Big Girl Panties Diaries - Entry #177: You’re Not Doing It Right Unless You Feel Like You’re Eating Glass

The wonderfully messy, occasionally terrifying journey of entrepreneurship.

Last week, I attended a dinner with a group of HR leaders. Great conversation, smart people, and the kind of honest discussion that happens when professionals get together without an agenda or a PowerPoint presentation in sight.

At some point, the conversation turned to entrepreneurship, and someone said something that stopped me in my tracks: "You're not doing it right unless you feel like you're eating glass."

I almost fell out of my chair. Not because I was shocked, but because I had never felt more validated in my life. FINALLY. Someone said it. Someone actually put into words what I've been experiencing for the past year.

Because here's the thing about entrepreneurship. From the outside, it can look pretty spectacular. You're your own boss. You set your schedule. You choose your clients. You get to pursue work you're passionate about and build something that belongs entirely to you. And all of that is true.

But what nobody puts in the brochure is that some days, building your dream feels an awful lot like chewing on a wineglass. And apparently, that's normal.

I cannot tell you how comforting that was to hear. Not because I want entrepreneurship to be painful. Believe me, I'd happily skip that part. But because sometimes you need to hear that the struggle isn't necessarily a sign that you've made a terrible mistake. Sometimes it's just part of building something from absolutely nothing.

Nobody Talks Enough About the Whiplash

Here's something I've learned since leaving the corporate world and starting my own business: Entrepreneurship is a master class in emotional whiplash.

One day, you're onstage delivering a keynote, connecting with an audience, and thinking, This. This is exactly what I'm supposed to be doing. The next day, you're staring at a proposal you spent hours developing, wondering why the person who was so enthusiastic during your conversation has suddenly disappeared into the witness protection program.

You celebrate a new client, then immediately start worrying about keeping that client. You land an exciting opportunity and find yourself thinking about where the next one will come from. You publish a book, something you once weren't even sure you could accomplish, and instead of sitting back and enjoying the moment, you're figuring out how to sell the next hundred copies.

It's exhausting, exhilarating, and occasionally makes you want to crawl under your desk with a bag of Doritos and reconsider every decision you've made since 1998.

And that's when I think back to that dinner. Apparently, I'm not the only one chewing glass.

Apparently, I've Started a Family Business

Here's another thing I didn't anticipate when I decided to become an entrepreneur. My family would apparently become employees. Unpaid employees, I should clarify, although I do occasionally provide meals.

My daughters have started alternating turns accompanying me to Barnes & Noble book signings. While other kids might spend their weekends doing just about anything else, mine are helping their mother sell books, meet readers, and navigate the glamorous world of author appearances.

Earlier this week, my parents came along to help me at a local conference. There I was, a grown woman with more than 25 years of professional experience, running my own consulting business, and still needing Mom and Dad (listed on the conference entry form as associates) to help me pull it all off. And you know what? I loved every minute of it.

Somewhere along the way, this thing I started building for myself has become something my family is helping me build, too. They're carrying boxes, helping at events, keeping me company, cheering me on, and occasionally reminding me that I might be taking myself a little too seriously.

Meanwhile, because apparently launching a consulting business, speaking at conferences, working with clients, and publishing one book wasn't enough to keep me occupied, I'm now writing my second book, The Panty Stack. Yes, another book. Because when life hands you a full plate, the obvious next step is to grab a bigger plate.

But there's something pretty special about all of this. My daughters are watching me build something from scratch. They're seeing the work behind the accomplishments, the uncertainty behind the confidence, and the persistence it takes to keep going when things don't happen as quickly as you'd hoped.

And my parents, who spent years supporting me as I figured out who I wanted to become, are still showing up. Only now, instead of helping me with a school project, they're helping me run a conference table.

I don't know if any of us anticipated this particular chapter, but I'm awfully grateful they're part of it. And if this whole entrepreneurship thing really does involve eating glass, at least I've got people willing to help me sweep up the pieces.

The Hardest Part Isn't the Work

I've worked hard my entire career. Long hours, complicated transformations, difficult personalities, impossible deadlines, and organizational politics. None of that is new. But entrepreneurship introduces an entirely different kind of difficulty.

There is no organizational safety net between you and uncertainty.

There's no established brand opening doors for you, no predictable paycheck arriving every other Friday, and no executive title that automatically tells people you're worth listening to. You have to build the credibility, create the opportunities, make the connections, and convince people that what you bring to the table is worth investing in. And then you have to do it all over again.

You can be exceptionally good at what you do and still struggle to sell it. That one has been particularly humbling, because being an experienced professional and being a successful business owner are not the same skill set. One requires expertise. The other requires expertise, salesmanship, marketing, financial discipline, resilience, patience, and a remarkable tolerance for hearing absolutely nothing after someone tells you how much they love your work.

There are moments when I miss the predictability of corporate life. Not necessarily the politics, the endless meetings, or the PowerPoint presentations about PowerPoint presentations. But the certainty. Knowing what my role was, knowing where the next paycheck was coming from, and knowing that if I did my job well, there was an established structure around me.

Entrepreneurship removes that structure and hands you a blank sheet of paper. At first, that's incredibly liberating. Then you realize you're responsible for filling the entire sheet. Some days, that feels like freedom. Other days, it feels like standing in the middle of a field during a thunderstorm holding a metal umbrella.

And then the questions start. Am I charging too much? Too little? Am I focusing on the right clients? Should I be doing more speaking, consulting, or writing? Should I be posting more, networking more, following up more? Am I building a business or just creating a very demanding job for myself?

And perhaps the most uncomfortable question of all: What if this doesn't work?

That's the one that really tastes like glass.

It's All One Big Experiment

Here's another thing I've figured out. Entrepreneurship is really just a series of experiments. Some work, some don't, some surprise the hell out of you, and some make you wonder why you thought they were such brilliant ideas in the first place.

You try a new service, pitch a different audience, develop a workshop, submit a speaking proposal, or write a book. Then, because apparently one book wasn't enough, you decide to write another. You put something out into the world and see what happens.

Sometimes the response is incredible. Sometimes it's crickets. And sometimes the thing you thought would be a huge success goes absolutely nowhere, while the idea you almost dismissed opens a door you never saw coming.

The trick is not to get so attached to any one idea that you stop experimenting.

I've spent more than 25 years helping organizations navigate change, and one of the biggest barriers I see is the expectation that we should have everything figured out before we begin. But that's not how change works, and it's certainly not how entrepreneurship works.

You learn by doing. You adjust based on what you discover. You stop doing things that aren't working and invest more energy in the things that are. And perhaps most importantly, you stop treating every experiment that doesn't work as a personal failure.

It wasn't a failure. It was information.

So keep trying new things. Keep putting yourself out there. Keep having conversations, testing ideas, and exploring possibilities. Not every door will open, not every opportunity will turn into business, and not every idea deserves a second attempt. But you won't know unless you try.

You can't build something new by only doing what you already know works.

And if you're going to eat glass occasionally, you might as well learn something from the experience.

Sometimes You Have to Be Your Own Sponsor

Here's something I've been thinking about lately. I spend a lot of my professional life helping leaders and organizations navigate uncertainty. I talk about the importance of leadership visibility, building confidence, creating clarity, and helping people move forward even when they don't have all the answers.

And then I go home and have to practice every single bit of it myself.

How do I help others lead through uncertainty? I set an example. Not by pretending I have everything figured out or acting like entrepreneurship is one long victory lap, but by showing up, trying new things, taking risks, acknowledging the hard parts, and continuing to move forward.

I've always said that successful organizational change requires active and visible sponsorship. Leaders can't just announce a change and disappear. They have to demonstrate their commitment through their actions. Well, guess what? The same principle applies when you're building something of your own.

You have to become an active and visible sponsor of yourself.

Nobody is going to advocate for your business more consistently than you. Nobody is going to magically appear and tell the world how talented you are, what you have to offer, or why your ideas deserve attention.

You have to get out there, make the connections, have the conversations, follow up, share your ideas, ask for the opportunity, and put yourself in rooms where nobody knows your name yet. You have to be willing to hear no without deciding it means never.

And when other entrepreneurs ask me what the secret is, I wish I had some brilliant formula to share. But I don't, because there is no silver bullet.

There's no magic LinkedIn post, perfect business plan, or networking event that suddenly makes everything fall into place. There's consistency, visibility, relationships, credibility, a willingness to experiment, and the ability to keep showing up even when you're not entirely sure what you're doing.

It's also learning when to pause, get some perspective, and trust yourself enough to take the next step. That's Calmfidence.

And perhaps the most important thing I've learned is that you don't have to wait until you feel successful to start acting like someone who believes in what they're building. You have to believe in it enough to keep showing up, even when your mouth is full of glass.

The Glass Isn't the Whole Story

For all the jokes about eating glass, I don't believe entrepreneurship has to be miserable to be meaningful. I don't believe exhaustion is proof of ambition, that suffering is some kind of admission ticket to success, or that we should celebrate running ourselves into the ground simply because we had the courage to start something.

But I do believe building something of your own requires a willingness to be uncomfortable in ways you never anticipated.

You have to become comfortable being a beginner again, even when you've spent decades becoming an expert. You have to learn how to hear no without allowing it to define your worth. You have to celebrate progress without immediately moving the finish line, and you have to stop expecting confidence to arrive before you take the next step.

Sometimes confidence comes afterward. After the pitch, the rejection, the awkward conversation, or the risk. After you discover that you survived something you were certain would break you.

That's what Calmfidence has come to mean to me in this chapter of my life. Not pretending everything is wonderful, but trusting myself to navigate the parts that aren't.

And sometimes, in the middle of all that uncertainty, something wonderful happens. A client tells you that your work made a difference. Someone who attended your presentation reaches out to tell you that something you said changed their perspective. A reader shares how your book helped them through a difficult moment. A conversation turns into an opportunity you never could have predicted.

Those moments matter because they remind me why I started.

So, Am I Doing It Right?

I don't know. And that's probably the most entrepreneurial answer I could give you.

I'm still figuring things out, experimenting, and learning what works and what doesn't. I'm still occasionally waking up at 3 a.m. with a brilliant business idea that seems considerably less brilliant by breakfast.

But here's what I do know.

I absolutely love working with amazing clients. I love the conversations, the challenges, the relationships, and the opportunity to help people and organizations navigate change in meaningful ways. I love building something of my own, something that reflects my experience, my perspective, my values, and the things I believe are worth saying.

And I love having the freedom to be as creative as I want. To dream up a new workshop, develop a keynote, write another book, try something completely different, or follow an idea simply because I think it has potential.

After spending so many years working within the boundaries of organizations, there's something incredibly liberating about realizing I get to decide what comes next.

That fills my cup.

And perhaps that's the part of entrepreneurship that doesn't get talked about enough, either.

Yes, there's uncertainty. Yes, there are disappointments. Yes, there are days when I question my sanity and wonder whether a predictable paycheck was really such a terrible thing. But there's also tremendous joy in creating something that is entirely yours.

And somewhere along the way, my family has become part of the adventure. My daughters are helping at book signings. My parents are showing up at conferences. They're getting a front-row seat to the wins, the work, and the occasional chaos.

I'm building a business, but I'm also building a life that feels more like me. And that matters.

So, to the person at dinner who told me entrepreneurship is supposed to feel like eating glass, thank you. I needed to hear that more than you know. You reminded me that the hard days don't necessarily mean I'm doing something wrong.

But you also reminded me of something else.

The glass might be part of the journey, but it doesn't have to be the whole meal.

Because at the end of the day, my cup is pretty full. And I'd much rather raise it in celebration than chew on it.

Big girl panties on. Glass optional.