The Confidence Trap
Why believing in yourself isn't the whole story.
Dear Fabulous Female Founders,
The other day, my friend Emily, founder of Wool & Palette, creator of naturally hand-dyed yarn, texted me an Instagram post from Eleanor Beaton, founder/CEO of SafiMedia, an education & coaching company for women entrepreneurs.
Eleanor’s premise: women entrepreneurs are often given the wrong advice. Instead of learning about capitalization, pricing power, operating leverage, distribution strategy, and financial instruments, we’re coached on confidence, branding, visibility, and marketing. As a result, we’re less prepared to access growth capital and build companies with enterprise value.
Emily asked me, “Do you think this is true?”
She went on to tell me about her business support group that was big on emotional support but weak on strategy.
At first, I wasn’t sure I agreed with Eleanor. After all, I’ve spent years coaching women through moments where confidence—not financial knowledge—was the thing holding them back. I’ve worked with founders who knew their numbers cold but struggled to negotiate with a business partner, fire an underperforming employee, take a risk on a new market or service or hire, navigate a difficult conversation, or convince investors of the value of what they’d built. Confidence matters. Emotional intelligence matters. The ability to lead through uncertainty matters.
But the more I sat with Emily’s question, the more I realized that Eleanor and I weren’t actually disagreeing.
🚲 ⚙️ 💡
Back in my Alta consulting days, I was a confident lady. Through a decade and a half of building, I understood our clients, our contracts, our pricing, our staffing model, our utilization rates, and our financials. I knew how we made money, where we lost money, and how one strategic decision rippled through the rest of the business. If someone asked me a difficult question, I usually knew the answer.
Alta Bicycle Share, our spin-off operations firm, was a different story. At first, that was no problem, for I played a supporting role safely in the land of comfort: business development, hiring, cheerleading. But then, just before what was supposed to be the launch of Citi Bike in the summer of 2012, we learned that our supplier had abandoned its software provider and was rebuilding the software from scratch, forcing delays and plunging us into crisis.
I was on maternity leave then, and when I returned I found myself in meetings discussing software architecture, equipment failures, manufacturing schedules, supply chain, warranties, station communications, performance penalties, and much more. I could follow the conversation well enough to stay afloat, but only just. Scratch the surface and I quickly realized how little I actually understood about the core of our business.
So I became a student.
I asked question after question, quite often bewildered. I spent time with engineers, operations staff, mechanics, software experts, attorneys, our supplier, and our finance team, slowly piecing together the totality of all we’d created and how everything worked. The more I learned, the more useful I became to the company, and almost without noticing it, my confidence returned—not because someone told me to believe in myself, but beause I finally understood what I was talking about.
📊 💪🚀
That experience has stayed with me through my years as a coach, advisor, and investor. The founders who impress me most aren’t necessarily the loudest or the most charismatic. They’re the ones who can explain, in plain English, how their business works. They understand their customers, their pricing, their margins, their cash flow, their hiring strategy, and their growth plan. If I ask a hard question, they don’t reach for buzzwords or polished talking points. They think for a moment, answer thoughtfully, and if they don’t know, they say so.
Their confidence isn’t performative; it’s grounded.
And I’ve noticed something else.
Many of these women have already lived through one startup. Some worked inside companies that scaled rapidly. Others built and sold smaller businesses before starting again. They didn’t wake up one morning magically confident. They earned that confidence by making mistakes, asking questions, surviving difficult moments, and gradually becoming fluent in the language of business.
The reality is that few women begin their entrepreneurial journeys with MBAs or investment banking backgrounds. Most of us weren’t raised around dinner tables where people debated valuations, capitalization tables, debt financing, acquisitions, or exits. We start businesses because we’re passionate about something. We are great designers, physicians, planners, engineers, HR professionals, publicists, or makers who see a problem or seize an opportunity.
That passion is a wonderful place to begin, but it isn’t the end of the journey.
Eventually every founder, whether building a venture-backed technology company or a lifestyle business, reaches the point where you need to understand cash flow, pricing, governance, hiring, financial statements, and the economics that drive your business—the tools, in other words, to allow your company to survive, grow, and create lasting value.
So perhaps the answer to Emily’s question is yes—and.
Yes, we coaches and advisors should absolutely continue helping women find their voices, negotiate boldly, lead courageously, and believe in themselves.
And yes, we should spend just as much if not more energy helping them become financially fluent, strategically sophisticated, and deeply knowledgeable about how businesses actually work.
The deepest confidence doesn’t come from positive affirmations. It comes from understanding your business so well that when someone asks a difficult question, you don’t have to fake an answer or hope they don’t dig too deeply.
You simply know.
And that’s the kind of confidence that earns the trust of investors, employees, customers, board members, and perhaps most importantly, yourself.
~ Mia
The corollary in my world, Mia--as we've talked about--is writers who do not educate themselves (and are often resistant to) the commerce side of writing. There's craft and creativity and confidence...oh yes...but there is understanding the world of publishing, the business of it. Then, of course, there are those who are ALL commerce and no art.