My Entrepreneurial Journey

Four “Staple” Footwear Options for Fall

The entrepreneurial journey for me started when I was in elementary school.

My sister, a neighborhood friend, and I would color pictures from a coloring book and then walk around to our neighbors’ homes asking if they want to buy them.

I mean, I was basically a door to door salesman, trying to make a dime. And I mean that literally, as we sold the pictures for a dime.

Back then, in the ’90s, people actually had dimes so the business was pretty successful. These days we would have struggled, needing a credit card reader or Venmo at age 10.

Around this same age, my sister and I starting creating friendship bracelets, and we would sell them by the first tee of the golf course on days when my dad was participating in a tournament. I remember taping the bracelets to the inside wall of the tee house, hoping we would sell out!

You may be wondering if I was trying to earn money to buy something in particular, but that wasn’t the case. I don’t remember having any sort of drive for earning money. It was all about the sale of the product, and the thrill of the transaction with the buyer. I loved the satisfaction of being able to offer something that someone wanted. I felt so proud and accomplished.

My first job working for someone else was in high school. I got a job at a local beauty store. I was a junior in high school, and also attending beauty school during the day at a trade school, so my world was pretty centralized around beauty. The store required that I stay later than I had expected, and it ended up not being a great fit for me at the time. I quit after about 3 weeks.

During my college years, I cut a few of my friends’ hair and worked at salons in the summers between semesters. I knew I wanted to be a stylist, I just had to finish my degree and there wasn’t any point to building a summertime clientele only to leave them all in the fall when I started back at school.

I loved working in the salon as an assistant and learned so much about doing hair from really talented artists.

I was so eager to work as a hairstylist that after I transferred down to East Carolina University, in Greenville North Carolina, I started working at a booth rental salon in the spring of my junior year. Booth rental was completely new to me but it aligned perfectly with my desire to own my own business and be in control of my career.

If you are unfamiliar, when you “rent a booth” at a salon, you essentially operate as a small business within a larger salon. It may look like a traditional hair salon with 8-10 chairs in a row, all with hairstylists working behind them, but each stylist is running their own show, managing their own product and inventory, charging their own rates, and being their own receptionists.

I couldn’t afford the weekly rent right away, and I knew it was going to take a bit of time to build up my clientele, so I met a sweet family at church that needed a nanny and took that job.

I was a junior in college, studying philosophy, managing a deeply intoxicating new love with my boyfriend Justin, working behind the chair at a new salon and babysitting a few times a week for 2 really sweet pre-school aged kids.

I enjoyed being busy.

Eventually, I was able to stop babysitting for the family (which I was horribly sad to leave!) and support myself and my business as a stylist. I found a new location for my business that better fit my needs and was happily enjoying the journey of working for myself, earning an income, and finishing my college degree.

I was so deeply settled in the notion of working for myself and building a business, it never even occurred to me to do anything different.

Over the next 10 years, I would go on to start a business selling cards, making jewelry (which is a business my sister and I began, but I left right before I had my first son) and starting my blog.

I was always meant to be an entrepreneur. I really believe that some people truly have that drive in them and some people simply don’t. One way is not better than the other, as there are downsides to really any kind of career or business, but it is so validating for me to have experienced the satisfaction of building my own business.

There are risks, challenges, struggles, lessons, accomplishments, and times of pure exhaustion on the entrepreneurial journey. It can come with a great deal of pressure and stress but also can provide great freedom and balance in your life as well.

I’m sharing all of this to encourage you if you have felt the pull toward starting your own business but you are afraid to start. I read e-mails and messages a few times a month from women who are considering the idea of going off on their own to start a business but they aren’t sure. Begin nervous or unsure about starting is normal, and I think it reveals that you really care about what you are about to do, but certainly, don’t let it steer you away from trying.

When you consider whether or not to start down your own entrepreneurial path, if your inner dialogue is focused around gaining freedom, flexibility, and money, you may be in for a tough ride for the first few (or several) years. Starting your own business takes an incredible amount of time and work. You will burn out quickly if the motivation for your business is to swiftly experience the perks that usually only come after years and years of work.

But if your drive is the heart of what the business is or the belief that you are fulfilling a need that people have by offering what you do or sell, you will find great satisfaction in that. That satisfaction and validation is the fuel that will push your business forward.


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Charmaine Ng | Architecture & Lifestyle Blog says · 09.11.19

You’re so inspiring, Kate! Thank you for sharing your journey – I’m sure it’s one many of us can relate to! ❤️✨

Charmaine Ng | Architecture & Lifestyle Blog

Rena says · 09.11.19

Wow, what a journey! I’m very impressed.
xx from Bavaria/Germany, Rena

Erin says · 09.11.19

I suggest reading Business Boutique by Christy Wright. It is a great book for women who are interested in building a business 🙂

Kate says · 09.11.19

Thanks for sharing!

laura says · 09.11.19

totally get it! My husband has spent close to a decade building a digital health company, we own a manufacturing company (made in the usa clamps used in dialysis- not sexy, but we own it). And, I am a realtor. Sometimes it feels like too much, but most days it feels great! Great message to never squash ambition! laura

Paige says · 09.11.19

One thing I’ve always been curious (fearful?) about when thinking about being an entrepreneur is health coverage. I hope this isn’t being too nosy but just curious if you’d be willing to share your thoughts on that.

Kate says · 09.11.19

Sure! It’s expensive but I purchase health coverage for myself and the 3 kids. My husband is covered through the VA due to a previous health issue that was discovered while he was in the Air Force. I have friends, though, that use an untraditional method of health insurance so I know there are at least a few different options out there!

Kacie DIx says · 09.11.19

THANK YOU for this post- as someone who has thought about starting a new career for many years, it is so refreshing to hear your perspective and have some validation from that! Thanks for what you do, and all your positivity, Kate!

Kathleen Van Surksum says · 09.11.19

Those last two paragraphs really hit home. I’ve re-read them several times to let that sink in. Well done.

Hilary says · 09.12.19

I loved reading this and hearing your experience! I truly believe it is something that is ingrained in you. The part you mentioned about expecting quick results is so important to share. My husband and I started a pest control business five years ago (he had been in the business for 15 years prior to that and I was in Finance for 15 years). We prepared for several years before taking the leap and five years in, while we live comfortably, it takes a conscious effort to budget judiciously especially when it comes to things like the cost of healthcare. We are still growing so the rewards have been in baby steps rather than giant leaps, but it gives me the flexibility to stay home with my children which you can’t put a price on!

Mindy says · 09.20.19

I have a 10 year old daughter that is very much like you described yourself. I am not at all entrepreneurial. I would love any advice for how to encourage her in this.

Thank you!

Krista says · 05.07.20

Thanks so much for sharing part of your story! It’s an encouragement as I am currently thinking about stepping out on my own as well.