re going to do about it.

Too often, we think that this is a bridge we can cross when we get to it. “Of course I’m going to miss the job and the people and the action,” you might think, “but I’ll find something else to take its place.” What we fail to consider is that we didn’t arrive at our jobs and in our positions overnight, and we won’t be able to find that “something else” overnight.

In the feeling/being questions, if your answers indicate that you have acquaintances but not friends, if you can’t identify people you love and want to be with, whether family or friends, this is even a larger danger signal. Most of us who have retired have been shocked by how fast those great folks we knew “in the business” simply faded from our radar screens, or we from theirs. When you retire, the reason for those relationships often disappears.

Now for a few small tips that can help you begin the transition, or if you’re already retired, can perhaps enrich or even help move you toward the next phase of your retirement life:

• If you’ve spent your work life dealing with people and being surrounded by people, learn to be alone. Spend time at it. Get comfortable with it.

• If your job has involved working alone, then do the opposite: Learn to be with people. Volunteer in some group activity, civic, church or otherwise.

• Do something different. Break the routine you now have and practice some things you might want to embrace in retirement.

• If you’ve spent your professional life working with words and numbers in an office setting, start working with your hands. Garden. Build something, even something small like a single bookshelf.

• If your job has been physical, then put your mind to work in your off hours. Read. Attend good films or plays or concerts. Take an adult education course.

• Don’t be afraid to get some psychological or spiritual counseling if you’re having real problems dealing with some of these questions or answers. Just as you may have engaged a financial planner or counselor as part of your retirement planning, you should consider calling on professionals for the personal aspects of retirement as well.

• Plan and have discussions with your spouse or partner. What are his or her expectations of retirement? How will your spouse or domestic partner’s life be enhanced or disrupted by your choices? If the honest answers to these questions demonstrate that there are likely to be diverging paths, this should be understood ahead of time so that you can maintain a strong relationship while involved in separate interests or activities.

By now you realize that the process of planning for a retirement of meaning and purpose, of personal and spiritual growth, and of deepening connections within yourself and with others is no minor task. You can’t add retirement planning to your weekend “to do” list and expect to whip through these questions and answers, then check them off along with mowing the lawn and repairing the gutters.

In fact, it is important to realize that answering these questions may lead you to no less than a complete realignment of how you choose to live your life from now on.

This article is adapted from James Autry’s book “The Spirit of Retirement: Creating a Life of Meaning and Personal Growth.”

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