Selling a Business and Designing a New Life: 10 Questions to Your Best Future

Marian Cook

February 16, 2010

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This is the second in a series of articles dedicated to the successful woman entrepreneur who, through her hard work and sharp wits, has successfully grown her enterprise to the point that it is salable. Selling a business, just like starting one, does require a thoughtful plan.

Just as you wrote a business plan when you started your business, you should draft an exit plan or exit strategy before selling it. Starting with the end in mind, you should thoughtfully design your future and direct the sale of your business to make that future a reality. Many owners aren’t willing to put their skills, relationships, and experience out to pasture in a traditional retirement after selling their business. As studies show and your already know, remaining active and engaged in purposeful ways serves to keep the brain and body vibrant and fit.

Developing an inspiring vision of the future requires you to tackle compelling questions such as those listed below. As you go through them, keep in mind these words from Mark Twain:

"Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."

And the discovery process starts by asking yourself questions such as:
  1. What does success mean to me now? What is most important to me in life? What values are important to me?
  2. How can I define my future life in accord with how I now define success and my values?
  3. What do I want my future life to look like"both day-to-day, and longer term? What changes must I make to achieve this?
  4. What have I enjoyed about my work and life and what do I want to continue with, and what to eliminate or disengage from?
  5. What other business ventures, ideas and work hold appeal to me? Can I begin to explore those now?
  6. How have my priorities changed over time, and what"and who"is important to me now?
  7. How can I best serve and enjoy my family? What activities do I want to share with them?
  8. What would I like to learn? Do? Where would I like to go? What dreams have been deferred to attend to my business? Is now the time to reignite them?
  9. What have I put off that needs my attention now? What needs less of my attention? What should I say “Yes” to, and what should I say “No” to?
  10. How do I want to be remembered and my life celebrated?
Keeping answers to these questions in mind, you should remember there are many paths to nirvana. Your path may be to stay on with your company, leave quickly, or remain in a role you and the buyer design. Once gone from the business, you can enter another, or perhaps you can move into a meaningful nonprofit role, choosing contribution over income. Another choice can be retirement to a life of leisure, which nonetheless you need to think through to decide how your time will be spent. Perhaps you should set aside time to decide the next option. Taking a break to rest, reset, and explore alternatives before defining the next chapter of your life can be very attractive.

Looking at your answers, sketch out at a high level the money needed to make these things happen. This becomes part of your financial requirements for life after the sale. If you choose a role inside your company or out where you will be making money through work or business-related income such as real estate, approximate what that inflow will be.

You are starting to breathe life into not just what your future life will look like, but how much money you will have to support it. Be conservative, and remember that you may need to invest more in your company to get the payout you want. When you consider when and how to sell a business, your eyes should be firmly set on the life you want after the sale is done.

I invite you to use these ideas to create your best-life business exit strategy.


Business transition expert, author of Selling Your Business For More: Maximizing Returns For You, Your Family and Your Business (Macmillan) and speaker Marian Cook, has helped hundreds of businesses to build value, ready for sale, and transition the business owner to new, productive lives. You can can connect with her at her blog: www.businesstransitionexperts.com/blog

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