By: Christina Salerno, Chief Dreamer of Dreamers & Doers, a curated community and PR Hype Machine® for extraordinary women entrepreneurs
Most career advice treats confidence as the price of admission. Build enough of it, the thinking goes, and you’ll finally be ready to make the move. For many women who have made big moves, it happened in the opposite order. They took the job, left the industry, or started the company first, and the confidence showed up later.
That pattern came through clearly in conversations with leaders from the Dreamers & Doers community. Some changed industries with no network to fall back on. Others were pushed into leadership by forces outside of their control. Here, they explain what those leaps taught them about readiness.
Saying Yes Before the Plan Was Clear
For many leaders, the turning point was a yes said before there was a plan to back it up.
Sometimes, those are big swings, like when Soraya Barrera said yes to the VP of Operations role at Translate.One before she had a playbook for how she would actually do the job of helping organizations communicate across borders, languages, and cultures. She built the plan as she went, staying visible in every decision instead of managing from a distance.
“Confidence doesn’t come from already knowing how to do the job, it’s built by saying yes anyway and closing the gap in real time,” Barrera says.
Michelle Bernier made a similar bet when she left law for venture capital with zero industry ties. She reached out cold, showed up in each and every room she could, and learned the business in real time.
“That experience taught me to trust my ability to figure things out rather than wait for permission to start,” Bernier says, adding that this mindset helped her in founding The Right Room, which designs gatherings that connect investors, founders, and leaders. “I wish I’d understood sooner that competence follows courage, not the other way around.”
But for those who are still working on their confidence, the bets can start smaller and add up. About a year ago, Janelle Ryan took a pay cut and went from working five days a week to four, without a mapped-out plan for the extra day. She used it to co-found Mass Pike Plumbing & Heating with her brother.
“Seeing what I could create with just one day a week gave me the confidence to recently quit my job and launch my own consulting business, The Disruption HQ,” Ryan says.
Whether you’re taking a major leap or trying a small experiment, the message here is clear: Do it before you feel ready. “Confidence became practical for me when I stopped measuring my readiness by how certain I felt,” explains Catharine Montgomery, who had to push past uncertainty when founding her communications and marketing agency, Better Together Agency.
Her advice to other women waiting to take a leap: “Make an informed choice you have been postponing, own the result, and let your track record become evidence you can trust.”
When Circumstances Force the Leap
Not all leaps are chosen. Sometimes the plan falls apart, and the only real option is to find a way to keep going.
Take the chaos so many business owners had to deal with during the pandemic. Sydney de Arenas watched her multiple businesses collapse, leaving her with significant debt and forcing her to take on several jobs.
“My confidence was decimated, but I kept taking opportunities, making decisions, building, and putting myself in rooms before I felt remotely ready,” de Arenas says. That resilience paid off when she founded The Hive, a growth engine for small businesses. “I learned how to keep leading even when I did not feel like the version of myself I had always relied on.”
When Hurricane Sandy put Red Hook underwater in 2012, Victoria Alexander was a broker and historic preservation grad student, not an organizer. “Nobody was coming with a plan, so I started showing up at meetings, asking the questions no one else would,” she says. She became a founding member of Resilient Red Hook, founded the Red Hook Business Alliance with Susan Povich, and started testifying in rooms where she had “no credential except that I lived and worked there.”
Today, Alexander runs Realty Collective, a women-owned boutique brokerage in Red Hook. “I wish I’d known earlier that ‘not ready’ is usually just code for ‘not invited,’” she adds, “and you don’t need the invitation.”
But sometimes the circumstances that force change can be more internal. Karen Hennessy Coles hit her turning point when she realized she was stuck and needed a different approach to working within her circumstances. “I wish I’d known I had ADHD and that my ‘struggles’ weren’t my fault, and I’d have leaned into my natural strengths and passions rather than pushing to prove I could do what was hard,” she says.
That mindset shift, along with regular yoga and support from a therapist and doctors, helped her build her own consultancy, Promovere People.
Training for Uncertainty
Many founders share that confidence in their ability to handle anything came through practice that made them feel more prepared.
“I developed the habit of becoming comfortable with pivots, listening to the data, accepting reality even when it was difficult, and being willing to change direction rather than treating a shift as failure,” explains Mathangi Swaminathan. Though it was far from linear, those pivots eventually led her to found social enterprise Parity Lab and grow it globally.
For Jen Blum, founder of JenAI Group, the pace of working in the constantly shifting fields of AI and cybersecurity taught her to get comfortable saying, “I don’t know yet, but I know how to figure it out.”
“Confidence isn’t certainty,” Blum adds. “It’s trusting yourself to move forward when you don’t have every answer, knowing you can learn, adapt, and figure out what comes next.”
If training for uncertainty within your work feels scary, look for opportunities to grow the muscle in your free time. Linda Du, co-founder and CEO of personal finance platform Moola, found the answer in long-distance cycling. Days of pushing through exhaustion, bad weather, mechanical problems, and uncertainty taught her to trust herself to figure things out as she goes, “which is exactly how I now approach building a company,” she says.
“You build confidence by repeatedly proving to yourself that when things go wrong, you’ll find a way forward,” Du adds.
For Melissa Withorn, the proving ground was moving her family from the U.S. to Portugal, where she now builds her American company, CAST Creative, a visual CRM for creative teams.
“Not only did we survive the big, scary move, but we thrived and grew inside the uncertainty,” Withorn says. “Now instead of second-guessing, I lead with the attitude of ‘what’s the worst that could happen’ and go for it.”
Ultimately, these women share that confidence is a muscle you have to keep working again and again throughout your life. “Confidence isn’t something you accumulate and keep; it’s something you have to keep re-earning,” shares Laura Meyer, who started Envision Horizons at 25, with no MBA and no decade of executive experience, and has found that success can actually erode confidence.
“The discomfort doesn’t go away as you move throughout life,” she explains. “It just shows up in bigger rooms, with higher stakes”, meaning you have to stay ready for it.
The Next Right Decision
It’s clear from these stories that confidence isn’t so much a character trait but a method: make the best decision you can in the moment, learn from it, and make the next one.
“I learned to stop confusing ‘I haven’t done this before’ with ‘I’m not capable of doing it,’” explains Kylee McGrane-Zarnoch, who founded A Moment of Magic Foundation in 2014 without a roadmap for building a national nonprofit. “I wish I’d understood earlier that you don’t need to have all the answers to lead well; you need to trust your ability to learn, adapt, and make the next right decision.”
Yéwándé Faloyin, CEO and founder of OTITỌ Leadership & People Development, has taken the fear out of mistakes by treating every outcome as useful. When something strikes a chord with a client, she uses it to sharpen her message. When something misses, she gets curious about what she misunderstood.
“Nothing is wasted; it’s all information,” Faloyin says. “I’m no longer afraid of making a ‘mistake’; I either win now or learn so that I can win later!”
Their circumstances could hardly be more different, but these women describe the same order of events. They moved first. The readiness caught up later.
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.)
