3 Sales Mistakes Keeping Your Business & Side Hustle Stagnant (And How to Break Free)
Scarcity 2 Sovereignty · 8 min read
You could have the best product in your niche and still be broke. Because it's not just what you sell. It's who you sell it to, and how.
I learned this firsthand when I ran a small business before college, selling hair and skincare essentials locally. Quality edge control, leave-in conditioners and natural hair butters. These were the kind of everyday products women went through constantly.
The market was right, because I started noticing almost every woman in the neighborhood needed these regularly, but the cost and inconsistent quality at the local stores was the gap I saw, and it birthed the business idea. With the help of one of my siblings, who is more outgoing and social, I sourced better, more affordable products from a wholesaler out of town.
I actually started with the right price, but after 13 straight days of zero sales, my sales confidence tanked, and I started selling at a lower price, terrified that asking for the right price would scare customers away. That business fell apart within a year, and I ended up in debt because I owed my suppliers. It was a painful experience.
Looking back, I realized one of my mistakes was marketing and selling to people who did not have purchasing power. Most of the men weren't too concerned about buying for their wives, while my regular customers kept buying on credit despite the price reduction.
This same mistake resurfaced years later when I first started selling my skills online. Being a newbie, I wasn't getting clients early enough, and when some eventually showed up, I undercharged constantly, also terrified that asking for what I was worth would scare my clients away. It resulted in burnout, but I made amends this time around and later started making amounts that blew my mind. I talked about this in some of my other posts.
Let's break down the three major sales mistakes keeping most business owners and those selling their skills stagnant. This happens both online and offline.
Mistake #1: Right product, wrong market
You're selling something genuinely valuable, but to the wrong audience. They don't get it. They don't feel the pain point you're solving. They don't care enough to actually buy.
Think about someone trying to sell real estate investment courses to people who are still struggling to make rent. The information might be excellent. The strategies might genuinely work. But someone stretching to cover this month's rent isn't thinking about acquiring property. They're thinking about surviving until payday. You could hand them the best real estate advice on the planet and it would bounce right off, not because it's bad advice, but because it's solving a problem two or three life stages ahead of where they actually are.
The product isn't the issue in this situation. The challenge is the room you're standing in, hoping to make sales.
Mistake #2: Wrong product, right market
You're targeting the right people this time, but your offer doesn't meet their real, current need. You understand them well. You just showed up solving a problem they've already moved past.
Picture a coach who spent months building an audience of beginner freelancers, people just starting to figure out how to land their first client. The audience is right there, engaged, paying attention. But the coach launches a course on scaling a six-figure agency. That's not what this audience needs yet. They're not thinking about hiring subcontractors or building systems. They're thinking about how to get client number one. The coach understood the room, but pitched next year's problem to today's audience.
You're one step ahead of where your audience actually is, and in business, that's just as fatal as being a step behind. Either way, you've lost the moment.
Mistake #3: Right product, right market, wrong message
This one stings the most, because you're doing almost everything right. The product fits. The audience fits. But your message doesn't connect, and nothing else matters if that piece fails.
Say you sell a genuinely effective budgeting course, and your audience is exactly who needs it, people drowning in financial stress. But your sales page reads like a syllabus: "12 modules covering cash flow, categorization, and forecasting." Technically accurate but completely lifeless. Meanwhile, your audience isn't lying awake at night thinking about categorization. They're lying awake wondering if they'll ever stop feeling behind, ever stop dreading their bank app, ever get to breathe again around money.
You're speaking features when your audience is buying relief. That mismatch alone can sink a genuinely good offer.
The fix, part one: solve your present problem
You are a target market. If you fix whatever's keeping you personally stuck right now, you'll automatically understand the right market, the right problem, and the right message, because you'll be living inside all three simultaneously.
You sell best what you've personally survived, not what you've only studied from a distance.
The fix, part two: solve your past problem
If you've already overcome a major struggle, teach that. Your past pain is someone else's present question. When you sell the exact solution you once needed yourself, your message becomes authentic in a way that's almost impossible to fake, and almost impossible to compete with.
The shortcut here is simple: sell to your past self. That's the truest, most precisely-targeted market you will ever serve, because you already know exactly what they're afraid of, exactly what they need to hear, and exactly which words will actually land.
Go back to your roots
Most business owners don't fail because of bad products. Also, most freelancers don't fail because they aren't talented or experts in their niche. They fail because they never truly understood who they were really selling to. If you're tired of spinning your wheels, stop looking outward for the next big product idea and look backward instead. Sell what you've overcome, or sell what you're actively fixing right now.
I showed the practicality of all this in one of my posts, The Real Reasons You Should Monetize Your Knowledge (Even If You Feel Insecure). I often used myself as an example during my classes back when I used to teach ghostwriting. I would tell my students that I was once in their shoes, and I'd always see myself in them when teaching. This made me understand them so well, and I taught in a way they found very profound. They usually gave feedback saying it was as if I'd been reading their mind on what they really wanted to learn.
That's how authenticity turns into profit.
If you want to see this exact principle applied to marketing psychology more broadly, The Crazy Bird That Outsmarts Everyone covers why resonating with your audience always beats shouting at them.