We caught up with the brilliant and insightful Jessica Gandara a few weeks ago and have shared our conversation below.
Jessica, so great to have you with us and we want to jump right into a really important question. In recent years, it’s become so clear that we’re living through a time where so many folks are lacking self-confidence and self-esteem. So, we’d love to hear about your journey and how you developed your self-confidence and self-esteem.
My parents divorced when I was just 2 years old. Growing up, I spent every other weekend at my dad’s house. But as I became a teenager, I wanted to spend more time with friends, like any 15-year-old would. My dad worked long weekend hours as a gas station manager, so on those weekends, he would drop me off at my grandmother’s house. There were no cell phones, no computers — and she was a strict, bitter woman who didn’t allow me to do anything.
I felt trapped. Frustrated. And for the first time, I found the courage to speak up. I handwrote him a heartfelt letter explaining how I felt, asking if we could adjust our time together so I wouldn’t have to sit alone at my grandmother’s. I mailed it to him… and he NEVER responded. No phone call. No visit. No explanation. Just silence.
That silence was devastating. It wasn’t just about a missed weekend. It was about feeling abandoned after finally finding my voice. And without realizing it at the time, that moment shaped so much of who I became.
Decades later, at 42 years old, I was in a women’s forum doing a blind spot exercise. One of the women said to me, “I see you as a leader, a strong woman with so much potential. But every time leadership presents itself… you run from it.” Hearing that shook me. And when the rest of the group agreed, I knew it was time to face something I had been carrying for years.
Together with these seven women, I peeled back the layers of my story. I realized that before that letter — before 15 — I had always put myself out there. I ran for school office, tried out for lead roles in plays, played sports. After that moment with my dad, all of it stopped. It was like my confidence left with him. From then on, I stayed in the background where it felt “safe.”
But once I saw that connection clearly, I couldn’t unsee it. I made a decision that changed everything: it was going to be my “Yes” year. I started saying yes to opportunities, even the ones that scared me. I said yes to projects I didn’t feel ready for, yes to putting myself back out there, and most importantly, yes to believing in me again.
I also did inner child work — speaking to that 15-year-old version of me, letting her know she wasn’t abandoned, that she was loved, seen, and safe. That healing moment gave me back my voice.
Today, I’ve written a book to help other women face their own turning points, and I lead a community where we push through our comfort zones together. We set goals, take action, and celebrate every win — big or small. Because confidence isn’t something you’re born with; it’s something you build, one courageous “yes” at a time.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
At the core of everything I do is one mission: to help people step out of their comfort zones and step into their power. I’m the founder of a personal growth movement that began with my book ‘It’s My Turn: 31 Daily Challenges for Women’ and has grown into a nationwide community called The Sisterhood.
What started as my own journey to rebuild confidence has become a space where women support, challenge, and celebrate one another through daily challenges, accountability programs, retreats, and shared experiences. Watching women transform — from doubting themselves to leading, launching businesses, writing books, finding healing or simply living fully again — is what excites me most.
Alongside my husband Joel, we host couples retreats where partners reconnect and grow together. It’s a blessing to do this work side by side, modeling what growth as a couple can look like.
We have some exciting things ahead — including a Couples Retreat in Park City, Utah, a 21-mile beach walk in South FL for men and women ready to push themselves and the 2nd Annual Sisterhood Retreat in February 2026. Every event and program we create is built on three pillars: community, courage, and growth. I believe real transformation happens when people around you see your potential — sometimes before you do. That’s the heartbeat of everything I build.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Looking back, there are three core qualities that have shaped everything I’ve built: self-awareness, courage, and consistency.
1. Self-awareness
For years, I was operating on autopilot, unaware of how one moment in my teens shaped my confidence and decisions as an adult. Once I developed the courage to look inward and understand my blind spots, everything changed. Self-awareness is the foundation of growth. My advice: slow down long enough to listen to yourself. Journal, get in community, ask for honest feedback. You can’t change what you can’t see.
2. Courage
Confidence didn’t come back into my life overnight — it came one “yes” at a time. I learned that courage doesn’t mean feeling ready; it means taking the step anyway. Say yes before you feel qualified. Step into rooms that make you stretch. My advice: Don’t wait for permission. Your growth lives on the other side of discomfort.
3. Consistency
The truth is, change happens in the everyday moments — the habits, the commitments, the follow-through. My confidence grew not from one big leap, but from showing up over and over again, even when it was hard. My advice: Start small but stay steady. Build daily habits that move you closer to who you want to become.
When you combine self-awareness with courage and consistency, you build unstoppable momentum. That’s what transformed my life — and it’s what I try to help others create every single day.
Tell us what your ideal client would be like?
My ideal client is a woman who knows deep down that she’s meant for more — even if she can’t fully see the path yet. She’s strong, capable, and has accomplished a lot, but somewhere along the way, she’s started playing small. Maybe she’s been putting everyone else first. Maybe she’s forgotten what it feels like to put herself at the center of her own story.
She’s not looking for a quick fix; she’s ready for real, lasting transformation. She craves connection, accountability, and a community that will challenge her — lovingly but firmly — to rise.
I work best with women who are willing to show up, even when it’s uncomfortable. Women who are open to self-reflection, growth, and taking action. Whether it’s saying yes to their first big challenge, leading from a place of courage, or simply remembering their worth — these are the women who thrive in the Sisterhood.
Ultimately, my ideal client is someone who’s done with standing on the sidelines of her own life and is ready to step forward — not just for herself, but for the ripple effect it will create in everyone around her.
Contact Info:
- Website: https://www.31dailychallenges.com
- Linkedin: https://www.linkedin.com/in/jessgandara/
- Twitter: https://x.com/jessicagandara
- Youtube: https://www.youtube.com/@jessicagandara24
Image Credits
The women pictured in these photos are the women I choose to surround myself with. These are women who are ready to conquer their fears and desire more out of life. They are writing books, pushing themselves physically by running their first 5ks/half-marathons/marathons, they are mending old relationships, seeking healing, growing exponentially in business and life.
so if you or someone you know deserves recognition please let us know here.
