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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 >>


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 to add to your content than anything else – journaling! But diving into journaling can be a little tough without some guidance – so in this post you'll find my top journal prompts for entrepreneurs to help you get started.

And it doesn't just help with your content either – Has your mind ever gone completely blank when someone asks you something or makes a comment? A total loss for words – except it’s not just ‘cause you’re surprised or caught off guard?

Later you come up with all sorts of brilliant things you could have responded with.

I hate that.

This isn’t just something that happens with arguments or witty banter either – for me, it used to happen all the time. Why does it seem like other people always have the perfect thing to say?

In a Facebook Group, someone would ask, What’s your biggest challenge with business right now? My mind goes blank.

Or at the beginning of a session, my coach would ask , How can I serve you today? My mind goes blank.

Trying to come up with my 1 year in business review? My mind went blank. I actually had to search through a year's worth of emails just to remember what I was doing. Don’t even bother asking me what I ate for breakfast.

But when I started keeping a weekly business journal everything changed.

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!

Benefits of Journaling

• Helps give your daily work meaning because you take the time 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 Peek at My Weekly Journal Prompts for Entrepreneurs Practice

Step One – I make it a part of my Sunday morning ritual

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)

• Relax and have fun for the rest of the day (every other week, I also run a session for 1 group of my year-long mastermind

The journaling piece is a non-negotiable starter for me!

Step Two – I automate it

I use a private Typeform-based form that gets emailed to me each week to complete and then sends me my responses so I can store them and refer back to them throughout the week and as needed in the future.

Step Three – Include a Variety of Questions

I answer a variety of questions and question types in my weekly business journal.

I include reflection-type questions – What milestones have I reached this week? What am I struggling with currently?

I also include information I’ll need to easily access that week – What am I wanting to let people know about this week? (including links and quick grab messages) What do I need help with this week?

And finally, I include content idea questions, such as – Who do I think is doing a really good job or a cool project that I want to help boost? What’s the best thing I’ve discovered this week?

How I Use My Weekly Business Journal In My Business

Here are some of the ways that I use my journal entries

• For coming up with new content ideas

• For coaching sessions (coming up with things I want to focus on)

• For stories to include in my blog posts

• For social media prompt answers

• For planning my week

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?

Next Steps

1. Create your journaling practice and system

2. Click on the image below to download the Monthly Content Planning Kit to turn these journaling ideas into Content You Can Use for Your Business

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