Managing the New Midlife

In 2015, The Kauffman Foundation reported that 26% of new entrepreneurs were ages 55 to 64.  Forbes predicts by 2020, 50% of businesses will be freelance and, with 10,000 Americans turning 50 every day and another 10,000 turning 65, the number of second acts will continue to rise.  Exciting, right?  Are you one of the 26% (or more) who are over 50 and eager to start a business?  Do you feel stagnant and are drawn to something new?  Or are you working on a project that is nudging you toward entrepreneurship?

Curious?  Read on!  The following information may help you to make a more informed decision.

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Early Phase:  Hints of a Second Act

You have the potential to become a second-act entrepreneur if:

  • You are getting restless—your everyday routine no longer motivates you.
  • You are tired of playing by the rules.
  • A major life change (e.g., job loss, divorce, health issues, or hitting a decade mark) has you itching to START OVER.
  • You’ve reviewed your first 50 years and aren’t where you thought you’d be.
  • You dream about turning your passion into a business.
  • You regularly think about how to use knowledge, skills, and experience to generate income ON YOUR OWN!
  • You are reading extensively about how to start a small business.
  • You are actively considering ways to fund your own business. 

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Mid-Phase:  Let the Risks Begin

You’ll know you’re well on the road to becoming a second-act entrepreneur when:

  • You quit a 60-hour/week job working for someone else to work 80+ hours for yourself—and you are much happier.
  • You give up retirement to build a business.
  • Or, you postpone retirement because your business idea really excites you!
  • Some friends and family think you are having a midlife crisis; others support and encourage you.
  • Your loved ones are concerned you are working too hard.
  • You dream (or have nightmares) about how to fund your business.
  • Your adult children ask you a minimum of two weeks in advance if you are available.
  • You forget it’s a holiday, your birthday, anniversary, or the weekend.
  • Your houseplants die, wither, or are covered in dust.
  • Your pets remind you when it’s time to eat.
  • During one-on-one networking meetings, your tummy grumbles loudly enough that your new connection offers to buy you a snack.
  • You find yourself drinking coffee at 1 am because your work isn’t done yet.
  • Your first paying client motivates you more than your first paycheck way back when.

Photo Credit: Rawpixel

DEEP into the Second Act:  The No-Turning Back Phase

You’ve arrived! You’re definitely a second-act entrepreneur if:

  • You go through withdrawal at just the thought of disconnecting from your devices for a day or more.
  • You take time off and you don’t know what to do with yourself.
  • You dream about how to grow your business.
  • Your lawn is officially recognized as a wildlife refuge area.
  • You keep water soluble pens in the shower to write new business development ideas on the shower wall.
  • You realize you are more content than ever and you are NOT DONE YET!


Are you still considering the possibility of becoming a second-act entrepreneur having read this column?  If yes, what attracts you most about the idea of entrepreneurship?  What scares you the most about pursuing such a dream?

Note:   I didn’t put timelines on any of these phases.  They can start at any time and can move us forward quickly, or they can sit and stew for years.

Advice:  Don’t let the idea sit and stew!  Age is no longer a limiting factor.  Once you turn 50, life makes more sense and you discover that you have something better to offer the world.  Whatever decade of life you are in, NOW is the time to reveal your second-act super powers!

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  1. Chris Burton on July 13, 2018 at 1:51 pm

    This article really resonates with me on many levels! I am well into the dreaming stage of becoming a Second-Act Entrepreneur—there really is so much to look forward to when we begin seeking new ways to express ourselves and connect to other like-minded people.

  2. Deb Gaut on July 13, 2018 at 2:19 pm

    So true, Chris! As you dream of what your second act will be like, take the actions necessary to make it real. Connect with those pursuing their own second acts, seek out the experts and mentors who can help you achieve your dream, and keep moving forward. It’s a fulfilling, worthwhile journey!