Three Months After Selling Her Business, Everything Changed

One of the stories I heard while researching people entering retirement took my breath away.

This lovely, smart, successful woman entrepreneur had sold her business. She was excited to be free of the constant stress of running an operation, caring for her staff, and carrying the responsibility that comes with owning a company.

Then, three months after the sale, her father died.

Six months later, she had heart surgery.

A few months into her recovery, her mother died.

Oh my.

She told me she had hardly had a moment to enjoy her retirement. In fact, she wasn’t even sure why she had sold the company. She was bored. The emotional stress she thought she had left behind had simply been replaced by life stresses she could never have anticipated.

And yet, as unsettling as her story was to me, what also came through was her resilience—and her hope for the future despite everything that had happened.

As I reflected on her story, three lessons stood out that I wanted to share with you.

First, this stage we call “retirement” is remarkably ill-formed—and completely subject to the uncertainties of life.

We talk about retirement as though it is a destination. You arrive, unpack your bags, and begin enjoying yourself.

But life doesn’t work that way.

Second, you can plan and plan some more. And then life happens.

Those of us in business know this well. We make elaborate plans, only to discover once we begin executing them that reality has other ideas.

Why would retirement be any different?

Planning matters. But perhaps what matters even more is our ability to adapt when the plan no longer fits the life we are actually living.

Third, you are going to rely on many of the same strengths that carried you through the rest of your life.

In fact, your past may be one of your greatest resources for whatever comes next.

Think about your own story. How did you respond when things didn’t go as planned? How did you reinvent yourself? What did you learn about your own resilience? How did you find your way through uncertainty?

Those experiences don’t disappear when you retire.

They come with you.

What continues to disturb me is how many myths we have created about retirement—and how confidently we have promoted them as truths.

Work hard. Save enough. Retire. Travel. Relax. Enjoy yourself.

If only life were that predictable.

The more people I interview, the more I realize that each of us arrives at this stage carrying an entire life history with us.

That history helps shape what comes next.

There isn’t one retirement reality waiting for all of us. And the myths aren’t suddenly going to become true simply because we reached a certain age or stopped working.

You are going to build your own reality.

And perhaps the better question isn’t, What is retirement supposed to look like?

Perhaps it is:

Given everything life has taught me so far, what do I want to build next?

What might that mean for you?

Or for me?