By: Christina Salerno, Chief Dreamer of Dreamers & Doers, a curated community and PR Hype Machine® for extraordinary women entrepreneurs
Ask founders which moments tested their confidence most, and many will point to the ones with an audience: naming a price, pitching an idea, launching something unfinished, or speaking up in a room full of longer résumés.
Leaders from the Dreamers & Doers community say those exposed moments are also where their confidence increased. Here, they share how they learned to ask for more, walk into rooms before anyone invited them, and let people see their work before it felt finished.
I Practiced Naming My Value
For many leaders, the first real test of confidence is whether they can stand behind the value they provide.
Hope Alcocer, owner and consultant of Wonder Woman Media, had to fight the all-too-common drive to lowball herself to win clients. She rebuilt her business around retainers, priced at what the work is actually worth.
She’s honest that it still takes practice. “If asking for what you are worth still gives you a nervous stomach or clammy hands, it’s okay… same! It’s like a muscle; the more you work it, the stronger it gets.”
Natanya Wachtel took a more inventive route. She built a game for her company New Solutions Network, using poker chips and index cards, where everyone gets to share what they’re carrying and the value it’s providing. One rule encourages players to round up after they estimate their contribution.
“I wrote that rule, in part, because I was the one who kept dramatically shorting myself in every dimension from effort, output, and financial outlay,” Wachtel says. “When you make the work look easy, nobody counts it, including you. Confidence turned out to be the willingness to say the number out loud and let the table agree to it.”
Faith Morris, an operations and scale strategist at Faith Morris LLC, worked on what she calls stepping into her expert energy: “Not ‘I can help with this’ but ‘I’m the best person for this job.’”
“I kept waiting to feel ready enough to say ‘I’m the best person for this’ , but that feeling doesn’t show up first,” Morris says. “You decide it, you act like it, and the confidence follows.”
I Made the Scary Ask
Every ask carries the risk of a no, which is exactly why so many people avoid making them. Confident leaders are the ones who become comfortable with that risk.
“I started treating embarrassment as a business expense,” explains Naomi Wynter, co-founder and CEO of The Two Do List, a couples planning platform. She made a habit of doing the things that made her cringe a little, like sending ambitious emails and talking about her work before she knew how people would respond.
“Confidence isn’t believing you’ll always get a yes; it’s knowing you’ll be fine when you don’t,” Wynter says.
Founder Julie Zhu agrees that a small but steady practice can grow confidence. “You don’t have to make a huge move,” she explains. “Sometimes confidence grows from taking one small step forward and seeing what happens next.”
Over the years, she has deliberately strengthened her habit of taking the lead, whether that means inviting someone for coffee, organizing a panel, or sending the email, helping her grow her marketing strategy business, Julie Zhu LLC.
And sometimes, it’s less about practice and more about a gentle mindset shift. Tianna Soto, the keynote speaker and journalist behind Stories With Heart, had to rethink her feelings on self-promotion when starting her business.
“Promoting my ideas and offerings isn’t cringe; it’s crucial for connecting with others in the spirit of service,” Soto says. “Once I adopted that mindset, it became much easier to have fun with outreach and speaking at events.”
I Walked Into Rooms Before I Felt Ready
Ready or not, some leaders share that confidence is grown simply by putting yourself in rooms that feel a little too big for you.
For instance, Nicole Leon, founder of L Leon Virtual Assistance, began pitching herself and pursuing opportunities before she had the credentials, recognition, or outside validation to prove she belonged.
“Every time I did, I collected more evidence that I was far more capable than I had given myself credit for,” Leon says. “The most powerful shift was realizing I could decide I belonged before anyone else had the opportunity to validate it for me.”
Lian Abad was forced by the pandemic to walk into rooms she felt she had no business being in. When COVID-19 shut down the hospitality industry overnight, she pivoted into B2B SaaS with no traditional tech background, betting that a decade of running hotel and food and beverage operations would translate. It did. “Once I proved that to myself, I left the corporate safety net behind entirely and went fractional, building my own business and working with clients on my own terms,” she says, which includes her work as Director of Operations at The Hive. “The skills that make you extraordinary in one room will absolutely translate to the next one, but only if you’re willing to walk through the door before anyone’s officially invited you.” She didn’t start until she was 42, after years as a full-time parent. Even before she felt like she was an expert, she was pushing herself to host master classes in communities where she had no built-in authority, building her public speaking skills on the fly.
“I wish I’d understood earlier that you don’t need to feel like the expert in the room to step up and contribute like one,” agrees Grace Tabib. While building DUPAY, she started hosting master classes before she felt like an expert and in communities where she had no built-in authority. “It forced me to realize I knew more than I gave myself credit for,” she explains.
Olivia Dufour, founder of Olivia Dufour Consulting, changed the question she asked herself. “My influence grew the moment I stopped asking ‘am I qualified for this?’ and started asking ‘what quality idea can I contribute?’” she says.
Working in global firms, she trained herself by observing high-stakes meetings with ambassadors from Japan, Italy, and the UK. One habit stayed the same in every setting: she made sure to contribute before the meeting ended, whether by raising her pen to signal a suggestion, passing a note to the strategist in charge, or unmuting as soon as she could.
For some, the room had to be rehearsed first. Lara Grant had to get comfortable being seen. Her pivot from travel editor to meditation and wellbeing coach at Lara Grant Wellness required facing her fear of public speaking, so she signed up for a cardio dance instructor training that required her to lead classes “in my best fitness instructor personality.”
“It helped me learn how to use my voice, lead despite nerves, and perhaps most importantly, have fun doing it,” Grant adds.
I Launched Before It Was Perfect
Some of the most uncomfortable moments leaders described came from putting unfinished work in front of the public. Those moments also taught them the most.
Kimberly Tara, CEO of The Tara CPA Firm, wanted to get the new tax strategy software she was building for small business owners exactly right before releasing it. A fellow CPA in her mastermind pod pushed back, telling her that holding TaxMove back until it was perfect was selfish. By putting it out there sooner, she was able to improve the product based on real feedback.
“The confidence showed up after I shared something imperfect, got parts of it wrong, and got to fix it with real people instead of guessing,” Tara says. Samantha Black, founder of AI-powered homework coach Methodwise, agrees that releasing her “unfinished” products ended up being one of the most confidence-boosting things she could do.
“I spent years waiting to feel qualified, when what I needed was one public thing with my name on it,” Black says. “Now, I talk openly about what I’m making while it’s still rough, which has brought me collaborators and opportunities that a polished launch never would have.”
“Confidence is usually the result of doing the thing, not the prerequisite for doing it,” agrees Amanda Riso, co-founder of divorce preparation platform McBeal AI. “Taking action earlier forced me to get comfortable learning in public, asking better questions, and making decisions with imperfect information, which ultimately made me much more confident as a leader.”
All individuals featured in this article are members of Dreamers & Doers, a highly curated community and PR Hype Machine® amplifying extraordinary women entrepreneurs and leaders through authentic connections, credibility-boosting visibility, and opportunities that accelerate big dreams. (Learn more about membership here.)
