Are you feeling stuck in the “messy middle” of scaling your business, unsure how to break past your current revenue plateau?
What if the key to reaching seven figures isn’t working harder or hiring more, but actually simplifying your business?
Success doesn't have to come at the expense of sustainability.
As a business grows its revenue and team, it doesn't always provide the freedom or increased profitability we expect. If you find that:
- You’re still making all the decisions
- Cash flow is tight and profits are shrinking
- Creating SOPs hasn’t gotten you out of the day-to-day
- Stability feels out of reach
- Stepping away would slow things down
You’re likely in the messy middle. Every business experiences it, the question is how long it lasts.
This stage often comes with challenges like feeling trapped in daily operations, fluctuating profitability, and dealing with complex systems and team dynamics.
In episode 218 of Lean Out Your Business Podcast, I discuss the messy middle and how to get out of it.
Simplifying is the key ingredient that helps get you out of the messy middle, but it also helps to unpack the following:
• Characteristics of the Messy Middle
• Personal Experience with the Messy Middle
• Common Misconceptions and Traps
• Steps to Break Through the Messy Middle
Tune into Episode 218 of the Lean Out Your Business Podcast or keep reading below.
Identifying the Messy Middle
Do you ever feel like the more your business grows, the less control you actually have?
It might seem like things should get easier once you hit certain milestones, but for many business owners, scaling brings an entirely new set of challenges.
If you’ve found yourself wondering why your to-do list keeps growing, your profit margins are shrinking, or your calendar feels more full than ever, you’re likely in the messy middle.
This is one of the most important phases of growth, yet it’s also one of the most misunderstood.
If not navigated strategically, it can become the very thing that keeps your business from reaching its full potential.
What Is the Messy Middle?
The messy middle is the chaotic and complex stage of business that typically shows up between multi-6 and multi-7 figures.
While it is not defined by a specific revenue range, it is marked by a set of common challenges:
- You’ve seen growth and had success, but that growth isn’t creating the time or freedom you expected.
- Your profit margins are shrinking, even though revenue is going up.
- You have a team, but too much still relies on you to keep everything running.
- You’ve invested in tools, systems, and SOPs, yet things still feel inefficient or disconnected.
- Your business has grown, but it hasn’t become more predictable or stable.
- You worry about what might happen if you step away for any length of time.
If any of the above sound familiar, you are likely in the messy middle.
Why Most Businesses Stay Stuck Here Too Long
It’s not the messy middle itself that causes problems, it’s what businesses do (or don’t do) when they’re in it.
Most owners respond to this phase by doing more. They sell more, hire more, and stack on more tools. But more does not always equal better.
Here are a few things that tend to keep businesses stuck in this phase longer than necessary:
- Not recognizing they’re in the messy middle so they misdiagnose the real problem.
- Trying to solve profit or time challenges by increasing revenue instead of increasing scalability.
- Adding new team members without redefining roles or streamlining what already exists.
- Creating systems that add complexity instead of simplifying operations.
- Building a business that is unintentionally centred around the CEO, which as a result makes it hard for the CEO to extract themselves from day-to-day delivery and decision making.
Scaling magnifies what already exists. If your business has strong foundations, scaling will amplify those strengths.
But if your business is weighed down by inefficiencies, bottlenecks, or low-margin offers, scaling will only increase the stress and chaos.
Signs You’re Scaling Something That Isn’t Scalable
One of the clearest indicators of a misaligned scaling strategy is when success feels more stressful than sustainable.
Some of the most common signs include:
- Revenue is increasing, but cash flow remains tight and unpredictable.
- You are selling more than ever, but your profitability continues to shrink.
- Team members require ongoing oversight, and hiring more people hasn’t created more freedom.
- Tools and systems are in place, but the business still feels disorganized or fragile.
- Every new milestone brings more operational headaches instead of stability.
In other words, the business is growing, but the impact and results are not aligned with that growth.
The Most Critical Shift to Make in the Messy Middle
If you want to move through the messy middle more quickly and with less friction, you must simplify and lean out before you scale further.
This does not mean scaling back your goals or ambitions. It means scaling with intention. It means optimizing what already exists and focusing on what will create the greatest impact and sustainability.
The businesses that move through the messy middle most effectively do so by focusing on five key areas: strategy, planning, systems, team, and insight.
The SPS-TI Framework for Scaling Simply and Sustainably
This framework is the foundation of what I teach inside Strategic Ops Institute and what we implement inside Lean Out Method. It includes:
- Strategy: Refining your business model and offer suite so they are profitable and scalable.
- Planning: Implementing a consistent planning cadence to ensure the business can grow while delivering an exceptional client experience.
- Systems: Creating systems that are designed for scale, not just to fix short-term problems.
- Team: Building a lean dream team with the right people in the right roles, and eliminating unnecessary hires or bloated org structures.
- Insight: Making data-driven decisions by regularly reviewing key metrics and understanding what is really driving results.
This framework is not something you do once and check off the list. It is a scaling ecosystem you continue to optimize over time.
You do not need to tackle all five areas at once. Start with the one that will create the biggest leverage for where you are right now.
What to Do Next If You Are in the Messy Middle
The most effective way to get out of the messy middle is to stop reacting and start intentionally designing the next stage of your business. That starts with simplifying what you already have.
Here are a few practical ways to get started:
- Review your offers and eliminate anything that is not profitable or scalable.
- Map out your current client journey and look for areas where complexity can be removed.
- Evaluate your team structure and clarify roles to reduce CEO dependency.
- Track expenses and margins regularly so small shifts don’t erode profitability.
- Identify one key area where streamlining would create immediate relief and results.
Most importantly, determine who in your business is responsible for scaling. If that person is you, do you have the support you need? If you have a strong operator or team member, do they have the tools and training to lead this phase of growth?
If you want a strategic partner to help bridge the gap between vision and execution, a CSOO (Chief Strategy and Operating Officer) or Scalable Ops Manager might be the missing piece.
These are the types of operational leaders I certify through Strategic Ops Institute, and they are specifically trained to install the full lean scaling ecosystem.
How to Move Through the Messy Middle with More Simplicity and Impact
To move through the messy middle without losing momentum or burning out, focus on:
- Simplifying before scaling
- Building a lean dream team instead of a bloated org chart
- Tracking profitability and cash flow as carefully as top-line revenue
- Creating systems that support, not complicate, your delivery
- Installing the SPS-TI framework to build a sustainable scaling ecosystem
Scaling should not feel like a sacrifice. It should increase your profit, impact, and time.
But that only happens when your growth is strategic, intentional, and supported by the right systems and team.
If you want to learn how to simplify and scale more sustainably: Download my free ebook, The Hidden Barriers Keeping You Trapped in the Day to Day.
by Crista Grasso
Crista Grasso is the go-to strategic planning expert for leading global businesses and online entrepreneurs when they want to scale. Known as the "Business Optimizer", Crista has the ability to quickly cut through noise and focus on optimizing the core things that will make the biggest impact to scale a business simply and sustainably. She specializes in helping businesses gain clarity on the most important things that will drive maximum value for their clients and maximum profits for their business. She is the creator of the Lean Out Method, 90 Day Lean Out Planner, and host of the Lean Out Your Business Podcast.
