Imagine getting to eavesdrop on a candid chat between trailblazing women founders and CEOs – the kind of conversation where they spill the hard truths and “aha” moments they earned on their way to the top. What would they tell their younger selves? What do they wish they had known at the start of their journeys? If you’re an aspiring female entrepreneur in the U.S., pull up a chair. We’ve gathered insights from successful women business leaders, backed by current data and expert advice, to fast-track your learning curve. The good news: women are launching businesses in record numbers (over 1,800 new women-owned businesses every day in the U.S.) and now represent about 42% of all U.S. businesses. The flip side? Female founders still face unique challenges – from raising capital (women-led startups attract only ~2% of venture funding on average) to battling biases (1 in 3 female entrepreneurs reports experiencing sexism as a business owner).
But as any of the seasoned leaders in our “conversation” will tell you, these challenges are surmountable. In fact, many wish they had tackled them with more confidence and less stress earlier on. In a friendly, relatable tone (because we’re in this together!), let’s walk through the lessons successful women in business most often emphasize. From embracing failure to owning your worth, from finding your support network to taking care of yourself, consider this a cheat sheet of wisdom – the kind these women wish someone had handed them years ago. Grab a coffee (or your beverage of choice) and let’s dive in.
Successful women entrepreneurs stress that failure isn’t the end – it’s part of the journey. In fact, many wish they’d learned to take risks and bounce back from setbacks much sooner.
One common refrain among women leaders is “don’t play it too safe.” Jean Case, CEO of the Case Foundation, reflects that in her early career she clung to her comfort zone more than she should have. “Success rarely follows a straight path, and it doesn’t come without taking risks,” Case says. Looking back, she realizes the toughest challenges often led to the biggest opportunities – a perspective she wishes she’d understood earlier to save herself “a lot of angst”. In other words, those detours and roadblocks are often where you develop the grit and new ideas that fuel major growth.
Fear of failure can be especially paralyzing. But failure, as experienced entrepreneurs will tell you, is not a badge of shame – it’s proof you’re trying. Kathy Hannan, former national president of Girl Scouts USA, observes that the best leaders became “stronger, wiser and more confident” by venturing beyond their comfort zones and sometimes falling flat. “Making a mistake is a learning opportunity that can only be realized when we take a risk,” she says, noting that if you fixate on perfection and never stumble, you’re probably playing too small. Understanding this sooner would have been a relief, Hannan admits, because it taught her that every misstep can teach you something and propel you forward.
A great real-life example comes from Spanx founder Sara Blakely, who credits her unusual upbringing with helping her embrace failure. Blakely’s father actually cheered at the dinner table when she talked about something she had failed at each week. “If I didn’t have something I had failed at, he’d be disappointed,” Blakely recalls. This reframed failure in her mind: failure wasn’t about the outcome at all – it was about not trying in the first place. Armed with this mindset, Blakely took a huge gamble in starting Spanx (she had no background in fashion or business) and became the world’s youngest self-made female billionaire by 2012. She observes that a lot of entrepreneurs are held back by fear of failure, and letting go of that fear was “a real gift” her dad gave her. Her advice: don’t wait until you feel 100% ready or certain – go for it, even if it scares you. As Blakely puts it, “What you don’t know can become your greatest asset if you let it”.
This theme comes up again and again in advice columns and interviews with top women entrepreneurs. Take more chances, sooner. Alexa von Tobel, who founded financial-planning startup LearnVest, urges young women to “dream bigger” and not hold back due to fear. “When people look back at their lives, they don’t regret the failures… but the things they didn’t do or the chances they didn’t take,” von Tobel says. “Do the things that scare you because they will pay off in the end.” Similarly, longtime leaders like Lourdes Martin-Rosa, president of Government Business Solutions, stress that thinking outside the box and taking calculated risks is how you expand and find your niche. She wishes she had tapped into certain opportunities earlier and diversified her business sooner, instead of hesitating.
The takeaway: Give yourself permission to be bold. Don’t let the need to be perfect or universally approved freeze you in place. As multiple women echoed: extraordinary things rarely come from playing it safe. If you stumble, it’s not a sign you don’t belong – it’s evidence you’re stretching yourself. Each “failure” is really just a step in progress. Adopt a “fearless mindset” by viewing setbacks as learning opportunities, not final verdicts. The sooner you start taking swings – even if some miss – the faster you’ll learn, adapt, and score that home run.
Imposter syndrome – that nagging self-doubt and feeling of being a fraud – is something even the most accomplished women confess to battling. “You’re not the only one who feels insecure – everyone does,” says Havenly co-founder Lee Mayer, who reminds her younger self (and all of us) not to let that insecurity hold you back from pursuing big dreams. In hindsight, many women leaders wish they had trusted their own abilities sooner instead of over-preparing, over-qualifying, and second-guessing themselves at every turn.
It doesn’t help that society often conditions women to be overly cautious. Studies have shown women tend to underestimate their readiness – for example, applying for jobs or opportunities only when they meet all the criteria, whereas men jump in when they meet about 60%. Leadership coach Sally Helgesen (co-author of How Women Rise) calls perfectionism one of the most common habits holding women back. Women often internalize the message that “I have to be perfect to get anywhere,” Helgesen notes, and as a result they shy away from risks or delegating tasks. The irony is that at higher levels, it’s bold vision and willingness to fail that are most valued – not flawless execution of small tasks. In Helgesen’s words, when women are passed over for top jobs, it’s often because “they’re not seen as sufficiently bold.” Her advice (and one she gives to her coaching clients): let go of the need to be the A+ student all the time. Striving for perfection and people-pleasing might have earned you praise early in your career, but it can become counterproductive as you grow. Give yourself permission to be “good enough” and confident in that, rather than overworking or quietly hoping others will notice your worth.
Many successful women echo this sentiment of cultivating confidence. “Be bold,” urges Amy Bowen, a communications director, who admits even after a decade as a leader she sometimes doubted herself. She realized that often “if you think someone else has it all figured out, chances are they don’t”. In other words, everyone is winging it to some degree – so don’t let intimidation or comparisons stop you from taking your shot. Trust your instincts. Nicole Opas, a VP at Zynga, spent years in the tech industry trying to “be one of the guys” to fit in, but eventually realized the immense value of her distinct perspective. “I’d tell my younger self that being one of the women is as valuable, if not more, than acting like one of the men,” Opas says. Once she started appreciating her own approach and insights, her leadership impact grew.
A powerful confidence-booster can be reminding yourself of what you already bring to the table. As entrepreneur Meera Oliva advises, “Work on developing your strengths, not your weaknesses…you will be far more successful being great in the areas where you naturally excel.” By playing to your strengths and acknowledging your expertise, you counteract that inner critic. At the same time, surround yourself with people who complement your skills (more on that in the next section) so you don’t feel pressure to be great at everything.
Also, don’t hesitate to seek feedback and mentorship as confidence-building tools. Instead of quietly worrying whether you’re doing it right, ask for input from trusted advisors or peers. As Sarah Gerber, co-founder of Zero Gap, learned, “worrying about perception and acceptance is wasted energy…Instead, seek thoughtful and productive feedback and ignore everyone else.” Proactively getting perspective can reassure you that you’re on the right track – or give you constructive tips to improve – both of which erode self-doubt.
The takeaway: You are more capable than you think! Almost every woman at the top will tell you she wrestled with insecurity at times. The difference is, she pushed through it. Remind yourself that feeling unsure is normal – it’s not a sign you can’t succeed. Silence that inner critic by focusing on your strengths and wins. Replace “I’m not ready” with “I’ll learn as I go.” And if the voice of doubt creeps in, channel your inner coach: Be bold, back yourself, and remember that even your role models had to adopt confidence before they had all the answers. As one female founder wisely noted, “chances are, everyone else is figuring it out just like you – and it will all be OK.”
Perhaps the biggest lesson many women entrepreneurs say they wish they’d learned earlier is this: Don’t try to be a one-woman show. Building a business (or a career) is not a solo sport, and believing you have to “do everything yourself” can hold you back or burn you out. Yet a striking statistic shows many women fall into the solo trap – about 82.5% of women entrepreneurs operate without any partners, compared to 69.8% of men. In other words, women are more likely to be solopreneurs, often out of a sense that they must prove themselves or because they haven’t found the right support. As a result, they carry 100% of the load, which can limit growth and make the journey unnecessarily hard.
Take it from Ursula Burns, who became the first Black female CEO of a Fortune 500 company (Xerox) and attributes much of her success to leaning on others. “Great leaders aren’t just confident and decisive — they also habitually lean on others,” Burns says. In her view, leadership means “bringing many people along” with you, not charging ahead alone. Even as CEO, Burns recognized that for “every great success we had, certain people knew more about pieces of it than I did”, and that she had to rely on their expertise. “I had to follow them as much as they had to follow me,” she explains, emphasizing that no one succeeds in isolation. If she could tell her younger self one thing, it might be this: build a strong team and trust them. You don’t have to have all the answers; you just need to surround yourself with people whose knowledge and talents fill in the gaps.
This applies whether you’re running a startup or climbing the corporate ranks. Mentors, sponsors, partners, employees, peers – cultivate your circle of support. Many female founders admit they waited too long to hire help or seek mentorship. They thought they were saving money or being tough by “figuring it all out” alone, but in hindsight that slowed their progress. “Something I wish I had known earlier in my career was the importance of networking and building relationships,” says Cherry Fermor, a small business owner. A strong network of contacts and collaborators can open doors to resources, advice, and opportunities that you’d never access on your own. Opportunities often come via people. As the saying goes, your network is your net worth – and women who embrace this sooner benefit greatly.
If you’re early in your journey, start by finding mentors and sponsors who believe in you. What’s the difference? Mentors give guidance and moral support, but sponsors actively advocate for you and create opportunities. Longtime business leader Gloria Larson urges young women to find both, noting that “mentors are great, but sponsors are even better.” A sponsor will use their clout to recommend you for high-visibility projects or alert you to opportunities and “hidden” pitfalls. Larson cites research showing that sponsored women are far more likely to ask for raises and stretch assignments than women without sponsors – and they report higher satisfaction with their career progress as a result. In short, having someone in your corner who will speak your name in a room of decision-makers is game-changing. Don’t be afraid to seek out that champion; often, experienced leaders want to pay it forward and help upcoming female talent. But (as one executive quipped) “they can’t help you if they don’t know where you want to go” – so voice your goals and welcome the support.
Beyond mentors, build your peer support network too. Other women entrepreneurs can be an invaluable source of strength and knowledge. There are formal groups, online communities, and local meetups for women in business – tap into them. Sharing experiences will remind you that you’re not alone in your struggles (someone else has faced that tricky client, that cash flow crunch, or that work-life dilemma). As business owner Natalie Arney notes, “Never underestimate the power of community… We [women] bounce ideas off one another, refer each other for work, and even provide a shoulder to cry on.” Sometimes just knowing that others get it is enough to keep you going on a tough day.
Finally, if you have co-founder or hiring opportunities, choose people who share your vision and values. A hard-won lesson for many: one negative or unsupportive team member can drain you. “Don’t spend time with people who sap your energy or are negative about the work,” advises entrepreneur Liza Kirsh, “In the long run, the success of your business depends on the power of your team. Find your people!”. It’s OK – even empowering – to admit you can’t do it all. Hire or partner with those who complement your skills and enthusiasm. Entrepreneur Cristina Mariani-May says she would tell her 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 when you feel overwhelmed.” When you have a circle of trust, you’ll be amazed how much farther and faster you can go.
The takeaway: Success is a team sport. Don’t isolate yourself out of pride or fear. Ask for help when you need it – it’s a sign of wisdom, not weakness. Proactively build a network of mentors, sponsors, peers, and partners. Invest in relationships as much as in your product or skills. As former Secretary of State Madeleine Albright famously said, “There’s a special place in hell for women who don’t help each other.” Flip that around, and there’s a special kind of heaven in the success we can achieve when we do lift each other up. Find your tribe, lean on them, and pay it forward when you can.
Many successful women in business share this retrospective insight: I wish I had advocated for myself more boldly. Early in their careers or ventures, they often hesitated to ask for what they wanted – whether it was a raise, a promotion, a funding deal, or a big client – and later realized the cost of that silence. Leadership coaches observe that women frequently expect hard work alone to merit rewards, whereas men are more likely to actively negotiate and promote themselves. The result? Women can get overlooked or underfunded not because they lack ability, but because they didn’t voice their value or aspirations. Don’t let that be you.
If you’re an entrepreneur seeking capital or a client contract, remember that business is often a negotiation. Know your worth – and add tax, as the saying goes. The data is sobering: female entrepreneurs receive only about 2% of venture capital dollars, and even in small business loans, the average loan for women-owned firms is roughly 50% smaller than for male-owned firms. Some of this is due to systemic bias, but experts also note women may be more conservative in what they ask for. In one survey, women founders reported needing only half as much startup capital as men, and were twice as likely to rely on personal or family funds instead of outside investors. While resourcefulness is good, undercapitalizing your business can stunt its growth. Lesson: Don’t shortchange yourself. If you need financing, go for it – and seek out investors who respect and understand your vision.
To that end, it can help to target “female-friendly” investors and support networks. Michelle Maiellaro, a startup founder, advises doing your homework to find venture firms or angel networks that “walk the talk of diversity and inclusion.” Connect with other women founders to get referrals to investors who have a track record of backing women-led companies. Not only will you increase your odds of funding, but you’ll feel less alone knowing others have navigated the same path. As Maiellaro points out, knowing you’re not alone in your struggles can boost your morale during the rough patches of fundraising.
In the workplace context, if you’re aiming for advancement or better pay, make your ambitions known. Krista Anderson, an executive at Okta, says one of her key lessons was realizing that “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.” Early on, she always assumed her bosses knew she was hungry for more – but people aren’t mind-readers. Once she began explicitly communicating her goals and asking for opportunities, she found much more support. It’s not bragging or pushy to share your aspirations; it shows initiative. Good managers will respond by helping you plot a path to get there. And if they don’t, it might be time to seek a new environment that will.
Speaking up also means learning to say “no” or set boundaries when needed – which is a part of knowing your value. Early in their careers, many women over-committed and said yes to every ask, often to avoid disappointing others. Over time they learned that this can lead to being overworked and under-valued (people can take advantage of a constant yes). As one entrepreneur put it, “we shouldn’t have to work harder and for less pay to prove our value.” If a client or partner doesn’t appreciate what you bring to the table, you have the power to walk away. “Only work with those who appreciate you and charge accordingly. Your services are valuable. Don’t sell yourself short,” advises business owner Alexis Ankersen. In hindsight, she wishes she hadn’t tolerated condescending clients or bargain pricing – respect yourself enough to set fair terms.
Finally, speaking up is essential not just for yourself, but for changing the culture. Successful women often become advocates for other women. They call out biases, push for fair policies, and insist on diversity. You can too, even in small ways. For example, if you catch someone talking over you in a meeting, politely reclaim the floor. If you notice only the men are being asked to lead a project, throw your hat in the ring. The more we assert our presence and value, the more the business world will adjust to hear us. As Sheryl Sandberg famously said, “I want every little girl who’s been told she’s bossy to be told again that she has leadership skills.” In practice, that means reframing assertive behavior as positive. Don’t shy away from being bold, decisive, and passionate in your communication – those are leadership qualities.
The takeaway: Closed mouths don’t get fed. Whether it’s negotiating your prices, pitching to an investor, or asking for a new role, don’t wait for permission to go after what you deserve. Be clear about your goals and needs. The answer might be a ‘yes’ more often than you think – and even if not, you’ll gain respect for advocating for yourself. Know your worth (in dollars and in talent), and don’t settle for less. By speaking up, you not only advance your own interests, but also pave the way for those coming up behind you.
If there’s one thing nearly all veteran women entrepreneurs agree on, it’s the importance of being true to yourself. Early in your career or when you’re the only woman in the room, you might feel pressure to conform – to act more like the (male) leaders you see, or to fit some corporate mold. But time and experience will prove that your authenticity is a superpower, not a liability. The sooner you embrace what makes you you, the sooner you’ll tap into your full potential.
Many women wish they’d learned this earlier. Linda Kozlowski, COO of Etsy, shares a piece of wisdom from her dad: “being successful is not about changing who you are to fit the circumstance or meet expectations…It is more important that you bring your true, authentic self to the table.” When she finally let go of trying to “play a role” and instead leaned into her own style and values, she found she became a better leader. Why? Because authenticity builds trust. People can sense when you’re genuine, and they’re drawn to it. It’s exhausting and ultimately ineffective to wear a persona that isn’t you. Kozlowski’s advice: Amplify the traits that make you uniquely qualified for your role – those might be empathy, creativity, attention to detail, humor, or anything else – and don’t worry if they’re different from how others lead. Different is good. In fact, difference can be your edge.
Being a woman in business is still a differentiator – there’s no denying that. Instead of seeing it as an awkward disadvantage (“ugh, I’m the only woman on this panel/team/etc.”), flip the script. Embrace that difference and use it. As Cristina Mariani-May puts it, “don’t be concerned with the fact that I’m usually the only woman in the room, but rather, embrace that difference and use it as an advantage.” Your perspective as a woman – shaped by your experiences – can lead to insights others in the room might miss. For example, women often excel at considering customers’ needs, fostering team collaboration, and spotting market gaps that male-dominated teams overlook. Countless successful products and companies (from 23andMe to Bumble to Spanx) were born precisely because a woman founder said, “hey, there’s a need here that’s not being met.” So, lean into the qualities and experiences that set you apart. As one female tech executive advised, “a woman’s perspective holds so much value…my approach to leadership as a woman is appreciated and valued” once she had the confidence to assert it.
Authenticity also means holding onto your core values as you climb. In the hustle, it’s easy to get swayed by others’ definitions of success or to mimic competitors. But the women who last and thrive in business do so on their own terms. Take Sara Blakely again as an example – she infused Spanx with her quirky, positive personality (e.g. including her own face and funny messages on product packaging) because that’s who she is. People found it refreshing and relatable, and it became part of the brand’s DNA. Similarly, if you value integrity, creativity, family – whatever it is – don’t feel you have to shelve those to “get ahead.” On the contrary, sticking to your values will attract the right partners and customers. As Kate DeGon, founder of an organizational change firm, says, “Never forget what made you successful. It’s likely grit, tenacity, self-confidence, intellect, willingness to take risks, dedication, belief, and a tribe of supporters that got you here…Always remain authentic to who you are; remember, it’s what got you here, and it’s what will get you there.” In short, know your “true north” and don’t stray from it. People are drawn to authenticity but back away from an impersonation.
Sometimes authenticity requires courage, especially in environments not used to diversity. But progress is being made. The business world is slowly recognizing that leaders come in many forms. You being yourself (and succeeding) expands the narrative of what a leader looks like – which helps everyone coming after you. As more women and people of color and varied backgrounds lead in their authentic ways, the old stereotypes break down. In the meantime, support systems (like the communities we discussed) can reinforce your resolve to stay true. When you swap stories with other women who succeeded by not conforming, it validates your choice to do the same.
The takeaway: Authenticity isn’t just a buzzword – it’s a practical strategy. You will perform better, have more genuine relationships, and differentiate your business if you are unapologetically yourself. Don’t dilute your personality or hide aspects of your identity; those might be the very things that spark new ideas or connect you with your audience. As one CEO said, bring your whole self to work – it’s the only way to become the best leader you can be. And if anyone ever comments that you’re “too this” or “too that” (e.g. too soft, too bold, too whatever), remember: what’s “too much” to them might be your magic. Own it. Your authenticity is your power.
In the frenzy of building a business or career, it’s easy to put yourself last – to burn the candle at both ends in the name of ambition. Many high-achieving women admit they ran themselves ragged at some point, trying to “have it all” or prove their dedication. The lesson they wish they learned sooner? Burnout helps no one. Success is a marathon, not a sprint (as Brooks Running CMO Melanie Allen likes to remind young professionals), and you can’t run that marathon if you’re running on empty.
So, let’s bust a myth: working 24/7 with no rest is not a badge of honor – it’s a recipe for poor performance and misery. As entrepreneur Jaime Ellithorpe notes, one of the toughest parts of being a female entrepreneur is juggling your business goals with personal needs and family commitments. The answer is not to neglect one or the other, but to plan intentionally for both. Ellithorpe’s practical tip is to literally schedule your life: “Create a calendar and make sure all your top priorities are penciled in first – the things that matter to you personally (self-care, family time, friends, etc.). After this, list the top 2-3 things that only you can do to grow your business. The rest can be delegated or postponed.” By structuring your time this way, you ensure that you’re tending to your health and relationships – the foundations that allow you to excel at work – while focusing your work hours on the most high-impact tasks only you can do. Everything else, automate it or get help. In short, work smarter, not just harder.
Several women leaders also mention the importance of setting boundaries. Early on, you might feel you have to be available around the clock to clients or that you can’t take a break lest everything falls apart. But in reality, taking breaks and recharging will make you more effective. It can be as small as not checking email after a certain hour, or as significant as saying no to projects that aren’t a hell-yes. As one founder quipped, “No is a complete sentence.” By carving out downtime, you’ll return to your venture with fresh energy and creativity. Remember, you are the driver of your business; if you break down, the business stalls too. So maintenance (sleep, exercise, mental health days) is non-negotiable.
Another aspect of sustainable success is keeping perspective. It’s okay (even normal) if your path is non-linear. Some days you might need to pause to care for a child or an elderly parent, or you might choose to take a year slower for personal reasons. These decisions do not make you less ambitious – they make you human. Many women who have had long, fruitful careers will tell you there were ebb and flow periods. “Treat your career as a marathon, not a sprint,” as Melanie Allen advises, meaning pace yourself and allow for life’s seasons. You can’t do everything at once, but over a span of years you can do a lot of amazing things.
It’s also worth noting that self-care isn’t just about you – it can be a leadership strategy. When your team (or future team) sees you modeling balance, they feel permission to take care of themselves too, which leads to a healthier, more productive workplace. Win-win. In contrast, if they see you never sleeping and never seeing your family, they’ll think that’s the expectation and likely feel unhappy or burnout-prone themselves. Leaders like Arianna Huffington have famously advocated for wellbeing, after she herself collapsed from exhaustion years ago. The bottom line is: you are not a robot, and that’s a good thing. Honor your human needs. As the saying goes, you can’t pour from an empty cup.
The takeaway: Your business thrives when you (the driving force behind it) are at your best. So prioritize the fundamentals: sleep, nutrition, exercise, time with loved ones, and hobbies that bring you joy or stress relief. Schedule personal time just as you schedule meetings. Don’t be afraid to delegate or delay tasks to protect your well-being. Remember that a sick, stressed, or chronically tired version of you won’t perform half as well as a healthy, inspired one. Taking care of you is not indulgent – it’s integral to long-term success. As one wise entrepreneur put it, if you drop a ceramic plate (your health, family), it could crack or shatter; if you drop a plastic plate (most work tasks), it will bounce back. Know which are which, and guard those ceramic plates with your life.
We’ve covered a lot of ground, so let’s summarize some practical, action-oriented tips drawn from these lessons and stories. Consider this your cheat sheet going forward:
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