What does it take to navigate the challenging journey between starting a business and achieving success? How can entrepreneurs maintain their drive and focus during the long, unpredictable middle years?
The Messy Middle, a book by Scott Belsky, dives deep into the often-overlooked phase of building a business. Drawing from his experience as the founder of Behance and an early investor in companies such as Uber and Pinterest, Belsky shares practical insights for surviving and thriving as an entrepreneur.
Read on to explore how to embrace uncertainty, maintain team motivation, and develop the resilience needed to turn your business vision into reality.
The Messy Middle Book Overview
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? The Messy Middle (2018), a book by 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 resilience you’ll need to see it through. The middle may be uncomfortable, but Belsky insists that it yields benefits that will make your success more likely in the end.
Belsky is an entrepreneur and investor with extensive experience in the tech field and creative industries. He’s best known as the cofounder of Behance, an online platform for showcasing creative work, which was acquired by Adobe in 2012. He would later serve as chief product officer and executive vice president. Belsky is a venture partner at Benchmark, a Silicon Valley venture capital firm, and he was an early investor in several well-known companies such as Uber, Pinterest, and Warby Parker. In addition to The Messy Middle, he is the author of Making Ideas Happen (2010), about seeing creative endeavors through to the finish.
In this overview, we’ll explore the difficulties you’ll encounter once your startup or project gets going, but after your initial excitement wears off. We’ll describe the skills you’ll need to cultivate as well as some weaknesses to beware of. We’ll discuss how to keep your team motivated, how to be patient through years of uncertainty, and how Belsky says you should cope with success if and when it finally comes.
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.
The first challenge an entrepreneur faces is dealing with uncertainty. When you start a new project or venture, you have no way of knowing whether it will succeed. Belsky argues that leaders must function without certainty and let the growth process play out. Part of this means resisting the urge to seek easy or simplistic solutions to business problems. This is an issue Belsky struggled with himself—when growing his business felt like a neverending uphill battle without a clear path forward, he had to fight the urge to sweep problems under the rug or settle for easy workaround solutions. He argues that patching over problems with easy fixes will often lead you to overlook truly original ideas that might make your business stand out.
Day-to-Day Entrepreneurship Isn’t Fun
Belsky argues that, as an entrepreneur, if you can accept uncertainty as a fact of life, part of your mind will always be working on creative solutions to your business problems. Belsky attests to this from personal experience—during his time as an entrepreneur, part of his mind remained focused on work no matter what else was going on in his life. Though intrusive at times, this ongoing mental work was a vital part of making good decisions. To manage this constant background noise, he recommends focusing on the individual problems before you, such as fixing a design flaw in your product, while keeping an eye on your broader concerns, such as the ultimate goal and financial health of your business.
The second challenge is dealing with setbacks and extended periods of hardship. To be clear—entrepreneurship isn’t fun. Belsky emphasizes that you and your team must accept discomfort as a necessary part of pursuing your goals. After all, many successful companies emerged from failed initial concepts, and your ability to pivot and start over, despite the psychological toll it takes, is crucial to success. To achieve this resilience, you need a deep commitment to your overall mission without becoming attached to one specific approach. Since this kind of resilience is so important, Belsky suggests that when hiring your team, you should evaluate your candidates’ ability to deal with uncertainty, challenges, and self-doubt.
Celebrate When You Can
Resilience can be hard to cultivate because humans evolved to prioritize short-term gains. Leaders must recognize this and find ways to help their teams stay motivated during long-term projects. Belsky says it’s important to provide your team with regular doses of positive reinforcement. Otherwise, you and your team may feel like you’re spinning your wheels. Traditional measures of success, like customer growth or financial gains, are often absent in the middle years of a venture, and the lack of external validation can be demoralizing. Therefore, you’ll have to create motivation by celebrating small victories and milestones, even if only by throwing a pizza party when your team successfully adds a new feature to your product.
However, Belsky cautions against celebrating false victories or giving positive feedback at the expense of confronting hard truths. Focusing only on positive outcomes or overstating praise can lead you to ignore problems. Instead, strive for an objective view of your venture’s progress, considering both its positive and negative trends. Look at your business from multiple points of view, such as those of investors or potential customers, and you’ll be able to keep a realistic view of your progress and the challenges still ahead. Be honest with yourself and your team about your business’s difficulties—don’t hide bad news while you celebrate progress.
Stay Aware of Your Strengths & 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.
The Benefits of Self-Awareness
Your emotional awareness isn’t just good for you—it’s also good for your business. For instance, being able to moderate your reactions during your venture’s ups and downs can help you stay open to feedback and criticism, which you need as a leader to make informed decisions and avoid critical mistakes. Belsky notes that the most successful entrepreneurs are those who can absorb input from others without becoming overly defensive. Plus, if you can notice your own defensiveness, you’ll also learn to spot when people on your team are having a similar reaction. That will help you guide them through the good and bad times by knowing how much emotionality is guiding the decisions they’re making for your project.
Another benefit of knowing yourself is that you can leverage your uniqueness to stand out from your competitors. Belsky encourages embracing your one-of-a-kind perspective as a source of potential innovations and breakthroughs. It may be tempting to establish your business in terms of what’s been done before, but conformity stifles new ideas. Belsky argues that you should lean into your distinctive vision instead of imitating your competitors. For instance, you might give your product a design that’s eye-catching to some while off-putting to others. Your ideas may strike some people as quirky, weird, or too far from the norm, but unique ideas will attract those who resonate strongly with your vision.
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 and using it to refine your intuition. He also emphasizes the value of doubt to equip you to make decisions in the face of uncertainty. Lastly, to make good decisions, you have to maintain your ability to think creatively. Belsky recommends blocking out time to tap into your creativity by turning off all your devices and letting your mind wander. Otherwise, your mind will stay reactive to every phone call and email notification, all of which stifles innovative thinking.
Business success also requires planning—and the willingness to adapt as circumstances change. Belsky suggests you view planning as a thought exercise that prepares you for your business’s unpredictability. However, you shouldn’t expect your business’s growth to follow your original plan. Instead, regularly reevaluate your progress and adjust your plans, letting go of projects and ideas that no longer serve your goals, even if you’ve already put significant resources into them. It’s natural to value a project that you’ve invested time and money into, but clinging to past investments can prevent you from making the changes your business may need so it can flourish.
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 picture.
However you achieve motivation, your team needs it to stay focused on the most important tasks. Belsky points out that, when progress feels slow, teams often dwell on small, easy problems instead of more significant issues. For instance, your team might fix an app’s fonts and color schemes instead of addressing functionality problems. This behavior comes from our deep-seated desire for the gratification of finishing a task, but it also leads to neglecting big problems that impact a project’s success. Belsky suggests that you clearly identify which tasks are the most significant and require your team to spend four-fifths of their time on important goals before moving to the quick, easy problems. Though difficult tasks take longer to achieve, explain to your team that accomplishing these tasks will be ultimately more rewarding.
Bureaucracy & Organizational Debt
If you avoid major issues for too long in favor of making small corrections here and there, your business will build up “organizational debt.” Belsky writes that organizational debt is the build-up of hard decisions that leaders avoid, often because of an aversion to conflict. Organizational debt manifests as retaining workers you should let go, maintaining outdated processes, or putting off needed restructuring. To reduce or prevent these problems from occurring, Belsky says to confront your challenges rather than working around them. Make it clear that this duty also falls on your team to identify and eliminate inefficiencies by being honest with themselves and seeking continuous improvement.
The larger your business grows, the more likely it is to become bureaucratic, focusing on rules and procedures while slowing down innovation. Belsky advises against blaming bureaucracy, since it’s often needed to keep a big business afloat. Instead, the key to innovation in such environments is to keep projects moving incrementally forward and take responsibility for maintaining momentum. As with reducing organizational debt, this job doesn’t solely fall on the business owner. Belsky suggests that anyone on your team, regardless of their position, can drive progress with the right motivation, which follows from your job to keep all team members invested in achieving your company’s goals.
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.
Patience & Curiosity
To endure the long stretch between beginning a project and seeing it succeed, you’ll need a lot of patience. Belsky points out that many business success stories ignore the need for patience, giving entrepreneurs unrealistic expectations, when some seemingly “overnight” successes come after years of persistence. While you may have conceived your business strategy quickly, it can only be carried out over a long time. Therefore, you need to adjust your expectations and how you measure your company’s progress.
The problem is that traditional measures of business success, such as earnings or profits, don’t leave room for patience on your quarterly income statement, so you’ll have to be creative with how you measure progress. Especially if your goal is far away, such as making a new type of business viable, traditional metrics such as short-term profits won’t suffice. Instead, Belsky says you should determine the most appropriate way to measure the steps that bring you closer to your goal, and use those to validate yourself and your team’s progress while you patiently wait for profits that might not materialize for years.
Belsky suggests that curiosity can keep you on track when traditional metrics such as profits aren’t available. He argues that, when you and your team work from a position of curiosity—such as whether a solution to a problem will work or if there are potential customers you haven’t considered—you won’t think about day-to-day success the same way that traditional businesses do. You might explore partnerships that aren’t obviously beneficial but lead to valuable connections in the future, or you may invest time in projects that don’t provide short-term payoffs but show potential for future success. Belsky says that if you find satisfaction in the learning process, you can stay energized when the road ahead seems never-ending.
Product Focus
Most of Belsky’s recommendations apply to any entrepreneurial venture, but since his experience is in product development, he offers some insights specifically for that sector. The long gestation time for any product significantly impacts the final form it takes, and successfully navigating the process is crucial for creating something truly valuable. As you spend the developmental years exploring everything your new product might do, Belsky emphasizes the need to stay focused on simplicity, user accessibility, and how the public will perceive your product once it’s eventually revealed.
Belsky describes a common pattern that befalls most new products—they start simple, get increasingly complicated, and then are replaced by something new and even simpler. The challenge in the middle of the development stage is to keep your product simple while adding enough features to meet your customers’ demands. Acknowledge that you’ll have to make trade-offs, such as removing older product features when you decide to add new ones. Belsky recommends identifying which aspects of your product will make it stand out and concentrating your efforts on those most impactful areas. Not every aspect of your product needs to be top-notch—only those that will be the most important to your users.
Keep It Intuitive
Your temptation in the middle of the development cycle will be to push your product to do as much as it can. However, Belsky argues that creating successful products requires balancing how powerful they are and making them easy to use. He suggests basing your product decisions on the idea that the best products help people save time. Therefore, your development teams should focus on making their product features intuitive so that users can quickly have a successful experience with them. Don’t pile on features that you’ll have to explain—instead, spend your developmental years exploring ways to make using your product so natural that customers won’t even need a manual.
In the end, the long years of product development must result in a product that customers want, which is why you must take human psychology into account when designing your product and its features. Belsky notes that people are often drawn to new products because of what makes them new and exciting before deciding if they’re actually useful. Once you introduce your product, this can shape your marketing, but during development, keep in mind that the features that excite customers at first may not be the ones they’ll most frequently use. Its most unique features give your product an edge, but Belsky recommends not losing sight of your product’s core strengths—the ones that will carry it into the future after the initial “wow factor” wears off.
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.
You must also watch out for psychological hurdles that can arise as a project nears completion. Some entrepreneurs may unintentionally sabotage the success of their business if they don’t feel worthy of it. Others give in to ego, which is also detrimental if you start ignoring feedback or anger the members of your team. Belsky writes that you should strive to stay humble as you achieve success, reminding yourself of the role your team played in getting you there, as well as remembering any lucky breaks you had along the way. However, don’t forget to affirm the hard work you and your team put in over the years. The road to success is a hard one, and everyone involved deserves the rewards, including yourself as the founder.
The End, for Better or Worse
Most of all, Belsky says, if your project’s truly over, whether you’ve succeeded or failed, it’s important to go out on a graceful note. If you didn’t succeed as planned, decide how you can learn from the experience. If you feel lost about what to do next, remind yourself that your identity isn’t defined by your work—a mindset that’s crucial for personal well-being regardless of how much success you enjoy. And if your dreams of success do come true, recognize that your journey isn’t over. A satisfying end to an entrepreneurial venture involves being content with your accomplishments while also being ready to embrace new challenges.
