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Imagine that your job of almost twenty years comes to an abrupt end. A job that at 61 you still enjoyed and continued to be very good at. Imagine further that your finances are such that retirement is an option. This is the situation that Mary Helen Conroy found herself in less than three years ago.

The course of action she landed on showed a remarkable amount of foresight and led to a pretty amazing journey that continues to unfold.

  • Mary Helen didn’t need to test the water to recognize that at 61 her chances of finding another comparable job were slim to none.
  • She had enough self knowledge to recognize that the concept of slowing down and transitioning to a traditional retirement was not for her.
  • She sincerely believed that she still had much to offer the world. She had always loved both learning and creating and felt compelled to test who she was at 61.

So after recently joining the ranks of the unemployed Mary Helen launched not one but two start-ups in January of 2014. Life’s A Daring Adventure: Personal Life Coach for Midlife and Retirement and Virtual Retirement Parties: A retirement party where the world can come…without the mess. If that wasn’t enough in October 2015 she co-founded Retiree Rebels, an audio blog/podcasting company that inspires the the nearly and newly retired to live the bonus years as the best years.

Life is either a daring adventure or nothing at all. – Helen Keller

I asked Mary Helen how, with no previous entrepreneurial experience, did she have the courage to launch three start-ups at 60+. She said that throughout her career she had always been an administrator so she had always run what she had done. So she didn’t view going the start-up route as such a large leap. Just as importantly she believed that she had a message that the world needed to hear.

So what are the lessons learned that Mary Helen would like to share with aspiring 50+ entrepreneurs.

  1. You are never too old. It is never too late to launch a next chapter. One of the great benefits about launching your own venture at 50+ is that there is no ageism when you are the boss.
  2. Know what it is that you are not done doing. Wayne Dyer famously said “Don’t die with your music still in you.”  The benefits of a purpose driven retirement years are evident. Think long and hard about your purpose in your 50’s and beyond.
  3. Be open to the unexpected. Mary Helen would never have imagined that she would become a podcaster. Retiree Rebel has quickly become her primary area of focus. She is also co-author of the forthcoming book – The Amazing Itty Bitty for the Nearly and Newly Retired (October 2016).
  4. It almost always takes longer to scale your business than initially anticipated. This is a common theme among most of the 50+ entrepreneurs that I have spoken to. Success requires a lot of hard work and almost always takes longer than anticipated. With that said chasing your own dream makes that journey and hard work so much more rewarding.
  5. Mary Helen’s 50 cups of coffee challenge. Mary knew that in order to scale her new business she needed to challenge herself to get out of her comfort zone. It was critical that she regularly network and meet new people. Her solution was to target to meet someone new for coffee every week of the year.

Business owner, public speaker, blogger, podcaster, soon to be published author, excuse-buster extraordinaire, all accomplished in her seventh decade. Mary Helen Conroy is fast becoming a role model to those of us who still believe that our best years are ahead of us.


As President of Your Future Reimagined (YFR) Coaching and Consulting, I help professionals/executives successfully transition to enjoyable and enriching Next Chapters. Please contact me to book one-on-one coaching, workshop and keynote speaking engagements.

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