3 Mistakes Keeping You in the ‘Messy Middle’ Stage of Your Business

There’s a part of being a solopreneur that nobody really talks about much, but we all go through it – I like to call it the ‘messy middle’.

It’s where you’ve seen some wins, you’re not a newbie, but suddenly, it feels like you’re just stuck, running in place. And no matter how much you try to make forward momentum, nothing seems to work.

The good thing is, you’re not alone. The other good thing is, there’s a way you can break free from this stage of business. It takes some mindset shifts and willingness to make some smart moves to get past it, but it’s totally possible.

So let’s break down these three common mistakes that keep you in this messy middle era and talk about how you can push through it.

Mistake #1: Viewing Expenses as Costs, Not Investments

The Mistake: When you first start out, it’s common to look at every expense like it’s a giant hole in your wallet. “How much is this gonna cost me?” becomes your mantra. You’re focused solely on saving bucks instead of looking at the big picture.

The Impact: When you’re always in save-mode, you might be holding your business back. Think of it like this: you’re so worried about the cost of, say, a new tool or hiring help, that you miss out on how these investments could actually bring in more dough or free up your time. It’s like being afraid to put gas in your car because it costs money, but then you can’t go anywhere. You’re stuck.

The Solution: Time to shift gears and start thinking like the boss you are. CEOs don’t just see the price tag; they see potential. They ask, “How is this investment going to pay off?” Maybe that new software speeds things up, or hiring someone frees you to focus on the big wins. Start making decisions like a seasoned CEO – weigh the costs, sure, but focus on the return those costs bring. It’s all about investing wisely to make your business boom.

Mistake #2: Sticking with Something That’s Not Working (The Sunk Cost Fallacy)

The Mistake: The sunk cost fallacy is a trap many solopreneurs fall into, believing that more time, money, or resources will turn a failing strategy or product into a success. It’s the “I’ve come this far, I can’t give up now” mindset, even when all signs suggest it’s time to pivot.

The Impact: Sticking to this mindset is like trying to fill a sieve with water – exhausting and futile. You end up draining the very resources and energy that could be put into projects or ideas with real potential. It’s a vicious cycle: the more you invest in these lost causes, the harder it becomes to cut your losses and move on to something that might actually work.

The Solution: Regularly review your business activities with a critical eye. Make it a regular thing to check in and honestly assess how things are going. Learn to recognize when something isn’t working and have the courage to stop and redirect your efforts. It’s okay to call it quits. Seriously, it’s not admitting defeat; it’s being smart. See these moments as lessons learned, not just failures. They’re valuable insights that can steer you toward better decisions down the road. Remember, knowing when to fold ’em is just as important as knowing when to hold ’em.

Mistake #3: Inconsistent and Non-Strategic Selling

The Mistake: Solopreneurs often fall into the rhythm of selling when they need immediate cash flow or happen to feel like it. Some months, you’re all about making those sales, pushing hard because, well, you gotta pay the bills. And then there are times when you’re just not feeling it, so you slack off. This hit-or-miss approach to selling will be a major setback in growing your business steadily.

The Impact: When you’re hot and cold with your sales efforts, your revenue starts looking like a rollercoaster – up one month, down the next. It’s a wild ride that can leave you and your customers feeling a bit dizzy. Customer engagement drops, and it makes it super tough to plan for the future when you don’t know what your cash flow’s gonna look like. And let’s be real, bouncing between those busy peaks and slow valleys is a fast track to burnout city because you’re stuck in a cycle of feast or famine.

The Solution: Develop a systematic sales plan that helps you get into a groove with your sales – think regular launches, promos, and reaching out to your audience. Don’t just wing it; actually map out when you’re gonna do these things so you can keep that cash flowing smoothly. Predicting your sales can be a game-changer, helping you plan better and stress less. Invest in automation tools like ManyChat; they can keep the conversation going with your customers, even when you’re not actively selling (or just not feeling it). This way, your biz stays on their radar, rain or shine.

Next Steps

Take a Hard Look at Your Decisions: Start separating your personal feelings from what’s best for your business. This might mean setting aside some passion projects that aren’t paying off or making tough calls that you’ve been avoiding. Maybe it’s about investing money into something to do some of the heavy lifting in your business. It’s all about what’s good for the biz.

Evaluate and Pivot: Got something that’s been a bit of a money pit? Time to get real about whether it’s time to cut your losses and shift directions. This could be anything from dropping a product line that’s not selling to changing up your marketing strategy.

Plan Your Sales Like a Boss: Get systematic with your selling. Lay out a calendar with promotions, product launches, and sales activities. Predictable sales efforts mean predictable income, and that’s a game-changer.

Build a Support Network: Whether it’s finding a mentor, joining a mastermind group, or just networking with other solopreneurs who get it, having a peer community can make all the difference. They’re your sounding board, your advice givers, and sometimes just the folks to give you that nudge when you need it.

Action Plan: With all this in mind, sketch out an action plan. What are the first three things you’re going to tackle? Break them down into bite-sized tasks and set some deadlines. There’s nothing like a bit of momentum to get you rolling out of the messy middle.

Celebrate the Wins: Don’t forget to cheer for yourself along the way. Every little victory is a step out of the messy middle and closer to where you want to be.


Getting out of the tricky messy middle spot means changing the way you’ve been doing things. What got you here won’t get you where you want to go.

So ditch the bootstrapping/passion-project way of operating for a more systematic, CEO-based approach, don’t get bogged down by what you’ve already sunk into your projects, and get super smart about how and when you sell.

Every move you make to tackle these issues will guide you towards the kind of growth and success you’ve been dreaming of.

And don’t forget, this whole solopreneur journey is a mix of growing yourself and your business. Every successful business owner you admire has been in the spot you’re at now, so keep steering towards your goals, with a ‘work smarter’ mentality, and you’ll get there sooner than you think.


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