Women Leaders

31 Powerful Women Share the Advice They'd Give Their Younger Selves

Check out these hard won lessons.
31 Powerful Women Share the Advice They'd Give Their Younger Selves
Image credit: FangXiaNuo | Getty Images
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
15+ min read

Entrepreneurial success is all about overcoming obstacles. While mentors are an integral part of navigating pitfalls and potential opportunities over the course of a career, it's important to remember that sometimes the moments that can feel like the worst setbacks can actually lead to some of your biggest opportunities.

Read on for encouraging advice from 31 women leaders.

Teresa C. Younger, president and CEO of The Ms. Foundation for Women

Teresa C. Younger, president and CEO of The Ms. Foundation for Women
Image credit: The Ms. Foundation for Women
"First, recognize that there is always a tomorrow, so you don't need to get everything done right away. Second, know that there is no right way, so it's OK if you take a left turn and go around the block a couple of times in life. Finally, to treat yourself kindly and to forgive the mistakes that you make, just as you forgive others."

Maggie Drake, co-founder and CEO of Bandolier

Maggie Drake, co-founder and CEO of Bandolier
Image credit: Courtesy of Maggie Drake

"I would tell my younger self to take more risks and reassure her that she is way more confident in her abilities than she thinks. I would tell her to chase the job she wants, not the money, and surround herself with role models she wants to emulate."

Nikki Pechet, VP of marketing at Thumbtack

Nikki Pechet, VP of marketing at Thumbtack
Image credit: Thumbtack

"That everything will turn out alright if you do two things: Consistently make decisions that are in line with your values, and be willing to work harder than the people around you 90 percent of the time.

Throughout my teenage years and well into my 20s, I spent a lot of time and energy worrying about the future, worrying if I would get where I wanted to go. I wish I could go back to tell myself in those moments of doubt at 16-years-old, 21, 27, 'work hard. Do the right thing. Not only will it all work out. It could be even better than you could ever imagine.'"

Monica Long, SVP of marketing at Ripple

Monica Long, SVP of marketing at Ripple
Image credit: Ripple

"Be more confident. You know more and are capable of more than you think. I read that women typically need to feel 100 percent certain they can do something before committing to do it, while men only need to feel about 60 percent certain. That uncertainty plays out as women missing more career-building or career-defining opportunities than men, when they're probably just as (if not more!) capable. At worst, you miss the mark or totally fail. Those experiences are valuable to learn from."

Beth Monaghan, CEO and co-founder of InkHouse

Beth Monaghan, CEO and co-founder of InkHouse
Image credit: InkHouse

"Trust yourself -- your talent, your ideas and your gut. You'll waste way too much time at the start of your career trying to mold myself into what you think success looks like (or what someone else tells you it should be). You can't build strong relationships or a strong business by turning yourself into someone else."

Donna Peeples, chief customer officer at Pypestream

Donna Peeples, chief customer officer at Pypestream
Image credit: Pypestream

"One of the biggest pieces of advice that I would give myself is not just 'lean in' -- you have to leap in! Take every opportunity that comes your way and run with it. When you come to a fork in the road, be brave and take the harder road -- it will certainly pay off in the long run.

It is equally important to think about the contribution you want to make through your career and not get stuck on the job title. There may be times that you will need to make lateral career moves for opportunities to do the things you love or work with people who will later be your mentors, but it's worth it. Continue to learn throughout your career."

Beth Devin, head of Innovation Network and Emerging Technologies at Citi Ventures

Beth Devin, head of Innovation Network and Emerging Technologies at Citi Ventures
Image credit: Citi Ventures

"Invest in knowing yourself. Don't be afraid to experiment, ask questions and be honest with yourself. Recognize when you are energized and excited about the day to come and pay attention to when you are stressed and/or bored. Avoid falling into a trap of pleasing others. The better able you are at identifying environments and roles that leverage your innate strengths and passions, the more work becomes rewarding vs 'just a job.'

Build your support system early. As you get started in your career and gain more experience, it's natural to want to break loose and go at it alone without any guidance. But it's never too soon to seek out advisors, mentors or a peer group to learn from and ask for help. This investment early on will pay dividends many times over as you grow, mature and rise up in your career. Always remember to give back and build up your 'chits' for when you need help.

Know you can do it all but not all at the same time. Give yourself a break."

Barbara Goose, CMO at John Hancock

Barbara Goose, CMO at John Hancock
Image credit: John Hancock

"Don't be afraid of a challenge. Take each obstacle as an opportunity to learn and grow into an even better version of yourself. Also know to accept help when it's offered and ask for help when it's needed. That's part of how you build a strong network, and the people you surround yourself with will be so valuable in the future, throughout not just your career but also your personal life."

Nidhi Gupta, SVP of product and engineering at Hired

Nidhi Gupta, SVP of product and engineering at Hired
Image credit: Hired
"The advice that I would give to my younger self is to be yourself. The worst thing we can do to ourselves as developing women is feeling compelled to assimilate. If you ever feel like you aren't in a position where you're constantly growing and learning, take a step back and ask yourself if you're staying true to yourself. Evaluate if you're surrounding yourself with people and environments that allow you to speak your mind and show your talents."

Jean Case, CEO of the Case Foundation and chairman of the board of trustees at National Geographic

Jean Case, CEO of the Case Foundation and chairman of the board of trustees at National Geographic
Image credit: National Geographic

"In my experience, success rarely follows a straight path, and it doesn't come without taking risks. Indeed, in my own life the road to achievement has been filled with bumps, potholes and extreme curves. I wish I had better understood that it was actually times of greatest challenge that led to the greatest opportunities -- it might have saved me a lot of angst along the way. I wish I had more fully embraced Albert Einstein's quote that 'failure is success in progress,' because looking back on my life now that is eminently clear to me. No one likes or wants failure but taking risks means the outcome is by definition, uncertain. But a fearless mindset in business and in life helps push through the fear or reality of failure with perseverance in pursuit of big ideas, big opportunities -- or simply to strike out toward a bold future. The easiest thing to do is to stay in the comfort zone and avoid taking risks, but the truth is rarely do extraordinary things in life come from playing it safe."

Kathy Hannan, national president and chairman of the board of Girl Scouts of the USA

Kathy Hannan, national president and chairman of the board of Girl Scouts of the USA
Image credit: Courtesy of Kathy Hannan

"Making a mistake is a learning opportunity that can only be realized when we take a risk. Being fixated on perfection may lead to playing it too safe, and stifle personal growth. The best leaders in every field have become better, stronger, wiser and more confident through taking risks, venturing beyond their comfort zones. As a result, these visionaries sometimes made mistakes and experienced failure. Ultimately, if you want to succeed in life, you need to get comfortable with knowing you will have those 'learning opportunity' moments; seize them, embrace them, learn from them and move forward! Understanding this sooner in life will prove very beneficial and will serve you well throughout your journey."

Maria Jimenez-Lara, CEO of the Naples Children & Education Foundation

Maria Jimenez-Lara, CEO of the Naples Children & Education Foundation
Image credit: Roland Scarpa Photography for Naples Illustrated
"I would advise my younger self to work hard and smart by approaching my goals with focus, discipline and sound planning. Once I learned to truly hone-in on projects that required focused planning, regardless of size, I was able to view them differently, more strategically, and thrive in helping others. I would also let my younger self know that there will be ups and downs, good days and difficult ones. Working with at-risk children is not for the faint of heart and I would want my younger self to come into this field knowing it's all worth it, because it really is."

Nicole Opas, VP of games at Zynga

Nicole Opas, VP of games at Zynga
Image credit: Zynga
"Being in the video game industry for nearly two decades, I've worked in mostly male workplaces. When I was younger, I felt like I had to be one of the guys to be included and talk like them to get my point across. What I've realized now is that a woman's perspective, especially in gaming, holds so much value to making a quality consumer experience, and my approach to leadership as a woman is appreciated and valued. I'd tell myself that being one of the women is as valuable, if not more, than having to act like one of the men."

Alexa von Tobel, CFP, founder and CEO of LearnVest.com

Alexa von Tobel, CFP, founder and CEO of LearnVest.com
Image credit: LearnVest.com
"If you have a dream, push yourself to dream bigger. You need to work hard and aim high because no one else is going to do it for you. Studies have shown that when people look back at their lives, they don't regret the failures or mistakes they made along the way, but the things that they didn't do or the chances they didn't take. So, take risks and do the things that scare you because they will pay off in the end."

Rachel Sumekh, founder and CEO of Swipe Out Hunge

Rachel Sumekh, founder and CEO of Swipe Out Hunge
Image credit: Swipe Out Hunge
"When I was starting out I would have six to eight coffee meetings a month. It's critical to hear how different people respond to your idea. I wish I knew that the value of these meetings wasn't so much about getting advice, no one had your solution, but rather realizing how much it strengthens you as a leader to be able to hear all types of feedback (even apathy) about your venture. It helps you better understand the different intentions behind people's feedback and prepares you to respond to any type of person when it matters and take things less personally.

Lisa Mae Brunson, founder of Wonder Women Tech

Lisa Mae Brunson, founder of Wonder Women Tech
Image credit: Wonder Women Tech
"First, I would grab my younger self and enfold her in a great big hug and let her know how worthy and loved she is. That sense of confidence is the foundation for all success. Then I would look her in the eyes and tell her that no matter what anyone says to you, no matter how 'qualified' you are, or the challenges you will face -- you are capable of great things, and you can and will succeed at whatever you set your mind and actions to achieve. Don't ever give up on what you feel in your heart is your purpose to do. There is no rule book, or guidelines, or a 'right way' to build a dream -- so take the risks, make those leaps of faith, and show up daily."

Sarah Gerber, co-founder and CEO of Zero Gap

Sarah Gerber, co-founder and CEO of Zero Gap
Image credit: Zero Gap

"Worry less about what other people think. Although I did this to a degree by carving my own path and taking an untraditional approach, any time or thought given to worrying about perception and acceptance is wasted energy. I could have used that energy to create even more. Instead, seek thoughtful and productive feedback and ignore everyone else. Also, be more aggressive and intentional in finding mentors, even if they are your peers. It is so important for learning what you don't know, you don't know."

Lee Mayer, CEO and co-founder of Havenly

Lee Mayer, CEO and co-founder of Havenly
Image credit: Havenly

"Don't minimize your goals. It's important to dream big! Just remember that you're not the only one who feels insecure -- everyone does. Don't let that hold you back from pursuing your dreams."

Gloria Larson, president of Bentley University

Gloria Larson, president of Bentley University
Image credit: Courtesy of Gloria Larson

"The best advice I would give my younger self and anyone starting their career, but particularly young women: find good people who will help guide you along your journey. Mentors are great but sponsors are even better. Here's why. A sponsor takes a more active role than a mentor in promoting his or her prot?g?'s success. For example, a sponsor will suggest a young professional for a highly visible project, put him or her forward for 'stretch' assignments, and secure approval for that person's professional training. Sponsors might alert their prot?g?s to hidden dangers like an unspoken problem with a colleague, or they might suggest connecting with one of an organization's hidden influencers.

And there is plenty of data that supports this. According to research conducted by the Center for Talent Innovation, the majority of women (70 percent) and men (67 percent) are hesitant to ask their boss for a raise, and that sponsored women are more likely to request pay increases and stretch assignments than unsponsored women. In addition, 70 percent of sponsored men and 68 percent of sponsored women report satisfaction with their pace of professional progression, while only 57 percent of their unsponsored peers report the same."

Amy Bowen, director of communications at Consigli Construction Co.

Amy Bowen, director of communications at Consigli Construction Co.
Image credit: Courtesy of Amy Bowen

"Be bold. Trust yourself and don't let the fear of failure or outside noise ever stop you from taking a chance at trying something different. If you think someone else has it all figured out, chances are they don't. They're figuring it out just like you. And it will all be OK.

When I was at a crossroads earlier in my career, I started my own business and followed my passion. I pushed myself outside my comfort zone and more than anything that experience gave me confidence to have an open mind when it comes to thinking about choosing pathways in life. I never realized how important that was at the time."

Meera Oliva, CMO at Gradifi

Meera Oliva, CMO at Gradifi
Image credit: Meera Oliva

"Work on developing your strengths, not your weaknesses. You will be far more successful by being great in the areas where you naturally excel, and surrounding yourself with people who are great in the areas where you are not."

Krista Anderson, chief customer officer at Okta

Krista Anderson, chief customer officer at Okta
Image credit: Courtesy of Krista Anderson

"Most leaders want to invest in your career, but they can't help you get there if they don't know where you want to go. I've always thought big and set my sights on roles where I saw I could have greater impact and influence. I made that clear to my managers -- and if you aren't doing that today, start sharing your aspirations with your leadership now. With that in mind, I also would tell my younger self to balance lateral career moves with vertical ones. While promotions and moving up the ladder show your value and ambition, it's important to expose yourself to different roles and organizations either within or outside of your company. Doing so allows you to explore areas that will define and fuel your interests and drive you to produce great work - not to mention they'll make you a much more well-rounded leader in the long run. Don't get caught up in advancing in your job just for the sake of advancement. Once you've identified what type of career you want to have, that's when you should focus on excelling in it. Early on, it's better to go broad, not up."

Glenda McNeal, president of enterprise strategic partnerships at American Express

Glenda McNeal, president of enterprise strategic partnerships at American Express
Image credit: Courtesy of Glenda McNeal

"Imagine the unimaginable and believe in the possibilities. While I have always been a planner and very responsible in my choices, I have learned there is far more in life that I do not control and letting go can create more opportunities. I would remind myself to make intentional choices and take deliberate actions. To live confidently and boldly, unapologetically."

Koel Thomae, co-founder of Noosa Yoghurt

Koel Thomae, co-founder of Noosa Yoghurt
Image credit: Courtesy of Koel Thomae

"To travel and explore the world while you're young. I wouldn't change much though, to be honest. I was really on this walkabout and adventure and didn't follow a linear career path to Noosa and the combination of all the different experiences. Traveling a lot, especially traveling alone, helped form this passion for food and entrepreneurial business. I would go back and tell myself to travel more because once you do get locked into a career path you don't get to do that quite as much. For me, traveling feeds my soul and now having this business, travel is so important to explore trends and new food ideas."

Cristina Mariani-May, CEO of Banfi Vintners

Cristina Mariani-May, CEO of Banfi Vintners
Image credit: Courtesy of Cristina Mariani-May

"I would tell my younger self, 'don't try to do everything, and don't expect to know everything. Surround yourself with smart, capable, creative people you can trust, and lean on them for help in situations where you feel overwhelmed. Be open to listening from everyone on your team -- you may be surprised at who gives you solutions and ideas that can ease a challenge or break new ground.' Also, I'd tell myself not to be concerned with the fact that I'm usually the only woman in the room, but rather, to embrace that difference, and use it as an advantage."

Lourdes Martin-Rosa, president of Government Business Solutions

Lourdes Martin-Rosa, president of Government Business Solutions
Image credit: Courtesy of Lourdes Martin-Rosa

"Take risks to help you expand and grow. As a young business owner, I would advise others like myself to explore 'thinking outside of the box.' Think about entrepreneurship. Harness innovation in every facet of business. Confidence builds reliability and trust, so believe in your mission and stay focused on your goals. From a tactical business perspective, I wish I would have tapped into certain opportunities earlier in my career. Women-owned businesses are underrepresented in so many places. Diversifying my business to serve both the public and private sectors has been instrumental to growing and finding my niche, which is one reason that I am so passionate about helping other businesses do the same."

Linda Kozlowski, chief operating officer at Etsy

Linda Kozlowski, chief operating officer at Etsy
Image credit: Courtesy of Linda Kozlowski

"When I was first starting out, my dad gave me a lot of valuable advice. I admittedly didn't fully grasp it all at the time, but have come to really appreciate his wisdom. The most powerful advice he gave was that being successful is not about changing who you are to fit the circumstance or meet expectations -- whether it be that you're the only woman in the room or have different experience then everyone else. It is more important that you bring your true, authentic self, to the table. It is only then that you're going to be the best leader and amplify the traits that make you uniquely qualified for the role you've been tasked with."

Melanie Allen, chief marketing officer at Brooks

Melanie Allen, chief marketing officer at Brooks
Image credit: Courtesy of Melanie Allen

"The biggest piece of advice I would give my younger self is that you should treat your career as if it's a marathon, not a sprint, and there is no right way to get from the start to the finish line. Similar to a marathon where you may need to adjust training based on how you feel, it's important to assess and adjust your career direction based on what's right for you in the moment. While advice from mentors along the way can help you recognize possibilities, your career is ultimately your own journey to own."

Jennifer Glanville, brewery manager and brewer at Sam Adams

Jennifer Glanville, brewery manager and brewer at Sam Adams
Image credit: Jennifer Glanville

"When I was younger, I'd have never thought about how important it was to establish my own brand and take ownership of my accomplishments. I've always been a natural leader and so focused on building up my teams, that at times my own successes took a back seat. It's not about accolades but more about owning your achievements and recognizing your success as an individual. As I've grown in my career, I've learned celebrating my successes only makes me a better, more respected leader."

Jessica Spaulding, owner and founder of Harlem Chocolate Factory

Jessica Spaulding, owner and founder of Harlem Chocolate Factory
Image credit: Courtesy of Jessica Spaulding

"Don't confuse advice with criticism. When I started Harlem Chocolate Factory, people would give me criticisms disguised as guidance. As a woman and new business owner, I felt obligated to take each of these suggestions to heart, but I quickly realized that advice without a plan or solution is not advice at all. I learned to weave out the criticism and focus on the mentorship that would add value to my business."

Sarah Gerber, co-founder and CEO of Zero Gap

Sarah Gerber, co-founder and CEO of Zero Gap
Image credit: Courtesy of Sarah Gerber

"Worry less about what other people think. Although I did this to a degree by carving my own path and taking an untraditional approach, any time or thought given to worrying about perception and acceptance is wasted energy. I could have used that energy to create even more. Instead, seek thoughtful and productive feedback and ignore everyone else. Also, be more aggressive and intentional in finding mentors, even if they are your peers. It is so important for learning what you don't know, you don't know."

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