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102 Journal Prompts for Entrepreneurs and Business Owners

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102 Journal Prompts for Entrepreneurs and Business Owners

Journal prompts are short questions that prompt you to write about something specific. They are great tools to help you get started with your writing projects.

If you can’t think of anything else, this article is all you need. We have also included some examples below so that it becomes easier for you to understand our suggestions. Don’t worry if most of them don’t seem like they would work for you.

You can always use our tips as inspiration and try out different ideas to see what works best for you. So, without further ado, here are our top journal prompts for entrepreneurs.

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Journal Prompts for Entrepreneurs and Business Owners to Attract Your Dream Client and Customers

  • 1. Write down one thing about yourself that people would never guess. What makes you unusual or unique in any way? How does that make you stand out from everyone else?
  • 2. Describe your ideal day at work. When do you want to start working? Do you have plans on how long you plan to stay until lunch time?
  • 3. Why did you choose entrepreneurship and to be a business owner? You got into entrepreneurship because… How did you know it was right for you? Why were you drawn towards this path?
  • 4. How do you feel when someone compliments you? Do you take it well or just ignore it?
  • 5. Write about a time where you made a mistake. Did you learn much from it? Were you able to move forward after you realized what happened?
  • 6. What has been your biggest setback in your professional life? Why was it such a big setback? Was there something you could have done differently to avoid getting caught up in the situation?
  • 7. Describe three things about yourself you like. What qualities do you possess that make you who you are today? Which personality traits do you appreciate more than others?
  • 8. Explain why being an entrepreneur is important to your future. Are you passionate about entrepreneurship? What kind of benefits will come from achieving success in this field?
  • 9. Name three things you want to achieve within two years. What are your goals? Who’s going to help you achieve those goals? Why should anyone listen to what you have to say?
  • 10. If you had $100,000 in cash lying around, what would you spend it on? How would you invest that money? Would you use part of it to finance your business? Or would you go on a vacation somewhere?
  • 11. What are the main factors that determine whether someone succeeds or not in his career? What influences people to fail? Is there something we can do to prevent failure from happening in the first place?
  • 12. What are your greatest strengths as an entrepreneur? What are your weaknesses? Is there something about yourself you wish you were better at?
  • 13. Do you have a special talent? If so, what is it? What do you enjoy doing most? How has it helped you become successful?
  • 14. Describe your worst experience and how you dealt with it. How did it affect you? Did you change anything in your life as a result of it?
  • 15. What are the biggest problems facing your industry today? What do you consider to be the biggest problem facing our country/world? Is there anything you think society needs to fix?
  • 16. List five things about yourself that people wouldn’t expect. How do these characteristics influence who you are?
  • 17. Describe three books you love reading. What genres do you read? What authors do you admire?
  • 18. Why do you get restless before bedtime? Try writing about each of these questions – what happens during the night? Does anything happen before falling asleep? What are you thinking about? What are you dreaming about? How is your relationship with your partner? What are you feeling? Can you hear anything? Do you talk in your dreams? What about your parents? What about friends?
  • 19. How does technology impact us now? What are some ways it has changed our lives? Has it impacted your life positively or negatively? Explain.
  • 20. Have you ever taken a risk that failed? If yes, describe what went wrong & explain what you learned from it. Did you try again? Will you still attempt the same thing? Why?
  • 21. Talk about how you achieved great success in the past. What motivates you to keep working hard every day?
  • 22. Do you believe in luck? What is luck? Why do we need to work harder instead of waiting for good luck?
  • 23. Describe your greatest achievement. Was it difficult to achieve? If so, why was it challenging? What was your motivation behind getting up early in the morning? After all that effort, what happened?
  • 24. Have you done anything embarrassing recently? If yes, what? How do you feel about it? What lessons have you learnt from it?
  • 25. When you look back over your life, where do you see yourself in 10 years time? Where do YOU want to be in 10 years time?
  • 26. What qualities are necessary to be a leader? What makes you a good leader? What are the best and worst traits of business leaders? Why?
  • 27. Write down everything you know about the person you want to emulate. Include details about their personality as well as achievements they may have made. Be sure to put in detail about their flaws along with their strengths.
  • 28. Tell us about a goal that you really want to accomplish by this year end. What inspired you to set such goals? What will help you succeed? When would you like to complete this task? Please describe how you plan on achieving this goal.
  • 29. In one word, describe your perfect job. Why are you passionate about this job?
  • 30. Describe your ideal situation. What kind of house will it be? Who are you going out with? Are you married or single? What type of car do you drive? What age group are you with? What are you wearing? Write about this dream home.
  • 31. Share an event or experience you had in your childhood which shaped you into the mature individual that you are today. What did you learn from it?
  • 32. What is the most important quality you possess? Why? How can you improve upon it?
  • 33. What is one habit which makes you happy? Why does it make you feel better?
  • 34. Write about something positive that someone says about you. Write down their words & repeat them throughout the week.
  • 35. What is the most powerful lesson you have learnt since becoming an entrepreneur? What were you doing when you learnt it?
  • 36. Write about a trait of yours you don’t like about yourself. Would you change it if you could? Which trait? Why not?
  • 37. How did you overcome a fear in your personal life? What were your fears? Were you able to conquer them? Why or why not?
  • 38. What characteristics do successful people share? How do you strive to be more like them?
  • 39. Tell us about the happiest moment in your life. How did it come about? How did you feel at that point? What caused this happiness? What motivated you to achieve this level of joy?
  • 40. Talk about a time when you felt very discouraged; tell me what you did and how you reacted to the problem. Did you feel happy after overcoming the challenge? Make note of the specific steps you took to get through the discouraging phase in your life.
  • 41. Talk about some time when you got lost. Why did you get lost? What did you think about during that time? Did you worry about finding your way? Why or why not. What did you learn?
  • 42. Give us an example of a challenge that you faced and overcame. When did you face it? Why did you choose to deal with it? How did it shape you? How did you react to it?
  • 43. What is the hardest part of running your own business? Is there any business advice you can remember on how to tackle these challenges?
  • 44. Discuss a recent success you achieved – whether small or large. Make note of the key points you needed to remember and take action on. Identify the habits that helped you reach your desired result.
  • 45. Outline who you consider to be your mentors: who inspires you and motivates you? Have you been successful following their footsteps?
  • 46. What has surprised you most about being an entrepreneur? What did you expect to see? How do you handle failure? How do you handle stress?
  • 47. Think of a person in this world whose character you admire. What qualities does he/she possess? What is his/her philosophy?
  • 48. What’s your biggest accomplishment so far?
  • 49 Write a letter to future you thanking past you for all the lessons learned.
  • 50. Have you ever experienced a loss of confidence? If yes, then describe the situation, and how you coped. If no, then write about a time when you had a low feeling. Explain why?
  • 51. Talk about a time you were confident enough to speak up. Describe the circumstances, and explain why you decided to stand by your opinion.
  • 52. Have you ever failed? At what age did this happen? What caused this failure? Was it your fault? Explain.
  • 53. Tell how it feels to fail. Describe the emotions, and identify the difference between a difficult experience and failure.
  • 54. Can you recall a time when you were really scared? What caused this fear? Was it justified? Why or why not.? Describe the feelings as they happened.
  • 55. Talk about a period in your life where you were extremely stressed out. Write about your thoughts at that time, and what helped you cope with stress.
  • 56. Talk about a stressful incident in your life. How was it handled? What did you learn from the encounter?
  • 57. Recall a time when you were extremely angry. How did this anger affect you? Describe how you dealt with this emotion.
  • 58. Share an instance when you were forced into a position where you had to make a tough decision. How did you react to the situation? Do you know the results?
  • 59. Talk about a time in your life when you faced a big decision and made the right choice.
  • 60. Name three people who have inspired you throughout your life. What is it about them that makes them inspiring? How do they make you feel?
  • 61. Imagine yourself going through one year without sleep. How would you feel? How will you manage?
  • 62. What are some of the things that keep you motivated? Are there times when you need a break? If yes, how do you recharge your energy?
  • 63. How was your first day of work? Did you enjoy it? Were you happy to be working? Would you like to repeat the same? Why or why not?
  • 64. What is it that keeps you determined and committed towards accomplishing goals? How do you motivate yourself? Are you alone in doing so? Or are you influenced by others?
  • 65. Reflect back on a defining moment in your career when everything changed for the better. What was it that triggered this change? How did you respond? Did you get discouraged? Where did you find the courage to deal with the problem?
  • 66. What would you say if someone asked you: “What motivates you?” Give reasons why this question affects you.
  • 67. What do you value most in life? Is money more important than love, friendship, family, health etc? Why?
  • 68. How has being successful affected your self-confidence to achieve more in life? Could you share stories in support of this affirmation?
  • 69. Do you believe that everyone should try their best at achieving success? Why?
  • 70. Do you believe that a person can strive without being productive? Why or why not. Explain?
  • 71. What is the biggest secret to happiness? How does it help us become content?
  • 72. What helps you focus? How well do you handle distractions?
  • 73. Your attitude towards work dictates the quality of your output. Talk about a time when you found something challenging. What did you decide to do about it?
  • 74. Do you think you are good at handling problems? Tell me about a time when you encountered difficulties. How did you react? Have you done anything similar since then?
  • 75. Talk about a time you experienced loss or grief. What steps did you take to overcome this experience?
  • 76. Share a story which shows what you are really capable of doing.
  • 77. If you were given the chance to come up with your idea again – what changes would you make? Describe the details of the new scheme/product/service.
  • 78. What qualities do you possess to succeed as an entrepreneur? What could you add to improve yourself?
  • 79. In five years from now, would you want to look back at your life? How much progress do you hope to see in between? If none, what will you do differently?
  • 80. How do you define greatness? Has anyone ever told you that you are living out all the characteristics needed to be great?
  • 81. What would you tell your younger version if he asks you: ‘what is my purpose in life?’ Explain your response.
  • 82. When faced with pressure, what do you do to relax yourself? Do you consider doing yoga, meditation or reading books, poetry or favorite quotes? Please explain.
  • 83. Talk about a time where you felt insecure but acted anyway because of your determination. How did you handle it?
  • 84. Did you ever encounter any form of rejection in your journey? What happened? Tell me about one such incident.
  • 85. Write down some areas of your life which require improvement. Identify the reasons behind their deterioration.
  • 86. Who are the role models that have had the greatest impact on your life? Would they be willing to read your journal entries and give feedback?
  • 87. As entrepreneurs, we need to learn that it is only our failures that teach us valuable lessons. What failure could you relate to so far? Was there a lesson learned? Explain.
  • 88. What are your weaknesses? Are you aware of them? Discuss how these affect your business. For example, an organization that has a weak sales team cannot expect high revenue.
  • 89. We often blame society for our shortcomings, when sometimes it is ourselves who prevent us from realizing our potential. Have you fallen into such trap? How did you overcome it?
  • 90. Most people feel the urge to do something extraordinary, but fail to act upon it. Why do you suppose this happens?
  • 91. What makes you confident enough to tackle issues head-on? How is it possible that you never procrastinate?
  • 92. How do you cope with setbacks? If you face more than three consecutive days without success, what is your immediate reaction?
  • 93. What would you like to achieve in the next five years of your business journey? Where do you see yourself?
  • 94. Write your own motto. Can it inspire others around you? What does it say?
  • 95. What drives you forward? What keeps you going even after tough times? What inspires you most?
  • 96. How would you rate yourself as a leader? Would you describe yourself as a visionary, an organizer or a visionary leading an organized team?
  • 97. What can you do better? What else should you improve? Have you thought of ways to increase productivity?
  • 98. What is the difference between a dreamer and an achiever? Do you think you have the ability to become both? Explain in detail.
  • 99. If you were asked to suggest ways to improve productivity in your workplace, what would you recommend?
  • 100. What will it take to move ahead in your career? What skills do you need to acquire? If no skills are required, then why not?
  • 101. What are the qualities which make up an entrepreneur? Who do you think possesses all these traits?
  • 102. What do you get out of running a business? Can it bring happiness or satisfaction to you? Will it change your lifestyle completely? What are your business priorities?

Conclusion

I hope that these journal prompts have helped you to be the best version you can be, especially in your journey as an entrepreneur, as well as achieving the business goals that you want.

Best of luck!

ABOUT THE AUTHOR

Felix Prasetyo is the founder and publisher at Lifengoal, covering relationships, social skills, and personal growth. Felix holds a degree in Computer Science from the University of British Columbia, and has also contributed to other media publications such as Addicted2Success.com and YogiApproved.

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