The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

The experience of using someone else’s creation comes from the path the creator took to make it.

Volatility is good for velocity. The faster you move and the more mistakes you make, the better your chances of learning and gaining the momentum you need to soar above competitors. Moving fast means conducting lots of experiments—many of which will fail—and making quick turns that are liable to leave you and your team dizzy.

Endurance is about much more than surviving late nights and laboring without reward. It’s about developing a source of renewable energy and tolerance that is not innate.

As you craft your team’s culture, lower the bar for how you define a “win.” Celebrate anything you can, from gaining a new customer to solving a particularly vexing problem.

Despite the temptation, don’t focus on “good news” at the expense of what’s going south and how to deliver bad news.

And when you find something worth celebrating, only applaud the progress and actions you want your team to repeat. It’s dangerous to celebrate accolades or circumstances that are not linked with productivity, like getting “press” that you paid for or winning awards that are not representative of your impact.

Another example of a dangerous fake win is raising capital. Funding shouldn’t be celebrated. If anything, raising money should make you nervous: It means you have more to lose and more people you are responsible to. For strong companies, financing is a tactic. For weak companies, financing is a goal.

What should you celebrate? Progress and impact. As your team takes action and works their way down the list of things to do, it is often hard for them to feel the granularity of their progress and you need to compensate. Celebrate the moments when aggressive deadlines are met or beaten. Pop champagne when the work you’ve done makes a real impact. Even if it’s just a few customers that make use of a new product or feature, these are the real milestones you want to celebrate.

“One of the main responsibilities of a leader or an executive is to make good decisions,” Soyer adds. “Yet, uncertainty makes this task difficult. Claiming an unwarranted degree of control on uncertain situations can harm the reputation of the leader in the long run. Whereas a leader who is behaving in harmony with the uncertain nature of a situation would be judged as fair and competent even if sometimes the outcomes are unsatisfactory due to bad luck.”

Despite whatever hacks and strategies you employ, you will get burned repeatedly. Society’s immune system is powerful and indiscriminate. Suffering is inevitable, but by expecting it, you can manage your expectations and those of your team. You can build a culture that is as much about the experience building the product together as it is about the product itself. By doing so, at least you’re in your own little world suffering among friends! As you hire people to join you, you can evaluate not only their skills and interests but also their tolerance and commitment to enduring the fight against the self-doubt and gut-wrenching hardships that real life and society will throw at you.

The thought of friction may make us bristle, but it’s not synonymous with difficulty. The standard linguistic definition recognizes this: Friction is derived from the Latin word fricare, meaning “to rub,” and … generally means a force that opposes relative motion between two objects. Rubbing in opposition to something instinctively sounds like an undesirable experience—a disagreement, a struggle, a fight—and so over time, we’ve come to connote friction with negativity. But on the whole, rubbing things together creates, not destroys. Friction gives us heat and fire. It quite literally moves mountains. Rubbing two people together may cause arguments—but it also makes babies. Friction is a positive force in all walks of life precisely because it’s only when we’re in opposition to something that we learn how to move forward. In order to advance both individually and societally, we need more friction in our lives, not less.

Whether you’re building a new business or transforming an old one, you’ll face an endless battery of painfully long conversations that have no outcome. Unresolved conversations are draining. People want resolution, and they want the confidence and motivation that comes along with a clear plan.

Your team needs energy transfusions, especially in the middle miles when circumstances feel dire and there is no end in sight. Acknowledge the trials and uncertainty you’re facing, followed by reiterating your plan of how to climb out, what you’re aiming to achieve, reminding your team why you’ve come together to do that, and then add your own enthusiasm and confidence. In the final moments of every meeting and communication, you need to reiterate purpose and leave people with the energy to achieve it.

It’s more important to be collaborative than to be correct. If an organization doesn’t let politics and burdensome processes get in the way, then size becomes an advantage. If not, well …

Perhaps all he needed was a reminder that some critical tasks—often the most difficult ones—will not be taken until the leader summons the courage to stop considering it and just does it.

Self-awareness starts with the realization that when you’re at a peak or in a valley, you’re not your greatest self. When things are going well, ego gets the best of you. When times are tough, insecurities run rampant for everyone involved. Only by recognizing these shifts in ourselves and others can we manage them and protect the integrity of our judgment and actions. We are not necessarily the cause of the situation, but we are the cause of how we see it. Our perspective is our promise or peril. With such insight, you can more carefully vet your reactions and decisions when things are going very well or poorly. Effective advisers and boards are most helpful at the extremes, when the tough questions are less apparent but critical.

You’re probably many decisions away from success, but always one decision away from failure. Clarity matters.

Don’t succumb to society’s gravitational force toward what is common and familiar. One of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy. Don’t let this happen to you. While society wants you to conform, it needs you to break the mold to help us see differently and make life better for the rest of us. And as American artist Sol LeWitt once advised, “Learn to say ‘fuck you’ to the world once in a while.” Do your thing.

You want to stay grounded as you make decisions, but sometimes you need to escape the gravity of reality to imagine the possibilities.

Knowing all that I know now, would I pursue the project all over again? Would I invest the money and energy all over again to get as far as I’ve come in solving this problem? If the answer is yes, don’t quit. Keep at it. Feeling impatient with progress and deflated by process is fine, so long as you still have conviction. But if your answer is “Hell, no! If I could go back to the day before I got into this mess, I would head in a totally different direction,” then ask yourself why you are still trying. Are the sunk costs keeping you from quitting? Are you still going only because of how much you’ve invested in it so far? Is it just ego? Try not to value the progress you’ve made thus far based on how hard it was and what leaving will cost you.

When you’re anxious about your business, there is no easier quick-relief antidote than checking things. The problem is that you could spend all day checking things and fail to do anything to change things. I call it insecurity work—stuff that you do that has no intended outcome, does not move the ball forward in any way, and is quick enough that you can do it unconsciously multiple times a day.

The purpose of reducing the hours you spend on insecurity work is to free up your mind, energy, and time for generating and taking action on new ideas instead of checking in on old ones.

The insecurity work we do every day is the equivalent of leading a journey focused only on what is immediately concerning us—beneath our feet—rather than focusing on where we want to be. But if you compartmentalize your ideas and look ahead, and worry less about day-to-day concerns, you’ll eventually look behind yourself to see the line you drew was much straighter. You will arrive much closer to your vision.

Whenever I meet with a team that lacks clarity or feels stuck, their breakthrough often comes from a new question or problem to solve rather than a better answer to the original question.

When you’re building something new, focus on asking the right questions instead of having the right answers.

Every storm better prepares us for the next. Trying again after getting beaten down is never easy—but the important things never are.

While many people claim to value long-term moves, few people have the patience. Curiosity is the fuel you need to play the long game. When you’re genuinely curious about something, you’re less likely to measure productivity in traditional ways. Instead, you’re content being in the muck and gain satisfaction from learning something new, not just ticking off to-do items. Rather than seeking a positive outcome, you’re exploring all options to satiate your own interests.

He’s not racing toward a transaction against a clock; he’s digging to learn.

“Invention requires a long-term willingness to be misunderstood,” he said. “When you do something that you genuinely believe in, that you have conviction about, for a long period of time, well-meaning people may criticize that effort.”

While a great strategy can be conceived quite quickly in a vacuum void of time and reality, it can be executed only over a long period of iteration, agony, and harsh reality (the messy middle!). To allow strategy to unfold, you need to refactor your own expectations and measures of progress while developing a culture and structure that ensures your team has the patience to stick it out with you.

Teams must therefore build systems to nourish patience, culturally or structurally, and you must be willing to defend your long game.

And when a new technology emerges, like Alexa, the company’s voice-driven user interface, it is allowed to evolve without being immediately subjected to measures of profit or utilization. So long as the team has conviction for the long-term strategy, judgment is kept in check.

Bezos has overhauled the natural human desires for immediate returns and near-term measures of progress.

Patience doesn’t mean tolerating inaction or slower progress: It means allowing alternative forms of measuring the impact of action. Aaron Levie, founder and CEO of enterprise cloud-storage provider Box, said it best on Twitter: “Startups win by being impatient over a long period of time.”

Seemingly quick wins have deep roots.

THE EASY PATH WILL ONLY TAKE YOU TO A CROWDED PLACE

I always prompt the questions: If we take the easy option, how quickly will our competitors be able to catch up? Is this an opportunity for us to make an investment that others cannot make to truly separate ourselves from the rest? If you want to be the industry leader, sometimes you need to take the difficult path. Be wary of the path of least resistance. It may look compelling in the short term but often proves less differentiating and defensible in the long term. Shortcuts tend to be less gratifying over time. The long game is the most difficult one to play and the most bountiful one to win.

Why conform to the average practices or timescale of the industry? My timescale is longer.”

So much of excellence is about just doing the work—even when it’s not yours to do.

So much energy goes into directing blame and expressing disappointment rather than just taking initiative to tackle what you’re criticizing.

Across so many teams I’ve worked with, I’ve marveled at just how quickly an idea takes hold when someone proactively does the underlying work no one else clearly owned. There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines.

Those who take initiative to contribute when it wasn’t their job become the leadership team of the newest stuff.

When you see something wrong, take the initiative to fix it.

The future is drafted by people doing work they don’t have to do. You need to be one of those people—and hire them, too. There is too much wondering and talking, and too little doing. So don’t talk: do. Care indiscriminately. If you’re willing to actually do the work, you’ll have more influence than those who simply do their jobs.

Your work habits and processes should be more efficient. You should be proud of what you’ve accomplished, but never satisfied. Optimization stems from the conviction that you can do better. It’s less about fixing what’s broken and more about improving what works.

I think taking time to understand why things succeed—whether they are your successes or others—is time well spent … you learn the most from things that go really well by asking why. Those are the things you want to understand and do more of.”

The problem with large, well-resourced businesses is that they have a well-defined path for everything—and tons of people employed to keep it clear and wide. The probability of discovering a new detour therefore disintegrates with time, as the known path becomes more established.

But optimization is the only path to excellence. A journey’s positive slope, where peaks are incrementally higher, is the result of the repeat cycle of evaluating, deconstructing, and building a better team, product, and self.

Great teams are more than the assembly of great people. On the contrary, great teams are ultimately grown, not gathered. They’re made through endless iteration of roles, cultures, processes, structures, and tackling toxins whenever they emerge. The only way to build a great team is through endless optimization of how a team works together, and clearing their path to solutions.

In an entrepreneurial environment, you must prioritize your team over your goals and tend to your team before your product.