The Pink Ink

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[DPA Interview] Achieving Success Through a Unique Productivity Solution with Designer Cara Dempsey

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This week we’d like to welcome Cara Dempsey, the founder of Wellnest Creations and one of our star students! Cara left her career of 19 years on a search for freedom and flexibility- which is exactly what she found with the help of the Digital Planner Academy®.

Cara has turned a creative idea into a successful digital product, which she now sells through Etsy and her personal website. We’re excited to share her experience with the Digital Planner Academy® and how it’s changed her life. Follow along with Cara’s story and think about lessons that you can apply to your own business. Let’s get started!

Could you go into detail as to what your planner’s purpose is?

“I want to help other women understand how they can use their cycle in becoming their most productive self. My planners teach women about each phase of their cycle and the intentions they should do to thrive in life.”

Cara Dempsey started her planner with a desire to take her own productivity to the next level, but it ultimately developed into a tool that helps other women better understand and follow their cycle to become the best versions of themselves. Cara says that women aren’t meant to do all things at all times, and instead, it’s healthy to align tasks with different parts of their cycle to make productivity their superpower. The planner teaches you about each menstrual phase and what movement, tasks, and nutrition the woman should follow in each phase to maximize productivity.

Pro tip! Notice how Cara focuses on a specific niche and topic: helping women become more productive using cycle vitality. This is a strategic method to reach a target audience and format your digital product to integrate your experience and knowledge. If you’re wondering how to choose a niche and share your skills, we’ll walk you through the process in our Digital Planner Academy®!

How did you discover the world of digital planning?

“I came across Shay and her work, I bought one of her planners, and then from there I saw that she offered a course to help other people.”

After leaving a 19 year career, Cara was searching for a path that would bring fulfillment and support, which led her to discover digital planners. She says in the interview that building productivity solutions has always been something she’s wanted to do, and finding The Pink Ink has given her the insight of what it takes to build a digital product on a software space. Cara joined the Digital Planner Academy® and with hard work and dedication, she found success!


Do you only have the planner as part of your digital product suite? Does it coincide with any other offerings that you have in your online business?

“I do coaching and strategizing with people, so it was a way that I could give something tangible to people and refer to something physical.”

Cara focuses on coaching to help women figure out how to create a life of purpose and ease based on how they’re built, not on what other people say it should be. She sells her planner individually through her Etsy page and personal website. This just goes to show that you can approach selling your product however works best, whether that’s joining a trusted platform or taking the step to create your own business.


How has the Digital Planner Academy helped you along your journey of creating this?

“The Digital Planner Academy really helped me understand the design aspect to teach myself and have a tangible way to go through.”

Cara says within the interview that while she’s always been into productivity, it reached a point where she was trying to do all things all the time, which can become overwhelming. The Digital Planner Academy® helped her understand the design aspect better and create an organized system that kept her on track in reaching success. It helped her understand what software she would end up using to create the best quality productivity solutions.

Think about this! Step-by-step programs are beneficial for those with a vision but not a strategic plan to reach those goals. Even seasoned entrepreneurs can profit from a guide, as it keeps students on track and provides a community to bounce ideas off of and stay accountable. Digital Planner Academy® was designed to make the design process easier while reducing time and creating a better quality product.


Have you had a positive outcome in terms of sales from your planner?

“I have found that the planners have helped me surpass what I needed in life, so it’s really supported me.”

Not only has Cara received positive feedback on her products, but she’s now making enough profit to surpass what she needs to support herself! Cara has taken her newly learned skills and knowledge a step further and is now working on some projects that could potentially be launched by next spring. She’s considering external projects that benefit other designers, as well as template-style products that allow others to create a more personalized planner.


Do you have any feedback or recommendations for others?

“I’d really recommend the Digital Planner Academy® because it really breaks it down into bite-size pieces.”


Cara points back to the Academy, even going as far as to say that “if I would’ve decided to go down this route without DPA, I would’ve given up.” That’s quite a big statement! But it makes sense when she attributes the planner to helping her utilize her gifts in the best way possible and streamline the process. Cara also hopes that other people can find power within themselves through their business journey.


Keep in mind! You’re not alone in this process. In fact, you have resources and community surrounding you, ready to help you succeed, but it’s important to take the opportunity. By joining the Digital Planner Academy®, you’ll connect with mentors that have succeeded in creating and selling digital planners. You’ll have the chance to ask questions, seek advice, learn from peers, and spur others on within their journey as well!


What are some positive aspects of that sort of lifestyle that you would like to share with people?

“I love that I can be in my comfortable clothes. I love that I can do it at home and my kids can be there. The flexibility- I can work when I want. There’s just so many benefits.”

Like many other designers, Cara absolutely loves the freedom that selling digital planners provides. She’s an ex-hairstylist and was craving a job with more freedom and flexibility- which is exactly what she found. Cara is able to work from the comfort of her own home and take time off whenever she wants. She works around her own schedule, not others’ schedules, and that’s the most freeing thing since leaving her career.

Follow along on Cara’s design journey!

We’re proud of Cara’s devotion to her craft and we encourage you to apply her strategies to your own business. There’s a lot we can learn! So check out Cara’s social media and Float Activity shop to stay updated with what she’s doing and show your support!


Cara has come a long way in her journey and overcome challenges with hard work and determination. She attributes a large part of her success to the Digital Planner Academy®, which is a step-by-step design program that teaches design skills, selling techniques, and strategies to building a successful business. Take this opportunity to connect with mentors and peers while gaining access to tools and resources that will guide you to success.


To achieve the freedom and flexibility you’ve always dreamed of, join the Digital Planner Academy® today!