Smart Entrepreneurs Don’t Overstay Their Welcome


startup exit

For most entrepreneurs their current business is not where they intend to stay indefinitely. At the right time they typically intend to make a graceful exit and leave while still perceived to be on top of their game. The challenge is how to know when and how to exit gracefully, avoiding trauma to either the company or themselves.

In his recent 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.

Heenan categorizes these leaders in 4 groups:

  • Timeless wonders. With their skills very much intact, these white-haired prodigies have no need to call it quits. Examples include Warren Buffett and Rupert Murdoch.
  • Aging despots. Reluctant to leave the spotlight, they are past their prime and should turn the reins over to a new generation.
  • Comeback kids. Whether to return their enterprises to their former glory or simply save themselves from boredom, these departed leaders have returned with a vengeance. Steve Jobs and Howard Schultz are two primary examples.
  • 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 and 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 and live life incrementally. Break your departure into manageable steps. Take things bit by bit so that 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, an unbridled ego can cost 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 and 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?

Reprinted with permission.

Image credit: CC by Maxime Guilbot

About the author: Martin Zwilling

Martin is the CEO & Founder of Startup Professionals, Inc., a consultancy focused on assisting entrepreneurs with mentoring, business strategy and planning, and networking.

Martin for years has provided entrepreneurs with first-hand advice, mentoring and business plan assistance as a startup consultant. He has a unique combination of business and high-tech experience, and executive mentoring and connecting startups with potential investors, board members, and service providers.

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