The Messy Middle: Why Scaling Feels So Hard

When you first start a business, the challenges are intense but straightforward: finding product-market fit, getting your first customers, convincing early believers to back you. It’s a whirlwind, but it has a certain simplicity.

At the other end of the spectrum, big established businesses benefit from infrastructure, resources, and processes that give them stability (even if bureaucracy creeps in).

But in between lies a stage that many founders underestimate: the messy middle. This is where growth gets complicated, risks multiply, and scaling can feel harder than starting up.

Why the Middle is Messy

1. Complexity multiplies
With more customers, more products, more markets, and more team members, the founder suddenly finds themselves running not a scrappy startup but a complex organisation. What worked when you were 10 people no longer works at 50, 100, or 200.

2. Cash is king – and under pressure
Growth eats cash. You’re hiring, investing in systems, expanding into new markets. Suddenly, what felt like healthy revenues are never quite enough to keep pace with the scale of ambition.

3. The founder’s role shifts dramatically
This is often the toughest transition. The founder who once did everything now has to let go, delegate, and step into a true leadership role. Many find this disorienting and emotionally challenging.

4. Culture is fragile
As the team grows, the values and spirit that bound the early group together can start to fray. Maintaining alignment and motivation becomes harder when you don’t know everyone personally.

5. The boardroom dynamics change
Investors are now around the table with higher expectations. The board is no longer just about cheerleading; it’s about governance, strategy, and accountability. For many founders, that feels like extra scrutiny just when they’re already stretched.

Why It Feels So Hard

The messy middle is tough because it requires a different kind of founder energy. Early stages are about hustle, invention, and speed. Scaling demands systems, leadership, resilience, and strategic clarity.

It’s no wonder that so many businesses stall - or fail - at this stage. Research from McKinsey shows that fewer than 1 in 200 startups actually scale to more than $100m in revenue. The leap from scrappy start-up to sustainable scale-up is vast.

How to Survive – and Thrive

1. Get the right people around you
This is the time to invest in leadership talent, advisors, and a strong board who can help you think strategically and hold the business together as complexity increases.

2. Shift your role – consciously
Founders who survive the messy middle are those who evolve from doer to leader. Your job now is to inspire, delegate, and set direction - not to run every detail.

3. Protect your culture fiercely
Codify your values, communicate them constantly, and make sure they are reflected in hiring, management, and decision-making.

4. Be financially ruthless
Don’t let growth get ahead of cash. Build realistic forecasts, keep a close eye on burn, and raise investment with enough runway to execute your plan properly.

5. Embrace the discomfort
Scaling is messy. Accept that. The founders who thrive are those who don’t resist the chaos, but instead find clarity within it and keep moving forward with purpose.

Closing Thoughts

If you’re finding the middle stage of growth hard, you’re not alone. This is the crucible where founders are tested most deeply - not just as entrepreneurs, but as leaders.

The messy middle may feel like the hardest part of the journey, but it’s also where businesses transform from fragile startups into resilient scale-ups. Get the right people, processes, and perspective in place, and this stage can become the launchpad to lasting success.