It is estimated that as many as 10,000 baby boomers are turning 65 each day. As people get closer to “retirement” they begin to think more about what this time will be like and questions enter their mind. I put the word retirement in quotations because it is becoming a term that is harder to define and it is changing. The retirement of the past generations is beginning to look and feel different. The questions of past generations retirement are somewhat different due to our longevity, health & activity levels, and still having “something in the tank” to offer. Many of us want and expect more during this time than our parents or grandparents.

As retirement gets closer, questions begin to creep into our thinking. Many of our questions are focused on either 1) our financial readiness (our “number”), and 2) our age. When either or both are attained, it leads us to declare ourselves ‘retired.” Don’t get me wrong, having an idea of the size of the portfolio needed to retire (your number) and an idea of the age you want to retire are important factors. But that is only part of what you need to make the decision to retire- to retire successfully with clarity, confidence, and control.

The questions to beware of are questions that creep into our thinking, often after we have made up our minds that we need to retire, or we have retired. Again, this decision is often based on our age or an accumulated number that says we can now enter retirement. Neither of these gives us permission to, nor does it prepare us, to make this transition successfully.

What happens quite often, though, is that once people decide to retire, it becomes a short-lived time of euphoria. This time is now all yours to do whatever you want. That means every hour of every day, week after week, month after month, year after year. You can pursue activities you have been planning to accomplish, perhaps planning these for years.

Oftentimes however, after the euphoria of retirement wears off, we are left in a state where we aren’t quite sure what direction to turn. We can’t seem to find the direction that puts us on a plan for retirement happiness.

The questions, or some combination of these, that often confront people when they encounter this inflection point of confusion and uncertainty in their lives are: 1) What’s next, is this it?, 2) This isn’t what I expected retirement to be like?, and/or 3) Who am I now?

Let’s examine each of these and provide some additions questions and points to consider to help answer to counter this uncertainty and confusion.

What’s next, is this it? This question creeps into our thoughts after spending some time in retirement. For some people this may be three months, for others it may be six months or a year or more. It tends to wander into our thoughts after we have done many of the things we planned to do in retirement. Typically, people go gung-ho on checking off items on their bucket list- including many travel-related places to visit.

The question can also become part of our thoughts if we have climbed the corporate ladder and attained a level of success nearing retirement but finding our lives unfulfilled. It can also confront our thoughts if we somehow lose our position later in our career. This typically occurs during a corporate reorganization, restructuring, or a new CEO or President takes over a company or division. You have probably encountered this or know someone who has gone through this.

What we are really asking (telling) ourselves is: I still am healthy and active and want to contribute, but what can I do to find what to do next? We are really searching for a new meaning, purpose, and legacy for the remainder of our lives both personally and professionally.

This isn’t what I expected retirement to be like? This question penetrates our psyche oftentimes, in my opinion, because we are attaching our future happiness to an incorrect belief (from what we have heard over the years, often in commercials and other advertising) that if we reach a certain level of financial success, and we reach a certain age, that retirement will be wonderful. After all, how could it be anything but? We are now the Chief of Our House, Vice President of My Time, and Head of Family Activities.

What we are really asking (telling) ourselves is: I used to be challenged at work and enjoyed (at least some) of the contributions I made to my company, industry (field of expertise), and how I helped clients or others if my position involved client focused work. You may or may not have liked your coworkers, but whatever your working relationships, they did provide personal connections. You were connected to something and somebody other than yourself and your spouse or significant other. We are seeking to fill the void left by our contributions and connections. We want to continue to feel wanted and needed.

Who am I now? This question can come up unexpectedly. We have always been defined by our title. It gave us standing in our organization and industry (field of expertise), and it provided us something (hopefully) that we could be proud of. The work we did was good work, we were a good employee and/or boss (or at least I hope you were?).
What we are really asking (telling) ourselves is: Now that I no longer have my work identity- my title, my standing in the company or industry, the perks, the staff I oversaw, the accomplishments, the awards, or the gold watch I was given (thank you very much for your service)- I don’t know who I am now. How do I now describe myself? How can I define a new me?

When I have clients who are dealing with these questions- sometimes people have a difficult time seeing they are being pulled down by these thoughts- I have them focus on these three things by asking and answering the associated questions.

Time– How do I want to spend my time now that I am in charge of every hour of every day? How do I want to spend what may be a significant amount of time due to my chances of living a longer, healthier, more active, and more connected life?

Direction– What is the most fulfilling way for me to spend my time? Start identifying things that are pulling you in a certain direction? Find something that moves you?

Purpose– At the heart of answering the tough questions (What’s next, This isn’t what I expected, Who am I now) that typically confront us in retirement and can make this transition less fulfilling is our purpose. What might have been purposeful to us at earlier stages of our life may not provide purpose to us as we transition into retirement. Don’t mistake being busy for doing things that are meaningful.

Your purpose is our reason to get up in the morning. It is knowing that what we do matters and being here- at this time, in this life- matters. Having a purpose provides direction to our lives and empowering. It allows us to see our future lives with more clarity and it is empowering.

Have you found your purpose as you transition into retirement? In future posts, I will provide some additional ideas for finding your purpose. Finding our purpose, I believe, is the key to a wildly exciting and meaningful retirement.

Contact me if you would like more information on finding your purpose in retirement. I can be reached at or at 952-994-8937.