How I Dealt with the Failure of Starting My Own Business

“About 96 percent of new businesses fail,” the banker told me as I opened up a bank account for my new business. This wasn’t exactly the “huzzah!” attitude I was hoping for as I embarked on my first entrepreneurial endeavor. But as a longtime overachiever, I was unabashed. I will be the four percent, I silently said to myself.


I will be the four percent, I silently said to myself.


Large cardboard boxes began stacking outside my door, resembling the makeshift wall of a childhood fort. I tore open the boxes with Christmas-morning excitement and my expectations were exceeded with each piece of clothing I pulled out. The pink shift dress with lace bodice! The purple chiffon top with the pearl-lined collar! Oh, the giraffe printed dress! These will sell out early.

They were all so pretty, I ordered more merchandise. I had $10,000 in my savings account and figured pulling out a few thousand to invest in inventory made sense since I felt confident everything would sell out. I figured when this clothing sold, I’d reinvest profits into next seasons merchandise.


You can’t do both.

I’d spent three months dedicating every spare moment to launching an online women’s clothing store. This was my chance to own my own business, to be an entrepreneur! I wanted to create something that inspired women to feel happy and I believed providing women with beautiful clothing (from size 2 to 22) could make them feel amazing. But just before I launched the site, I received a call at work.

“You can’t do both,” an HR representative said as I sat in my cubicle. “We have a policy which prohibits employees from participating in any outside business endeavors.”

My stomach twisted; the idea of losing my guaranteed weekly paycheck was daunting. I’d already tapped into my savings to start this business. Could I afford to launch a new business without this day job? I imagined the work and money I’d already invested: the mountain of legal paperwork, the research to find clothing vendors who represented my brand, the hours on hold with tech support as I struggled to set up my shopping cart platform.

I wasn’t entirely sure how I’d make it work without a steady income, but my intuition and desire spoke louder than my fear. If this is what you really want, find a way to make it happen. I officially put in my two weeks’ notice and launched my store.

The instant high I received from quitting my day job to pursue my entrepreneurial dream quickly diminished when I wasn’t receiving enough online orders to pay my bills. I marketed my new store by partnering with fashion bloggers, posting to Facebook, and sending email newsletters with special offers. Every time I sent out a newsletter or posted a picture to Facebook, I felt like my marketing efforts were being thrown into a black hole. I sold three shirts and a dress in the first month. This wasn’t going to cut it and I started waiting tables to supplement my income.


The money just wasn’t coming.

I was happy at first, walking out at the end of my shift with a wad of cash in my pocket. But I quickly loathed heading into work. I had spent years waitressing in high school and college. Reverting back to my adolescent job felt like I was taking a step back. Suddenly, I didn’t have as much tolerance for screaming children demanding more hot fudge on their sundaes and senior ladies bogarting one table for an entire afternoon. Plus, I wasn’t earning enough tips to pay my rent. I began making withdrawals from my savings account to pay bills.

Withdrawing a couple hundred dollars each week without ever depositing into my savings account became a frightening ritual. Soon cash disappeared from my savings like leftovers from a refrigerator after Thanksgiving — slowly yet deliberately, until mere scraps remained.

I logged in to pay my credit card. My stomach churned with the kind of fear you get after turning down a desolate city street late at night, uncertainty and desperation pulsing through your veins. My eyes widened in disbelief. Total amount due: $3,400.00. I logged in to my bank account to check my balance: $1,008.56.


My heart pounded. I couldn’t breathe. I don’t have any money. I’ve lost it all. How did I let this happen?

Frantic, I called my mom. I needed a sounding board. With each ring, I could hear my own heart pound against my chest like crescendoing drums. She answered and the mere sound of her voice ignited a flood of tears, the way one tiny matchstick could send an entire house up in flames. In between my sobs, my mom calmly requested I stop crying, take a deep breath, and listen to her.

“How much money do you need?”

“I can’t take your money,” I sniffled.

“Kate, this isn’t a negotiation. You need help. We’re your parents and that’s what we’re here for.”

“I will pay you back,” I said. “I won’t take it otherwise. I got myself into this mess. I don’t want to feel like you had to do this” — I stopped to blow my nose — “that you had to give me this money” — sniffle — “because of my poor judgment.”

Their money allowed me to step off the financial tilt-a-whirl I’d been spinning on, just before I’d need to vomit — but then, why did I still feel sick?


I was proud to support myself and now, for the first time since being a child, I couldn’t.

I became increasingly embarrassed that my parents had to rescue me with their money. I hadn’t even borrowed money from them to pay for college. I’d had a job since I was 16 and while my mom would treat me to a new outfit or to getting my hair done, I never expected her to front the costs for my superfluous purchases. I was proud to support myself and now, for the first time since being a child, I couldn’t.

Embarrassment and guilt grew from needing to borrow money but then, a worse feeling began to marinate within me: I was a failure.

Each of the clothes-filled cardboard boxes lining my apartment floor now mocked me with every step I took past them.

What were you thinking?
You invested thousands of dollars into us.
You can kiss that money goodbye.


Failure doesn’t mean you’re done. It’s simply there to guide you to your next adventure.


The end… but really the beginning.

I didn’t want to close my business. After all, this was supposed to be my big thing—my calling to make a positive impact with women realized! Closing would be admitting defeat. But the business was a money-suck with no profitably in sight. Plus, I didn’t want to have to borrow any more money from my parents. Shutting down the business made logistical and logical sense but it also made me feel like a failure; a defeated doe-eyed girl who should have known better than to embark on such a fanciful dream. I failed at my dream—what am I supposed to do now with my life?

After I shut down the online store, I sold some of the leftover inventory to a local resale shop and donated the rest to Dress for Success, an organization that provides women in need with professional attire. Then I searched for a job: one that would provide a paycheck and professional fulfillment.

Growing up in the Midwest, it had always been my dream to work in New York City. I used the milestone of closing my business to open up the possibility for this other dream to come true. After submitting countless job applications, several phone interviews, and lots of LinkedIn stalking—I found the right career match. Today I’m working as the Director of Account Management for a tech savvy digital content studio in Manhattan. I work with top publishers and share unique ideas for how they can increase engagement with their readers. I enjoy my day job and it stretches my strategic muscle but I still have a desire to create something that inspires women to feel happier! This is a cup my day job cannot fill. I decided I’m not going to give up on this dream simply because my online clothing store didn’t succeed.

Riding the train to work one morning, a thought occurred: Why don’t you write more often? You used to write all the time. Why not reignite that creative calling?

I made a vow somewhere between Christopher street and 9th: I will write every day. Even if just for a few minutes, I wanted the consistency. I wanted to create a habit. The daily habit of making sure I met with my laptop for at least a few minutes a day turned into a complete lifestyle change. Now I wake up one hour earlier to write before work. I’ve completed my first manuscript for a book focused on how women can bring more happiness into their lives by creating healthy habits, and I just launched a blog focused on this same topic.

They say about 96 percent of new businesses fail, but I now know that I did not. My dreams just look differently than I had originally imagined, and I’m chasing new ones, with a new belief: failure doesn’t mean you’re done. It’s simply there to guide you to your next adventure.

  • Nikki Laraja

    I love this, as a struggling small business owner myself, I find this so inspiring!

    • Thank you, Nikki!! Best of luck with your business! When profits don’t come from the struggle, at least lessons do.

  • Sandra McNeill

    This is so refreshing! So many entrepreneurs share their stories of successes, which are wonderful and inspiring, but can lead others who are struggling to feel rather alone or like failures. I really appreciate the honesty and vulnerability in this article – as well as the message that if a business fails, YOU aren’t a failure.

    • This is really great to hear, Sandra. I know what you mean and I’m glad you do not feel alone. Best of luck with your yoga practice and spreading the love and your light through what you do!

  • Thank you for writing this post. I am lucky enough to be able to have both- a full time job plus my jewelry business on the side – I can’t imagine giving up my full time job, not just because of the money, but because I enjoy it!

    I work at a financial institution, and so I know firsthand about the failure rate for new businesses, but that’s not a reason to not give it a shot. In fact, going in, I was completely prepared to fail (less so prepared for success, but that’s a story for another time).

    Congratulations on your new gig!

    • So true! I love writing and building my blog but I really enjoy my day job too and I find my passions feed each other. What a great balance for you to have the financial knowledge while you grow your own business.

      Thanks for reading!

      P.S. You offer some beautiful pieces on your site!

  • Thank you so much for writing this! I tried to create a small Buisness and failed, and now I am jut trying to grow a blog. People don’t realize that success isn’t easy, and I love how honest/inspiring that this is

    • Thank you for taking the time to read it, Jessica. I’m really happy it spoke to you. Best of luck with your blog!

  • Shanice

    Such an inspiring article, thank you! I would love to check out your blog.

    • Hey Shanice! Please do! It’s and you can sign up for my newsletter to receive more goodness!

  • Linda Sivertsen

    Great post, Katelyn! Beautiful. xx

  • Jessica

    Thank you for sharing your story. I am trying to launch a business while still working full time. I’m thankful that I have the option to do both and am very optimistic as you are. Appreciate you sharing your truth!

    • How wonderful that you can do both. It can be so hard juggling two jobs at once but when you love what you do, and you’re as ambitious as you sound, you go after what you want. It may evolve over time and that’s okay too! It’s all part of YOUR journey. Best of luck with your business, Jessica!!

  • Omg I love this!! Thank you for sharing and being so honest. As I was reading I was thinking “why don’t you become a writer, you have a writing gift” and then I read about your writing LOL! I think there’s alot of pressure these days to be this mega success as a young person and a perception of “just quit your job it’ll happen” but that’s not always the case. You’re definitely a gifted writer and I believe your writing would help women much more than some clothes would 🙂 Congrats!!

    • Thank you so much Ashley! I have always felt called to write but for some reason it took me over 20 years to listen to that voice!! Really appreciate your feedback. It inspires me and my message as a writer! 🙂 Please keep in touch!!

  • Melissa A

    Do you think your business would have “failed” if you were able to keep your full time job and have this business as a side hustle or passion project?

    • That’s a great question, Melissa! I think it really depends on my definition of “failure” or success” in this case. For me, I had wanted the clothing website to be my full time job but I couldn’t do that from day one, without any other income. I believe a day job you enjoy is a great thing to support you and grow your experience while you hussle on the side with your passion project. Then, at some point, your passion project can hopefully transition into your full time work. That’s my way of seeing it now at least!

  • Candace N. Bisram

    Such a captivating story. This reminds me of when I started my online store to sell necklaces — which was a failure and I ended giving them out as Christmas presents.

    I believe everything happens to redirect us closer to our real purpose in life. Perhaps you were not meant for retail. Maybe you’re meant for something greater like using your creativity and passion for helping women, to make a positive impact in many lives.

    Whatever you venture into, whether it works or fails, is a stepping stone that will lead you closer to your real purpose in life.

    All the best 🙂

  • Thank you for sharing, very refreshing to hear a different story of entrepreneurship.

  • Lynn Shaw

    Definitely not a fail. An inspirational example of courage and taking responsibility!


  • Jasmine Callender

    This was really inspiring. I have been trying to launch my business for a few years now and have dealt with major pitfalls along the way. I definitely understand the stress of having a job that doesn’t limits your ability to pursue your passion on the side. After a bit of searching I was able to find a 9-5 job that gave me a bit of freedom. Have a consistent salary is definitely a safe net. I’m hoping to dive in full time soon but I’m patient 🙂