Pivoting at 35, Courtney Cowan Tells Us How a Business Really Begins

Imagine having a career that allows you to work in an adorable space, bake cookies nonstop, and interact with fellow chocoholics all day long. To us, that sounds like a dream — but for Courtney Cowan, it’s reality. We chatted with this cookie-baking #GirlBoss about her time in the entertainment industry and how she pursued her dreams of opening her own bakery, LA-based Milk Jar Cookies.

Name: Courtney Cowan
Age: 38
Current job/profession: Owner, Milk Jar Cookies
Education: B.S., English, Indiana University

Prior to launching Milk Jar Cookies, you worked as in television post-production as a producer — a very different environment than the culinary space — while baking cookies on the side. How did you manage a side project while working full-time? 
Lots of late nights and super early mornings were involved, that’s for sure. My job in television was definitely not a 9 to 5, so there were many nights I would get home from work at 10 p.m. and have to bake 12 dozen cookies for delivery the next morning on my way into the office. Needless to say, it wasn’t always the easiest balance, but in some ways that helped me realize how much I truly loved baking and sharing a little joy with others.

Did you always plan on turning Milk Jar Cookies into your full-time gig? How did you know it was the right time to do so?
I definitely dreamt of it being my full-time gig from the inception, but for a very long time, I didn’t know exactly what that meant. My job in television allowed for pockets of time when my show was on hiatus where I could focus all of my time on my cookie dream. However, as soon as I would get the call to go back to work, I would take the job and be back to doing both.

I went back and forth for about seven years, and there were times I resented each endeavor and struggled to figure out which path to take.

I went back and forth for about seven years, and there were times I resented each endeavor and struggled to figure out which path to take. I remember a time in late 2011 when I was working on a particularly intense show and felt like I needed to shut down the cookie side hustle because I wasn’t able to do it in a way that made me proud. So, I packed up all of the packaging supplies and everything related to it and put it in the garage. Barely two days passed before I knew that was a mistake and my heart ached for my cookie business. Shortly thereafter, I had back surgery and found myself at a fork in the road. I decided to utilize my eight-week recovery time to write a business plan and start laying the groundwork for a brick and mortar store. I was so enraptured and excited by the process that there was no looking back. 

What was the initial transition like — going from a ‘corporate’ environment to becoming your own boss? 
While I was always a very dedicated and conscientious employee, the sense of responsibility that comes with being your own boss, and thereby the boss of others, is immense. Thankfully, I’m an extremely organized self-starter who’s good under pressure, so I took to the initial transition well. I lived a life full of lists and long hours, but I was getting it done because I knew I had to. My dad always told me that the best way to eat an elephant is one bite at a time, and that’s a mantra I have absolutely repeated to myself over the last four years.

The sense of responsibility that comes with being your own boss, and thereby the boss of others, is immense.

You officially opened Milk Jar Cookies in 2013. How far ahead did you begin planning for the launch of the brick and mortar store? What steps did you take to ensure the business was set up for success?
Looking back, it all happened rather quickly, albeit after seven years of recipe development, research, and dreaming. I wrote the first draft of my business plan in July 2012, signed the lease for the space in December 2012, and opened the doors in April 2013. The months in between were filled with logo design, branding and packaging development, designing the interior of the shop, demolition and build-out of the space, and everything else that goes into launching a business. It was very intense, and my husband and several friends were instrumental in the process of eventually getting it all done. I did my best to stay two steps ahead by arming myself with as much research and knowledge as I could, which also helped. Every bit of this was uncharted territory for me, so I googled and asked A TON of questions. 

What was the biggest challenge you faced as you switched industries? 
Confidence! I was a self-taught baker, and aside from my babysitter club when I was 12, a first-time business owner. I struggled with whether the public would see my product as a viable delicacy because it was created by someone in their apartment and not a trained pastry chef. To combat that self-consciousness before we opened, I just kept baking my cookies and giving them to people. Each time people’s eyes lit up or gave an “mmmm,” my confidence was boosted a bit. 

As for the business side of things, I found anyone and everyone I could and asked them as many questions as I could. So often, I think our fear is simply of the unknown, so I did my best to just lean in and unveil the mysteries of owning a bakery by scheduling informational interviews with other bakery owners and renting a commercial kitchen space a few times to see how it worked to use a convection oven or a large mixer. Turns out, there wasn’t much to fear in those things once I had been exposed to them. 

Do your research and then go for it! Don’t let your fear hold you back.

Were there any skills from your previous job that translated to running your own company? 
There have actually been several skills that I honed in my entertainment career that have come in handy in this venture. An overall awareness of several different projects, their statuses, and knowing how to prioritize the variety of things that need to get done in a day are skills that I exercise daily. While I typically only managed two or three people in my producer role, having the experience of being a leader and a boss has helped as I’ve grown my team to 20. The most unexpected skill that translated has been my knowledge of the city of LA, as it has allowed me to strategize our deliveries each day. My days of being a runner and planning delivery routes for the runners on my shows have definitely proven useful.

What advice do you have for women looking to do a professional 360? 
Do your research and then go for it! Don’t let your fear hold you back, but instead let it drive you and push right through it. What awaits you on the other side is better than you even imagined. There’s a possibility you may eventually realize you don’t love your new path as much as you thought you would, but don’t let that hold you back either. That can be just as valuable as finding out that it truly is your passion, and then you take that knowledge and choose a new path.

You had a hand in many aspects of starting the business, from decorating the interior to supervising the logo, branding, and menus. Were there any aspects you took a more hands-off approach to, and if so, how did you know when to pull back? 
Pulling back has been one of my biggest struggles thus far. I can honestly say that it’s because I really do love what I’m doing and even packing a box of cookies still brings me great joy. That being said, I have a wonderful team and my value is in growing the business. This year, I have mindfully handed a great deal of responsibility over to my team, so that I can focus on that growth. It’s been wonderful to see them run with it and how the business has evolved and grown. 

How did you initially market Milk Jar Cookies?
There was not a lot of money for marketing or promotion in the beginning, so I did my best to utilize social media to generate interest and establish the fun, welcoming personality of the brand. We also hung a banner on the storefront and a poster in the window that was a direct letter to the people walking by, inviting them to be a part of this experience with us. If nothing else, I think it created intrigue because it was so personal. And, I’m sure the fact that it was cookies didn’t hurt either. 

What does your current day-to-day look like? 
Every day is different, and I love it that way. I generally wake up early and snuggle with my dog for a few minutes before the day begins and then hit the ground running. Once I arrive at the shop, it’s a combination of emailing, strategizing, managing my staff, ordering supplies, decorating the window, and everything in between. We have taken possession of a second baking space that is our Shipping & Delivery hub, so there has been a lot of planning, problem-solving, and new process development as we transition to this new way of working. There are new challenges daily, and it’s certainly never dull.

What do you look for when hiring potential employees?
I look for people who have a great attitude, want to work hard, and enjoy learning new things. Experience is nothing if those three attributes aren’t there. 

Believe in yourself and chase your craziest dreams. Even if people tell you that you can’t, do it anyway. You’re young, but you’re able, and the world is yours for the taking. 

What’s the most challenging part of running your own company? The most rewarding? 
For me, the answer would be the same for both — managing the growth of the business. Milk Jar has consistently been growing at a rate of 20% each month, compared with the year before, with this year set to have several months that were double that of last year. Keeping up with that growth and maintaining the highest quality product and customer service is challenging, but I am so proud to say that we’ve done it. 

What’s your proudest professional achievement to date? 
I am very proud of the consistent experience that we are able to provide our customers, both in our product and in hosting them at the shop. Despite the growth in our production volume that has brought about changes in our processes and new faces to our staff, we have been able to continue to produce the same quality of product and the same friendly, hands-on service to our customers. There is something to be said for people knowing exactly what they can expect from you with each and every order. 

Where do you see Milk Jar Cookies five years from now? 
In the next five years, I’d love to open two or three more locations and serve people of other areas. There are several cities across the country that I personally adore and feel Milk Jar would thrive in. At the moment, we’re focusing on growing our Shipping & Delivery, but I’ve got my sights set on a couple more shops, that’s for sure!

What advice would you give your 23-year-old self?
Believe in yourself and chase your craziest dreams. Even if people tell you that you can’t, do it anyway. You’re young, but you’re able, and the world is yours for the taking. 

Courtney Cowan Is The Everygirl…

Favorite Milk Jar Cookies recipe? 
That’s like asking me to pick a favorite child! But, if I had to choose one, I’d have to go with my first — Chocolate Chip.

I wish I knew how to…
Play the banjo.

Quote you live by? 
Make it happen.

If you could have lunch with any woman, who would it be and what would you order? 
Just one?! Can’t I throw a party? I’d have to go with Michelle Obama, and I’d order some carrots from her garden. 

Show Comments +