I never really thought of myself as an entrepreneur. Sure, I worked hard and had ideas, but “business owner” wasn’t on my vision board. That all changed when I started Mad Lizzie’s Flower Farm. What began as a creative side project quickly turned into my first real taste of building something from scratch. From planting seeds and selling bouquets to sending newsletters and writing blog posts, I got hooked. Not just on the work itself, but on the challenge, freedom, and sheer possibility of running my own thing.
But there’s a big difference between feeling entrepreneurial and actually taking the leap into self-employment. When I finally did it, I went in with nothing but faith and a “what’s the worst that could happen?” attitude. Spoiler: a lot can happen.
Over the years—through both successes and “learning experiences” (aka failures)—I’ve collected a list of lessons I wish someone had told me before I started. Today, I’m sharing five of the big ones, along with practical steps so you can avoid some of the headaches I went through.
1. Your Closest People Won’t Always Be Your Best Customers — And That’s Okay
This sounds crazy, I know.
When I first launched my business, I assumed my friends and family would be my biggest cheerleaders and first paying clients. Some were… but many weren’t. At first, it hurt.
That’s when I developed what I call the First Circle, Second Circle theory:
- First Circle: Your partners, lifelong friends, parents, siblings—your ride-or-dies. They love you deeply, but their role isn’t to buy from you; it’s to keep you grounded, give you perspective, and sometimes protect you from risks (even if that protection comes in the form of skeptical questions).
- Second Circle: A much wider group—acquaintances, social media followers, friends of friends, customers, colleagues, fellow entrepreneurs. These are often your most loyal supporters, even if you barely know them in real life. They get it.
Practical Step: Don’t take it personally if your First Circle doesn’t whip out their credit cards. Instead, focus your marketing and networking on expanding and nurturing your Second Circle. These are the people who will sustain your business.
2. Boundaries Are Not Optional—They’re a Survival Skill
In the beginning, I said “yes” to everything: coffee chats, volunteer opportunities, “quick” projects that somehow morphed into full-blown commitments. I was so afraid of missing an opportunity that I burned myself out before I even found my stride.
This is especially dangerous if you’re a giver by nature. If you identify as a people-pleaser, you’re walking into a minefield here. I learned the hard way when I first started Mad Lizzie’s. I gave away so many flowers, poured endless glasses of wine, and opened up my time, energy, and even my physical spaces—all in the name of “getting my name out there.”
Here’s the problem: when you give without clear limits, you train people to expect it. Word got around that I was generous and perpetually “new,” which made it easy for others to take advantage—often without even realizing they were doing it. Before I knew it, my generosity wasn’t building my business; it was draining it.
The solution? Have rules from the very beginning. Mine are simple and non-negotiable:
- I either give it away or I charge full price. No discounts for friends or family. It’s not because I’m not generous—it’s because this makes it incredibly easy to say yes or no without guilt.
- I only donate my time, energy, or space if it benefits our immediate area or school district. Since we own a coffee shop and ice cream store, this means things like local baseball teams, school band programs, or community events. We stay away from big, national charities—nothing against them, but the impact on our community is more meaningful when it’s local.
And here’s the kicker: we get asked for silent auction donations all the time. So we made another hard-and-fast rule: either a gift card for a set dollar amount or a pre-made basket of products. No custom, last-minute creations. No “just this once.” Trust me—without this rule, it spirals out of control faster than you think.
Bottom line: Boundaries aren’t about being selfish; they’re about protecting your resources so you can keep doing what you love without burning out.
Practical Step: Decide early on when you’re available, how clients can communicate with you, and what you will and won’t do. Write it down. Put it in your contracts, your calendar, and your inbox autoresponder. Boundaries aren’t rude—they’re respect for your time and energy.
3. Cash Flow Matters More Than Profit (At First)
I thought as long as my profit-and-loss statement looked decent, I was golden. Wrong. You can have a profitable business and still run out of money if your cash flow is a mess.
Practical Step: Track money coming in and going out weekly—not just monthly or quarterly. Use a simple spreadsheet or an accounting tool like QuickBooks or Wave. Pay attention to payment terms and late invoices. Your business can’t grow if you’re constantly in “waiting for payment” mode.
4. Community is Your Competitive Advantage
Business ownership can be lonely, and going it alone slows your growth. I didn’t realize how much I needed a network until I found one. Surrounding yourself with other business owners isn’t just about referrals—it’s about encouragement, ideas, and having people who get what you’re going through.
Practical Step: Join a mastermind, networking group, or online community where entrepreneurs actually connect—not just pitch to each other. Contribute, collaborate, and don’t be afraid to ask for help.
5. Not Everyone Will Like You (Or Your Business)—Ignore the Noise
There’s a “third ring” beyond your circles of support—people who criticize, question, or even mock your choices. It’s usually about their own fear or envy, not you.
Practical Step: When criticism comes from someone you wouldn’t take advice from, don’t take it personally. Respond with kindness (or not at all), and redirect your energy toward serving the people who do want what you offer.
Final Thought
Starting a business is equal parts thrilling and terrifying. You’ll make mistakes—everyone does. But if you go in knowing your closest people might not be your customers, your boundaries matter, cash flow is critical, community is essential, and not everyone’s opinion deserves your attention… you’ll save yourself a lot of unnecessary stress.
Focus on the people and practices that fuel you, and the rest will fall into place.
