Helene Lerner on Taking Smarter Risks
MASTERCLASS
October 27, 2025
Helene Lerner is an award-winning producer, author, and the founder of WomenWorking.com, one of the premier websites for career women.

Helene Lerner is a trailblazing influencer and empowerment expert who has dedicated her career to inspiring individuals to live boldly and authentically. A prolific author, accomplished public television host, Emmy Award-winning executive producer, keynote speaker, and workplace consultant, Helene has built a legacy rooted in uplifting others. As the founder of the WomenWorking brand, Helene has cultivated a robust presence globally. She is the CEO of Creative Expansions, Inc., a multimedia company with a mission to empower individuals, particularly women and girls, to achieve their full potential. Helene’s expertise has made her a trusted voice in personal and professional development. She has appeared on major national programs such as Good Morning America, The Today Show, CNN, and Fox News.

With an unrelenting passion for making a difference, Helene continues to inspire individuals across the globe to embrace their power, Live Richly, and lead with purpose. Her new book Smart Women Live Richly, No Matter What's in Their Wallet! is available now.

Helene Lerner has built her career on helping women move through fear and toward fulfillment. Drawing from her new book, Smart Women Live Richly: Six Keys to Unlocking True Wealth and Prosperity, Lerner shared a deeply personal roadmap for navigating change and fear with confidence, purpose, and grace.

Redefine What It Means to Take a Risk

“Many women have been told we’re risk averse. I don’t believe that’s true. The difference is that we take smart risks – strategic, calculated ones,” said Lerner.

Her framework for assessing a risk begins with a simple inventory: write down the pluses and minuses of moving forward. Then ask yourself three questions: Where am I in my life cycle? What are my core beliefs? Does this action align with them?

If the answers point toward growth and integrity, it’s what she calls a “best bet.” If not, it may just be a “not now.” “When things align, go for it. Because if you don’t, you’ll regret it.”

Confidence Doesn’t Mean Fearlessness

Lerner rejects the idea of being fearless. “There is no such thing as fearlessness,” she said. “When we step out of our comfort zone, there will be fear. The most important thing is not to stop.”

Her own leap came when she left a stable 13-year job at a newspaper during the 1980s recession, guided not by logic, but intuition. “I walked into the building, pressed the wrong elevator button, and found myself resigning in HR,” she recalled. That instinctive decision became the foundation for a decades-long media career. “Confidence is moving forward when you think you can make a difference, even with shaky knees.”

Ask for Help – It’s a Sign of Strength

For Lerner, no risk is truly smart if it’s taken in isolation. “Reaching out for help is a sign of strength, not weakness,” she said.

She credits her mentors and collaborators for shaping her early television career, reminding women that support systems are essential. “If I didn’t have people to talk to, to get feedback from, I don’t know if I would have been able to do it,” she noted. “We are strong, but we don’t have to do it alone.”

Mentor with Praise, Not Perfection

As a workplace consultant, Lerner sees mentorship as both an opportunity and a responsibility. Her approach centers on encouragement. “We are already so critical of ourselves,” she said. “Praise, both for others and for yourself, is like water to a parched garden. It helps everything grow.”

She encourages leaders to help younger colleagues name their strengths and to model creative risk-taking without fear of failure. “Stop and say, ‘Why am I thinking about what I haven’t done? Look at what I just did. Good job, Helene.’ Our bosses won’t always give it to us, so we must give it to ourselves.”

Cultivate a Prosperity Mindset

At the heart of Lerner’s message is a simple truth: fulfillment is not just about achievement, but appreciation. “A prosperity mindset is about kindness, gratitude, and seeing the richness that’s already around us,” she said.

Her reminder to pause – to recognize small joys and give yourself credit – is as practical as it is powerful. “Little things are really big things. It’s about choosing to look at what you do have, not what you don’t.”

Helene Lerner’s Smart Women Live Richly is available now.

/*video overlay play button*/