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Ask Yourself the Right Questions

For your choices about future work and retirement to be good ones, you need to assess the realities of your situation, consider your needs and goals, and evaluate your options. The following questions can help you make thoughtful decisions and lead you to your optimal choices:

  • Reality assessment—What are your strengths and limitations? What are your critical capabilities? What is your financial picture? What are the assets on which you can rely?

  • Career accomplishments—How can you leverage your experience? What are the specialty skill sets and competencies of which you are most proud? What professional and social networks can you tap to assist in your search to define your next steps?

  • Goals and aspirations—What do you want to experience that you’ve missed so far in life? What interests you? What turns you on? If you had more time and resources, what would you most like to do? With whom do you want to spend your time? What do you want to accomplish? For what do you want to be known? What do you want your legacy to be? How do you hope to make a difference?

  • Opportunities and options—What is your attitude about retirement? When is the right time for you to retire? What are the opportunities that are out there for you? What are the different options? What are their pros and cons? What are the obstacles that lie in your way? What is keeping you from achieving/accomplishing what you want? What risks are you willing to take?

  • Visioning—How do you see your future? Among your circle of family and friends, who else shares your vision for the future? What would your life look like if the changes you envision were to occur? What will you gain? What would you lose? What do you want to be careful to avoid?

  • Action steps—What life changes are you willing to make? What help or resources do you need to initiate change? What are your next steps? What is your timeline for action-taking?

In practice, making choices is often a step-by-step, evolutionary process. Decision-making is typically iterative as you jump from one choice point to another. Often we find ourselves taking action steps that make sense to us, but we aren’t sure why or how to explain our decisions. Sometimes you may think you know exactly what would make you happy but then later find out life didn’t turn out as you anticipated. When this occurs, you need to rethink your priorities and plans.

Often important life choices are serendipitous. We embrace opportunities as they arise, often without a lot of careful analysis or planning. For example, many of us got into our first jobs based on our college major (which was often not an entirely rational choice) or based on inputs from recruiters with whom we talked and offers we received. Opportunities to change jobs or companies are often responses to opportunities that arise or the result of initiatives taken by others recruiting you. At this time in your life, think about how you can be proactive—the initiator who identifies options and pursues opportunities.

Peter Drucker once said that strategy is not about future decisions, but about the future of today’s decisions. Your good choices include consideration of both your immediate options and your longer-term future. You need to consider both the facts as you know them today—and also your expectations for the future. This is like a zoom lens. You focus close-up, but expand your lens to include wider considerations and changes that may possibly occur in the future that influence your decisions. Choices are decisions about actions you will take in the short-term, with consequences for the long-term. For example, you may decide at age 60 to start a business, but will you still want to be building it ten years in the future—working long hours and risking your retirement assets as investments in your endeavor? Alternatively, if you decide to retire early in order to travel to exotic places—a desire you and your spouse have long had—what are you likely to do in three or four years, after you have done “enough” traveling? If you expect to live twenty or thirty active years in the future, you are well advised to make today’s choices with your future view in mind and be flexible enough to revisit your choices as the years go by.

  • When you climb a rock face you move up one small space at a time, sinking your grappling hook into a rock crevice just within your reach, pause to look around, and then move up and repeat the process. You climb the mountain, with a goal in mind, but it is an exploratory process, with each part of the climb within your immediate reach as you progress.
  • —Rob Cahill
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