Meet Lady Jenny Bolivar

We recently connected with Lady Jenny Bolivar and have shared our conversation below.

Lady Jenny, so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.

For a long time, imposter syndrome quietly followed me — especially as I transitioned out of corporate America and into the entrepreneurial space. After over 20 years working in high-level, structured environments where roles and outcomes were clearly defined, stepping into a leadership position where I was creating the path as I walked it felt… unsettling. I would catch myself wondering, Who am I to lead this? To consult other businesses? To speak up on behalf of my community and advocate for the change we deserve?

But here’s the truth: I didn’t overcome imposter syndrome by suddenly becoming fearless. I overcame it by acting despite the fear — over and over again. Every time I showed up to a meeting, every time someone pulled me aside to say, “Thank you for saying what I was too afraid to,” every time I connected the dots between someone’s vision and real resources — I built evidence that I belong here.

I began to understand that imposter syndrome doesn’t go away just because we achieve more — it quiets down when we own our story. I’ve lived the journey. I’ve seen the gaps. I’ve stood in rooms where decisions are made and made sure our voices were heard. And most importantly, I’ve helped others step into their power as well. My lived experience is not just valid — it’s valuable.

Now, I don’t try to “fix” imposter syndrome. I see it for what it is: a signal that I care deeply and that I’m stretching. And when that voice tries to whisper doubt, I remind myself of what I’ve built, who I serve, and why I show up. I don’t have to know everything — I just have to keep showing up with integrity, strategy, and heart. And that, I do well.

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

I’m Jenny Bolivar, founder of LJB Strategies — a consulting firm built to support and elevate small businesses, especially those that are woman-owned, Latin-owned, or part of historically underserved communities. My background is rooted in corporate America, where I spent over 2o years navigating the structures and resources that many small businesses just don’t have access to. And at first, when I started helping entrepreneurs, I didn’t even realize it was advocacy — I just knew they needed support.

But over time, I began to see the pattern: these weren’t just individual business owners struggling to grow — they were pillars of our communities trying to keep the doors open without the tools, funding, or network that bigger companies take for granted. That’s when it clicked for me — this is advocacy. Supporting small businesses isn’t just good business — it’s essential for community sustainability, job creation, and economic equity.

What I do through LJB Strategies is help close that gap. I bring strategy, clarity, and resources to the table — the kind of knowledge that’s often locked behind expensive consultants or corporate playbooks. And I believe that if we’re fortunate enough to have that knowledge, and if we can translate it in a way that empowers others, then it’s not just a gift — it’s a responsibility.

What’s special about this work is that it’s never just about business. It’s about people. Legacy. Belonging. I help clients not only grow their companies, but understand their role in a much bigger ecosystem.

Right now, I’m focused on expanding my workshop series Confidence Through Clarity, working closely with chambers and community groups, and continuing to advocate for small business owners to be seen, supported, and set up to thrive. Because when they win — we all do.

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, the three most impactful qualities in my journey have been adaptability, strategic thinking, and relationship-building — all of which align closely with what I learned from my 16 Personalities test as an ENTJ, or “The Commander.”

1. Adaptability
As someone who naturally leans into structure and progress, stepping into entrepreneurship and community work required me to embrace a different kind of flexibility. Things don’t always go as planned — and that’s okay. I’ve learned that adaptability isn’t about lowering your standards; it’s about staying grounded while adjusting your approach. If you’re just starting out: trust that your ability to pivot is just as important as your ability to plan.

2. Strategic Thinking
My ENTJ traits came through loud and clear here — I’m wired to seek efficiency and improvement. Strategy has always been my anchor. Whether I’m helping a business scale, walking someone through certification, or developing a chamber roadmap, I can see the bigger picture and help others connect the dots. If you want to sharpen this skill, practice asking better questions. Get curious about why something isn’t working, and train yourself to find the root, not just the symptoms.

3. Relationship-Building
While I may lead with vision and decisiveness, what I’ve come to truly value is the human side of all of this. No strategy works without trust. No impact lasts without relationships. I’ve learned to slow down, listen, and collaborate — and those relationships have become the heart of everything I do. My advice? Don’t just build a network — nurture it. Your relationships will carry you farther than any business plan.

One of the most valuable tools I’ve used in this reflection process was taking the 16 Personalities test. It gave me language for strengths I had but didn’t fully understand, and helped me recognize where I could grow. If you’re curious about your own leadership style or how you show up in business and life, I highly recommend taking the free assessment — it’s a great way to better understand how you operate and where your power really lies.

Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?

Without a doubt, my husband has been one of my biggest sources of strength. His support is steady and unwavering — the kind that reminds me I’m capable even when I start to doubt myself. Whether I’m jumping into something new or regrouping after a challenge, he’s right there, encouraging me to keep moving forward and stay true to my purpose.

But something people might not know is that when I first stepped into this phase of my life — transitioning from corporate to consulting, stepping into entrepreneurship, and planting roots in a brand-new community — I was starting from scratch. I didn’t have the relationships or local connections yet. So I said yes to the invitations, joined The Women’s Network, connected with Women in Business, and started showing up even when it felt uncomfortable. And honestly? That changed everything.

Building those relationships didn’t just give me referrals or resources — they helped me discover my passion for supporting local businesses and advocating for economic equity in my own backyard. It’s through those connections that I found clarity on how I wanted to structure my business and what kind of impact I wanted to make. Being rooted in community helped me define my own boundaries — how I spend my time, who I partner with, and how I show up for my clients. I learned to lead with purpose, not pressure.

And at the heart of all of this is a lesson I carry with me daily: growth begins when you’re willing to step into the unknown, build new relationships, and stay open to what they can teach you. I came in new — and I found my voice, my mission, and my people

Contact Info:

• Website: https://www.ljbstrategies.com
• Instagram: https://www.instagram.com/ljb_strategies/
• Linkedin: https://www.linkedin.com/in/jennybconsults/

Image Credits

Photo Credit Sonia Tapia Photography