Journal Prompts for Overcoming Common Entrepreneurial Struggles

When you’re running a business, there’s always going to be struggles. Often, we all struggle with the same things.

It’s my belief that we all have the answers inside of us to overcome most things.

Often, it’s helpful to have a guide, coach or therapist to help us uncover these answers.

Journaling can be another way to get to the bottom of what’s holding us back. It’s free and it’s available at any time during the day or night.

I’m covering a handful of common struggles here and giving you questions to journal on. Reflecting on these prompts will likely give you a different perspective on your struggle.

So let’s dive into some journal prompts that can help you get over…

  • imposter syndrome,

  • making decisions,

  • pivoting,

  • pricing your products,

  • and receiving money.

Journal Prompts for Overcoming Imposter Syndrome

What are three specific moments in my life or business where I created a positive impact or achieved something meaningful?

How can I remind myself that I am capable and deserving of my success?

What are the negative thoughts I tell myself when imposter syndrome shows up?

How can I reframe these into empowering, truth-based statements?

Am I measuring my worth based on external validation (like social media, money, or approval from others)?

How can I shift my focus to internal validation and trust in my own skills?

What do I believe people might "find out" about me if they looked closely?

Are these beliefs based on facts, or are they fear-based assumptions?

How can I own my imperfections as part of my growth journey?

If I fully trusted in my expertise, skills, and worth, how would I show up differently in my business or life?

What’s one small action I can take today to embody that confidence?

Read my full blog on overcoming imposter syndrome HERE.

Journal Prompts for Making Decisions in Your Business

Does this decision align with my core values, long-term vision, and the impact I want to create?

If not, what adjustments would make it more aligned?

Am I hesitating because of fear, or is my intuition telling me something important?

How can I tune into my gut feeling and separate limiting beliefs from true guidance?

What is the worst case scenario that could happen if I make this decision? Why would this worst case scenario be the best thing that could happen?

What is the best possible outcome that could happen after making this decision?

How does focusing on possibility instead of fear shift my perspective?

When I imagine saying yes to this decision, do I feel expansive, excited, and energized?

Or do I feel drained, anxious, or hesitant? What is my body telling me?

If I were already the successful, confident version of myself five years from now, what advice would I give myself about this decision?

Journal Prompts for Making a Pivot in Your Business

What is calling me to shift directions in my business?

Is this coming from inspiration, frustration, or a deeper alignment with my purpose?

What aspects of my current business do I love and want to carry forward?

What no longer feels aligned and needs to be released?

What fears or doubts are coming up around making this pivot?

How can I distinguish between fear that’s keeping me stuck and intuition guiding me toward growth? To help on this one, where do I feel fear in my body? Where do I feel intuition and knowing in my body?

Has my ideal client or audience changed?

If so, what do they need most, and how can I position my new direction to support them powerfully?

If my business pivot is wildly successful, what does my life and work look like in a year?

How do I feel in this new version of my business?

Journal Prompts Before you Price your Products

What are the key benefits and transformations my product or service provides?Take each feature and re-write it as a benefit. For example: “these beautiful, bright flowers will transform your home” becomes “ these mood-lifting flowers will fill everyone in your home with happy thoughts”

How does it improve my customers’ lives?

Am I pricing it in alignment with the true value it offers?

Do I feel uncomfortable charging higher prices? If so, what fears or doubts come up?

Do I worry about people thinking it's "too expensive" or that they "won’t pay"? Where do these beliefs come from?

Does my current pricing feel like a fair and balanced exchange of energy for the time, effort, and expertise I put into my work? If not, what adjustments would make it feel more aligned?

Am I underpricing because I fear people won’t buy if I charge more?

How can I shift my mindset from focusing on affordability to attracting aligned customers who see the value in what I offer?

Imagine confidently setting and receiving your ideal price for your product or service. How does it feel? What changes when I fully embrace this level of abundance and trust in my worth?

Journal Prompts to Help you Receive Money

What messages did I receive about money growing up? How have these beliefs shaped my ability to receive and feel deserving of financial abundance?

Do I believe I am worthy of financial success? If not, what specific fears or doubts come up? How can I reframe these into empowering beliefs?

When someone gives me a compliment, gift, or financial opportunity, how do I typically respond? Do I accept it with gratitude, or do I deflect? What does this tell me about my ability to receive?

If I were to receive a large sum of money today, how would I feel? Excited? Overwhelmed? Undeserving? What would I need to shift in my mindset to fully welcome and enjoy financial abundance?

Anytime one of these common business struggles comes up, you now have a reference guide for working through your next steps.

Now, go ahead and share this post with one business bestie.

Thanks for being here!

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