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“Where will you be five years from today?”

  |   retirement transition, Baby Boomers, reinventing yourself after 50

by Beth Davis – STPI Transition Planning Consultant and founder of of Planning What’s Next

That’s the question asked by Compendium in their little inspirational book Five. It reminds me of the ubiquitous answer to the retirement transition question in the CEO peer groups I ran for nearly fifteen years. Regardless of age, years in business, or any other pertinent demographic if a CEO was asked when he or she might want to sell their business, the answer was almost always, “in five years”.

What do you make of that?  In my speculation, it means that the question is relevant and close but the answer far enough away that the owner doesn’t have to do anything about it just now – a decision that can be delayed. The problem is that the five-year window keeps slipping and the planning doesn’t happen.

Deciding what’s next – start with what you value

A good place to start is with your values. What’s important to you? Be honest with yourself – it’s too easy to create the “God, family, country” list. Where do you spend your time and your money? That’s a good indicator of what’s important to you. When I looked at it that way, I saw that I spend a lot of time and money on training, books, exercise and home goods – so some of the things that are important to me are education, life-long learning, health & fitness and good design (I won’t get into “the hair expense” – something most women of a certain age know a lot about).

What did you discover? Did that exercise make you wince? If so, you might want to start down a path of self-examination and redefinition. In re-examining your values, start with the traits or qualities that describe the people you admire, the places you love, the programs you support – from this list you can choose your top five lifetime values. Write them down and keep them near so you can frequently reflect on them. How are you living those values? On a scale of 1 to 5, how consistently do you live what you value? What would you like to change? How would you like to be different in this? Identifying your top five values and answering these questions is a short-cut to naming the top goals for your “what’s next”.

Create a personal mission statement

I love this quote, “Your life is worth a noble motive”.  Most leaders I know are good at making things happen, not just letting things happen. And yet, in this arena of business transition, I often see “the deer in the headlights” look.

Once you’ve clarified your values, consider creating a mission statement for your life. Just as your business has a mission or purpose, so can your life. When you dedicate your life to something greater than yourself life is a bigger adventure, something you can organize around. Ask yourself, what services or activities do my values call me toward? What is my legacy? What is the contribution I want to make? Can you start to sense a direction here?

Satisfaction and the wheel of life

Once you’ve defined what’s important to you and gotten clear on what your life is all about, you can take a look at each spoke on the Wheel of Life and measure your level of satisfaction in each domain.  Many business owners speak to me about the lack of balance in their lives. Here’s the place where you can gauge what you’re attending to (or not) and what your goals and options are in each “spoke”.

When I coach owners through the Successful Transition Planning Institute’s programs, I help you decide how you want to live your life going forward:

Framework Purposeful Living


We look at six options for each spoke of the wheel and then further, within each option we look at both the upside and downside, so that both your thinking and your life is balanced. From this investigation, you can create a life plan.

Define your own success

In the end, you need to define success in your own terms. I think Viktor Frankl said it best, “success is the side-effect of your personal dedication to a course greater than yourself”. Enough said.


If you want to learn more about defining the “next version of yourself”, get the FREE download of chapter one of the new book by Jack Beauregard, “7 Principles for Living With Authenticity”, click the image below:

7 Principles book image