26 Questions to Help You Decide If a Late-in-Life Business Is Right for You

Instead of just asking "Why me?" ask yourself these questions to determine if becoming an entrepreneur after you retire from your job is a smart move for you.

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By Rick Terrien

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The following excerpt is from Rick Terrien's Ageless Startup. Buy it now from Amazon | Barnes & Noble | IndieBound

How do you know if starting a business is the right path for you? And how do you know when the time is right to lay the groundwork for the next chapter of your work life? If your answer is that you'll figure it out when you get there, then you'd better start figuring it out soon. Creating new income streams with a new enterprise is entirely possible, but it takes time and resources. It's always best to start small, start slow and start smart—with some self-assessment.

When you ask yourself some simple questions about where you'll be working at 60 or 65, don't see work as a burden to live through. See it as a path to liberation in the later years of your life. Ask yourself:

  • Do you understand that staying active and engaged is better for your health and longevity?
  • Can you afford to invest a small amount of money to launch a new enterprise?
  • Can you invest the time needed to plan, launch and grow a small enterprise?
  • Can you work through adversity?

Start asking yourself questions like these now so you can get ready for a future that is bright with opportunity and resilience. Sure, it can be scary, but it's much scarier to have no answer the question "Where will you be working when you're 60 or 65?"

Read on to discover some of the most common questions people ask when they're considering a new business adventure later in life. They'll help you take stock of your own situation so you can make those first moves toward starting a business.


Why is an ageless startup right for you? When you consider your options, you'll likely see that the question perhaps shouldn't be "Why me?" but rather "Why not me?" Consider this:

  • You have skills and knowledge that have taken most of a lifetime to accumulate.
  • You have the time to build a new career slowly and thoughtfully that can reflect the values you want to leave for those who follow.
  • You have networks of friends, colleagues and connections and that are unique in history.
  • You have the passion to make a difference and time enough on the planet to not care what others think about you.

Why should you start a life of entrepreneurship at this point in the game? Your entrepreneurship self-assessment should be focused on how you want to conduct the rest your life. When you ask yourself, "Why me?" and wonder if an entrepreneurial this path is right for you, here are a few questions to guide that inquiry:

  • What goals do you have for your new enterprise?
  • What parts of your life would you like your startup to enhance?
  • What parts of your life would you like to keep separate from your startup?
  • How much money can you invest to launch your startup? Make sure this is money you can afford to live your life without.
  • What in your personality is most professionally important to others?
  • Are there other areas of your personality that you don't want to expose to your customers?
  • What milestones in your work life can you highlight as important to your startup?
  • Are you willing to share your workload with other professionals (accounting, tax, etc.), or do you need to do it all?
  • Are you good at meeting new people?
  • Are you good at listening?
  • Are you good at empathizing with people describing their problems?
  • Do you have the personality that can see problems as opportunities?
  • Can you refine your passion or mission into a single compelling sentence or two?
  • Can you describe who the customers for your future enterprise will be?
  • What problems will you solve for your target consumer?
  • Can you motivate yourself and work independently?
  • Are you comfortable asking for help?
  • Are you willing to work outside traditional work hours?
  • Can you learn to meet new people and insert yourself into new situations?
  • Are you comfortable using social media, even at an entry level?
  • Can you admit you don't know something when appropriate?
  • Can you learn from mistakes and failure and accept outcomes that aren't perfect?
  • Can you say no to people and projects that don't fit your business model?
  • Can you work in business with people you may disagree with per­sonally?
  • Can you be satisfied with not being recognized as the smartest per­son in the room?
  • Can you work in ambiguous situations, in which no clear outcome is initially visible?

Take some time to journal your answers to these questions or create a working document that you can return to later and review your answers. You'll likely find that the question of "Why me?" is a multifaceted one that touches on several areas of your entrepreneurial spirit, reality and worldview.

Older entrepreneurs can create significant value for themselves and their communities by focusing on the life skills and traits that got them here: common sense, tenacity and a strong ethic of helping. You can apply your extensive knowledge of what doesn't work to bypass entrepreneurial roadblocks. You have the time and resiliency to launch new businesses that may be slow to grow but rich in benefits. You don't need immediate returns as many investor-backed startups led by younger thrill-seekers do. You possess the self-discipline needed to see tasks through to fruition. By this time in your life, you've likely figured out what you're truly passionate about and can build new enterprises to serve those goals.

Rick Terrien


I am a lifelong entrepreneur with a focus on sustainability. My own business launches that have exceeded 40 years, 20 years, 10 years and five years. I was awarded U.S. Small Business New Product of the Year, as well as Fast Company's Fast 50 (now The World's 50 Most Innovative Companies).

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