Learn what 10 top Take The Lead leaders, colleagues and allies say about the value of risk.

Some may find the scary business of Halloween entertaining, but in real life, entrepreneurship and business shifts are also scary and risky-- and maybe not so fun. Here 10 top leaders share how the discomfort of risk is worth it all and why.

For Take The Lead’s 10-year anniversary, here is a treasure chest of insights and strategies from Take The Lead’s co-founder, allies, colleagues, friends, and business associates in an array of fields and disciplines. With the latest research and data on how women value risk and how that impacts financial behaviors, this can hopefully and helpfully deliver a path to turning risk into reality.

1. Gloria Feldt, co-founder and president of Take The Lead: “We grow our courage muscles like we grow our physical muscles — by using them. Same with risk taking.” She adds, “When I started my journey to leadership, women thought we had to become men (metaphorically in their behaviors, and even dress — anybody else remember the sincere navy suits and floppy ties?) to succeed. Today, it is clear that the world needs what women have to offer. In the 20th century, women marched to get the vote and change discriminatory laws. In the 21st century, we must actualize the opportunities we have created for ourselves to take our rightful place in the fair and equal share of leadership. Every step of the way forward for women or any other kind of progress has required some kind of risk taking. Otherwise, no progress would be made.”

“In the #20thcentury, women marched to get the vote and change #discriminatory laws. In the #21stcentury, we must actualize the #opportunities we have created for ourselves to take our place in the fair and equal share of #leadership. — @GloriaFeldt1”

2. Michele Wucker, author, TED speaker, commentator and policy analyst specializing in the world economy and crisis anticipation: “If risk takers succeed, we worship them. If they fail, we’re likely to demonize them.“ The author of You Are What You Risk: The New Art and Science of Navigating an Uncertain World, The Gray Rhino: How to Recognize and Act on the Obvious Dangers We Ignore, and other books, adds, “Looking at risk is like going into a room full of fun house mirrors. But the very act of recognizing a risk makes you more likely to do something about it. Risk stereotypes affect how both genders think they are supposed to behave and can create conflicts when one member of either gender is not acting typically. In other words, they hurt men as well as women.”

A 2023 study on gender differences in attitudes toward risks finds, “gender differences in financial optimism and financial loss aversion – the stronger psychological response to monetary losses than monetary gains – explain a substantial proportion of the parallel gender difference in willingness to take risks.”

Yes, women generally take fewer risks, due to an anticipation of negative outcomes.

“Gender differences in attitudes towards risk may originate from differences in how the genders evaluate the probabilities and/or the costs of risky decisions,” researchers report. “Females report experiencing both negative and positive affect more often than males.”

This ability to effectively weigh outcomes on both sides contributes to better decisions, another study on the inclusion of women on corporate boards shows. “Women’s presence on corporate boards plays a critical role in the board’s involvement in risk-taking. Hence, investors and stakeholders should consider women on corporate boards as a crucial risk-mitigating factor.”

Women in leadership offer crucial insight into effective risk-taking.

3. Carla Harris, senior client advisor at Morgan Stanley, author, acclaimed singer, leadership icon: “If you consider yourself a leader, you must be comfortable taking risks. Fear has no place in your success equation personally or professionally. Failure always brings you a gift of experience.” Harris, a Take The Lead Leading Woman Award winner, says, “Your authenticity is your distinct competitive advantage. People will trust you. Your success depends on your ability to successfully penetrate relationships. Performance is the currency generated by delivery of what is requested—and going beyond. People will always tell you what they value. Then you can strategize on how you will deliver on that value.”

“If you consider yourself a #leader, you must be comfortable taking #risks. Fear has no place in your success equation. #Failure always brings you a gift of #experience. — @carlaannharris #wordsofwisdom”

4. Stefanie Salem, entrepreneur and founder of the Newport Beach Wine & Food Festival: “I weigh fear against, ‘What if I didn’t try that?’ There is so much rejection and so many letdowns, you have to keep trying. There is no easy way to the top, you have to take the stairs. Most people do not see the stairs.” Salem adds, “If you are on a train, and do not like the scenery, it will change. There is always Plan B, C, D, E, F and G. Maybe it was G all along. Everyone has every opportunity to build from scratch and do something. If you talk about it too much, you will come up with a million reasons not to do it. Check off the obstacles one by one as they arrive. What are you waiting for? You learn something from every failure.”

5. Kathleen Turner, iconic actor, performer, author, Take The Lead Wear The Shirt Award winner: “Risk is everything. I don’t take a job I know I can do. For me, every job is a risk to the point of failure. If you are a talented communicator and have the power to change ideas, then the stories you choose to tell are essential. I want to leave a legacy as someone having the guts to do what they think is right. You want to go knowing you did the very best you could do that day.”

“#Risk is everything. I don’t take a job I know I can do. For me, every job is a risk to the point of #failure. If you have the #power to change ideas, then the #stories you choose to tell are essential. — @RealKTurner”

Feldt writes about her friend: “ The actress Kathleen Turner, a very smart cookie when it comes to leadership and life, says that she never repeats her successes — she always seeks new roles unlike those she already has done, roles that will stretch her abilities. She once told me, ‘A full and meaningful life must involve some risks or there can be no growth.’”

6. Kate Isler, co-founder and CEO of TheWMarketplace, author, gender equity, activist, wife, mother, partner, friend, businessperson, and sister: “I never want anyone to think I go into this blindly, especially when you are the breadwinner and have responsibility for five people.” What she calls, “an economic engine for women” is to “focus on harnessing the purchasing power of women to buy from women-owned businesses, professional services, and gender-balanced national brands to change the culture and promote gender equality.” Isler adds, “When you hear about successful women, you usually hear about their trajectory forward and up. That is not always the case, and sometimes the path involves mistakes and missteps. What I did was be very intentional about learning and understanding and taking risks on what I was ready to do, to make that step. When women talk to one another, they immediately find the common ground. Then they think, ‘If she can do that, I can do that.’ We need to feel empowered by one another, not intimidated. We hear it and we can do it if we see it done.”

“Focus on harnessing the #purchasingpower of women to buy from #womenownedbusinesses, professional services, and gender-balanced national brands to change the culture and promote #genderequality. — @IslerKate”

7. Elaine Welteroth, author, journalist, “Project Runway” judge and former editor in chief of Teen Vogue: “Appoint yourself. We have a responsibility to make a difference right where we are. There’s this thing that happens. About age 9, a girl enters into the world with a limitless sense of possibility and it is the world’s labels and stereotypes that hurt the way we dream. It is through the hero’s journey that you recognize all you have lost along the way, and you can look back and claim the parts of yourself. We can all put ourselves in spaces where we are the only one who looks like us and it is a really important learning opportunity to learn what it is like to be a minority and to understand the privilege you have.” She adds, You have to be the risk taker to change the data and change the mission to empower, enlighten, inspire, and amplify the voices of people who do not see themselves reflected. “When you decide to make a bold mission and have a broad impact and you change the stories, it’s not just a nice thing to do, it’s a business imperative.”

“You have to be the #risktaker to change the data and change the mission to #empower, #inspire, and #amplify the voices of people who do not see themselves reflected, it’s not just a nice thing to do, it’s a #businessimperative. — @ElaineWelteroth”

8. Hope Timberlake, coach, trainer and author: “You may be the only woman, only POC, only neurotype, oldest or youngest. But your perspective matters and you are in the room for a reason,” says Timberlake, the author of Speak Up, Dammit: How To Quiet Your Fears, Polish Your Presence and Share Your Voice. “Offer the benefit and impact for your listeners, then you will feel more comfortable sharing your ideas. Set the tone, as you lean in, set the expectation. You can be vocally assertive and name the behavior. Demonstrate the balance of strength and warmth to be effective. It’s so important because we need to celebrate different ideas. Build discomfort immunity.”

9. Priya Rajendran, tech developer, innovator, creator: “Over the last 10 years, I have learned how to take on risks, raise my hand, and welcome and actively chase new challenges. The fear of the unknown will always follow you. But if you approach it with research, data, and objectivity you’ll have clarity and a fearlessness that will make it easy for you to jump into the great unknown that is your future. I enjoy bringing some order to chaos and leading the teams through ambiguity without feeling lost. Risk is the seed that will create beautiful new flowers and a new future. Take risks aggressively – and take them strategically.” A technology expert who lead the team that built Paypal's Wallet, adds, “New opportunities found their way to me instead of me pushing to find new projects. So don’t push to find the next step in your career – leave a little room for some pull.” It is so easy to get comfortable with a job that you are good at and just ‘cruise’ through the years. When you’ve become a domain expert in something that makes you successful at your job, you’ll probably continue doing it for many years. But there is a boundary you must never cross: it’s when you become complacent, comfortable, and things become too easy. This is where your career stalls and your growth gets stumped. You will never be completely ready for a bigger risk, a bigger challenge, or a bigger role. When an opportunity presents itself, go for it and don’t worry about whether you have done that kind of work before or not. As long as you have the curiosity and a learning mindset, you will be able to take on any challenge.”

10. Sarah Saffari, founder of CEOwned. “You can choose to resist and be in a position of struggle with the unknown, or you can become comfortable with uncertainty. You can see the beauty in a potentially negative situation. What I like to think is we are responsible for wiring our own brain.” Saffari adds, “I think there’s never, ever going to be a right time, never the level of certainty you may need. If your goal is financial and location freedom, come to grips that there is no right time. Do you want to work in corporate and live a life fulfilling someone else’s dream? It is a massive risk but the risk of not doing it is much higher.”

A new study of career paths of 757 female leaders (of all races) in the U.S. between 1850 and 2019 “finds that the hurdles they have to clear in order to reach the top are largely the same as those they faced 200 years ago – and that Black women not only have to work harder but also have to take more career-focused risks than their counterparts in order to break through.”

The study shows, “As their careers progressed, white women tended to reduce their risk-taking behaviors, whereas Black women increased theirs. The dual challenges of racism and sexism mean that their leadership journey often involves navigating a ‘double jeopardy.’”

As these leaders attest, the risk you take today is worth it for the tomorrow you envision.

Leadership Takeaway of The Week:

“We need to feel empowered by one another, not intimidated. We hear it and we can do it if we see it done.”

Kate Isler, co-founder and CEO of TheWMarketplace, author, gender equity advocate

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About the Author

Michele Weldon is editorial director of Take The Lead, an award-winning author, journalist, emerita faculty in journalism at Northwestern University and a senior leader with The OpEd Project. @micheleweldon www.micheleweldon.com