It's okay to want more

You don't need permission to want more ,you only need the courage to take the next step.

What is your name and what do you want the world to call you?

Ashley Chamberlain

Where are you from and where do you call home now?

Athens, GA grown; Louisville, KY made

If someone met you for the first time at a dinner party, how would you want them to describe you after the conversation ended?

I hope they'd say I was warm, ridiculously funny, and someone they genuinely wanted to keep talking to.

Take me back. What were you like as a little girl? What did you dream about becoming before the world told you what was realistic?

As a little girl, I was wild—in the best way. I looked at the world and believed absolutely anything was possible. I wanted to be everything. The world really was my oyster.

I'm the oldest of three girls, and I always wanted to be seen. I'll never forget wanting to be a gymnast in kindergarten... mostly because of the sparkly costumes and makeup. As I got older, my definition of success became pretty simple: I wanted to be rich enough to take vacations because, in my mind, that's what wealthy people did.

Was there a moment, a person, or an experience early in your life that shaped how you see yourself today?

Without question, my husband, Richard.

When we met, my dreams were small. I just wanted to be "enough." Richard has this incredible way of letting me borrow his glasses whenever I need them so I can see myself the way he sees me. Over and over again, he reminded me, "You're made for more."

Sometimes all it takes is one person believing in you before you're able to believe it yourself!

Sometimes all it takes is one person believing in you before you're able to believe it yourself!

What is something about your upbringing that explains who you are now, even if it does not seem obvious on the surface?

Being the oldest daughter taught me how to take care of people. It taught me responsibility, leadership, and how to carry things that weren't always mine to carry. Looking back, I think I became a leader because someone had to and eventually, I realized I actually loved leading.

What was happening in your life right before you decided to build what you are building now?

I found myself in a top position at a very early age of 30 years old. I no longer had a position I could work towards and that felt helpless. I wanted to provide a different lifestyle for my children but didn’t have any other steps towards promotions available. That’s when I started to think outside the box. How can I earn more to provide for my family? I guess I have to start my own income earning machine.

Was there a breaking point? A moment you knew something had to change?

The breaking point was realizing I had hit my salary ceiling, and I wasn’t thrilled. I had a great job. Great benefits. Great stability.

But "great" wasn't the life I wanted. I wanted more.

What did you have to walk away from to become who you are today?

I had to walk away from the pressures of living a “normal” life. I told myself, for so long, that I was asking for too much. I was being greedy and wanting too much. I had to leave behind the idea that you are “supposed” to follow some life guide in order to be happy. I had to create my own guide.

If you could go back and tell yourself one thing in that moment, what would it be? It’s ok to want more.

Ashley Chamberlain proves that wanting more isn't greed ,it's the courage to build a life on your own terms.

How did you land in this specific field? Was it intentional or did it find you?

Becoming an accountant was intentional. Becoming a business owner happened almost by accident.

I'd always known I was good with numbers. What surprised me was realizing I was also good at building businesses.

What is the real reason you do this work? Not the polished answer. The true one. Freedom.

People laugh when business owners talk about freedom because, let's be honest, we usually work more than anyone else.

But my freedom looks different.

I don't miss baseball games anymore. I don't have to choose between work and Christmas parties. I can have a random Tuesday phone calls with my sisters or take my kids where they need to go without asking permission.

The flexibility has transformed my relationships, and that's worth every late night.

What is the transformation you are actually trying to create in the people you serve?

I am trying to create freedom for others by taking ahold of their books for them. My dream for our clients is for them to spend their days exactly how they want, and with who they want, not behind the screen worrying about their accounting.

If your business disappeared tomorrow, what is the one thing you would want people to remember it stood for?

Community.

I hope people remember that we made them feel like family. We have the heart of a mom-and-pop shop with the systems and professionalism of a much larger company.

That's always been the goal.

When you are not working, who are you? What lights you up that has nothing to do with your business?

I'm what I like to call a hobby collector.

If there's a creative hobby out there, I've probably tried it. Reading, crocheting, photography, coloring, crafting, you name it, I've probably convinced myself I needed supplies for it.

What does a perfect ordinary Tuesday look like for you right now?

I spend about 4-6 hours working and honestly no two days look the same. It could be zoom calls, coffee chats, or client fulfillment. I love working from home because I get to walk my dogs, get my nails or hair done during business hours, or binge watch a show.

What is something most people do not know about you that you wish they did?

I wish people embraced multi-passionate women more.

You don't have to fit neatly into one box.

I wish people embraced multi-passionate women more. You don't have to fit neatly into one box.

I can be deeply creative and deeply analytical. I love spreadsheets just as much as I love photography and crafting.

Turns out, you can be both, and be really good at both.

What are you most afraid of, and how has that fear shaped the way you move through the world?

My biggest fear is having to work for someone else again. If every business failed tomorrow and I had to clock in somewhere, I would struggle with that more than almost anything.

That fear pushes me to keep building, learning, and creating opportunities, not just for myself, but for other people too.

If you let yourself dream without limits, what does your life look like in five years?

I want to keep buying businesses, hiring incredible operators to run them, and building companies that don't rely on me every minute of every day. I want to own five or six more businesses, cheer my kids on from the sidelines, walk my dogs in the middle of the afternoon, and yes... continue getting my nails done during business hours.

That's the dream.

What is the legacy you want to leave behind, separate from money or titles?

I want to leave behind the legacy of unexpected success. I don’t think anyone in my life would’ve dreamed up the life I’m living today. I wasn’t the child my parents banked on being “something big”...but my past does not define me.

What is one thing you are still working to become, even now?

I am constantly working on celebrating the wins. Big and small. I have a habit of checking things off the goals list and moving forward…I’m learning to pause more often and tell myself, “I’m proud of you”.

If a woman reading this is standing exactly where you stood before everything changed, what do you want her to know?

There isn't one right way to build the life you want. Everyone's journey looks different.

Stop waiting for permission, stop worrying about doing it perfectly, and start taking the next step.

You'll figure out the rest along the way.

What is the one sentence you want people to remember about you?

That Ashley girl, she’s even funnier in person!

Ashley Chamberlain — Founder of Chamberlain and Good Company

Meet the expert:

Ashley Chamberlain is an accountant and bookkeeping expert who has helped hundreds of small business owners get financially organized, tax-ready, and profitable. As the founder of Chamberlain and Good Company, she combines real-world experience with practical strategy to help entrepreneurs run smarter, more sustainable businesses. Her no-fluff approach makes complex financial concepts easy to understand and even easier to implement.

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