20 Journal Prompts For Entrepreneurs To Reflect, Learn, And Thrive
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20 Journal Prompts For Entrepreneurs To Reflect, Learn, And Thrive

Add a bit of structured exploration of your thoughts, goals, and strategies with these picks.


Many have touted the benefits of journaling, especially when it comes to one's mental health. I've always been one to keep a diary, but in recent years, journaling has become quite challenging for me. Nowadays, I feel like my thoughts are moving way faster than my hands can write, which frustrates me to the point of not even bothering to write them down. (And I'm not a fan of putting my personal business online or on my phone via an app. I'm one of those people who fears that there's always somebody who either has access or can gain access and the possibility is just too creepy and scary for me to even attempt to use any digital form of a journal—cybersecurity be damned.)

One day, I was trying to think of ways to recommit to journaling, especially since I've been through quite a few career and life transitions (Weight loss and master's degree, anyone?), and came across the concept of journal prompts.

They're basically targeted, open-ended questions that lead to a more structured way of writing down your thoughts. The premise reminds me of the training I've recently completed for my master's studies, where coaches are able to guide their clients toward successful outcomes versus just telling them what to do.

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Journal prompts have offered me a method of self-exploration, reflection, and focus that takes a bit of the overwhelming annoyance out of trying to obsessively control the process of journaling (which, for me, is a self-defeating and counter-productive habit). I feel more at peace answering such questions and I'm less apt to rush through the journaling process, something that is supposed to add peace to my day, not lump-in-the-throat loathing.

Here are a few favorites I've turned to as a self-employed, type-A Capricorn who always has 50 million things going on, is constantly in her head, and needs brain-dump release with a side of return-on-my-time-investment:

  • What personal milestones did you reach last week related to your business or work?
  • What was your “a-ha moment” this week? (If there wasn't one, explain why).
  • Who is your ideal client? Why?
  • What motivates you to continue doing what you do?
  • What does a great work-life balance look like for you?
  • What business win did you experience this week? (And how did it make you feel?)
  • How did you feel after taking meetings today? Which one was your favorite? Which was your least favorite? Why?
  • Who is one business leader you admire? Why?
  • Who is someone who you consider your competition and what are three things you admire about them?
  • Where do you see yourself revenue- or earnings-wise in 30 days?
  • What actions are you taking today to reach a revenue goal in 60 days?
  • For you, what is the most annoying part of doing business?
  • What are three daily routines you could possibly automate or delegate? (And explain how.)
  • Who are three people who contribute to your daily business or work-related success? Why?
  • What are three of your best qualities in doing business? (Describe why.)
  • What's one new idea you'd like to make a reality for your work or business?
  • What are three skills you could upgrade or improve on when it comes to how you run your business?
  • What are three resources you'd like to tap into in order to grow your business or brand?
  • What are three activities you could add to your workday that will make it fun?
  • What are three Fortune 500 companies that have similar missions or values as you or your business? (Detail why.)

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Featured image by LaylaBird/Getty Images

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