What Business Owners Can Learn from the Retirement of 3 TV Personalities

June 6, 2015

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We find frequently that business owners who are looking to transfer out of their businesses focus a lot on the financial aspects of the process. However, as we’ve often discussed, there are a number of non-financial aspects of a business transition that need attention, as well. The non-financial issues are equally important and, if not addressed, can leave owners feeling irrelevant.

The potential lack of identity that some owners may feel outside the business can cause feelings of emptiness and regret, which is the last thing that should happen after spending your life building a successful career and business. A recent article from Next Avenue, “Top 10 List: Lessons From Letterman’s Retirement,” holds some great lessons for business owners who are transferring out of their businesses.

The article got us thinking about the differences between the post-retirement plans of various TV personalities and some of the examples they can provide for exiting business owners. Let’s take a look at some of the unique ways that these individuals have approached their post-retirement lives.

Jay Leno – While Jay Leno’s exit from The Tonight Show was fraught with challenges, rumors, and negative feelings, once all was said and done, he had a plan for the foreseeable future – continuing to do stand-up comedy. Since leaving the show, he is doing more than 200 shows a year on the road. He also is extremely passionate about cars of all kinds and has an online presence through Jay Leno’s Garage.


  • Keep doing what you love in a modified way.
  • Sometimes you can finish by going back to the beginning.
  • Be mindful of your work/life balance.

Bob Schieffer – After 46 years, Schieffer is retiring from CBS News. He has tried to retire a number of times over the last decade, yet continued working. Apparently, CBS had been reluctant to let him leave over the years because succession plans were unclear, until recently. Following his departure, Face the Nation will be hosted by John Dickerson. And, by all accounts, Schieffer has built and is leaving Dickerson with a strong platform – ratings are at an all-time high. In a recent interview, Schieffer said his decision to leave now is partly due to the fact that he wants to allow his successor, Dickerson, the time and space to gear up for the upcoming presidential season.

While he has not announced his future plans, Schieffer says the only thing he’s not doing is Dancing with the Stars (because his wife won’t let him).


  • Understand that the best laid retirement plans may be altered due to unforeseeable circumstances.
  • Don’t stay too long – leave on a high note when things are going well.
  • Be ready to let go of the reins when it’s time for your successor to take over.
  • Make sure you heed the advice of your spouse when planning for the future!

David Letterman – Following a 33-year career, Letterman signed off for the last time as a talk-show host. While he publicly announced his planned retirement a year ago, it’s probably something that he has been planning for some time. Even with the significant time and planning for his transition out, it was obviously an emotional and difficult time for him. This was especially evident in the weeks leading up to his last show. And, despite the ups and downs, scandals, and challenges, he has been extremely gracious and generous by thanking those who enabled his success as a television personality.


  • Give yourself sufficient time and space to plan and adjust to your transition out of your business.
  • Acknowledge those who helped you throughout your career and in your business.
  • Understand that, even with time and planning, the transition is most likely going to be an emotional one. It may take you some time to really figure out what you want to do.

Of course from a financial perspective, these folks don’t need to worry; yet they too struggle with their personal transition. It’s not just about the money. They are great examples of how business owners can handle the non-financial aspects of retirement. Business owners who are planning for their post-retirement should ponder these questions:

  • What are your personal post-transition plans?
  • What do you really want to accomplish with this transition?
  • How will each transition option impact and affect employees, family (those involved and not involved in the business), customers, community, and your legacy?
  • What matters most to you?

These questions can only be answered by you and it takes time to figure it all out. With the proper planning, your next phase of life can be what you hope and envision — excitement and the fulfillment of lifelong dreams and goals!

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