The Startup
Published in

The Startup

9 Confidence Lessons I’ve Learned From Starting a Fashion Business

If you don’t believe in you, no one will.

Photo by Nicola Styles on Unsplash

Good day, entrepreneurs.

Starting a business has been like everything else new that happens in life. Have challenges come up? Yes. Have people talked to me like I’m an idiot? Yes. Have I been having fun? Yes.

I recently launched my clothing brand (woo!) and would like to share the lessons I’ve learned along the way in hopes they help you in your business journey.

Whether you’re starting a business from scratch, buying a franchise, or even starting a new workout routine, the bottom line is…if you aren’t confident in what you’re doing, you’re going to struggle.

I’m here today to make you feel less alone in your bravery pursuits, give you some confident lessons, and hopefully make you laugh.

1. Acting like you know what you’re talking about (when you don’t) will backfire.

Ask the questions that need to be asked without fearing you will look stupid. In the beginning, you probably will. And who cares if you do.

Like Rebecca Minkoff says, “If you don’t have thick skin in business, you’re not going to get very far.” So thick skin I grew!

2. Comparing yourself to other people who have been in the game for 40+ years makes NO SENSE.

Or 5 years or really any length of time longer than what you have put into it. You should only be comparing yourself to the person you were yesterday. Truly.

Comparison really is the thief of joy. Nothing productive comes from comparing yourself to someone else.

3. If you are not being 100 percent you, you are setting yourself up for failure.

This can sometimes be a difficult thing to be in business because you’re supposed to be “professional.”

For someone who preaches mantras to BE YOURSELF!! for a living, I really surprised myself as to how not myself I was when discussing my brand with veterans in the industry.

While there is a tactful way to finesse your personality in situations that call for more “business speak,” you still have to be you. Your you-ness is what dictates your success.

4. Going with your gut is always the right answer.

Again, for someone who shouts this concept from the rooftops, I was surprised at the times I leaned into someone else’s advice over my own intuition.

I assume this gets clearer over time, but in the beginning, it’s tricky to decide what’s right for your business when you have so much newness and uncertainty thrown at you. Give yourself grace, but always go with that initial gut feeling.

5. Reminding yourself of your “Business Why” is crucial to your success.

I learned this from fashion business experts Ana & Klas Kristiansson.

During a fashion business course I took with them, they hammered the idea into our heads that the “Why” of your business will guide every single decision you make — from the fabric you choose to the manufacturer that’s right for you to the language you use on your website.

Anytime I’m stuck on a design decision or don’t know who I should collaborate with for an event, I ask myself my “Business Why” and the answer becomes clear immediately.

6. Finding the right people to work with is key.

I’ve said this once and I will say it again — I would rather be raking leaves with someone who makes me a laugh for a living than having my dream job with a boss who is a nightmare.

Even if you’re a one-man team, you work with your customers at the very least. On that note, keep in mind your vibe attracts your tribe.

7. If you don’t believe in what you’re selling, no one else will.

I almost fainted when my dressmaker showed me the kimonos she handmade for me. I was so in awe of them — and of her for her beautiful craftsmanship. There is no cooler feeling than seeing something you’ve dreamed up in your mind sit right there in front of you to touch and ogle over.

The kimonos I designed (and my fashion taste in general) are a very specific look. They are not for everyone, which is what makes them so cool and special and exclusive.

I don’t say this to brag. I say it to show you that if you are not completely in love and totally obsessed with your product, no one else will be.

8. You MUST find ways to keep yourself motivated every day.

And it has to be more than looking forward to your morning cup of coffee and your evening glass of wine.

For me, it’s listening to business podcasts, humor podcasts, and loud music, taking long walks, forgetting about my phone, perusing pretty places like boutiques, book stores, and organic markets for inspiration, reaching out to people in the industry for advice, and committing to four solid hours of work per day.

Any entrepreneur will tell you that “the highs are sky high and the lows are dirt low,” and they are correct. Both of those extremes are fleeting, so you have to find ways to keep yourself excited about your business in the in-between times.

9. Doing one thing that makes you uncomfortable every day goes a long way.

Another self-helpery tidbit of advice that works wonders.

For me, this is telling a mom at a park about my line, showing her photos and asking her opinion about the looks.

Instead of thinking, “What if she thinks I’m being self-promote-y?” I think, “What if this is the clothing brand she has been searching for all her life and I am the one giving it to her?!”

Being delusional can work. At the very least, it’s a true mental health hack.


Your you-ness is what makes you amazing, and it is what will separate you in business. Don’t water your personality down for someone who thinks you’re too extra. If you believe in yourself and in your business, you will be successful.

Thank you for reading :)

Ashley is a Connecticut-based writer & fashion designer specializing in mental health. Her work has been featured in Forbes, POPSUGAR, Well + Good, and more. She believes our weirdness is what makes us great, and advocates for everyone to be themselves, always.

Sign up for her cheeky mental health newsletter here.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store