Navigating the Messy Middle: Lessons in Building and Learning



Aug 18, 20233 min read


Navigating the Messy Middle: Lessons in Building and Learning


When it comes to building something from scratch, whether it's a business or personal growth, we tend to focus on the exciting beginning and the satisfying end. However, Scott Belsky's book, "The Messy Middle," reminds us that the most crucial part of any journey is often the middle stretch, which is frequently overlooked and misunderstood. This article aims to explore the insights from Belsky's book and provide actionable advice on navigating the unpredictable and challenging middle phase of any endeavor.

The Turbulence of Creation:

Belsky highlights that the journey of creating something new is far from linear. It is a volatile process filled with ups and downs, uncertainty, and struggle. The initial excitement of a new idea quickly dissipates, and the reality sets in. This "trough of reality" is where the true journey begins. It is normal to feel overwhelmed during this phase, but it is crucial to focus on creating value and pushing through the challenges.

Enduring the Lows and Optimizing the Highs:

In the messy middle, endurance is vital. Belsky emphasizes the importance of developing a source of renewal energy and tolerance that is not innate. To endure the lows, it is necessary to celebrate even the smallest wins, fostering a sense of manufactured optimism. By hacking our reward system and finding reasons to celebrate progress, we can maintain motivation and push through the challenges.

Optimizing What Works:

While navigating the middle, it is essential to optimize what works. Belsky suggests evaluating the successes and analyzing why they worked. This process allows us to understand how to replicate and spread those successes within our team or project. Rather than focusing solely on fixing what is broken, the emphasis should be on improving what already works.

Resourcefulness Over Resources:

Businesses often die due to indigestion rather than starvation. Belsky reminds us that resourcefulness is more valuable than resources themselves. Developing the ability to do more with less and being creative with limited resources can lead to new value creation. Additionally, staying within our circle of competence and focusing on what we do best can be a powerful superpower in both life and business.

Fostering Apprenticeship and Free Radicals:

Belsky introduces the concept of fostering apprenticeship and encouraging a culture of constant learning and teaching. Devoting a percentage of our energy to mentoring others not only prepares emerging leaders but also creates a culture of growth within the organization. Additionally, Belsky discusses the emergence of "free radicals," individuals who bring unbound energy to the professional world. Embracing these free radicals and allowing others to take credit for their contributions can lead to increased productivity and collaboration.

Embracing the Journey of Building:

Building a company or embarking on a personal growth journey is not a one-size-fits-all process. Belsky emphasizes the importance of creating our own unique playbook, learning from past successes, and breaking new ground. While there may be best practices to consider, it is crucial to discern which path aligns with our goals and circumstances.


Navigating the messy middle requires resilience, resourcefulness, and a willingness to adapt. By enduring the lows, optimizing what works, and fostering a culture of learning, we can navigate the unpredictable nature of the middle phase and emerge stronger. Embracing the journey and constantly refining our approach will ultimately lead to personal and professional growth.

Actionable Advice:

1. Manufacture optimism by celebrating even the smallest wins. Find reasons to reward yourself and your team, fostering a sense of motivation and progress.

2. Optimize what works by evaluating successes and understanding why they were successful. Replicate and spread these successes within your team or project.

3. Foster apprenticeship and embrace the energy of free radicals. Share knowledge and mentor others, creating a culture of growth and collaboration.

Remember, the messy middle is where the real growth happens. Embrace the challenges, learn from them, and continue building your unique path to success.


  1. "Lessons from Scott Belsky’s Book “The Messy Middle”", (Glasp)
  2. "The Top 3 Most Effective Ways to Take Notes While Reading", (Glasp)

Want to hatch new ideas?

Glasp AI allows you to hatch new ideas based on your curated content. Let's curate and create with Glasp AI :)