I started my first business when I was only 22 years old, ten days before I gave birth to my first child. That was over 20 years ago. If I could sit down with that version of myself and share the lessons learned as a woman entrepreneur over two decades of business ownership, I’d pull up a chair, pour some coffee, and talk for hours.
My coaching business, where I work with high-achieving women in business and leadership, is almost 10 years old now. (I can’t even believe that.) I’ve made a lot of my own mistakes, celebrated wins I didn’t fully understand yet, and picked myself up more times than I can count. So I want to pull back the curtain and be super honest about the lessons I’ve learned along the way, and sometimes the hard way.
Whether you’re still in the early stages of business or navigating a new season of growth, I hope these can help shortcut some of the struggles you might be going through. Because hindsight is a gift, but foresight? That’s even better.
[IMAGE: Warm, candid photo of a woman entrepreneur at her desk or workspace reflecting | Alt text: Woman entrepreneur reflecting on lessons learned in business]
Growth Brings Criticism (And That’s Part of the Deal)
Here’s the thing. The bigger your platform, the more visible you become, and criticism comes with that visibility. I’m not going to tell you to get thicker skin or just deal with it. I want to point out that it’s real, and it can hurt.
I’m coming off a month where I’ve had some pretty substantial criticism. Some constructive, some not so great. And I’ll be honest with you: sometimes it makes me want to stay small. It makes me afraid to grow.
But I don’t want that for myself, and I don’t want that for you either. So my encouragement is this: try not to take it personally, and whatever you do, don’t let it slow you down. Growth will always invite opinions from people on the outside. Your job is to keep building anyway. If you’re struggling with this right now, I wrote about how to handle negative feedback about your business with grace and professionalism that I think might help.
Revenue Does Not Equal Profit
I remember one of my earliest big months in business. I saw that revenue number come in, and I was ready to pop the champagne. Then I looked at payroll, rent, license fees, software, supplies, subscriptions, taxes, and suddenly I realized I barely had any money left.
That was a hard truth. Sales numbers look glamorous, but profit is what actually pays the bills and gives us freedom.
I see this all the time, especially when women undercharge for their products or services because they don’t fully understand what it actually costs to deliver. And honestly? I wish I had spent more time earlier in my business on financial literacy. Understanding my cash flow. Being able to read a profit and loss statement. Knowing enough to make educated decisions about how and when I was spending money and what I was charging.
The biggest thing I see when I’m coaching women today is that they really don’t feel comfortable or knowledgeable in their finances. And that’s not a character flaw. It’s a skill gap that can be closed. Getting comfortable with your numbers is one of the most powerful things you can do for your business.
You Can’t Do It All Alone
I actually hate the myth of the Superwoman entrepreneur. It’s exhausting.
The lesson here took me a while to learn. When I started hiring, I kept bringing on people who were a lot like me, with similar strengths. And guess what? Now we just had two people who were really good at one thing but not great at another. Not exactly the dream team.
What changed everything was building a team that thinks differently from me, that works differently from me, that can hold me accountable in areas where I struggle. People I can delegate to with full confidence that they’re competent and able to deliver.
So if you’re hiring (or thinking about it), don’t look for another you. Look for someone who fills the gaps you can’t. That’s where the real support lives.
Boundaries Are a Business Strategy
Saying yes to everything leads to burnout. That’s not an opinion. That’s a fact.
I recently had someone reach out who wanted to carve out some time to go through something together, and my whole body was telling me this was not in alignment. Not with me, not with my business, not with my values. And I really struggled with saying no. I never want to be perceived as someone who doesn’t compromise, doesn’t hear people out, or isn’t open.
But I knew with my whole chest that this was not the right path. And I knew that the momentary discomfort of saying no was going to be so much better than the long-term discomfort of saying yes to something I didn’t want to do and then having to follow through with it. Or even worse, starting it and having to back out.
“No” is a complete sentence. And it’s one of the most powerful ways to protect your energy, creativity, and business growth. Say no to things that aren’t aligned so you can say a wholehearted yes to things that are.
Your Network Is Your Net Worth
Business success is deeply tied to your relationships. I truly believe that. And building community isn’t something that just happens by accident. It takes intention, generosity, and a real commitment to the idea that we’re better together.
I am beyond thankful for the Leading Lady community. The women who show up with a mindset of community over competition. Women who amplify each other’s businesses. Women who talk about each other positively in rooms even when the other person isn’t there.
Whether it’s online in my free Leading Ladies Facebook group, in The Hub, or in person at the Annapolis Collective, these communities were built because I believe in quality connection with like-minded women who live to uplift one another. And research backs this up: entrepreneurs with strong support networks are significantly more likely to succeed and sustain their businesses long-term.
If you don’t have that kind of community yet, go find it. Or build it. It will change everything.
Your Brand Is More Than Your Logo
I’ve probably said this 1,000,003 times, but I’ll say it again, because I feel passionately about it: your brand is the way people feel when they interact with you.
I want people to know they are valued and welcome and that they’re entering a safe space without judgment. That’s the experience I’m building, whether it’s in-person, online, or anywhere in between. And while your fonts and colors absolutely matter, your brand goes so much deeper than that. It’s your consistency in values. Your messaging. The customer experience you create.
Focus less on making things look perfect and more on making people feel something when they connect with your business.
Rest Fuels Results
Let me tell you something. I subscribed to the hustle culture mentality. I worked hard. I pushed through. I put rest at the bottom of every priority list. Sound familiar?
And then at the end of 2022, my body told me it was done. I got really sick, and I spent most of 2023 allowing myself to heal. I needed that wake-up call. That slap to the forehead that said, “Hey girl, sit down. Rest.”
Here’s what I know now: you cannot survive and thrive at the same time. We need to prioritize our health, our family, and our joy, because that’s what keeps us in the game long-term.
I used to feel so guilty about rest. About sleep. About not being productive every second. Once I was able to flip that script and recognize that rest IS productive, that we need rest in order to show up whole and energized and prepared, everything changed. And the numbers tell the story, too. Studies show that entrepreneurs who don’t prioritize personal time are 2.25 times more likely to report high levels of burnout. If you need permission to rest, consider this it.
If you want more on building a sustainable pace, check out my post on working smarter, not harder.
Systems Are Sexy (Yes, Really)
I love systems. There, I said it. My brain is chaos, but because my brain is chaos, I need those systems more than ever.
Chaos is what kills businesses. Not competition, not the economy. Chaos. And systems are the antidote. They remove decision fatigue. They calm the noise. They free you up for what you actually got into business to do: vision and leadership.
Invest in your processes. Know your standard operating procedures. Put automation in place early. And here’s a big one: do frequent and thorough audits of your systems. They’re living, breathing things. You can’t just set it and forget it. Go back and check in with your tools. Make sure things are working as smoothly and efficiently as they need to be, because you don’t want to create bottlenecks that block your progress.
Leaders Are Learners
Your expertise gives you credibility, but learning keeps you relevant. I think about this one a lot.
It can be tempting to settle into what you know, to lean on your expertise and stop being curious. But expertise can become a trap if you close yourself off to feedback and new ideas. Leaders are learners. Always. And you’re either learning or you’re dying. (Okay, that sounds dramatic, but you know what I mean.)
So what are you reading? What kind of content are you consuming? What professional development are you investing in? How are you nurturing your hobbies and keeping an open mind? And this one’s big: do the people around you feel comfortable giving you honest feedback?
Build rituals into your life that nurture a learner’s mindset. That’s what keeps us evolving, adaptable, and ready for whatever comes next.
Your Business Is Not Your Identity
This might be the most important lesson on this list.
It is so easy to tie your self-worth to your success or failure as a business owner. I know because I’ve done it. As high-achieving women, we get wrapped up in roles: wife, mother, business owner, community leader. And we forget that those are small parts of who we are as a whole person.
I lost myself at points in my life. And when I’m able to reconnect with who I really am, separate from my preschool business, my coaching business, the Leading Lady community, my role as a mother, that’s when everything else comes into perspective.
You are more than your business. Your worth is not in what you produce. Hold space for your life outside of work. Nurture your hobbies. Invest in friendships that have nothing to do with your profession. Build a life that’s filled with joy, because joy is so much more than what we do for a living.
Be Better, Not Bitter
I’ll close with a motto I kind of live by: the goal is to always be better, not bitter.
Lessons are hard. Sometimes they leave a bitter taste, and it would be easy to let them harden us. You might feel like you’re getting knocked down over and over and start thinking, what’s even the point?
The point is to be better. Don’t let these lessons harden you so much that you stop adapting, growing, and evolving into the best version of yourself. Give yourself time to process. To assess. To pull the insight out of the experience. To refine. And then get up. Be resilient. Do better. Be the best version of yourself.
If any of this resonated with you, I’d love to hear from you. What’s something you wish you knew earlier, or something you’re just now learning that you’d love to share with others? I read and respond to every message.
Ready to take your next step? Grab my free Strategic Planning Wheel to map out your priorities, join the Leading Ladies Facebook group for real conversations with women who get it, or check out The Hub for ongoing coaching, community, and support.
