Meet Jese Gary

We were lucky to catch up with Jese Gary recently and have shared our conversation below.

Hi Jese, thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.

Honestly, I’m still navigating it. I don’t believe imposter syndrome is something you fully overcome—it evolves with each new chapter of life. While I have a solid level of confidence, stepping into new opportunities often stirs up internal doubts about my qualifications and self-worth. For me, it’s less about how others perceive me and more about the narratives I tell myself.

Recently, I started working with someone on my resume and career development. It was eye-opening to realize that I was disqualifying myself from roles I could do. That was a turning point. I’ve learned to pause when resistance shows up and ask, “Is this a true thought, or is it fear speaking?”

Even when I may not check every box, my faith in Jesus Christ reminds me that doors can open beyond what I think I’m capable of. That belief helps me keep going. I’ve started intentionally putting myself in rooms where growth happens and shifting my perspective to ask, “What’s the best thing that can happen?” instead of dwelling on what could go wrong. That mindset keeps me from staying stuck in self-doubt.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I was born and raised in Washington, D.C., where I witnessed entrepreneurship firsthand. My mother successfully ran a daycare business before selling it when I was 18, all while working full-time as a teacher. Watching her balance both roles showed me the power of ownership, hard work, and creating impact. I always thought I’d pursue entrepreneurship later in life—but “later” came at 29, when I felt a deep desire to build something that brought me joy and made a difference.

Today, I run a boutique community event agency that focuses on creating meaningful experiences. As I’ve grown personally and professionally, I’ve felt called to expand how I show up and use my voice. That’s led me to launch two podcast platforms that reflect this next chapter.

The first is Life Over 40, a podcast designed to spark honest, roundtable-style conversations about the real-life shifts women face as they grow older. From wellness to career pivots to identity changes, it’s about creating space for often overlooked stories.

The second is The Hustle Free Entrepreneur, a podcast tailored for event industry business owners. We hear about the glamorous side of events so often, but rarely do we talk about the behind-the-scenes challenges of running a business. This show offers support, strategy, and solidarity to help others succeed without burnout.

What excites me most about both platforms is their ability to build a community rooted in authenticity and shared experience. At 44, I’ve realized that so many of us are navigating similar transitions—we just need a space where we feel seen, supported, and inspired.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Looking back, I realize that curiosity, flexibility, and perseverance have had the most impact on my journey.

Being raised around educators, I’ve always been naturally curious. I love learning, reading, and discovering new things. As a business owner, that curiosity has fueled continuous growth and helped me stay ahead of the curve. Lifelong learning isn’t optional—it’s the foundation for innovation and long-term success.

Flexibility has also been key. The vision I started with doesn’t look the same five years later—and that’s a good thing. Being open to change allows your ideas to evolve into something even better. If you become too rigid, you risk building a business that no longer serves you or your audience. Surrounding yourself with a trusted circle or mastermind can help you stay grounded and gain honest, constructive feedback. Inviting others into your vision is important, not just for validation, but for growth.

Lastly, perseverance has carried me through the most challenging moments. You have to be connected to your “why”—your purpose and the impact you’re striving to make. If money is your only motivator, it will be hard to keep going when your income dips or things get tough. Your perseverance, purpose, and faith must work together to sustain you through wins and setbacks.

For anyone just starting out, stay curious, remain open to evolving, and build your vision on something deeper than profits. That’s how you create lasting things.

Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?

My mom has been my biggest cheerleader through this process. She was always playing big in her life despite obstacles or challenges. By watching her journey, I learned what it took to make it to the other side of entrepreneurship. The most impactful thing a parent can do is lead by example in their own lives.

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