The Messy Middle: Embracing the Challenges of Progress

Have you ever started a project or embarked on a journey brimming with enthusiasm and excitement, only to find yourself struggling midway through?

This often-overlooked phase is frequently referred to as the messy middle—the challenging and unpredictable part of any journey that lies between the initial burst of excitement and the satisfaction of reaching the end.

Whether you’re launching a new business, writing a book, pursuing a fitness goal, or engaging in personal development, the messy middle is where the real work happens. It’s the phase where many people get stuck, lose momentum, or even consider giving up altogether. Understanding and navigating this stage effectively is often the key to pushing through and achieving the success you’ve envisioned.

But is the messy middle just a one-time challenge? Isn’t it a recurring theme in our lives? While some tasks have clear beginnings and ends, like planning and going on a holiday, there are parts of our lives that are in a constant state of transformation. We are often, in some way, always living in the messy middle, continually adapting, learning, and growing amidst the complexities and uncertainties that define our journeys. Life itself, with its endless cycles of change and growth, is a perpetual messy middle that shapes who we are and who we become.

What Is the Messy Middle?

The term “messy middle” gained popularity through Google’s research on purchasing behaviors within digital marketing and e-commerce. Their work specifically focused on how consumers search, compare information, and make decisions online. While Google played a key role in formalizing the concept through various publications, the idea of the messy middle has grown and evolved through the collective contributions of researchers, practitioners, and organizations—all aiming to better understand and enhance the customer journey.

The concept has been popularized to qualify the point in any project or journey where plans often go awry, unexpected challenges arise, and the straightforward path you envisioned suddenly becomes murky and complex. It’s where the thrill of starting something new is replaced by the grind of daily effort, and it’s easy to feel overwhelmed or even lost.

The messy middle is more than just a figurative term; it’s a real and tangible part of any journey.

Why does It matter? The Realities of the Messy Middle

The messy middle is where the growth happens. While it can last weeks, months, or even years, this phase tests your resolve, refines your skills, and forces you to adapt and overcome obstacles. Navigating it effectively can lead to personal and professional transformation, making you more resilient and capable. It is usually characterized by several key realities:

Uncertainty: Plans rarely go perfectly, and the messy middle is where you encounter unforeseen challenges that require adjustments and flexibility.

Resistance: As outlined by Steven Pressfield in his book “The War of Art,” resistance often shows up strongest in the messy middle. This can take the form of procrastination, self-doubt, or fear of failure.

Complexity: What seemed simple in theory can become increasingly complicated in practice, requiring problem-solving skills and persistence.

Emotional Rollercoaster: The messy middle is fraught with emotional ups and downs. One day, you may feel like you’re making progress, and the next, you might feel like you’re back to square one.

Parenthood, in many ways, embodies the essence of the messy middle. As a parent, you live in a constant state of flux, where what works one day with your child may completely fail the next. Each stage of your child’s growth brings new challenges that require constant adaptation.

Perhaps the greatest lesson from parenting as a messy middle is that it forces you to embrace imperfection. Just as you grow alongside your child, they are learning from your willingness to adapt, to show up despite uncertainty, and to find joy in the small victories—a peaceful bedtime, a shared laugh, or the pride in their first accomplishment. Parenting is a reminder that the messy middle is not just a phase to endure but a life to embrace, one where growth is ongoing and the journey itself is the reward.

Navigating the Messy Middle

By now, you understand that every great journey has a messy middle. Like many things in life, this phase often comes with common identifiable obstacles, regardless of the situation. The good news? With the right mindset and strategies, you can learn how to address these challenges, stay on track, and move closer to your goals.

Lack of Motivation

One of the most significant challenges in the messy middle is maintaining motivation. When you start a project, the excitement of new possibilities fuels your drive. However, as time goes on and progress slows, that initial burst of energy can fizzle out. The everyday grind can make your goal feel less appealing, and it becomes easier to justify skipping a task or putting off work.

Much like attempting to learn a new language, where the first few lessons are exciting as you pick up basic phrases, but over time, grammar rules and vocabulary drills feel tedious.

• Reconnect with Your ‘Why’: Revisit the reasons why you started this journey. Reminding yourself of the bigger picture and the long-term benefits can reignite your passion.
• Set Smaller Milestones: Breaking down your goal into smaller, manageable tasks can make the process feel less overwhelming and provide frequent opportunities to celebrate progress.
• Create a Routine: Establishing a consistent routine can help you stay disciplined even when motivation is low. Sometimes, showing up is half the battle.

Facing Setbacks

Setbacks are inevitable in the messy middle. Whether it’s a failed experiment, a missed deadline, or a roadblock you didn’t anticipate, setbacks can make you question your path and your ability to succeed. The key is not to let these setbacks define your journey, but to use them as learning opportunities.

Who has never forgotten to buy an essential ingredient for a recipe they planned to make for dinner? Rather than abandoning the meal, you adapt—substituting another ingredient or changing your dinner plans. The result, while not what you originally envisioned, can be surprising and certainly different, but not necessarily bad.

• Reframe Failures as Learning Opportunities: Every setback provides valuable feedback. Instead of viewing failures as negative, see them as a chance to refine your approach.
• Develop a Problem-Solving Mindset: Cultivate a proactive approach to challenges. When a setback occurs, focus on finding solutions rather than dwelling on the problem.
• Keep Moving Forward: Progress doesn’t have to be perfect. Even small steps forward are better than standing still.

Overwhelm and Complexity

As you delve deeper into your project, things can become increasingly complex. The more you learn, the more you realize how much you still don’t know. This complexity can be overwhelming, making it difficult to see the path forward. When I think of complexity, I often think of technological or legal restrictions.

For instance, when you have a clear vision of what you want your website to do, but technical requirements or coding limitations make it far more complicated than anticipated, it can leave you feeling stuck and overwhelmed. Similarly, this happens when you attempt to build furniture from scratch. You might start with a straightforward idea, but as you deal with precise measurements, unexpected material challenges, or assembly issues, the project can feel far more daunting.

• Simplify Where Possible: Break down complex tasks into simpler steps. Focus on one thing at a time rather than trying to tackle everything at once.
• Prioritize Tasks: Not everything needs to be done immediately. Prioritize tasks that will have the most significant impact and tackle those first.
• Seek Help When Needed: Don’t be afraid to ask for help or delegate tasks that are outside your expertise.

Self-Doubt

The messy middle is prime territory for self-doubt. As progress slows and challenges mount, it’s easy to start questioning your abilities, your decisions, and even the value of your goal. Self-doubt can be paralyzing, leading you to second-guess every step and potentially abandoning your efforts.

In fact, we live in a culture of instant gratification, where everything—from food delivery to entertainment—is available at the touch of a button. It’s no wonder that when progress feels slow, I’ve found myself questioning whether my efforts were worth it, whether I had the skills to succeed, or if continuing was even the right choice.

• Acknowledge Your Achievements: Take time to reflect on how far you’ve come. Celebrating small wins can boost your confidence and remind you of your capabilities.
• Surround Yourself with Supportive People: Seek mentors, peers, or a community that understands your journey. Positive reinforcement from others can help counteract self-doubt.
• Focus on Growth, Not Perfection: Remember that progress, not perfection, is the goal. Every step, no matter how small, is a step in the right direction.

Embracing the Mess

Embracing the messy middle is not about avoiding challenges but recognizing them as an integral part of any meaningful journey.

It’s where you learn the skills, habits, and mindset that will carry you through not just this journey, but countless others to come. So the next time you find yourself struggling midway, remind yourself: this is where the magic happens. Lean into the mess, adapt, and keep moving forward—you’re closer to the end than you think.

Ana McFee – Business Development Senior Manager – Consultant at EHL. Connect with Ana on LinkedIn.

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This article originally appeared on EHL Insights.