After building a business, selling it, and “retiring,” I am among those who say, “I’m so busy I don’t know how I ever had the time to work!” It seems to be a common feeling for today’s retirees. I learned this especially in researching small business owners for my book Exit Signs. There’s a big difference between what Boomers and their parents looked for in their “golden years.” Today, we see many choices in the road ahead.

Only 14 percent of those looking ahead to retirement see it as a time to “take a well-deserved rest.” An estimated 31 million Americans age 44 to 70 are interested in “pursuits that enable individuals to put their passion to work for the greater good.” When asked about their ideal retirement work arrangement, the most common choices were to:

  • Repeatedly “cycle” between periods of work and leisure (42%)
  • Have part-time work (16%)
  • Start a business (13%)
  • Work full time (6%)

The Book We All Need

Seems we need a book for the millions of experienced, wise, energized Boomers (15 million of whom own businesses) thinking about starting a new venture. Maybe it’s called Encore Start-Ups for Boomers.

Like Exit Signs, it would go beyond the transactional advice about financing, branding, and legal entity choices. This new book would pose the strategic questions that when overlooked give us headaches later. Here are the major chapters of my imaginary Encore Start-Ups for Boomers.

Each chapter would address a question at the heart of the motivation and tenacity needed to start and sustain an entrepreneurial dream, whether it is a for-profit business or not-for-profit organization.

Chapter 1: Am I Crazy to Consider an Encore Start-Up? No, it’s not a sanity question. It’s a motivation question. What’s the need IN ME I am trying to meet? Is it building and innovating, making a difference in this world, maybe running something bigger than yourself? If your reason to launch an Encore Start-Up is to recreate the past, hit pause. What is it about the past that feels unfinished, or what is the feeling you want to recapture? Can you find another path to experience that feeling or complete what’s unfinished that doesn’t involve ditto marks?

Chapter 2: What Counts? What is the purpose of your encore venture? Are you building equity to fund an estate? Is your goal to leave a business for others to carry on, or more simply create a nice income for the next X years? Or is your measure of success about a higher purpose you’ve yet to achieve? These end-games are all valid. It’s a question of what counts to you as you enter the game.

Chapter 3: Who Gets To Play? Is this a solo endeavor or a team effort? Are you willing to let others work as true partners? If so, what values and end-game goals must others share with you? You will hire, develop, and work with others differently depending on how you answer these questions AND those in Chapter 2.

Chapter 4: What’s Big Enough? If you type “grow your business” into a search engine, you will get 53 million results. In Exit Signs I ask “How Big?” because growth is the seductress in start-ups and endings.

Whether a solo encorist or a partner in one, the answer to “How Big?” is a volatile one if it isn’t decided early and revisited frequently. It’s a question with three parts: the hook, the hazard, and hindsight.

  • The Hook: ask yourself what hooks you about size and growth? Bragging rights? Impact? Security?
  • The Hazard: ask yourself what, if any, are the repercussions of Big Growth on health, relationships, other long-unfulfilled dreams?
  • Hindsight: ask yourself what you know about yourself when growth and size were part of your previous work or business? What was its impact on you, your family, and your colleagues?

Chapter 5: What Does “That’s All Folks!” Look Like? Having a sense of our own mortality tends to guide the definition of milestones and timelines. It can also cause anxiety and fear about “is that all there is?” So write down the milestones or timelines that define when “The End” is as you begin your encore venture. What end-game will let you say, as Dr. Seuss wrote, “Don’t cry because it’s over; smile because it happened”?

Endings and Beginnings Are Exciting Times

Depositphotostypewriter bwBoomers have redefined “retirement” with aspirations for continuing activity, contribution, and satisfaction. The options for encore careers, start-ups, and endeavors are ours to decide. Whatever your choice, take the time to ask yourself what drives your imagination; what excites you; what needs must be met? What’s the title of your next chapter?

Are there other chapters and questions you would add to my imaginary book, Encore Start-Ups?