Journaling for Entrepreneurial Confidence

In this interview with CanadianSME Small Business Magazine, Lisa Simone Richards, co-founder and CEO of Pearl Spark Pages, opens up about her entrepreneurial journey and the powerful role of self-reflection in building confidence. Through her luxury stationery brand, Lisa is helping female founders tackle imposter syndrome and embrace their true potential. In this conversation, she shares the personal experiences that led to the creation of the Female Founders Journal and discusses the profound impact that intentional journaling and community-building can have on women entrepreneurs.

Lisa Simone Richards is the co-founder and CEO of Pearl Spark Pages, a luxury stationery brand designed to help female founders push past imposter syndrome and build confidence through mindful self-reflection. As the host of The Messy Middle, both an online community and the private podcast, Lisa creates safe spaces for women entrepreneurs to get real about the ups and downs of business and celebrate their growth.


Your journey from publicist to product entrepreneur is inspiring. What personal experiences led you to create Pearl Spark Pages and, specifically, the Female Founders Journal?

After speaking at an event for 150 founders about pushing past imposter syndrome to boost visibility, I posted a short clip on Instagram.

A few hours later, a friend from university DMed me: “You’re SO cool!”

Without thinking, I replied: “I feel like a fraud half the time.”

Ironic, right?

Even with 20 years as a publicist and speaker, imposter syndrome still had a front-row seat in my mind. It constantly said that I wasn’t good enough and didn’t know enough. That voice showed up in masterminds, meetings, and conferences, often urging me to shrink.

Some quick Googling confirmed that I wasn’t alone. A KPMG study found 75% of women leaders have experienced imposter syndrome.

It became clear that if the voice in our head shapes how we show up, we need tools to take back control of that voice. So I made it!

Within weeks, I created two daily journalling frameworks—one for the morning, one for the evening—to help me feel as confident inside as I looked outside. And they worked.That’s what inspired me to create Pearl Spark Pages, a luxury stationery line for female founders, and our first product, the Female Founders Journal, the only guided journal specifically for women entrepreneurs to help them rewire their inner dialogue, build authentic inner-confidence, and celebrate their progress.


Imposter syndrome is a recurring theme in your story and your products. How have your own struggles informed the journaling frameworks you developed, and what makes them uniquely effective for women entrepreneurs?

Since my first internship straight out of undergrad, I’ve worked with female founders. After nearly two decades in PR, I knew this audience intimately because I am them. I created the Female Founders Journal not only from my own lived experience, but also had it reviewed and approved by a therapist to ensure it would be a truly supportive tool.

My whole life people have told me how it looks like I’ve got it all together. But only I know what’s happening behind the scenes—like starting my day reacting to emails and ending it in a blur of unfinished tasks. I rarely paused to acknowledge progress. And I definitely wasn’t celebrating myself.

That’s where the journalling frameworks came from: a need to start my day with intention and end it with celebration. I built journalling frameworks that would fuel confidence and reinforce positive growth.

What makes this journal uniquely effective for women entrepreneurs is that it has nothing to do with productivity or goal setting. It’s about YOU as the founder. Fun fact: PEARL stands for Passionate, Empowered, Ambitious, Resilient Leader. It’s about building the kind of self-belief that fuels resilience and long-term success.


Pearl Spark Pages is positioned as a luxury stationery brand with a mission to empower female founders. How do design and intentionality play a role in fostering confidence and self-belief through your products?

I really want to make sure that every product we design is created with intention and is very aligned with the brand. It’s not just about journalling or writing for the sake of it. It’s about reflection. We often overlook our own progress, focusing on what’s next instead of what we’ve already achieved. The journal helps you tap into your personal database of accomplishments and use them to build confidence from the inside out.

Taking a moment to recognize yourself—whether for something big or something small—shifts your mindset from pressure to pride. I don’t want women to fill these pages and then forget them. Come back to them and reflect because they’re living proof of your growth. That’s why the journal includes monthly reflection prompts to review what made you feel most accomplished, what lessons you’ve learned, and what limiting beliefs you’re ready to release.

I was really specific in making sure that this journal isn’t about strategy, productivity or habit tracking.  The thoughtful, luxurious design invites you to slow down and see yourself clearly. It’s beautiful because we deserve beautiful things in our lives and on our desks.

For female founders, it’s easy for us to feel like we’re never doing enough. This journal reminds you that you are. Even on the hard days, you’re making progress—one page at a time.


Transitioning from a service-based PR career to launching a product-based business is a significant leap. What were your biggest challenges in making this shift, and what advice would you offer to other founders considering a similar transition?

It was definitely a leap—but one I was able to make surprisingly quickly. The idea for the journal came to me while I was in Indigo with my husband, back in September 2024, and by January I had a physical prototype in-hand.

The biggest reason I was able to fast-track that process was community. Honestly, I did not encounter many challenges along the way because I connected with women who’d already walked the path. Being part of The Entreprenista League, a network of women entrepreneurs, gave me direct access to other female founders who were willing to hop on 30-minute calls and share the behind-the-scenes of their product journeys. They helped me skip the learning tax and avoid expensive mistakes. That kind of generosity changed everything.

My advice is don’t do it alone. Especially if you’re transitioning from services to products, find people who are already in that space. Ask questions, get curious, and lean on your community.


As you look to the future, what is your vision for Pearl Spark Pages and the community you hope to build around it?

My vision is for Pearl Spark Pages to become the leading provider of journals and tools that cultivate self-belief, confidence, vulnerability, and authentic expression in women entrepreneurs. I want our products to feel like a trusted companion in the messy, meaningful process of building a business—offering more than structure, offering support.

And I’m definitely not guessing my way forward. I already know what our next three core products will be. One of them has already pre-sold over 200 units! That tells me we’re building something women are craving.

Just as important as the products is the community around them. Entrepreneurship can feel isolating, especially when you’re second-guessing yourself. I want Pearl Spark Pages to be a brand where women feel seen, supported, and celebrated—where they can show up as their full selves, not just the curated version.

Through journalling, storytelling, and intentional reflection, we’re helping women reconnect with their vision, push past imposter syndrome, and build businesses that reflect who they really are.

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CanadianSME
With an aim to contribute to the development of Canada’s Small and Medium Enterprises (SME’s), Cmarketing Inc is a potential marketing agency and a boutique business management company progressing rapidly in its scope. By acknowledging a firm reliance of the Canadian economy over its SMEs, the agency has resolved to launch a magazine, the pure focus of which will be the furtherance of Canadian SMEs, and to assist their progress with the scheduled token of enlightenment via the magazine’s pertinent content.
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