When you look at someone who has worked at CNN, Entertainment Weekly, Madison Square Garden, and now runs her own media strategy company, it is tempting to assume they had a perfect plan.
From the outside, it looks linear. Impressive. Maybe even a little intimidating.
But in my conversation with Brittany Kaplan on From a Woman to a Leader, what emerged was something different. Not a perfect plan, but a series of very human choices:
To say yes.
To move.
To be uncomfortable.
To raise her hand.
To be a “big fish in a small pond.”
And to keep doing that, again and again.
Being “Raised By CNN”
Brittany describes her early years in media as being “raised by CNN.” She went to school for broadcasting, fell in love with news, and landed an internship at CNN that turned into a job before she even graduated.
Her dad had always told her, “Be a big fish in a small pond. Make sure you get noticed.”
She took that seriously.
She worked hard, showed up early, stayed late, and made herself useful. She loved the newsroom so much she joked she could sleep there. Those years became her training ground – “Camp CNN” as she and her colleagues called it.
What most people do not see is how many times she packed her life into boxes and moved to sustain that career. Across the United States seven times. New York to LA and back again. New roles, new shows, new teams.
It sounds bold, even glamorous. But the reality included friends’ couches, shared bedrooms, and a lot of logistics made possible by supportive parents and a willingness to say yes quickly.
The Myth Of “Having It All”
Brittany and I are from the generation that was told women could “have it all.”
Career. Family. Relationship. Social life. The shiny, balanced package.
She shared that she takes issue with that phrase, not because she does not want it to be true, but because the systems around us were not designed to support it.
We created better access to careers. We opened more doors. But we did not always create the structures that make it realistic for women to be fully supported at work and at home at the same time.
The result for many women in high pressure fields is guilt, exhaustion, and a quiet sense of failure when reality does not match the slogan.
In Brittany’s words, the environment is slowly course correcting, but we are not there yet.
Standing Out By Being Helpful
One of my favorite parts of our conversation was when Brittany talked about how to stand out early in your career.
Her advice is refreshingly practical:
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Always raise your hand.
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Offer to help.
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Be honest that you do not know everything.
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Show where you can make someone’s day easier.
At CNN, one of the first ways she became truly useful was at the Daytime Emmys. No one on the team knew much about daytime TV. Brittany did. She had grown up watching the shows and knew the actors, storylines, and relationships.
She did not push to be in front of the camera. She simply went to the producer and said, “I think I can help here.” She suggested questions, connected dots between people and shows, and quietly made the coverage better.
That is how you become a big fish in a small pond. Not by being loud, but by being genuinely valuable.
Confidence Without Knowing Everything
Like many women listening to this podcast, Brittany works with clients who are experts in fields she is not.
Her job is media strategy, brand partnerships, and positioning. Their job is to be the expert in their industry.
She is clear about that. She does not pretend to know their business better than they do. And she is not afraid to say, “I do not know yet, teach me.”
Real confidence, she reminds us, is not knowing everything. It is knowing your lane and being willing to learn.
Mentorship And The Ripple Effect Of Kindness
Brittany’s career is full of mentors, from local community leaders in her youth group to senior figures in media.
One story stood out.
At 17, she sent a faxed press release (this was before email was standard) to New York news stations, inviting them to cover a youth summit. That night, her home phone rang.
On the line was Bill Ritter, one of the most respected anchors in New York.
He told her he had received her press release, could not send a crew, but was impressed by what she had done. He stayed on the phone with her, encouraging her and asking about her goals.
She never forgot it.
Today, when someone reaches out to her for advice, she does her best to respond. Not because she has endless time, but because she knows what a single act of kindness can do for a young person who is just starting out.
Growing Through Discomfort
Later in the episode, Brittany shares something her therapist told her:
We grow the most when we are in uncomfortable situations.
Sometimes, the win is not having an incredible night at the event or walking away with ten new connections. Sometimes, the win is simply that you went. You walked into the room where you knew no one. You did the thing that scared you.
If you are an ambitious woman who finds networking, big moves, or reinvention uncomfortable, this reframe matters.
You can be proud of yourself just for showing up.
Final Takeaways
From my conversation with Brittany, here are a few lessons to take into your own career:
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Say yes, then figure it out.
You do not need a perfect plan to accept an opportunity. You can move, ask for help, and build the plane as you fly. -
Be a big fish in a small pond.
Look for places where your skills and energy will be noticed, not just where the brand name is impressive. -
Be helpful and curious.
Raise your hand, look for ways to make someone’s day easier, and use the knowledge you already have. -
You do not have to know everything.
Confidence comes from knowing your expertise and being open to learning from others. -
Growth is uncomfortable.
You are allowed to be nervous and still walk into the room. That alone is worth celebrating.
Listen And Go Deeper
If this resonates, I highly recommend listening to the full episode with Brittany.
🎧 Listen to the episode: limorbergman.com/podcast
📺 Watch on YouTube:
Want More Personal Stories & Deeper Insights?
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About Brittany Kaplan
Brittany Kaplan is a powerhouse in sports, entertainment, and media, known for turning brands, events, and talent collaborations into culture-shaping moments. With a career spanning high-profile talent booking, brand strategy, and VIP event production, Brittany has a proven track record of transforming bold ideas into measurable results — boosting visibility, deepening audience engagement, and driving major revenue growth. From managing celebrity relations at Madison Square Garden to producing headline-making events for Entertainment Weekly, Brittany knows how to create experiences that don’t just capture attention — they build lasting brand loyalty. Her expertise spans client services, experiential marketing, strategic partnerships, and influencer strategy, all rooted in a deep commitment to diversity, inclusion, and authentic storytelling. Today, Brittany works with leading brands, talent, and media companies to craft campaigns, events, and partnerships that break through the noise. She’s passionate about helping organizations move from good to unforgettable — and she brings that same energy to every conversation.
Follow her on LinkedIn: https://www.linkedin.com/in/brittanylkaplan/
Instagram: https://www.instagram.com/brittanylkaplan/