9 Hard-Won Lessons After 8 Years in Business

Eight years ago, I had no idea what I was doing. I knew I loved organizing things, building systems, and helping creative people bring their big ideas to life. But running a business? That’s a whole different beast. Safe to say, those eight years have taught me a lot. 

As you know, it’s not always easy. You’ve been on the cusp of overwhelm more times than you can count. 

But if that’s how you feel right now, in this moment, these lessons are for you. Because I learned most of them the hard way — by doing the opposite first, crashing and burning, and then (finally) figuring out what actually works.

Here’s what eight years of business have taught me about how to stop being overwhelmed and actually enjoy what you’ve built.

Lesson #1: Your Skills Are Valuable, Even If They Come Easy

I can build a beautifully custom, color-coded Asana board with my eyes closed. For years, I thought that was just “something people did.” (LOL because I now know…it’s not). 

You’re allowed to charge for the things you’re good at, even if they feel effortless to you. Especially if they feel effortless to you! Because what’s easy for you is impossible for someone else.

I can’t write worth a shit, so I hire a copywriter. My clients ask me for spreadsheet help. We all help each other. That’s how this works. Stop devaluing your skills because they come naturally. 

The ease you feel is your expertise showing. 

Lesson #2: Your Business is Not Your Identity

There was a long period where if my business was struggling, I was a failure. Professionally AND personally. If for some reason I’d had to close my business, I would have had a mental breakdown.

Over time, I learned to separate my work from my personal worth. If I closed my business tomorrow because there wasn’t a need for it anymore, or if I wanted to scale back and take a full-time job? I’d do it. (I’m not, to be clear. But I wouldn’t beat myself up about it.)

Your business is not your identity. It’s a thing you do. And you’re allowed to change your mind about how you do it.

Lesson #3: Everyone Knows Everyone. Don’t Burn Bridges.

The online space is a tiny little corner of the internet, even if it feels like our entire world. I’ve always tried to be a person who keeps options open and doesn’t burn bridges. I’m grateful for that because I would have shot myself in the foot multiple times if I hadn’t.

It’s not uncommon for potential clients to see case studies on my website and book a discovery call saying, “I know XYZ that you worked with!” It would be a real bummer (and hella awkward) if I had to say, “Yeah, we don’t talk anymore.”

Be professional. Be kind. Even when it’s hard. The online business world is smaller than you think.

Lesson #4: Everything Takes Longer Than You Think

This is one of the biggest reasons us business owners feel overwhelmed — we consistently underestimate how long things take and then beat ourselves up when we can’t meet impossible deadlines we set for ourselves.

Whatever timeline you have in mind, double it. So stop pushing yourself to get things done in an impossible amount of time. You’re just burning yourself out, and you’re the only person who knows how long it actually took anyway.

(And if someone IS paying that close attention to your timeline? Fuck ’em.)

Lesson #5: If It’s Not a Hell Yes, It’s a Hell No

Every. Single. Time. I’ve said yes to something that didn’t feel like a 1000% YES from the start, it turned into a living hellscape. If I took on a client with a few red flags? I only found 10 more.

If I said yes to a timeline that felt like a squeeze for my capacity? My mental health suffered.

But every time my gut screamed “DO IT” or “FIGURE OUT A WAY TO DO IT”? I’ve never regretted it. Trust your gut. It knows things your brain is trying to rationalize away.

Lesson #6: Ignore the Noise

You don’t have to make $10K working 3 hours a week to be happy. (If you were traumatized by the 2018-2021 online course/coaches internet wave, you’ll understand this.)

I started an online course because I thought that was what you HAD to do to scale. I thought I needed a team so I could work less. I tried both because that’s what the internet told me I needed.

Guess what? I hated both. I don’t want to sell all the time (introvert). I don’t want the responsibility of employees. I want to help creative people grow passion-driven businesses in a strategic way. Staying solo and working 1:1 with clients lets me do that best.

Learning to ignore the noise of what I “should” do and listening to advice from a few trusted people has been one of the best things I’ve done.

Lesson #7: There Will Always Be Something You Could Be Doing. Take the Day Off Anyway.

Having a completed to-do list is not a luxury we get as business owners. It’s important to realize (or learn the hard way… ahem) that you can take a break anyway. The world won’t burn down because you took one day off. 

Give yourself permission to step away even when the to-do list isn’t done. Because it will never be done.

Lesson #8: Authentic Networking Actually Works

I wish I could go back and tell Penn State Student Chynna to go to every career fair and talk to every guest expert she could. My introverted personality kept me from that. Now? I know that jobs, clients, and opportunities come from the people you know.

Looking back at the last eight years, nearly every positive thing that’s happened to me came from someone I had a real, personal connection with:

• Clients who referred their friends
• OBM friends who sent referrals
• Podcast interviews because of the blog posts my copywriter wrote
• Guest speaking invitations because someone shared my name

All because I’ve met new people, gotten on coffee chats, and genuinely tried to help other business owners. Community over competition isn’t just a cute saying. It’s how you scale your creative business systematically — with support, referrals, and relationships.

Lesson #9: No One Is Paying That Close Attention

It’s easy to think “omg what will people think?!?” when you change your mind about something. But either people aren’t paying that close attention, or if they are, they probably don’t care (a hard truth, but a freeing one). 

I once launched a new service, did one project, realized I hated the work, and never offered it again. No one noticed. But I beat myself up for weeks, thinking people would judge me or lose trust in my work. Spoiler alert: They didn’t.

People are too wrapped up in themselves to worry about what you’re doing. So just do it anyway.

Bonus Lesson: Chaos-Proof Your Business Will Save Your Ass More Times Than You Can Count

Here’s what eight years have really taught me: Business chaos is inevitable, but not permanent.

You can build systems that protect your time. You can set boundaries that stick. You can create infrastructure that lets you take a day off without everything falling apart. That’s what chaos-proofing looks like.

You may just need a little guidance and gentle hand-holding as you do it.

If that’s you, go ahead and grab the free Chaos-Proof Guide to learn exactly which systems to build first so you can scale without burning out. I walk you through each step, explain it all in simplified language (no operational jargon here!), and show you a few next steps to take depending on your situation. 

If getting your business organized is on your to-do list this year, this guide is a great place to start!