Believe that you are loved. This might mean working through negative thought patterns or childhood trauma, but believing that you are loved is the first step toward becoming free from the fear of failure.

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Jennifer Pepito.

Jennifer Pepito is the author of Mothering by the Book and the founder of The Peaceful Press. Jennifer is on a mission to help moms overcome fear and love their life, and her homeschool curriculum empowers this through heroic stories, heartwarming poetry, and engaging life skills development. She’s a Wild and Free podcast host and has made guest appearances on popular podcasts such as 1000 Hours Outside, At Home with Sally, and Charlotte Mason Poetry. Jennifer lives in the mountains with her beloved family, where she enjoys reading aloud, working in her garden, and watching the sunset. Learn more at

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I was a stay-at-home mother until 2016 when I began writing learning resources for young children, birthed out of my love of educating my own children. Mothers worldwide saw the value in my resources, and my business, The Peaceful Press, grew quickly as families discovered the joy of learning together.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

I listened to a podcast by Donald Miller where he talked about writing your eulogy and working backward from there. This was very moving for me as a mother and a business owner because, while I love helping people through my offerings, I want to be known at the end of my life as someone who put relationships first. This relieved so much pressure from my work life. Now, I can work toward reasonable monthly business goals while still preserving time for connection with the people I love the most. It’s made my business life more enjoyable and helped to clarify what is really important to me.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Many virtues help a person succeed in business; one of the most important ones for me is bravery. So many people are afraid to take the first step toward pursuing their dreams, but when I approach my goals with a sense of courage, I can make things happen. I also attribute my success to a sense of playfulness. I’ve tried things that didn’t sell well, and conversely, I’ve created life-changing resources for people. I don’t look at success as an end goal but more of a journey of creativity and fun, and that makes it easier to focus on the process than on creating a perfect product. The last virtue is one I’ve mentioned already, and that is balance. Taking time away from business to be with my family and recharge has helped me be open to creative new ideas and to pace my growth.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

I think people deal with fear because they don’t trust that they are loved. When we approach life as a contest that we must master in order to prove our worth, it makes the stakes much higher. However, if we can start from a place of knowing that we are loved and loveable, then failure doesn’t indicate a loss of personhood or identity, and it becomes much less frightening.

What are the downsides of being afraid of failure? How can it limit people?

The fear of failure keeps people locked into a rut and inhibits them from creating a life of purpose and joy.

In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?

When we no longer fear failure, we can take chances, make mistakes, and acquire new skills. When we aren’t afraid of losing our identity by making a mistake but accept mistakes as a natural part of a well-lived life, we are free to be who we were made to be.

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

I had a dream of writing a book in order to encourage my community of mothers, and after a few years of researching the process and building my platform, I signed with a respected agent. We began working on revising my book content, but after several months of working together, he abruptly canceled our contract. I was understandably dismayed and subsequently discouraged as the next several agents I reached out to also declined to work with me.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

I didn’t give up on my dream of writing a book but kept it as a yearly goal and continued working to build contacts and refine my writing. I was persistent about pursuing this dream and finally had a chance to acquire an agent who believed in my project. Now, that book dream is a reality, and mothers everywhere are overcoming fear as they read my words in Mothering by the Book.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

Believe that you are loved. This might mean working through negative thought patterns or childhood trauma, but believing that you are loved is the first step toward becoming free from the fear of failure.

Develop good habits. As you develop the habit of persistence, refining your craft even when you don’t feel like it, you will conquer fear.

Speak life. Instead of speaking negatively about yourself and your progress, make a conscious effort to say kind and uplifting words about yourself.

Be thankful. Notice your progress and be present in the process. Life is a gift, and when we are thankful for the present joys, we are equipped to receive greater blessings.

Be playful. Approach life in a brave and fun way, looking at your progress as a process in which mistakes are inevitable. Accepting that the process might be messy will disempower fear and help you be more courageous.

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

I disagree with this quote because, while failure might be a natural part of learning, there is the opportunity for many successes along the journey. Each time you overcome a setback, try something new, or acquire a skill is a small success that should be acknowledged and celebrated.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

My dream is to inspire a movement of connected families because so many of the ills we are seeing in society today could be solved simply by having healthier relationships.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them 🙂

I’m a huge fan of Amy Porterfield and Jenna Kutcher because they value their business and their personal lives and live with integrity in both arenas.

How can our readers further follow your work online?

I’m most active on Instagram @thepeacefulpress, but readers can find a free family connection challenge and learning resources at and find my book on overcoming fear at

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.