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Your Guide to the Top Journaling Prompts for Entrepreneurs

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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Your Guide to the Top Journaling Prompts for Entrepreneurs

If you're a business owner who creates content there is one practice that will help you come up with more stories, more original ideas and just more words overall—journaling! But diving into journaling can be a little tough without some guidance (and great questions) so in this post you'll find my top journal prompts for entrepreneurs to help you get started.

When I started journaling I found that I was more focused on the right things, reflective on what needed to change and how and more tuned into my own voice. I can’t wait to show you a behind-the-scenes of my process and hope it’ll inspire you to come up with your own!

Prefer to watch this blog post instead? Click on the video below!

Benefits of Journaling

There’s a reason journaling has become such a popular trend, as it: 

  • Helps give your daily work meaning because you take the time to reflect
  • Keeps a record of the progress you’ve made
  • Helps you identify patterns preventing you from reaching goals or finishing projects
  • Developing and strengthening your own voice
  • Makes a memory of milestones that might just pass you by without notice

There are so many other benefits of keeping a regular business journal – but my favourite – using your weekly journal as a GOLDMINE for content to share through blogging, social media, and other content outlets.

So in addition to all of the ways journaling has benefited me personally, it’s also been one of the best things I’ve done for my content strategy.

A Behind-the-Scenes Look at My Business Journaling Practice

Step One – Create My Weekly Business Journal

The biggest thing that I use my journal for is to help me create content—like my newsletters, some extra shares for social, thinking through presentations, even mapping out new systems. So once a week (Sundays), I’ll start by coming up with the areas I need to journal on. For instance, this week I’m working on my next month’s newsletters, a new welcome sequence and updating our team onboarding systems. 

Then once I have the general areas decided, I come up with the questions for each individual email, post or project. For each piece of writing, I come up with 1-3 questions to guide the writing. 

So for instance, with the weekly newsletter that sends this blog post to my community, I might write: 

  • Why do I bookend my day with writing?
  • How does it help me output an extra 10,000+ words a week without really trying? (And yes, I really did go back and check the word counts on my last 5 journals!)
  • What are the first steps someone can take to get started with business journaling?

And I’d repeat this process for each of my pieces. 

Then I format the journal by having 1 page for each piece of writing with the questions at the top and a box for writing. I create this in Google Sheets and then export it as a PDF to my iPad. 

Step Two – Start and End My Day With Writing

Every morning, after my am routine, I start my workday by completing one page. This wakes my brain up, starts my day working on something creative and primes the rest of my day to be more creative too. 

I do the same thing as a way of wrapping up my workday too. I move to my couch, snuggle with my pup and complete one more page. 

Depending on how many pages I have, I may do one mid-day as well or spend Saturday wrapping up the rest of the pages.

Step Three – Process My Weekly Journal During My Sunday Routine

My Sunday morning ritual includes everything I need to do to prep for a great week ahead:

  • I reflect on my goals using this weekly business journal and Power Sheets (link)
  • I plan my week and prioritize my tasks and projects to see what I need to do next and when
  • I prep for the week (grocery shop, meal prep, tidy my space, laundry)
  • Relax and have fun for the rest of the day 

For my business journal, this is also when I process my previous week’s writing. I’ll type out my writing for the week. While the app I use (Noteshelf 2) lets you auto-transcribe your writing, I like to take the opportunity to edit things as I go. Once I’m finished typing it up, I move the pieces of writing to their proper spots (my editorial calendar, project folder, etc.) and then create the next week’s journal. 

Here are 25 Journal Prompts for Entrepreneurs that You Can Use Today

  1. What are you working on this coming week?
  2. What would you like help with this week?
  3. What milestones did you reach last week?
  4. If next week went completely as planned, what would you get finished?
  5. What was the best thing that happened last week?
  6. What’s a challenge you struggled with last week?
  7. What did you learn last week?
  8. What was your favourite discovery last week?
  9. What 2 people do you want to connect with this week? Someone old. Someone new.
  10. Favourite tip about [your area of expertise]
  11. Any big ahas or realizations this week about your work or business?
  12. Who is one person who’s doing great things that you want to thank and spotlight this week?
  13. Are you working on anything (a blog post or new offer) that you need some market research for? Form a question.
  14. Do you know of any opportunities or resources that others might find interesting?
  15. What progress did you make on your yearly/quarterly/monthly goals?
  16. What is something FUN that you want to do next week?
  17. What is something that you want to create next week?
  18. What are you most looking forward to next week?
  19. What things are you most grateful for from last week?
  20. How was your work-life balance last week? What would you change about it – if anything – this week?
  21. Snapshot (choose two to jot down): Book, Song, Podcast, Blog, Movie, TV Show, YouTube Video, Quote, Recipe, Tool, Online Community, Resource
  22. What’s your latest blog post? Link? What will readers get from it?
  23. What’s your latest freebie? Link? What will people get from using it?
  24. What’s your current offer? Link? What will customers get from it?
  25. How can you love yourself this week?

Ready to get started with business journaling?

I can say with confidence that journaling has been one of the best things I’ve done for my content strategy. By creating a weekly business journal, building journaling into my am and pm routines, and processing my journal as part of my Sunday routine, I’m guaranteed to have a goldmine of content always on hand that I can share through blogging, social media, and other content outlets. 

I promise that adding journaling into your schedule will do so much for you, personally and for your content. 

Download one of my themed business journals to try it out for FREE!

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