The Messy Reality of Entrepreneurship: 5 Hard Lessons I Learned Along the Way

When I first became self-employed in 2014, I had no idea what I was walking into. I thought my experience as a marketer would mean I’d have everything sorted when it came to running my own business. Spoiler alert: it didn’t! Eleven years later, as CEO and Franchisor of activ Marketing Franchise, a nationwide company, I can say with confidence that those early days were full of hard lessons.

But here’s the thing about lessons learned the hard way—they stick. And every one of them has helped me scale activ since stepping into the CEO role in 2021. Here are five of the biggest ones, straight from the trenches of entrepreneurship.

1. Get a Good Accountant—It’s Non-Negotiable

When I first started out, I made one of the most common mistakes new entrepreneurs make: I didn’t save enough for my tax bill. Coming from employment, where tax was taken care of automatically, I had no idea how much money I’d need to set aside for HMRC. The shock of my first tax bill was a painful lesson in financial planning.

That’s when I realised the value of having a brilliant accountant. A good accountant doesn’t just crunch numbers—they help you stay on top of your finances, plan for growth, and avoid sleepless nights. Now, my accountant is one of the most trusted advisors in my business.

Lesson: Don’t wait for a financial crisis to get expert help. A great accountant is worth every penny, giving you the confidence to focus on running and growing your business.

2. Delaying Project Management Software Was a Costly Mistake

In the early days, I relied on email chains, sticky notes, and a whole lot of chaos to manage client projects. At the time, I didn’t think project management software was a priority. I figured we could get by without it. Big mistake.

Without a proper system, and as my client base grew, deadlines were missed, balls were dropped, and opportunities were lost. It wasn’t until we implemented project management tools that everything changed. Suddenly, we had structure, visibility, and efficiency. Clients noticed the difference, and it gave us the ability to grow without the chaos.

Lesson: Don’t underestimate the importance of being organised. The right tools aren’t just for big businesses—they’re for businesses that want to become big.

3. Reactive Marketing is What I Call ScatterGun—Don’t Do It

When I started as a self-employed marketer, I did do marketing for my business—but it was ad hoc, unplanned, and reactive. I’d throw out the odd social media post, run a quick ad here or there, and hope for the best. I call it ScatterGun marketing—random efforts that although with a goal, were executed without a strategy or a defined plan.

Having been there and done it, I’m always banging on to clients about why this approach doesn’t work. Yes, I filled my capacity mainly through referrals, but when I wanted to scale, I realised I was starting from scratch. I had no pipeline, no strategy, and no consistent messaging.

Lesson: A marketing plan is essential, no matter how small your business is. It doesn’t have to be complicated, but it does need to exist. A good plan ensures that every effort is focused, intentional, and aligned with your goals.

4. Don’t Stop Marketing (Even When You’re Busy)

One of the biggest mistakes I see clients make—and one I made myself—is stopping marketing when things are going well. When your diary is full and the phone is ringing, it’s tempting to scale back on marketing efforts. But this is a dangerous trap.

I have clients who say they don’t need marketing because they’ve got enough work. But what happens when a big client drops off or the phone stops ringing? If you haven’t been consistently marketing, it’s much harder to generate leads quickly when you need them.

Lesson: Marketing is an ongoing investment in your business’s future. Even when you’re busy, keep your brand visible and your pipeline full. Future you will thank you.

5. The Pareto Principle is Real: Beware of the 80/20 Rule

The Pareto Principle—often called the 80/20 rule—says that 80% of your revenue comes from just 20% of your clients. While it’s great to have high-value clients, it also puts your business at risk.

I’ve seen it firsthand: losing one top-tier client can have a massive impact on your bottom line. That’s why it’s so important to keep building your pipeline and diversifying your client base. You can’t alwyas rely too heavily on a few big contracts long term—it’s not sustainable.

Lesson: Always have an eye on your pipeline. Nurture your top clients, but make sure you’re actively bringing in new ones to protect your business from unexpected losses.