Why Selling Yourself as an Entrepreneur Feels Like Playing Dress-up (And Why That’s Okay)

By Tricia Scott.

If you've ever tried to sell your business, whether through a website, pitch, or social media post, you know the struggle is real. Selling yourself as an entrepreneur isn't just hard; it feels downright unnatural at times.

There's something about putting your whole self out there, your ideas, your business, your face that makes you want to crawl into a hole, Gollum-style, and talk gibberish about rings until you die.

It's not just you. It's all of us. Most entrepreneurs I meet, even the ones with huge followings and shiny success stories, wrestle with the same thing: the deep, gut-wrenching fear of coming across as too much. Or worse, not enough. It feels like you're playing dress-up in your business clothes, and the moment you step out the door, you're convinced someone's going to tell you, "Get back inside you big faker, you're not really an entrepreneur." It's a vicious cycle of self-doubt that can make you question every decision.

So why, when we know the value we bring, is this so hard? Well, let's break it down.

You Don't Always Know What You're Selling 

Most of us get into business with a passion, a skill, or a vision. But when it comes time to put that vision into words, you know, to sell it, things start to get funky. Why? Because entrepreneurs are always evolving. We change, pivot, adapt. One day, we're selling our expertise in one area, and the next, we're refining our product or service to serve a different purpose.

This constant iteration isn't a flaw though, it's actually a huge strength. Your business doesn't have a set, "fixed" title like in the corporate world. You're constantly shifting, growing, learning and tweaking your offering, which makes it hard to articulate exactly what you're selling. But the reality is that it's okay not to have everything figured out. What matters is that you keep going, pushing through the uncertainty, and learning what works along the way.

Imposter Syndrome Is Real (And It's Not Your Fault) 

One of the biggest roadblocks for entrepreneurs is feeling like a fraud. "Who am I to sell myself like this?" or "What if they find out I'm just winging it?" Sound familiar?

You're not alone. Even the most seasoned entrepreneurs feel like impostors at some (most) points. The truth is, imposter syndrome isn't something you "get over"; it's something you learn to work with. It shows up because you're trailblazing, pushing boundaries, trying new things, and questioning the status quo. That discomfort is a sign that you're doing something bold, something worth pursuing. The key is not to let that voice of doubt hold you back.

One of my biz faves, Ash Ambirge, sums it up perfectly: entrepreneurs are some of the most capable people on the planet, but they're also the ones most likely to feel insecure or unsure of themselves. The challenge, then, is learning to sell your work anyway. Even if you don't feel 100% sure, you have to own that you have something valuable to offer.

The Fear of Being Too Much (Or Not Enough) 

Let's talk about the elephant in the room: the fear of sounding too confident. Or worse, the fear of coming across as arrogant or self-centred. As women in business, we're often conditioned to downplay our achievements or belittle our successes because society doesn't want us to be "too much."

You need to let go of that fear. Stat. Selling yourself isn't about boasting; it's about owning your worth. Of course, there's also the other end of the spectrum: you know when you feel like a child in its mother's heels, playing dress-up, and you want to be the grown-up but your voice shakes, you trip over your too-long dress and you feel like a giant fraud? Yeah, that.

Both ends of this spectrum are suuuper uncomfortable, so naturally, the answer lies in the balance. Knowing (and believing) your worth, asking for what you want, and showing up confidently. Because when you can master that, you send a message to the world: "I'm here, and I'm ready." Will it still be uncomfortable? Probably, but a little nervousness reminds us that it matters. Get comfortable with the uncomfortable.

The Cycle of Reinvention (And Why It's Not a Bad Thing) 

Entrepreneurs are constantly changing. Whether it's a new product, a refined service, or a fresh direction for the business, we're continually evolving. And as much as this can make you feel like you're always starting over, it's a necessary part of growth.

Instead of viewing this constant reinvention as a source of doubt, start seeing it as a sign of strength. It means you're not stuck. It means you're agile, flexible, open to new ideas and always striving to be better. And as you embrace that constant evolution, your ability to sell yourself will grow right along with it.

Selling yourself as an entrepreneur is hard, no doubt. It's uncomfortable, messy, and filled with moments of doubt. But you're not alone. Every entrepreneur goes through this struggle. The key is to push through the discomfort, own your worth, and embrace the beauty of reinvention. Your business is a living, breathing entity, and so are you.

Own that power and watch your business grow.

I believe in you (always).

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 Tricia Scott is a passionate startup business mentor and the Founder and Editor of The Female CEO - Create Evolve Overcome, a platform and digital magazine holding the space to showcase female entrepreneurs from all over the world. 

The Female CEO is gaining global recognition daily and Tricia is able to bring her own level of expertise as a start-up mentor and multi-company director to her very exclusive table along with her team of brilliant Guest Editors and Contributors. You'll usually find her with her MacBook in one hand and a coffee or a glass of something fizzy in the other. Reach out anytime!