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

by Scott Belsky

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. This volatility can hurt morale and cause anxiety, but you have a better chance of extraordinary results.

The easiest route to take is to glide in the direction of wherever fate pushes. But living at the mercy of circumstance makes you a passive participant in your own story.

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.

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 old adage “Friction polishes stones” is true: Friction not only reveals character, it creates it. By avoiding conflict, we don’t smooth out the rough edges of our ideas and plans.

Hugo Macdonald, the former design editor of Monocle magazine, made the case for friction: 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.

By participating, everyone feels more in control of their destiny.

“It’s amazing what you can achieve if you refuse to be discouraged, refuse to let down your team, and you check your ego at the door,”

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.

Self-awareness means understanding your own feelings enough to recognize what bothers you. Whatever triggers your frustration or irritates you is rooted in a core value you have, something you vehemently stand for or against. For example, injustice really bothers me. Whenever I see unfairness, I need to right it. When I am taken advantage of, I will opt to right the wrong even if the economic cost of doing so exceeds the economic impact of letting it go. This behavior could potentially be destructive, and it is tied to one of my core values. But now that I have made myself aware of it, I can see it bubbling up in myself and learn how to mitigate it. At least I try. Being conscious of your triggers helps you take your finger off that trigger.

However big your project or ambition, your journey is nothing more than a sequence of decisions: You’re probably many decisions away from success, but always one decision away from failure.

“In most cases, if the fundamental reasons for why the product or service should exist are still valid, then the team will always take on the challenge, assuming you didn’t burn way too much time or cash and it was an intelligent—albeit sometimes crazy and unexpected—way to get to the learnings.

When you feel lost in ambiguity, ask a different question.

The perfect question is a key to clarity. It unlocks truth and opens minds. It is distilled by having empathy for your customers’ struggles and ignoring sunk costs and past assumptions to get at the root of a problem. When you’re building something new, focus on asking the right questions instead of having the right answers.

Conflict prompts disappointment, followed by perspective and self-examination, and ultimately another attempt with a renewed sense of purpose.

Leading a reset happens in six phases: feeling anger, removing yourself, dissecting the situation, acknowledging your role, drafting your narrative, and then getting back in the game.

Feel the Anger If you’re seething with anger and disappointment, let yourself feel it. The emotion is real, and denying it keeps you angry or, even worse, leaks into other parts of your life. Remove Yourself The second phase is giving yourself space to get some perspective. Something went wrong, you’re angry and upset—but you also have one life to live. While you may feel the urge to jump back in and vindicate yourself, your brain—and judgment—will benefit from a context switch first. It can be hard to remove yourself from the situation you’re in, but when you take a time-out—perhaps a week abroad or simply a trip to the beach—you’ll wonder how you could have recovered without it. You’re free and you’re alive—don’t forget it. Dissect the Situation After the anger has subsided and you’ve put some distance between you and the instigating incident, it is time to dissect the situation with a sound mind and some perspective. What went down? Did you see it coming? Why or why not? Play back lines in your head: Who said what, and why? What other external factors were at play? Also ask your partner, spouse, or close friends for their perspective. Were they surprised? What do they think h...

When I find myself debating a road map with a product team at Adobe, or making decisions about the technical architecture of a product, there is often an “easy option” that provides most of the desired functionality and a “best option” that is inevitably a step function more difficult and costly to achieve. 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.

Sure, we value speed, but just because an industry moves fast doesn’t mean we always have to be obsessed with moving fast.

Each chapter requires a fresh perspective on the product, renewed empathy with the product’s users, and a candid assessment of the team you have and the team you need. A chapter is a clear goal, underscored by why it is important, and then every team determines its tactics.

you need a mission that can generate the many mini narratives required to carry you through a chapter.” Without a clear mission we’re all liable to get lost.

When you find yourself frustrated or critical, channel that energy into persistent creation.

When you want to learn to be a great runner—do you study slow people or fast people? 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.”

In an entrepreneurial environment, you must prioritize your team over your goals and tend to your team before your product. If your team is not in a good place or your office culture is lacking, your most valuable resources will not be able to make great products or execute well over time. Your team genuinely needs to be as important to you as what you’re making.

The more different your team, the more different and innovative your product.

People disagree and fight for their beliefs only when they are engaged enough to care. Those who are especially argumentative, opinionated, and polarizing therefore play an important role in your company, as they prevent you from settling for the familiar or easy solution and keep you questioning your norms. So long as they share your mission, these instigators are your greatest protection from groupthink and harmful compromise.

In my experience, some degree of stubbornness and frustration are common attributes of technical geniuses; people who are ahead of their time are intolerant of business practices behind the times.

Teach your team to value conflict and develop a tolerance for passionate and respectful disagreement.

no one wants to put on a ‘work face’ when they get to the office. No one wants to leave part of their personality and inner life at home,”

Apprenticeship is an investment in future talent, so actively encourage it.

If you don’t weed out the sources of angst, you risk losing your key players. People join an exciting project or high-performing venture to do the best work of their lives. If they’re not working with people they admire—creators who are fully committed to one another and to the work—they leave. If you’re hesitant to let underperformers go, you’re punishing the best performers by limiting their potential, and you’re strangling the team’s prospects. The best reason to fire people who are not performing well is to keep your best people. The short-term pain of letting a troublesome employee go outweighs the long-term gain of keeping the rest of your employees engaged.

culture is not in any manager’s control: It’s organically formed through the stories your team tells.

ourselves—we want to make a real and lasting impact in the world around us.

We want to always be doing our best work and making the greatest impact we can.

Employees need to be delighted by their own work experience as much as they hope to delight your customer’s experience using your product.

The underlying system that helps align work with the best people to own it is attribution. When you and the rest of your team know who did what, a natural intuition develops for pairing projects with people outside of traditional hierarchical structures. Each person’s expertise becomes clearer, and the team is naturally supportive of those empowered to lead certain projects, regardless of their seniority. Respect is bred for those at the source of the work rather than those a level up. With such alignment, decisions about who should do what are supported by the larger team rather than being questioned and doubted.

The person who did the work should present the work.

As you recognize people who work for you, assign credit as you would influence. Ultimately, you want the people who really did the work to get rewarded and have more influence next time around. While you may think assigning credit is about rewards, it’s really about assigning influence for future decisions.

Embrace best practices until you need to change them. Then break them.

“Powerful enough for professionals, accessible enough for everyone”

When you must implement a new process, give it some beauty. Loyalty to a new system comes from believing in it and being attracted to it. The design, nomenclature, virtual confetti that explodes from a completed task—these little touches can go a long way in spurring utilization.

Progress is the best motivator of future progress, but it must be merchandised sufficiently so that people feel it.

Ideas are misunderstood unless they can be visualized. Doubts and confusion can be cleared in one fell swoop by a simple image of visualizing a potential solution. When a visual is put up on a screen or a prototype is passed around, the whole conversation becomes more productive and specific.

Going forward, every meeting for this project started with our lead designers “showing” the rest of the group where we were and what we had to discuss rather than just telling people.

Whether you are sharing an idea with colleagues or pitching an idea to investors, be less polished and more real. A little texture in the form of uncertainty and admission of challenge is helpful for everyone. The right partners will see your challenges as potential rather than weakness, and your honesty will set the right tone for future collaboration and navigating the ups and downs of the journey together.

No one ever did anything awesome or great because they were told to.

Telling people what to do is the opposite of responsibility. . . . The danger is people are “doing” their jobs, not “thinking” them.

“I love the idea of every person understanding how their small role aligns with the broader mission. . . . Elon Musk says that you can stop anyone on the SpaceX factory floor and ask them what they’re doing and why it’s important. Someone could be making bolts and you could say, ‘Why do you do it? What’s your job?’ And they’ll say, ‘Oh, I’m making these bolts so that we can have a landable vehicle, because if we do a landable vehicle, then we can get to Mars. And if we can get to Mars, then humanity will da-da-da-da . . .’” When people know where their small part fits in the whole, they recognize how indispensable their work is. They feel more accountable.

Before shooting a blasé email to a new client or pinging a colleague about a problem on Slack, consider the following: Is this a one-way share of information or is it conversational? Email is a great way of blasting off information for people to consider on their own schedule; they can respond whenever they like, and you are likewise not pressured to reply until you’ve gathered your thoughts. As casual as it can sometimes feel, however, emails are not conversational: They lump all of your thoughts together rather than allowing two people (or more) to spar point to point. This means they also come with a high chance of misunderstanding. Email is an effective way to inform people of something, but if you’re aiming to influence others and generate a deep understanding, choose a conversational format instead, like back-and-forth messaging, picking up the phone, or an in-person conversation. Is the topic collegial or is it sensitive and potentially controversial? Whether it is via Slack, Facebook Messenger, WhatsApp, iMessage, or whatever your preferred texting service, casual conversations best take place over a real-time messaging system. However, the bite-size quality of this form of messaging means it’s not well suited to discussing complex matters. Its text-based nature also strips away the tonal nuances of voice and the inaudible visual cues of discomfort. If your topic is sensitive, push yourself toward a more intimate medium—especially if you find yourself preferring te...

People tend to dislike solutions until they feel like they understand the problem itself. Proposals must come after personally postulating the problem and the consequences of not solving it. Simple truths resonate; they stick in your mind, whether you like it or not.