You’ve heard all the clichés about hindsight and regret—and there’s a reason they exist. If only you knew then what you know now!
Consider this your shortcut. With insights from 14 savvy entrepreneurs from the Dreamers & Doers collective, we’re here to help you sidestep rookie mistakes and launch your business with confidence. Your future self will thank you.
From mindset shifts and financial strategies to sales tactics and hiring tips, these gems of wisdom from powerful women prove just how invaluable it is to learn from those who’ve been there before.
Ogaga Johnson
Founder & CEO of Verisult, empowering career professionals and immigrants by connecting them to meaningful careers and helps businesses recruit, train, and build a high-performing workforce.
Stephen NEJ
“In my first year, I did everything myself and saw growth, but it was limited. Once I started bringing in experts for tasks beyond my strengths or those that didn’t require my direct involvement, my business grew ten times faster. I could focus on what truly mattered. As women, we’re often conditioned to believe we must do everything by ourselves, but real success comes from building a team that complements your skills and asking for help when needed.”
Amanda Hofman
Chief Swag Officer & Co-Founder of Go To Market, the anti-boring branded merch and swag experts changing the way the world handles swag.
Julia Guignard
“I wish I knew that all the stories of massive business success I was seeing daily on Instagram were either overstated or fake. I felt awful about my ‘slow’ social media growth when, in reality, I was completely on track for the stage of my business. If I had understood this earlier on, I could have focused my energy on more creative and practical business pursuits than chasing a follower count.”
Marissa Badgley
Founder & CEO of Reloveution, LLC, a consulting and professional development services provider that helps leverage the magic of humanity to strengthen team culture and deepen leadership impact.
Holly Todd
“In my first year of business, I thought success hinged on a perfectly-crafted strategy and a seamless sales funnel. I quickly learned that, for me, the most effective and authentic business development strategy is less about selling and more about listening and responding, less about chasing clients and more about deeply engaging with people at their point of need. I wish somebody had told me back then to ditch the playbook, the packages, and the status quo of ‘business development’ and instead rely on my superpowers of human connection and co-creation.”
Mathangi Swaminathan
Founder & CEO of Parity Lab, a pioneering movement breaking cycles of trauma and healing communities through innovative mental wellness and transformational leadership development.
Mathangi Swaminathan
“I wish someone had told me that building a business is as much about managing your own energy and mental well-being as it is about strategy and execution. Lean into your own power and wisdom—there will always be unsolicited advice, but not all of it deserves your attention. If I had known this earlier, I would have spent less time taking everyone’s advice and feeling small and frustrated. Instead, I would have focused more on speaking my mind and being intentional about who I asked for guidance, surrounding myself with those who saw my vision and amplified my strength.”
Kellie Okonek
Founder & CEO of Iron Lady Consulting, transforming organizations from functioning to flourishing by building high-vitality teams—teams in coordinated and effective action, fueled by the principles of adventure.
Tarryn Megan
“In my first year of business, I wondered why I wasn’t ‘going for it’ with the same relentless drive I’d always had. But looking back, I see that I was in a season of learning, much like the Earth cycles through its own rhythms. I needed time to practice, refine my skill set, and discover my true calling—not just coaching, but organizational vitality. Just like in nature, growth doesn’t happen all at once; it emerges when the foundation is strong. If I had understood that sooner, I would have given myself more grace and trusted that the right path would reveal itself in time.”
Ellen Hockley
Principal & Founder of Ellen Hockley Consulting, empowering early-stage, purpose-driven female founders to overcome career challenges postpartum and build thriving businesses.
Jen Chanyi
“I wish I had better understood the power of saying no and how it relates to my mental, physical, and emotional health—as well as my bottom line—in a very positive way. When you say no to what doesn’t serve you, it leaves you open to say yes to what does. In my early years, I was so terrified that I wouldn’t make any money and succeed that I said yes to nearly everyone, including clients who were a horrible fit. I couldn’t give the time or energy to the great clients because I spent so much time dealing with the awful ones, and it nearly broke me and my business. Saying no is extremely scary, but will help you grow in ways you never thought possible.”
Clara Ma
Founder & CEO of Ask a Chief of Staff, the premier resource for Chiefs of Staff looking to secure high-impact roles and drive results.
Clara Ma
“Early on, I was focused on quick wins: closing my first deal, generating revenue, and proving to myself and others that this idea had legs. And while that initial momentum was crucial, I quickly learned that the real challenge wasn’t in starting but in sustaining. If I had approached things with a longer-term mindset from the start, I could have smoothed out the highs and lows. Entrepreneurship feels like a sprint, but long-term success comes from building with stability in mind.”
Kelly Hubbell
Founder & CEO of Sage Haus, helping busy parents reclaim time by building their village.
Colleen Amelia
“I spent a lot of time early on trying to create the ‘perfect’ offer when, in reality, the best thing I did was listen to my audience. The more I paid attention to what my ideal customer actually needed, the more I was able to refine my services and create solutions that solved their problems. If I had embraced this mindset earlier, I would have spent less time second-guessing myself and more time experimenting, gathering feedback, and adapting. Business isn’t about having all the answers upfront—it’s about being willing to try, listen, and adjust as you go.”
Emylee Williams
Growth Strategist at Creative’s Catalyst, helping women-led micro agencies uncover sustainable growth opportunities to build aligned multi-million dollar companies.
Beth Barbosa
“I wish someone had normalized the power of a strategic pivot instead of making me feel flaky for evolving my business. I took the ‘consistency is everything’ advice so literally that I felt guilty every time I needed to shift, even when those shifts were clearly what my audience and clients needed. Now I know that being able to pivot strategically based on real results and energetic alignment isn’t flakiness—it’s actually the most consistent thing you can do as a leader. If I’d understood this sooner, I would have spent less time forcing myself down paths that didn’t serve my business just because I thought that’s what consistency meant.”
Elle Wilson
Founder & CEO of Met Through Friends, hosting IRL dating events where everyone brings a friend, and offers dating coaching for those who want support building a kinder, braver, more fun in-person dating life.
LinkedIn Headshots
“I’m just now closing my first year of business, so these realizations are fresh. I wish someone had told me to simply get started rather than trying to get everything right first. There can be a big temptation to make sure things are perfect before you put yourself out there and to spend time planning rather than executing. While I do think it’s important to be thoughtful and to have high standards, I’ve learned the value of starting small, experimenting, and iterating. The lessons you learn from just getting started and the confidence you get from small wins can end up being wind in your sails!”
Brittany Buxton
Founder & CEO of Ardent Impact Collective LLC, leading the Post-Baby Renaissance™, a movement redefining how law firms and corporations support working mothers during the pre-maternity, maternity, and postpartum reintegration phases.
Savannah Scott Photography
“In my first year of launching my business, I felt immense pressure to build the traditional way: raising capital fast, scaling aggressively, posting constantly, and conforming to a rigid definition of what a successful entrepreneur should look like. But as a new founder with two young daughters under five, I quickly realized that the standard startup playbook hadn’t been written for women like me. Instead of trying to force my life into a model that didn’t fit, I needed to rewrite the model entirely, designing my company in a way that actually aligned with my vision, values, and reality as a working lawyer mom.”
Sydney de Arenas
CEO of The Hive, helping small businesses streamline operations, scale sustainably, and reclaim their time with expert support and strategic initiatives.
The Hive
“Once I raised funds, I wish I had brought in someone else to manage our finances. Scaling took longer than expected, and I found myself in a constant fundraising cycle. While I’ve always been good with money, handling larger amounts at a faster pace was a new challenge, and the cash burned quicker than I anticipated. Had I been more strategic with spending, I could have navigated the pandemic smoothly instead of temporarily shutting down that business. That experience taught me the importance of financial oversight to protect them from unexpected challenges.”
Anouck Gotlib
CEO of Belgian Boys, creating whole ingredient breakfast options with a European twist so families can prep less, smile more, and indulge better.
Ursula Prinz
“Early on, it’s hard to release all the little things, but letting go and asking for advice from the right people is the best thing I’ve done in the last few years. Building a strong team and not micromanaging is key. I aim to immerse myself in the company of smart, passionate people who have more experience and knowledge than I do in their field.”
Chandler J. Esq
Attorney & Founder of Lethal Legal, an intellectual property law firm helping business owners in all 50 states gain exclusive rights to their brand, stop copycats in their tracks, and scale their business with confidence.
Chandler J. Esq
“I wish someone had told me to implement systems and processes from day one instead of waiting until I was drowning in work to figure them out. Looking back, I spent so many late nights creating SOPs, developing workflows, and streamlining client communication, all while trying to manage a full client load. If I had built these foundations from the start, I could have scaled much faster and avoided the growing pains that come with playing catch-up. This is exactly why I now prioritize systems in everything I do. True growth requires a strong operational foundation.”
All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources.
Join us on this journey of self-discovery, empowerment, and celebration! Here’s to strong women – may we know them, may we be them, may we inspire them!
With love and inspiration,
Women on Topp Magazine
By subscribing, you accept the privacy rules of our website.
