For most entrepreneurs, their current business is not where they intend to stay until they die. At the right time, they all intend to make a graceful exit, and leave while still perceived to be on top of their game. The challenge is how to know and exit gracefully when the right time has come, without trauma to either the company or themselves.

I don’t have any solid insight on this subject, so I was intrigued by the classic book “Leaving on Top: Graceful Exits for Leaders,” by David Heenan, a business executive and Georgetown professor. He did some good research on 20 top leaders, and why some leaders ‘get out while they’re on top’ while others ‘overstay their welcome.’

First of all, both Heenan and I agree that most exiting business leaders can be categorized into one of four major groups:

• Timeless wonders. With their skills very much intact, these white-haired prodigies have no need to call it quits. Warren Buffett and Rupert Murdoch clearly fall into this category.
• Aging despots. Reluctant to leave the spotlight, they are past their prime and should turn the reins over to a new generation. We won’t mention any names here, but we al-l know a couple of these.
• Comeback kids. Whether to return their enterprises to their former glory, or simply save themselves from boredom, these leaders left their company, but then returned with a vengeance. Steve Jobs and Howard Schultz are a couple that come to mind.
• Graceful exiters. Quitting while ahead, these leave a sterling reputation as they move on. Bill Gates and Oprah Winfrey are business examples in this category.

After many stories of leaders in all these categories, he offers some good tips on how to get counted in the category you prefer:

1. Know thyself. What matters most to you? Fame? Fortune? Family? Friends? Helping others? Listen to your heart. Look at yourself as objectively as possible and analyze what’s truly important. Be open and responsive to the inputs of others.

2. Know thy situation. When everything is clicking, it’s easy to overstay your welcome. Staying power is elusive at best. Know where you stand, and don’t wait for the annual review. Move on before someone else decides to move you on.

3. Take risks. Don’t shackle yourself to the past. Accept change as a natural part of your transition, just as you always have for your company. Strike out anew while you are still hardy enough to face new challenges. Push your comfort zone.

4. Keep good company. Stay connected. Cast a wide net, including people inside and outside your fields of interest. Ignore the naysayers. Keep the company of sunny characters, those with an upbeat disposition. Avoid humorless people.

5. Check your ego at the door. While we still treat some personalities like royalty, a new view of leadership is beginning to see them more as stewards than kings. In addition to muffling hubris, graceful exiters functions as talent spotters, so everyone wins.

6. Keep learning. Graceful exiters remain curious. They are intellectually interested, alert, and adaptable. They read, explore new places, and engage their senses. The more diverse your experiences, the better the prospects for forging a new chapter in your life.

7. Stage your exit. The transition to what’s next may take a while. Back into it. Live life incrementally. Break your departure into manageable steps. Take things bit by bit. By carefully staging your departure, you’ll build confidence for your new life.

8. Know when to walk away. Many give up everything to stay in the saddle. As their legacy erodes, they fail to prepare for the next season of their lives. However brilliant they may once have been, their unbridled egos cost them soul and substance.

9. Know when to stay put. If you are happy and productive, stick with your day job – the one you love. Give it your all. Remain passionate about it. Not everyone has to pack it in. A long, healthy, and productive life awaits those people who prepare for it.

10. Start now! Life’s prolonged course offers everyone the opportunity to chart new horizons. But you need to set your priorities early and put the building blocks in place to achieve them. Don’t dillydally or let procrastination steal your dreams.

Leaving on top, and exiting gracefully, begins with recognizing that a job, like a life stage or a relationship, has peaked. After that, I’m reminded of the old quote by John Richardson "When it comes to the future, there are three kinds of people: those who let it happen, those who make it happen, and those who wonder what happened." Which category will you fall into?

Marty Zwilling

https://blog.startupprofessionals.com/2021/03/how-to-know-its-time-to-exit-your.html