PDF Summary:The Messy Middle, by Scott Belsky

The time between starting a business and success is marked by endless ups and downs. This is normal and necessary for growth, and in The Messy Middle, Scott Belsky argues that you should embrace this often overlooked aspect of entrepreneurship. During the “middle years” of your business, you’ll develop the skills you need to realize your goals. The uphill climb will be uncomfortable, but Belsky insists that it’s worth it.

Belsky is an entrepreneur best known for cofounding Behance, an online platform for creative artists. In this guide, we’ll explore the difficulties he says you’ll encounter once your startup gets going, as well as the skills you’ll need to cultivate. We’ll discuss how to keep your team motivated and how to cope with success if and when it comes. We’ll also cover writings from other business experts who expand on Belsky’s ideas or approach his views from a different perspective.

(continued)...

Perspectives on Focus

Belsky references many skills to learn and make use of in relation to staying focused on your business priorities. That’s because the concept of “focus” is very broad. Let’s explore how other experts on productivity and the brain have addressed the topic.

One way to define focus is as selective attention. In his book Focus, psychologist Daniel Goleman contrasts open awareness and selective attention as two mental states your brain engages in. Open awareness is fluid, passive attention in which you’re not focusing on one specific task, whereas selective attention is the effortful focus you use to filter through the flood of sensory stimuli and narrow your attention to what is relevant. As Belsky suggests, selective attention is the mode your brain engages in to decide what’s relevant to your current task and what’s a distraction you should try to avoid.

Another way to look at focus is as deep work. In his book Deep Work, computer scientist Cal Newport discusses focus as uninterrupted concentration on a task that pushes your cognitive abilities to their limit. Newport explains that skills you need to succeed in the modern economy—like complex problem-solving, data analysis, and computer programming—require deep work to learn and execute. Deep work is also what you’ll have to engage in to improve the business instincts and decision-making skills that Belsky highlights.

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.

(Shortform note: In addition to the business situations Belsky describes, flexible planning has long been vital to success in military operations. In Made to Stick, Chip and Dan Heath relate the adage that “no plan of battle survives contact with the enemy.” In business, this means that no business plan survives the real-world market unchanged. The Heath brothers explain that the US Army distills all aspects and details of a plan to a central point—the “commander’s intent” that defines an intended outcome. In a business sense, your intent may be to reduce costs or open new markets, so when you periodically reevaluate your plan, use your overall intent as a guide so you don’t become attached to specific details as to how to achieve it.)

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.

(Shortform note: Belsky presents team motivation in terms of advertising, but in Empowered, Cagan and Jones recommend something different—that you lead like a coach. To coach your workers toward success, you have to inspire them as a team and as individuals, create personal development plans for each member, and maintain a constant dialogue as everyone moves forward. Instead of “selling” them on your business goals—as Belsky suggests—you should motivate them by posing challenges that encourage your team members to think creatively and stretch their abilities. According to Cagan and Jones, this increases buy-in and motivation more than simply aligning workers with your ideas—coaching makes business success personal.)

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.

(Shortform note: The ratio Belsky describes—that your team should spend 80% of their time on high-priority goals—appears to be a spiritual descendant of Italian economist Vilfredo Pareto’s rule that 80% of outputs stem from 20% of inputs. In The 80/20 Principle, Richard Koch explains how this ratio appears in many areas of life. For example, we derive 80% of our happiness from 20% of our life experiences, and 80% of our best relationships are with 20% of the people we know. Koch asserts that you can apply the 80/20 rule to clear out waste in your business and focus your energy on the projects that matter most. In Belsky’s middle years of startup growth, the 80/20 rule helps you eliminate the needless work that slowly accumulates over time.)

Bureaucracy and 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.

(Shortform note: The organizational debt that Belsky warns against is similar to the concept of “technical debt,” a software industry term for issues that designers put off solving in favor of short-term workarounds. Technical debt takes the form of software bugs, wasted resources, and misleading documentation, and incurring it lets developers move ahead on projects that are at least partially working. The assumption many developers make is that they or someone else in the future will resolve the problems they leave unfinished, but left unchecked, technical debt leads to faulty products and disgruntled customers. Organizational debt is arguably worse than technical debt, since it directly affects the company as a whole.)

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.

(Shortform note: The incremental progress that Belsky recommends will surely move you forward, but there is another option—a “design sprint.” In Sprint, Jake Knapp, John Zeratsky, and Braden Kowitz describe the idea as an event in which a team is given one project to delve into for a week, while postponing all other meetings and bureaucratic obligations. A sprint lets your team focus all of its output on a single task, which can jump-start momentum on a particular problem. A design sprint begins by identifying the outcome you want to accomplish, gathering ideas on how to achieve it, and narrowing your team’s focus to a few priorities. At the end of the week, your team will feel a boost from having achieved an important stepping stone.)

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 Impossible, Steven Kotler points out that from a brain science perspective, achieving intrinsically motivated goals generates more pleasurable neurochemicals than achieving goals tied to external motivation. The trick is to identify what your internal motivations are and align them with the goals of your business. Kotler recommends exploring your personal interests and finding ways to link them together. You should also expand your social network to include people whose goals complement yours to engage a positive feedback cycle of social support and mutually motivated progress, whether in business or your personal life.)

Patience and 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.

(Shortform note: Though your urge may be to push yourself and your team to get results as soon as possible, the best way to cultivate the long-term patience that Belsky recommends may be for you to slow down. In The Ruthless Elimination of Hurry, pastor John Mark Comer argues that when your life is lively, it brims with meaningful purpose, but when you’re merely busy, the work overwhelming you is probably meaningless, and you need to cut back and be patient with your progress. He suggests that if this is hard, you can gamify patience—in other words, turn slowing down into a game. For instance, make a game of reducing your meaningless phone use by creating rules for when and how to use it and challenging yourself to follow them.)

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.

(Shortform note: The most conventional way people use to determine success is to measure results, but to be more creative, as Belsky suggests, you should consider tracking your efforts instead. The authors of The 4 Disciplines of Execution argue that past results don’t give you any information on how to proceed. If you track your current efforts—or “lead measures,” as they call them—you’ll find them a much more effective guide. Lead measures are predictive and influenceable, in that a change in your efforts yields a change in results. For instance, if you’re trying to save money, you can focus on working more and spending less (efforts) instead of dwelling on how much your expenses were in the past.)

Belsky suggests that curiosity can keep you on track when traditional metrics like 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.

Questions to Shape Your Progress

If Belsky’s description of curiosity seems open-ended and vague, journalist Warren Berger offers more specific guidelines in A More Beautiful Question. Berger suggests that business leaders should always be asking fundamental questions, such as:

• Why do some people choose our competitors instead of us?

• Why not try to reach a new demographic? How could we do that?

• What if we updated our mission statement to better reflect today’s values?

• What if a new startup disrupts our market, as Uber did to taxis?

• Why not let our employees work from home?

Berger asserts that the most successful companies are those that encourage employees to ask questions and search for innovative answers. To foster curiosity throughout your organization, Berger says to replace brainstorming sessions with question-storming sessions in which employees are asked to come up with questions instead of ideas. Since there’s no pressure to answer those questions right away, these sessions help people’s thoughts flow freely, without the urge to censor themselves. In Belsky’s “messy middle” of company growth, these sessions would also keep workers energized and promote continued engagement.

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.

(Shortform note: Even the simplest product isn’t going to please everyone, and the trade-offs Belsky says you’ll have to make will inevitably open some doors for your business while closing others. Therefore, your trade-off decisions must be strategic. For instance, tailoring a product to suit one need makes it less capable of servicing another need. Willfully ignoring some of your customers may feel like leaving potential revenue on the table, but straddling the gap between different customer needs leads to inefficiencies that open the door for competitors to produce a better product. You sometimes have to choose not to serve all potential customers, because in trying, you’ll risk doing a poor job of serving any customers and their needs.)

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.

Designing for Humans

The simplicity Belsky talks about isn’t easy to achieve, but it can be done. In The Design of Everyday Things, Don Norman characterizes simple, intuitive design in terms of two principles related to the user experience—discoverability and understanding. “Discoverability” refers to whether a user can figure out what an object is and how to use it. “Understanding,” on the other hand, refers to the user’s ability to make meaning out of the discoverable features of the object. Human-centered design, therefore, focuses on human needs and behaviors first, rather than designing a product and hoping that users figure out how to use it.

However, simple designs don't necessarily have to be logical. In Alchemy, marketing expert Rory Sutherland suggests that effective design can leverage humans’ illogical thinking. Just as Belsky says to play into psychology with design and market strategies, Sutherland suggests ways to tap into the instinctive, unconscious reasoning behind how people make decisions. The first tool is signaling—things you do to demonstrate your trustworthiness to others, such as using a professional-looking font in your time-management app. The second tool is the placebo effect, such as hinting that your app will make your users’ time more fun. Whether these things make logical sense is irrelevant to your users’ positive experience.

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 Transitions, Bruce Feiler writes that you’ll see yourself as a different person than before this major change in your life, as you integrate the experience into your life story. In addition to coping with the complicated feelings or bringing a major part of your life to a close, you’ll also have to decide on your next steps. In the wake of change, you’ll have to let your old habits and priorities die and replace them with new ones that align with your current reality.)

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.

Credit Where Credit’s Due

It may seem counterintuitive that anyone would act counter to their own success right at the end of their journey, but Belsky insists that it happens, and in The Now Habit, Neil A. Fiore explains why. People fear success because they’re afraid they’ll alienate their friends and colleagues, they worry about the major life changes success can bring, and they fear that success will raise others’ expectations to the point they can’t be met. They may even fear that success will change them in the way Belsky describes—into an egocentric person not worthy of the pride of accomplishment.

You can proactively counter the latter outcome and maintain the sense of humility Belsky praises by adopting a habit of recognizing others’ importance. In The Magic of Thinking Big, David J. Schwartz lists this as one of the key mindsets that let you lead people effectively. If you acknowledge other people’s importance—and go out of your way to make them feel important—they’ll work harder for you, cooperate more, and offer more help as you near the finish line. Show sincere appreciation and recognize that accomplishments are the result of team effort.

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.

Bounce Back From Failure

As we noted earlier in this guide, success in entrepreneurship is far from guaranteed, no matter how hard you work or follow Belsky’s principles. However, before you even begin, consider whether how you define success might be setting you up for failure. In Anatomy of a Breakthrough, Adam Alter states that many of our concepts of success are too extreme, such as becoming a millionaire or winning major awards. Setting more realistic expectations means success will be hard but achievable.

However, what characterizes even those people we perceive as great successes is how they build upon failure and adjust their courses of action. Alter explains that failure makes you re-examine your approach and try new strategies to reach your goals. If you never fail and question yourself, then you don’t push yourself, and you become blind to opportunities that can only be found by straying from the easy path. If you fail too often, then maybe your goals really are too ambitious—but if you don’t fail at all, you’re not stretching to meet your potential. Therefore, don’t beat yourself up when you fail. Simply look at what happened, figure out what it can teach you, and jump back into the drawn-out process that Belsky lays out for success.