101 Questions to Help Business Owners Determine What to Do After Exit

By: Patrick Ungashick


Figuring out what you want to do after you exit from your company is a crucial step to exiting successfully and happily.

Many business owners have heard stories or know another owner first-hand who exited only to realize he or she was bored, frustrated, and regretted the decision to leave behind the daily challenges and sense of purpose that comes with owning and leading a company.

It will not matter how much money you have in the bank after you exit if you wake up every day lacking something meaningful and relevant to do with your time and talent.

Yet too many owners do not know what they are going to do after exit. Or, just as dangerously, some owners assume they know but have not tested their assumption by trying the activity in real life for any meaningful period of time.

Have a Clear Vision for Your Exit

Before you exit, you should have a clear vision for what you are going to do next and should verify that plan by actually trying the activity or endeavor. Once you exit, you cannot go back.

The following list of 101 brainstorming questions will help owners research and reflect on what to do with their time and talent after exiting from their business. Go through the questions, either on your own or with your spouse or a trusted advisor. (Spouses may consider answering selected questions as a couple, if helpful.)

Answer only those questions that prove helpful. Write down your answers and keep them for reference. Consider doing this exercise several times as exit draws near because your answers may evolve

  1. What did I want to be when growing up?
  2. What drives me?
  3. Do I live exactly where I want to live?
  4. Is there a cause in which I would like to be involved? What about that cause interests me?
  5. What would I change most about my community?
  6. Do I have dreams that I have not yet accomplished?
  7. Do I spend my time and talent doing what I most want to do?
  8. What do I want more of in life?
  9. What do I want less of in life?
  10. Over the next five years, what do I really want to do?
  11. Who is the happiest person I know? What makes him or her so happy?
  12. What is my personal mission?
  13. What would I attempt if I knew that I would not fail?
  14. Who are three people in my life who could help me achieve my dreams and goals?
  15. What are the things I have most wanted to do during the last five years but have not yet done?
  16. What are my greatest talents?
  17. What have I always wanted to be great at? If I am not there yet, what has stopped me?
  18. What are the important lessons I learned in business?
  19. Over the last five years, what have I wanted to change about my business and my role in it?
  20. What activities make me lose track of time?
  21. What makes me feel great about myself?
  22. What are my core values?
  23. What do other people often ask me to help them with?
  24. If I had to teach something, what would it be?
  25. What are some of the biggest challenges I have overcome in life? In my business?
  26. If I could share a message with a large group of people, who would they be? What would I say?
  27. What are the important lessons I learned in business? List them.
  28. What adjectives would people who know me use to describe me?
  29. What am I known for?
  30. What activities do I enjoy so much that I never tire of them?
  31. What would I have done differently in my career?
  32. If I could test drive three different jobs, what would they be?
  33. What important lessons about myself have I learned from my failures and mistakes?
  34. Is there anything in my life that feels unfinished?
  35. What sayings, quotes, or mottos do I often turn to for guidance?
  36. Who do I most enjoy serving?
  37. What do other people see in me that I do not?
  38. What is the world calling me to take on?
  39. What did I most enjoy doing as a child?
  40. What do I dislike about today’s society?
  41. How do I introduce myself to other people?
  42. If I had to repeat my career as a business owner, what would I absolutely not change?
  43. If could swap my business for a different one, which would I swap it for? Why?
  44. What dreams have I deferred in order to attend to my business?
  45. What personal qualities have I most developed through owning a business?
  46. What have been my biggest challenges as a business owner and leader?
  47. How do my employees perceive me?
  48. How do my peers perceive me?
  49. What is the difference to me between living and existing?
  50. What are my greatest life accomplishments?
  51. What am I most thankful for in my life? In my business?
  52. Who am I most thankful for in my life? In my business?
  53. What is/are the greatest gift(s) another person(s) has ever given me?
  54. What is/are the greatest gift(s) that I have ever given to somebody?
  55. When was the last time that I did something for the first time?
  56. Do I “go” through life or “grow” through life?
  57. What skill do I most want to master?
  58. What am I passionate about?
  59. What have I always wanted to do but have never done?
  60. If I had to donate a half-day per week of my time, to whom or what would I give it to?
  61. What do I most enjoy giving to others?
  62. What does success look like to me?
  63. Over the last five years, what I have most enjoyed doing outside of my business?
  64. What skills or attributes do I have that most contributed to my business success?
  65. If I had no fear, what would I do after exit?
  66. What interest or passion am I afraid to admit that I have?
  67. If I could spend my time doing anything at all, what would I do?
  68. How would I like to make the world a better place?
  69. What would I regret on my deathbed if I had not done it?
  70. What bores me?
  71. At what time in my recent past have I felt the most passionate and alive?
  72. What makes me excited to get out of bed in the morning?
  73. What is it that I know deep down inside that I can do as well as anybody?
  74. What is it that I do with ease?
  75. Who are three people who taught me something worthwhile? What did each of them teach me?
  76. What do other people often thank me for?
  77. What about me typically earns the most compliments from other people?
  78. What types of people do I most like to be around?
  79. What have I most enjoyed about owning a business?
  80. What have I least enjoyed about owning a business?
  81. What topics do I like to read about?
  82. What recurring dreams do I have?
  83. What would I be doing if I absolutely, 100%, did not care about what other people think?
  84. What is on my bucket list?
  85. What am I world-class at doing?
  86. What drives me?
  87. What frustrates me?
  88. What do I resent doing?
  89. When I need help, how comfortable am I asking for it?
  90. What would I do if I had one billion dollars?
  91. What makes me feel great about myself?
  92. What am I naturally good at?
  93. What has been my greatest joy as a business owner and leader?
  94. What do people need that I enjoy providing?
  95. What would I stand for if I knew nobody would judge me?
  96. What does a perfect day for me look like?
  97. If I had to go back to school tomorrow, what would I major in?
  98. If I could be the most influential person in the world, what would I change?
  99. Which of these questions have stayed with me? Why?
  100. Who should I share my answers with?
  101. What do I need to do next?

Exiting happily requires more than just selling your company for top dollar. It also requires having a solid plan for what you want to do next in life that is engaging, rewarding, and meaningful. Use these questions as a starting point, and let us know if we can be of further assistance.

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