The Messy Middle Summary

1-Sentence-Summary: The Messy Middle challenges the notion that projects grow slowly and smoothly toward success by outlining the rocky but important intermediate stages of any journey and how to survive them.

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What was the last big project you started that eventually failed? Did you found a start-up, launch a blog, or engage in a massive art project? It’s tough to see our passion projects crash and burn. This makes it all the more critical to discover what parts of our journey led to our fall.

An estimated 90 percent of startups fail miserably before impacting the marketplace significantly. Why does this happen so frequently? It’s as if we never hear about this ugly side of entrepreneurship. The news is full of examples of highly-valued startups and their humble beginnings. But what about all those that die out? What’s the great stumbling block that makes it so hard for them to succeed? The Messy Middle will teach us the answer.

Author Scott Belsky founded and was once the CEO of Behance, the top digital networking company for creatives. Making ideas into reality isn’t anything new to Belsky, as he also wrote the book Making Ideas Happen. In The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture, he explains how to keep that new idea moving forward. It’s possible to progress even when you get into the middle, which contains the most burdensome troubles. With these tips, you can make any project or venture prosperous by learning to weather the storms that will come your way.

Here are the 3 biggest lessons I’ve learned from this book:

  1. Making it through the messy middle determines victory or failure.
  2. Maintaining self-awareness in times of difficulty and prosperity is vital to surviving after your journey’s start. 
  3. Double down on what works well to accomplish the most

Let’s get our hands dirty in the messy middle!

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Lesson 1: Failure or success of your project is the result of perseverance through the chaotic center.

No matter what type of journey you are setting out on, whether it’s entrepreneurial or a personal project, the messy middle is inevitable. Whenever you initiate a new endeavor, you need to give a significant amount of initial energy. While this power is necessary to get your project off the ground, it also isn’t as hard to find because the puppy-love phase has you enamored with your new idea. With fairytale-like wonder, we often only see the beginning or the end of ventures. 

What we fail to recognize is all of the hard work and pain that occurred in the space between the founding and end. In the middle portion of your project, you’ll experience a rollercoaster of challenges. Your endeavor itself and your own emotional connection to it will go through many highs and lows. At times you may lack enthusiasm and feel lost. This portion of the journey will make or break you. Whenever we persist through this challenging part, however, we later see an upward trending curve, even if that graph has multiple highs and lows along the way.

The author, Scott Belsky, is no stranger to the laborious center of any project. His online platform and company Behance struggled through a messy middle for years. At times no-one cared about his idea, many expressed doubts, and he felt like the entire company would fall apart. Belsky’s struggles through the middle of Behance’s journey helped him learn to keep going when times get tough in the middle.

Lesson 2: If you want to last through the hard middle of your journey, remain self-aware through trials and triumphs.

Inevitably, you will go through numerous moments of success and failure along your journey, especially in the intermediate portion. What does it take to survive the messy middle? Belsky says that to come out on top, we should maintain self-awareness amid the lows and the highs. We don’t realize that both the ups and the downs impact us personally in ways that can hinder our progress.

When we are going through a great time, we let our ego take charge. This hinders our ability to make decisions effectively because our psyche makes us overconfident. Good advice falls on deaf ears when shared with one who thinks they’ve got it made and that they don’t need to improve.

On the flip side, when our venture is struggling, we grow insecure and vulnerable. This leads to leaders blaming others for the difficulties the company is experiencing, which can undermine the effectiveness of the team.

Self-awareness can be as simple as remaining open to feedback. From the experience of the author, leaders who are less defensive and more receptive of correction, have the highest potential. Additionally, outstanding founders of startups not only receive correction and feedback well, but they also seek it out.

Lesson 3: Your greatest victories come from focusing on improving what works well.

I remember well the moment I read about working on strengths rather than weaknesses. Being a perfectionist for much of my life I’ve struggled with my shortcomings, always wanting to eliminate every one of them. I didn’t see the power and potential of doubling down on what works well until I tried it myself. Once I made this practice a habit, my self-confidence and success began to skyrocket. The same is true for any business venture or project you begin.

As you are mudding your way through the messy middle, you will experience times of prosperity. The key to hastening your progression toward the final goal is riding those waves and focusing on what created them in the first place. Whenever something works well, examine the why and how, and seek to replicate and spread the improvement across your entire team.

One way to do this is through what’s called A/B testing. If you have a clickable button on your site, for example, you may send half of the people who click to one sales page and half to another. Whichever page converts the most sales is the one that you continue to use. This process can be implemented across multiple aspects of your company as well.

The Messy Middle Review

Wow, what a great book! I was excited to take a closer look at The Messy Middle because I’m all too familiar with this stage of my own projects. After reading the book, I now have a much more realistic idea of what it takes to make it through that crucial and most painful intermediate section of any project. This is a fantastic book, and I would definitely recommend it!

Who would I recommend The Messy Middle summary to?

The 31-year-old employee of a new start-up who is working too hard and discouraged, a 45-year-old entrepreneur who has started many projects but gives up when they get hard, and anyone who has a hard time finding motivation when life gets tough.

Last Updated on August 18, 2022

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Luke Rowley

With over 450 summaries that he contributed to Four Minute Books, first as a part-time writer, then as our full-time Managing Editor until late 2021, Luke is our second-most prolific writer. He's also a professional, licensed engineer, working in the solar industry. Next to his day job, he also runs Goal Engineering, a website dedicated to achieving your goals with a unique, 4-4-4 system. Luke is also a husband, father, 75 Hard finisher, and lover of the outdoors. He lives in Utah with his wife and 3 kids.