8 Things I Wish I'd Known Before Starting a Fashion Business

8 Things I wish I'd known before I started a fashion business from A Leap of Style designer Karissa Lindsay

“But, how did you know it was time to leave? How did you really know?”

I get this question a lot. These days I get many requests to share my story and journey into entrepreneurship, both in small intimate settings, and on larger scales like blog posts and other publications. 

I’ll give you the short of how I got here: I dreamt of being a designer as a kid, pursued a degree in print journalism because I thought there was no money in design (catch that irony please), chased a career in education because it was stable and I was decent at it, nearly had a breakdown, found Christ, took a chance on a clothing line, and here we are three years and one very long sentence later. 

Designer Karissa Lindsay of A Leap of Style wearing the African Print off the shoulder Jumpsuit

That's me, Karissa CEO & Lead Designer, being silly in the Olivia Jumpsuit at Melodrama Boutique in Houston. 


How’d I know it was time to jump from my nice, stable job? I knew it when I spent more waking hours thinking about my side business than about the work I once felt so passionately about. I knew it when I started to feel overwhelmingly underutilized, and more importantly, underperforming. I was…disappointed. In myself. In my career path. With my life. So I decided to move on. I believe God called me to something new, something creative, something that would stretch me and my faith. Maybe I’ll write more about that later – drop me a line in the comments if you’d like to hear it.

Anywho, so I left. I made the decision, and a year later I took the official leap into full-time entrepreneurship. And without further ado, here are the top 8 things I wish I’d known before starting my fashion business:

Get in the business of running your business

I remember my first full day as a fashion entrepreneur. That first Monday, I jumped in to creating. I was free as a bird! I was liberated! I was ready to make things! Wrong move. I think the rule is something like 15% of your time “should” be spent creating and about 85% should be spent on the business itself. You’ve got to make a plan that works for you, and figure out how to work it if you want to see all those beautiful creations move from your hands, to your customers, and let’s be honest – into money in the bank. I’ll be honest that I’m still working this time ratio out, but it makes a serious difference. Getting the business foundation firm allows you the mental space to be creative. It’s a MESS when your business is all over the place and you’re trying to create. Trust me here. 

A name and a website do not equal a business, or a brand

Very few people know that I bought the A Leap of Style domain long before there were any African print maxi skirts or Von Me Dresses. I built an initial site, took some crappy pics on an iPad, and thought I was good to go. Your brand is everything from the images you put out, to the fonts you use in your emails. Your brand is the story of your company – it is the why behind what you do, and it is the thing people will remember about your company, and you, once you’ve left the room.

There’s an awesome TED talk from a guy named Simon Sinek that I love. I think he breaks down the why behind a brand in a super-understandable way. You’ve got to figure out your brand in order to market it – and you’ve got to market so people know you exist. You can have the best product in the world, but if no one knows it exists, you can't expect to make sales.

Get out there

I read a Rebecca Minkoff interview where she urged emerging designers to get out and do trunk shows and pop ups and anything that would get their products in the hands of customers. I can be pretty shy at times and so this was a little unnerving for me. I did (and still do) get a great boost of confidence because I believe deeply in my product. I also know that a huge part of my life’s purpose is to empower and inspire women – the pieces I design allow me to do that on so many levels. Anyway, getting your product in the hands of real customers, in person is invaluable. You get to see reactions and get feedback and know for sure whether you've got the juice. It’s much needed, time well-spent to interact with the people willing to give you their money for your creative pursuit. I don’t think there’s a much better feeling than seeing a woman’s face when she puts on the Von Me Dress and it’s perfect for her. I live for those moments!

Stay true to you, boo 

It's easy to be swayed by trends. You’ve got to keep an eye to what’s in fashion now, but don't waver from what your customers want. I love to hear, “I saw [insert piece of A Leap of Style clothing here] and I just knew it was yours!” You've got to be consistent to build brand recognition. And that means incorporating some trends, and letting some go. For example, I was really inspired by the trend toward Victorian and antebellum pieces for fall of 2016, and also really into dashiki prints, but not the classic dashiki itself. So, we blended those two trends into the Victoria Dashiki Top to make this beautiful piece that is work-appropriate for my customers who have corporate jobs, but also a really fun piece to throw on for a Beyoncè concert with a pair of distressed jeans. Know what makes sense for your brand.

Victoria Dashiki Top in Yellow Dashiki from A Leap of Style


…but know your girl (or guy), too!

You’ve GOT TO narrow down your target customer! I kind of touched on this above, but one of the best things I’ve learned to do is to design for and market to a specific customer. I’ll give you this example: say you’ve started a line of handbags, and you think your target customer is between the ages of 25-34 and living in a metro area. But you stop there. At that point, you’ve included a woman who is 25 and in graduate school and gets the bag as a gift from her parents and only wears it for special occasions, a mom who is 30 and buys the bag because it’s beautiful, but functional enough to tote her kids’ stuff around, and a 34 year old socialite whose husband bought the bag for her. Each of these women’s needs is different, and the way you market to them should be as well. I have one customer in particular who I imagine when I’m designing and when I’m creating many of my marketing materials – we aim for her in all that we do, with the understanding that other people who are not the “target” will still be attracted to our bold, African prints and fun aesthetic too.

Learn your craft

I remember prepping for my first show. I wanted to take about 25 pieces to the event. I thought I needed a factory and I needed one fast. So, I called one of the cut and sew shops in town. The manager asked me a series of questions, and at the end of my stumbling through the answers, her assessment was, “You’re not ready! Call back when you’re ready!” I was crushed, but I knew there was more to learn. So, I sought out the information. I learned about textiles, patterns, grading, sewing techniques, and sourcing fabrics. Most of it I learned from the blog www.fashion-incubator.com and a book published by the blog’s author, Kathleen Fasanella. I recommend it to every emerging designer. It’s an easy read and will give you the basics. YOU NEED TO KNOW THE BASICS! You’ll especially need to know the basics if you don’t have any formal training. You’ll save yourself a ton of time and money by doing some learning upfront.

Know what you know, outsource what you don’t

I learned early that if I wanted perfect fits, I'd have to work with professionals. So I contracted with people who are awesome at the things I’m not so awesome at. And I’m still learning this lesson along the way. There are things about running a business that I am good at and where my gifts and talents are best used – where my time is best spent and I am able to not only enjoy my career, but also make my money honey. And then, there are things that I am not so good at. You wear many hats as an entrepreneur. Many. In the beginning you’ll try to wear too many. Why not do it all? Don’t fall into that. Your talents and gifts are ridiculously valuable when you put your energy into using them. Free yourself up to use them and hand off the rest.

Keep your faith, and your head

I love memes, so I’m going to reference another one. This one is a favorite: 

I don't have a 9-5 I have a "when I open my eyes to when I close my eyes"

I call bull on that. You’ve got to grind. Got to. There are times when I have to turn down invitations because there is so much work to do. Man, I mean I’m up cranking this post out at the end of a 15-hour day, but best believe I’m going to take some moments of peace for myself this week. When I first started, I’d work nonstop, but I realized that the work does not end. It took my sister getting really sick for me to realize that not even my dream was worth overworking myself for. You've got to rest and listen to your body; listen for God or the universe or whatever you believe drives you forward. Make that time as often as you can by writing it in to your schedule. I have an alert on my phone to remind me to stop and pray everyday. Your business is worth your all. Your health and sanity are worth a few minutes of that all. Oh, and go see a counselor if you need to. I read a stat about the increasing rate of suicide amongst entrepreneurs. If you’re at that point, or even just overwhelmed, definitely get help or at least talk to a coach about how to make the healthiest decisions for you and your business.


Whew! That got kind of deep huh? I hope this helps someone out there. Share this post with your entrepreneur friends – especially the ones thinking about a career in fashion! Leave your comments, too and let me know if you'd like to know more!





  • Wow! What a great blog and so on time. Funny thing is, I think I’ve already gotten to the it’s time to leave part but I don’t know what I’m supposed to do next…actually, I just figured it out this weekend ?. I also suggest folks read “Before You Quit Your Job” by Robert Kiosaki (spelling?). That book has helped me over the years with the litmus test and also teaches the running of the business aspects of being an entrepreneur.

    Good luck everyone! There is no better time than now to follow your dreams!

    K Ashade
  • I loved this! I actually ran across your post while taking a 10 minute break…from sewing! I love hearing tips from other industry professionals regarding what it takes to be successful. The grind is REAL! But the reward is tremendous. I knew it was time for me to take the leap into fashion when I became increasingly annoyed at everything that kept me away from designing, including the job I currently had. Your gift will make room for you. Ignore it (your gift) if you will, but it will continue to float to the top. It is persistent because God intended for it to be Used.

    Kenya Carter
  • This really hit home today. I’m just starting this journey ….getting laid off…coming to the reality that it was the best thing for me..knowing in my head my heart was so over being at my job…. Making the decision too not send out anymore resumes…I had only sent three and got interviews with all three but knew in the pit of my stomach…,It wouldn’t work…living my dream is where I need too be. Finding true balance…Your words were golden…..Thanks!!!

  • Thank you for sharing your information. It’s funny, I started out studying Marketing at university then switched to Speech Pathology when I moved to the USA. Now I am doing a Masters degree in Education….with a view to Literacy therapy. . A stable job….like you said. Some parallels there. I will check out the ted talk vid you suggested. I’d like to ask a question though. I sew my own stuff, and it’s so exhausting. When I go national with my brand how do I produce enough inventory to meet the demand. if my brand is hansmade? Do i hire workers? Do i outsource? I keep worrying about that. If you have time look at @Gewel2 on Instagram. Thanks


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