3 Must Do’s When Reinventing Your Career


There is a prevailing sentiment that once past 40 you’re too old to reinvent your career. The transition is too risky. You have too many responsibilities and you may put your reputation in jeopardy. Taking chances are for the young. Besides, reinventing means starting over. And starting over is daunting.

I definitely don’t believe that to be true. You should not confuse reinvention with starting over. Case in point, Phyllis Diller who recently passed away at the age of 95. She had a career writing advertising copy for a radio station. At the age of 40 with a brood of five kids, she wrote her last copy line and turned to comedy. She reinvented her career while raising her family and being the primary breadwinner. She didn’t know exactly how she was going to do it. There was no road map to follow but it was full steam ahead. And by all accounts she never looked back. It was a risky time for a female comedian to be out on the circuit doing a solo act. All the others were part of a male/female act, most famous at the time, Gracie Allen playing dumb to George Burns.

Not only did she burst onto the scene at the age of 40, her comedic career spanned over 50 years performing into her 90’s. So, what can we learn from Phyllis Diller. Here are few pointers on how to reinvent your career:

  • Leverage your strengths: As an advertising writer she was adept at creating humorous headlines. At the same time, she was cultivating a local audience that marveled in her humorous stories. She turned her focus to crafting and delivering rapid-fire one-liners. This served as the centerpiece of her act.
  • Make it your own: She created a unique persona around being the anti- housewife, wearing wacky outfits and bellowing her trademark laugh.
  • Gather support: She had the support of her husband as well as a cadre of other like-minded comedians breaking through at that time.

Think of what we would have missed if she had thought she was too old to reinvent her career. Make no mistake reinventing your career is hard work. Phyllis Diller is fond of saying that she ordered a bucket of guts every morning. But you could tell that she loved what she was doing.

I end this with a quote that was given to me 30 years ago and has been visible in my life ever since.

“To be what we are, and to become what we are capable of becoming, is the only end of life.” – Robert Louis Stevenson