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Legacy, the Giving of Life’s Greatest Treasures, and a Life Worth Living

An important part of selling your business is deciding what you are going to do in the next chapter of your life. A growing number of us reach a certain point in our lives when we look up from our desk and wonder if there is more to life than this? This is the concept of “Halftime” – that point in your life when you realize that simply having more success is not enough, and you begin to think about what can give the second half of your life more meaning, purpose, joy,and balance.

After a flourishing career in real estate, I transitioned to helping other successful men and women through their Halftimes. For 17 years I’ve been with the Halftime Institute, and throughout more than 11,000 hours in one-on-one coaching, I have helped people reinvent themselves in the second half of their lives.

The concept of Halftime is relatively new. 100 years ago, the average life expectancy was only 47. Today when you reach 47, you still have 30 or more bonus years of your life left. Will you continue to do the same thing, or will you explore the other callings in your heart?

The type of work performed back then was different too. 100 years ago you likely had a physically demanding job on a farm or in a factory. We are now knowledge workers, and our best contributions can be made after the age of 50. When we sell the company and retire, we don’t think that our best years are behind us. We look forward, eager to make it so that our best years still lay ahead of us.

That said, there is no university for the second half of your life. People often go into it unprepared, which is why we’ve set out to create a university of peer learning to help you think about your second half. Here are some key lessons that can help you navigate your own Halftime.

Reflection and the Learning Curve

Halftime is a time for reflection. It is a midlife pause when you take the time to look back, take stock of who you are and what matters, then look ahead to dream and reinvent yourself. It’s important to take a Halftime break because when you follow your first-half dream too long and too hard, it always turns over on itself.

Perhaps the thrill of the deal is gone. Or maybe a close friend dies at your age, and you wonder how much time you have left. Your last child may leave for college, making you realize that you have your whole like in front of you. And some people sell their company and lose their identity, only to cling to it later on as they use who they used to be to define who they are today.

Halftime is the realization that you can put your passions and skills to work and reinvent yourself – to create a vision for the second half of your life, a clear sense of what your purpose or mission is.

That said, there is a learning curve that must be tackled. You must learn new things and form a new identity. You have been rewarded for working at a feverish pace, and now you must detox, step back, and reflect. You may be used to managing your own team and company, but in Halftime you have to learn how to manage yourself and your own life.

Because of the learning curve, it’s best to start thinking about your second half before your exit:

  • What do you really care about?
  • What kind of difference do you want to make in your life? In the world?

If you can take the experience and wisdom that you have gained in your first half and combine it with what you care most about, you can create a beautiful, captivating second half, which may or may not involve selling your company.

Common Halftime Mistakes

In the hundreds of people I have mentored, I have noticed a number of common mistakes that people make during Halftime. Understanding these missteps will help you avoid them when you’re planning your own second half.

1 – No Long Term Metrics

Even the most seasoned executive very often has no long-term metrics for their second half. They don’t know what their goals are and what they want to achieve during the second part of life. It is important that you have a plan and that it is measurable.

2 – Jumping Too Quickly

Many don’t take adequate time to define their purpose and mission statement. They find multiple opportunities coming to them; they just start saying “yes” to everything, and they end up getting “sloppy busy.” Don’t jump to a solution right away. Take time to think about who you are, what you are about, and what you would do the rest of your life even if you were not paid for it. Find the thing that will bring you joy and money will follow.

3 – Going Alone

Others decide to go on the journey alone, but you should align yourself with those around you, for example, your spouse and your children. Creating a plan for what you will do with your life requires you and your spouse to dream separately and then plan together.

4 – Not Detoxing After the Sale

After the sale (or ideally before the sale) you should go through a detox period where you contemplate the future. Many people start the second half of their life on the wrong foot because they did not take the time to reflect and then determine their next steps. Think of it like an Olympic swimmer approaching the wall. After the turn, they take a moment to glide and calculate where their next stroke will be.

Two Important Elements of Halftime

If you are thinking about reinventing yourself after the first half of your life (whether you are selling your business or just transitioning to a new role), there are two essential things you need.

1 – A Process

The process I encourage my mentees to use is “Get clear, get free, get going.” Start out by getting clear about who you are. Think about your passions and strengths then create a clear and measurable mission statement for the second half of your life. Next, look at your time and money and decide what you are doing now that is low value and that can be cut out. This will free up your time and money so you can start listening to your heart and people around you. Finally, get going by trying things out. Explore your options to find what suits you best.

2 – Case Studies

If you isolate yourself and try to think through Halftime on your own, you will miss the perspective that peers and coaches can bring. Often times they can see your strengths and see opportunities that you might have missed. At the Symposium I shared several case studies, including:

  • Clark Millspaugh – A Tulsa oil and gas businessman who, after a trip to South Africa, realized he wanted to help the less fortunate. He came back to Tulsa, sold his company and created a nonprofit grocery store and many educational programs. He died of cancer five years later, but with a vision and focus, he was able to enjoy a meaningful second half.
  • Tana Greene – Tana had gotten pregnant at 16 and was then abused by her husband. When she broke free, she swore that she would own a home by 26 and own her own business by 30. She built her business then used the second half of her life to help those involved in domestic violence. She is currently a chairwoman at a domestic violence center and has written a book about her experience.
  • Kenneth Young – Kenneth was a 57-year-old owner of a tea company. In his Halftime reflections, he identified his passions – photography and orphans in China. Instead of selling his company, he hired a COO and moved into a chairman role. He went to China to capture compelling photographs of disabled orphans, put them on the back of the company’s tea boxes, and drove people to a non-profit website where they could donate to the cause. He ended up winning the nonprofit of the year award in China


Each one of these people got clear on who they are and what they care about. They built long-term metrics into their life before launching their second half. Their stories can help disrupt your mental model so you can think about your own second half in a different light.

The second half of your life – after the sale of your company – could be the best season of your life. Take time for reflection during Halftime so you can reinvent yourself and add more purpose and meaning to your life in the second half.