Lots of us will want to continue to work after 50, whether we’re retired or not, and for a variety of personal, professional and financial reasons.  We may work part time for our old employer, take a full-time job with a new one, or become self-employed.

Entrepreneurs make up a special subset of the self-employed.  They’re different from normal self-employment businesses, such as piano instruction or a dry cleaning operation, because entrepreneurs:

  • Bring something new into the marketplace: a product, service or way of doing business
  • Possibly introduce disruption into the industry and marketplace
  • Face higher than usual risk
  • Enjoy higher than usual possibility of great return
  • Place both reputation and money on the line; it’s the ultimate example of having your own skin in the game.

SNN Sarasota News Network and I have been featuring keys to entrepreneurial success during my weekly television appearances.  These keys are particularly important because entrepreneurship, while attractive on the surface, can be (and usually is) a supremely complex and emotional combination of invention, improvisation,  intuition and moxie.  It requires honoring your past experience without  being defined or limited by it.  The more you know before you commit to entrepreneurship, the better––no matter how previously successful you may have been with other business ventures, entrepreneurial or not.


  1. Purpose. Why is the entrepreneur choosing this route? What needs does it meet? What is it that the entrepreneur needs from the experience?
  2. Energy. Being an entrepreneur can be incredibly time-intensive, especially during the startup phase. Does the entrepreneur have both the energy and the freedom from other obligations to take this path successfully?
  3. Aptitude. Does the entrepreneur have the necessary skills and leadership qualities to run his or her own business? Entrepreneurs may need to act as CEO, accountant, social media expert, marketing maven, legal eagle, strategic sourcer, senior engineer and HR specialist in rotation within just a few hours’ time.
  4. Interest and Expertise. How interested is the entrepreneur in running the actual business, willing to make really tough, important decisions quickly? Does the entrepreneur have the expertise to run the business? For those functions which are not part of the entrepreneur’s interest and expertise set, is there funding for inside or outside staff to take up the slack?
  5. Network of Business and Professional Connections. Does the entrepreneur have the professional and personal networks to tap as needs arise? Can the entrepreneur’s network open doors, find resources and answers, and create opportunities when the entrepreneur’s own group of contacts is lacking in some aspect?
  6. Discipline and Tenacity. Is this venture a lark or a hobby, or is it a wholehearted commitment? Does the entrepreneur have both the professional discipline and tenacity to start it and stick with it throughout the ride?
  7. Planning. How good is the entrepreneur at planning? How good is the he or she at adapting rapidly and thoughtfully? If you can name one entrepreneurial venture for which everything occurred according to plan without any surprises and changes, please let George know.
  8. Financing. How much of the entrepreneur’s own money will be invested? What will happen to his or her personal finances if the venture fails—or takes much longer than expected to become profitable? How much other funding will be needed, and are the sources and commitments secured? This may not only include startup capital but operating funding for some period of time.
  9. Raison d’Etre. What is it that the entrepreneur is really offering in the marketplace? Is it primarily the product/service itself or is it the benefits to the buyer from owning or using it? What will create the market and sustain it in the long run?
  10. Understanding the Market Itself. What is happening in the marketplace now, and where is it heading? Who, if any, are the competitors? How can the entrepreneur get ahead of the market or, even better, redirect it towards his company and its offerings?
  11. Profitability and ROI. How much profit does the entrepreneur expect to make in the first and ensuing years? Will it be enough to lure and satisfy investors? How about the return on investment? Will the entrepreneur and the business be able to prove they are the ultimately great investment of others’ monies?
  12. Exit Strategy. Starting an entrepreneurial business is NOT like getting married forever. The entrepreneur changes. So does the business and the market. The entrepreneur should always have an intelligent, workable exit strategy on the back burner.

My suggestion: Consider each of these keys, and take your time answering all the questions. Then discuss the questions and answers with people who know you well, perhaps who have worked with you, and/or have gone through the entrepreneurial experience themselves. You may be surprised at what a great series of conversations this can trigger. And the insights you gain will help inform your decision to go for it or take a pass . . . for now.

Whatever you decide, good luck!

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