Book SummaryThe Messy Middle, by Scott Belsky

1-Page Summary1-Page Book Summary of The Messy Middle

The time between starting a business and its eventual success or failure is marked by a seemingly endless series of ups and downs. With patience, endurance, and no small amount of luck, you may find that each of your lows is less of a setback while each high pushes you a bit further. This back-and-forth is normal and even necessary for growth, so what if you embraced it instead of trying to avoid it? In The Messy Middle (2018), Scott Belsky argues that if you charge headfirst into the challenges you’ll face during these drawn-out “middle years,” you’ll develop the skills and insights you’ll need to ultimately realize your goals.

Belsky explores the challenging and often overlooked middle phase of entrepreneurial projects. He argues that while we often focus on the beginning and the end of success stories we admire, the middle is where the most important work happens, and it’s where the real learning and development occurs. The problems you’ll face during this time will force you to fine-tune your approach to success while developing...

The Messy Middle Summary The Road Forward Is a Maze

Most business leaders like to brag about how their companies started and how much success they found in the end, but Belsky points out that recounting these dramatic moments reveals little about their actual journeys. The time between launching an idea and seeing it realized isn’t glamorous, and many successful entrepreneurs never talk about it, because doing so requires a level of vulnerability. However, skipping over the important “middle years” leaves aspiring entrepreneurs with an incomplete and unrealistic picture of what to expect. Belsky discusses two challenges during these middle years as well as the importance of celebrating progress even when your ultimate goal is far away.

(Shortform note: Though Belsky discusses the twists and turns you’ll face on the way to becoming a successful entrepreneur, he doesn’t directly acknowledge the high rate at which most entrepreneurial startups fail. In The E-Myth Revisited, Michael E. Gerber points out that 40% of new businesses fail within the first year and 80% fail within five years. Like Belsky, Gerber disparages romantic notions about how businesses are born and...

The Messy Middle Summary Stay Aware of Your Strengths and Weaknesses

To stay objective about your business’s progress, you need to also be realistic about yourself. Belsky emphasizes the critical importance of self-awareness as you deal with the challenges of bringing your ideas to fruition. Knowing who you are and how you react to stress can keep you on an even keel through ups and downs, leave you open to other people’s ideas, and turn your uniqueness into a competitive edge.

Belsky writes that understanding your emotional responses and values lets you maintain perspective during both the good times and the bad. During periods of success, some people develop an overblown sense of their abilities and become less receptive to other people's advice. You may also ignore warning signs that you don’t want to acknowledge. This overconfidence can lead to poor decisions and even a disconnect from reality. Conversely, during hard times, you might become defensive and blame others for your problems. If you’re able to recognize—and hopefully curb—these behaviors in yourself, you're more likely to maintain a good sense of judgment and take appropriate actions when you need to.

(Shortform note: While Belsky describes the pitfalls of not understanding...

The Messy Middle Summary Stay Focused but Flexible

In addition to knowing your strengths, you also have to work to constantly improve yourself as a business leader while nursing your startup through its growing pains. In particular, Belsky says to work on your ability to focus, make instinctive decisions, and plan for the future while remaining flexible about the inevitable changes you’re bound to face in this time.

Belsky writes that to be successful, you must focus your efforts and say no to distractions. This can be tricky because as your business grows, you'll encounter more opportunities and have to choose between them. Belsky advises analyzing opportunities based on whether they match up with your goals or will help you develop a skill. By being selective, you don’t waste your time and energy on pursuits that won’t pay off for your business. However, you must also learn to make those decisions without getting bogged down by overthinking—sometimes it's best to go with your instinct rather than endlessly weighing your options.

Surviving a growing startup’s middle years requires constantly improving your business instincts and decision-making skills. Belsky suggests seeking advice from sources who don’t always agree...

The Messy Middle Summary Keep Your Team on Track

It’s unlikely that your new startup venture will be a one-person operation, and the burden of pushing through the hard middle years shouldn’t fall on your shoulders alone. Instead, achieving your overall business goals will doubtless be a team effort. Here, we’ll discuss how your team will need to maintain their collective motivation, stay focused on the tasks most important to their success, and avoid the distractions that will try to drag them down.

Motivating Your Team

We often think of marketing as something directed at potential customers, but during the growing phase of your business, you must constantly market your vision to your team. Belsky suggests using graphics, slogans, and regular communications to reinforce your company’s key goals and milestones. You can create internal “advertising” that highlights your team’s achievements while pointing them toward the next steps in their process. By consistently promoting your vision and making progress visible, you keep your business’s reason for existence at the top of your team members’ minds. If done well, this will maintain enthusiasm and give people a clear sense of how their work contributes to the bigger...

The Messy Middle Summary The Long Haul

The highs and lows of the road to success aren’t the only struggles you’re going to face. According to Belsky, the chief factor that makes growing a business so difficult is the sheer amount of time it takes. Surmounting this barrier takes determination, a great deal of patience, and a curious mind that can find its own rewards in the midst of the process long before you reach the end.

Determination

Belsky argues that short-term thinking is only natural, which makes it hard to focus on long-term goals and strategies. That’s why enduring the challenges of growing a startup requires tremendous fortitude. However, to sustain your momentum over the long haul, you can’t rely on personal praise, good reviews, or even other people’s understanding. Though it’s only natural to crave those things, not getting noticed for all your hard work could easily frustrate you and cloud your judgment if that’s your only motive for success. Therefore, Belsky says that instead of relying on external validation, your motivation must come from within.

(Shortform note: Belsky’s advice to create your own motivation may sound hard to do, but in _[The Art of...

The Messy Middle Summary The Pitfalls of Success

As difficult as the meandering journey of growing your startup can be, achieving success at the end of that road presents an entirely new set of difficulties. As you near your original goal, you’ll have to work not to jump to the finish too soon, be mindful of your own mental state, and conclude your project with humility and poise.

Belsky says the first thing to do when rushing toward a project's end is slow down. Perhaps you’re about to bring a product to market, or maybe a large corporation has offered to buy your startup for a healthy sum. It’s here that Belsky stresses the importance of seeking guidance. Even experienced leaders can feel like novices when navigating the complexities of finishing a venture, and the skills that served you well in the beginning may no longer apply in this phase. Therefore, enlist a few trusted advisers, break down decisions into simple questions, and try hard not to rush through making important choices.

(Shortform note: The changes that hit you at the end of a project go beyond the technical complexities Belsky describes—there are many emotional hurdles as well. In _[Life Is in the...

Shortform Exercise: How Well Do You Navigate the Middle of a Project?

Belsky describes the middle period of any business venture, whether it’s an entrepreneurial startup or a project within a larger business, as a maze of setbacks and successes. The same could be said for any project in life, such as finishing your education or mastering a new skill. Think about a long-term project you’ve engaged in, whether in your professional or personal life, and what the road was like between the start and finish.

In your long-term project, how long did it take for your initial sense of energy and excitement to wear off? Once it did, describe the feelings that replaced it.