Meet Jenny Geska

We caught up with the brilliant and insightful Jenny Geska a few weeks ago and have shared our conversation below.

Jenny, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

My confidence didn’t come overnight — it was built through experience, evolution, and plenty of moments where I had to remind myself of who I am and what I’m capable of.

I developed my confidence by saying “yes” to opportunities that scared me and “no” to things that didn’t align with my values. From performing on stage to leading as a realtor and travel agent, every chapter of my life added a new layer to my self-worth.

When I became a mother, an entrepreneur, and a woman navigating both personal and professional pivots, I had to dig deep and learn to trust myself — not just when everything was going right, but especially when things were uncertain.

I’ve learned that confidence isn’t about having all the answers — it’s about having the courage to keep showing up and believing you belong in every room you enter. That belief — paired with hard work, self-care, and surrounding myself with purpose-driven people — is how I continue to grow into the most authentic version of myself.

Thanks, so before we move on maybe you can share a bit more about yourself?

I wear a few different hats — and I love it that way. I’m a travel agent, realtor, UGC creator, and social media strategist — but at the heart of it all, I’m a storyteller and entrepreneur. I help people experience the world, find their dream homes, elevate their businesses through content, and ultimately create lives they’re excited to wake up to.

What excites me most is the freedom to create and connect. Whether I’m planning a Disney vacation for a family, creating UGC for a major brand, or coaching someone through Pinterest marketing to grow their visibility — it’s all about empowering others and helping them dream bigger.

Lately, I’ve been diving into digital education with the launch of my Pinterest Marketing Guide, which helps entrepreneurs across industries — especially in travel, real estate, and solar — harness the power of Pinterest to grow their business. It’s part of a larger mission I have to simplify digital growth strategies for everyday dreamers who want more freedom in their lives.

I’m also in the process of building a supportive online community where creative entrepreneurs and multi-passionate women can share resources, stay inspired, and grow together. And on a personal note, I’m navigating some big life transitions — including separation and building a new chapter for myself and my daughter — which has only deepened my commitment to showing others what’s possible when you lead with purpose and resilience.

There’s so much more to come — but what grounds me is knowing that everything I do comes back to helping people realize they’re not stuck, they’re just one bold step away from something amazing.

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?

The three most impactful qualities in my journey have been resilience, adaptability, and strategic storytelling.

Resilience – Life hasn’t always gone as planned, but resilience has been my anchor. Whether I was navigating motherhood, a career pivot, or personal heartbreak, I kept going. I always tell others: allow yourself the grace to grow through hard seasons. Strength doesn’t mean never falling — it means getting back up with intention.

Adaptability – The world changes fast, especially in industries like real estate, travel, and digital marketing. My ability to shift gears — from client meetings to creating content, or from UGC work to launching digital products — has been key. My advice: stay curious. Learn new platforms, trends, and skills. The more flexible you are, the more doors you can walk through.

Strategic Storytelling – Whether I’m pitching a vacation, a property, or a brand, I lead with connection. Knowing how to tell a compelling story — through content, copy, or conversations — has been a game changer. If you’re just starting out, practice sharing your “why.” People connect with purpose more than polish, so don’t wait until everything’s perfect. Start now and let your voice evolve with you.

At the end of the day, success is rarely linear. It’s made of small, consistent steps — and a belief that you’re worthy of what you’re building.

If you knew you only had a decade of life left, how would you spend that decade?

If I had just ten years left, I’d live even more unapologetically — leaning fully into love, freedom, and purpose.

I’d spend as much time as possible traveling with my daughter, showing her the world, chasing sunsets, and making memories we could feel in our bones. I’d make sure she knows she can do anything — that she comes from strength, softness, and grit.

I’d keep building — not just a business, but a legacy. Something that could live on in the lives I’ve touched. I’d create tools and spaces that empower other women to rewrite their own stories. I’d mentor boldly, love fearlessly, and stop waiting for “perfect timing.”

I’d buy the beach house. Dance barefoot in the living room. Laugh loudly. Cry when it’s real. Show up for people even when I’m hurting.

Most of all, I’d choose joy on purpose — every single day.

Because the truth is, none of us are guaranteed time. So why not live like our lives are already precious?

Contact Info:

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Highlighter Series
What do the first 90 minutes of your day look like?

Coffee? Workouts? Hitting the snooze button 14 times? Everyone has their morning ritual and we

Highlighter Series
What have been the defining wounds of your life—and how have you healed them?

Our deepest wounds often shape us as much as our greatest joys. The pain we

Highlighter Series
Are you doing what you were born to do—or what you were told to do?

Culture, economic circumstances, family traditions, local customs and more can often influence us more than