The Messy Middle: What I Learned in My First 3 Years of Business

Eight years ago, I was ready to get back to work after having my daughter. But instead of going back to a traditional role or continuing to freelance, I did something that felt both terrifying and inevitable: I started my own business.

That decision came as no surprise to the people who know me best. I come from a family of entrepreneurs—my mom, dad, sister, and brother have all owned or currently own businesses they built themselves. So it's safe to say my closest relatives were just waiting for me to take the leap. As for me? I'd like to think I was destined to be a business owner. It runs in my blood, after all. 😉

Starting a business felt like the logical next step in my career. But despite all the guidance I received from the seasoned pros around me, I couldn't have anticipated the joys, growing pains, and unexpected plot twists that were waiting for me in those early years.

Here's the thing: running a business is NOT for the faint of heart.

It demands so much more of you than a traditional career path. Early mornings, late nights, being stretched to your limit—especially in the early days—it's all par for the course. I remember reworking my backend systems over and over until they finally felt right, making sacrifices when finances were tight, and saying no to things I really wanted to say yes to.

But as challenging as my journey has been, the decision to set out on my own has been far more rewarding and worthwhile than anything I've had to sacrifice to get here.

Here's what the last three years of owning my business have taught me. Hopefully, you can learn a thing or two from what I've walked through, too.


Year One: Saying Yes to Everything (And Burning Out Fast)

When I started my business, I was reacting to needs I saw in the market and taking on any project that came my way. I said yes to everything—partly because I was grateful for the work, partly because I wasn't sure what my "thing" was yet.

I was constantly putting my clients' needs before my own, staying on top of every new tool and trend, and trying to create systems for myself while simultaneously learning how to run a business. I felt incredibly lucky to make a living doing what I loved (in my PJs, no less!), but that gratitude came with a cost: business burnout.

And let me tell you, it was NOT pretty.

I felt like my work was starting to impact my family negatively. I remember one Friday, I left a family dinner early because a client needed something ASAP. If you find yourself consistently sacrificing your personal life for the sake of your work, tread carefully. Not maintaining healthy boundaries can cripple even the most experienced business owner.

Eventually, I was pulled in to help clients in a bigger capacity—and that's when things started to click. I realized that, of all the projects and roles I'd taken on, I found the most fulfillment in helping creative entrepreneurs streamline the backend of their businesses. I saw that the impact of creating systems was immediate, measurable, and allowed my clients to have more clarity with way less overwhelm.

So I refined my offers, pivoted my positioning, and stepped boldly into the world of operations consulting.

The lesson: Sometimes you have to say yes to everything before you figure out what deserves your "hell yes."


Year Two: Finding My People (And Ditching the Friction)

Year two felt different from the jump. I had found my happy place working in operations, but I quickly realized that many of the clients I was attracting weren't aligned with who I was as a person or the core values at the heart of my business.

I'd been working with creatives long enough to know that some corners of the industry can feel... a little snooty. And as a jeans-and-t-shirt, hanging-out-on-the-porch kind of gal, I experienced a LOT of friction the more I encountered that vibe in my working relationships.

Seriously, the second I hopped on certain calls, I would feel all sweaty and stiff. It felt so unnatural and performative—and I knew I had to make a change.

So I set out to better understand who my ideal client was and how I could speak directly to them. That's when my messaging started to shift. I leaned into phrases like "warm-hearted creatives" and "life-first business," and the response was immediate. What started as an experiment turned into something people really resonated with.

That year, I was able to turn the tide on my working relationships and found myself working with insanely talented, approachable, and downright wonderful people who valued the same things I did: simplicity, balance, community, and authenticity.

Here's what I learned: Your brand isn't just what you do—it's who you're for.

And when you get clear on your values and let them guide your messaging, you start attracting the right people. The ones who get it. The ones who feel like friends, not just clients.

The lesson: When you try to be everything to everyone, you end up feeling like yourself for no one. Get clear on your values and let them steer the ship.


Year Three: Burning It All Down to Build It Over Right

The third year of business was all about systems and strategy. Looking back, I get the sense that I burned everything to the ground so I could correct course and rebuild with all the valuable insights I'd gained along the way.

I knew exactly what type of services I wanted to offer and had a much better understanding of who "my people" were. For the first time, I had the opportunity to bring fully realized values to the forefront of my business and nail down my brand messaging to match.

I worked on my backend systems so they could better serve my clients. I tweaked and fine-tuned my workflows so I could deliver the care and attention my people deserved. I focused on building my support network so I could maintain some sense of balance as I expanded—which proved to be the right move because I had a baby that year!

This was also the year I started asking myself harder questions:

  • What do I actually want my day-to-day to look like?

  • What kind of work lights me up vs. drains me?

  • How can I build a business that supports my life, not one that runs me into the ground?

And those questions? They changed everything.

The lesson: Growth isn't always about doing more. Sometimes it's about getting intentional, simplifying, and making space for what actually matters.


The Takeaways (And What's Next for You)

I'm sharing all of this with you to pull back the curtain and give you an honest look at what the first few years of business can feel like. The messy middle is real, and if you're in it right now, I want you to know: you're not alone.

Ultimately, there are no one-size-fits-all solutions when it comes to owning a business. My journey may not reflect your personal experience, or you may see pieces of your own story here that make you feel a little less alone.

If you haven't taken the leap yet, I hope you know that it's possible to create the business and life you want for yourself—one baby step at a time, one year at a time.

If you've already gone all in and started your journey, I'm here to remind you that it's okay to take time to reflect, change your mind, and change course. Building a business that aligns with your values and supports your lifestyle isn't just possible—it's what you deserve.

One of my favorite quotes that's carried me through every season of business is this: "If you don't build your dream, someone else will hire you to help them build theirs."

Rest assured, your dreams are worth investing in. And you can make them a reality—just as I have, and am still continuing to do.


Want More Real Talk Like This?

If you're craving honest conversations about what it really looks like to build a sustainable creative business, I'd love for you to check out my podcast, Taking Five. It's a space where creative entrepreneurs can exhale, reflect, and find clarity in the chaos.

Each episode features real stories from women who are redefining success on their own terms—from navigating maternity leave and pivots, to saying no, raising rates, and creating whitespace by design.

Think of it as a coffee break with friends who totally get it. ☕

And if you want more behind-the-scenes updates, practical tips, and stories from my own journey, join my newsletter In the Margins. It's a gentle reminder that you don't have to move faster to grow—you just have to move intentionally.

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