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6 min read

The entrepreneurial mindset that helped me grow my business

By Rebecca Miller · March 10, 2021
Hero image of a pink pie with strawberries

Six years ago, I left my career as a full-time attorney to open a pie business, Peggy Jean's Pies, with my mom. I had never baked a pie in my life.

I know, right? Who makes that sort of decision?

Because I was naïve about entrepreneurship, I fully expected smooth sailing through calm seas as we ventured into world pie domination. I really believed that because my mom had some entrepreneurial experience and that because I practiced law, the world would watch as we slayed the pie market. 


Spoiler alert: starting, managing, and growing a successful company is a million times harder than what most people expect. What I saw in my head was Meg Ryan in You've Got Mail. The reality was 90-hour work weeks and a tremendous time of personal, emotional, and mental health growth that felt mostly like an uphill battle. (Uphill both ways. In the snow.) 

Also, my hair never looked as cute as Meg's. Not even once. And no one ever brought me a bouquet of freshly sharpened pencils. 

A headshot of Rebecca Miller
That's me, not Meg Ryan.

If you're considering entrepreneurship—or if you're already there and are struggling—I've got two insights for you.

Love your business 

You must love your business. Not like it or tolerate it or decide it's just ok for now. It requires loving it on the best days, the worst days, and probably most importantly, all the mundane days that are between. The mundane is where your life goes from Meg Ryan in You've Got Mail to Bill Murray in Groundhog Day. Loving your business requires the same work and attention every single day, in good sales and in slow sales, in times of creativity and times without, and in times of certainty and times of insecurity. 

I can't emphasize enough the work that this commitment requires. There was nothing easy about most of our earliest days: we baked all the pies, washed all the dishes, took out all the trash, paid all the bills, waited on all the customers, and so much more. More than once, I looked around and wondered when someone in charge was going to show up. And then I remembered it was me.

After six years, I look around less for that person on a regular basis...but I still want to retreat when it's time to categorize expenses or solve staffing woes. Those skills aren't in my preferred tasks, but my business requires it, and so I continually commit to learning those skills. (And before that sounds overly sanctimonious, please know that I struggle the whole time, often question my life goals, and give side-eye to my phone when the accountant texts to ask if I've updated our books for her review.) 

Without cultivating so much love for our business, it would have been extraordinarily easy to give 10% instead of 100%—or actually just to walk away when we went through dark days. 

Have you ever been in a store that feels like it just gave up? When people walk into our store, it looks and feels like it's well loved and cared for. Our storefront is clean, bright, and cheery, and our staff is trained to greet each customer as they enter the front door. Our commitment to this environment helps build our loyal customer base that is so very important to our success. Our superfans love our pies, obviously, but they really connect with our storefront and our brand

The inside of Peggy Jean's Pies

We've had customers order pizza for our staff in the busy days prior to Thanksgiving because they worry we aren't taking breaks from our busy baking schedule! Our December days are generally 16 hours long to meet demand, but they are also full of customers stopping by with well wishes, cards, gifts, and before the pandemic, lots of hugs. They give us their business, and we give them a place to feel welcomed, a story to watch unfold, and someone to root for. If we didn't love our business so much, I'm certain we couldn't convince an ardent group of followers to do the same. 

Go the distance 

The entrepreneurial finish line is never going to arrive. If you're starting a business, you're signing up for a marathon that never concludes. I spent my first few years convincing myself that the hard work and the pressure to grow my skill set would eventually end. And when it did, I would take a deep breath, relax a little, and watch my little business grow while I watched from a distance

The moment simply never arrived. And the realization that it wasn't coming hit me so hard that I remember every detail. 

It was a Thursday in April. I was wearing a black company logo T-shirt. I had just picked up coffee, and I was sipping it in silence for a few minutes before I turned off my car, unlocked our front doors, and welcomed our staff to start the day. I was thinking about what I needed to accomplish that day, and it had a fair amount of projects I had delayed because I didn't really know how to do one or more things on the list. As in, didn't have the knowledge or resources to get to my end goal—seriously. And then I realized, welp, self, THIS IS NEVER GOING TO END.

That actually helped me a bit. It helped me avoid dumping projects onto a never-ending to-do list and focus more on figuring out what I didn't know how to do and why. From there, I scheduled one-on-one meetings with people who had expertise in areas I didn't (hello, accountants), did a lot of online research, and read a lot of books about business, creativity, and mindset. 

As we grew, the company kept needing more from me in different ways. We were different in year three than year one. And different in year five than year three. As our business evolved, it required me to evolve to lead us in the right way. That sounds daunting, but if you can appreciate the opportunity it brings you to grow as an entrepreneur and as a person, you will realize what a gift you have been given.

A picture of a pie

Just between you and me, I keep a running list in my planner of things that annoy me about my own store. It allows me to continually question the way we do things and why it works or doesn't work. I've found that the answer is often that we've always done it like that since we started or that's the only way we know how to do it. Challenging those ideas has been a rewarding experience. Remember, I started a business because it sounded fun (plus I thought a tousled pixie haircut would make me endearing), so what did I know when we started about business? Continually reviewing, adjusting, and changing our mindset of our day-to-day tasks is an integral piece of the puzzle of entrepreneurial success. 

Remember I mentioned that my mother had entrepreneurial experience—she owned an iteration of our business with her best friend while I was an undergraduate and in law school. And eventually, as her best friend became too ill to be a co-owner, we had to have a difficult conversation about what it meant if my mother no longer could—or actually wanted—to own the business. Despite rooting for her, she was just over it. And she closed the store, at peace with her decision. When you're running a long race, there are times you just have to tap out when your body and mind can't move forward another foot. In long races, there are golf carts that will come get you when you just can't carry on, and they drive you back to your car. 

It happens, and when it does, that's ok too

Hang on for dear life 

We're starting to work on the concept of a second location, which is akin to a dump truck backing up and unloading a pile of work at our back door that seems inconceivable. Can I be a woman responsible for two storefronts? Did I ever envision myself being a woman that owns two grease traps? These are the things I ask myself late at night. I think so. I hope so. I've decided this: I'll wrap my arms around my store(s), put my head down, and hang on for dear life. 

If you can do these two things—love your business and work like there is no finish line—you'll find yourself in love with the entrepreneurial game.

Just shy of our seventh anniversary, we are celebrating our first $1M year. I feel like NYC152 would approve.

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