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.

Society has a grand immune system designed to suppress new ideas.

In order to fight against the resistance, you’ll need more than passion and empathy. You’ll need to commit to suffering for the years required to push your idea to fruition.

Not just a willingness to suffer, but a commitment.

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.

we need more friction in our lives, not less.

As a leader, you can’t always provide answers. And you shouldn’t, as the correct solution may still be premature. But what you can do is always add energy. This ability to turn negative conversations into positive ones is a trait I’ve always admired.

Your job is to be an energy giver rather than taker, which is common among founders and leaders I admire.

most of the time, the right answer is clear, and the next step is yours. You need to do your fucking job.

Don’t blame yourself for feeling skittish. Avoiding conflict and hesitating before you disappoint others is not a weakness, it is having a conscience.

just as a common cold can become full-blown pneumonia if left unchecked, infections in a team grow when not addressed. Your job is to detect infection, determine whether it is viral, and nip it in the bud if it is.

“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.

Effective advisers and boards are most helpful at the extremes, when the tough questions are less apparent but critical.

The leaders I admire most have invested a great deal of time understanding their own psychology and unpacking their past. Whether through executive coaching, psychoanalysis, or some form of group therapy, your effort to understand how your own mind works is the only path to reliable self-awareness during times of stress.

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.

I’ve attended workshops that James puts on for his students, and a theme throughout is resisting the urge to fit in. I asked James to explain why he seeks work that, at first, strikes others as strange, and how he handles it: I do the work I do because I have to. I can’t help it. I was born this way—I can’t be false to any man.

the future always starts as fringe.

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.

Jeff Bezos, legendary for his long-term vision, reiterated this point. “Invention requires a long-term willingness to be misunderstood,”

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.

Great teams are more than the assembly of great people. On the contrary, great teams are ultimately grown, not gathered.

Too many teams hire when they should be optimizing the people they’ve already got. You can always get more resources, but resourcefulness is a competitive advantage. Resources become depleted. Resourcefulness does not.

What your team lacks in experience they can make up for with initiative.

Inexperienced yet smart people with initiative will almost always exceed your expectations.

Initiative is contagious, expertise is not.

Past initiative is the best indicator of future initiative.

gauge whether the candidate has a history of being proactive in advancing their interests.

Initiative comes from obsession. The more infatuated you are with something, the more likely you are to know (or want to find out) more about

technologist Nicholas Negroponte said it best: “Where do new ideas come from? The answer is simple: differences. Creativity comes from unlikely juxtapositions.”

look to build a team of people who have endured adversity and overcome substantial challenges in their own lives.

In a world of pithy sound bites and smooth pitches, aim to work with people who are always building on your ideas and inviting you to build on their own.

I’ve always ascribed to the philosophy, often attributed to Carl Jung, that “everything that irritates us about others can lead us to an understanding of ourselves.”

The easiest way to deal with people who make you uncomfortable is to find fault with them; judging others is an easier and more cowardly path than reconciling yourself.

Typically, the type A “doers” on the team are the powerful antibodies that extinguish new ideas that put time lines and budgets at risk. In contrast, the wide-eyed “dreamers” are the foreign bodies that infect a team with new ideas that challenge the status quo.

When building a team, hire both doers and dreamers in relatively equal proportions.

Don’t just recruit great members; graft them, too.

Setting up new talent to succeed is an active process that doesn’t happen on its own.

Amy Edmondson, now a Harvard Business School professor, studied medical teams at hospitals nationwide. She sought to discover what made the most successful teams so adept. To her surprise, she learned that top teams actually reported more mistakes than low-performing teams. She coined the term “psychological safety,” which refers to “a shared belief that the team is safe for interpersonal risk taking,” to explain this finding. It wasn’t that the best teams made the most errors, she realized, but that the best teams were willing to admit and discuss their mistakes more often than other teams.

Psychological safety, Edmondson wrote in a study published in 1999, is “a sense of confidence that the team will not embarrass, reject or punish someone for speaking up. . . . It describes a team climate characterized by interpersonal trust and mutual respect in which people are comfortable being themselves.”

encourage managers to schedule regular check-ins with new employees. New organ rejection can sneak up on you, so you need to ask questions to make sure new employees are in the stream of communication and building relationships with their new colleagues.

I learned about the 70/20/10 model for leadership development. The model suggests that when it comes to training leaders, only 10 percent happens in a classroom through formal instruction, 20 percent is all about feedback exchange and coaching, and a whopping 70 percent is experiential.

after the initial shock of someone leaving us rather than being dismissed, I realized that our team’s immune system was working as it should.

some people grow out of their roles, or their roles outgrow them. Others become destructive to a team’s chemistry or develop into a liability.

comfort also breeds complacency.

if your staff become too comfortable socializing only in small groups, you lose the opportunity for cross-collaboration and overall team building that comes from chance meetings.

Change is painful and especially unwelcome when there is nothing dire to fix. But what you must realize—and relay to your team—is that proactive changes that feel premature are far better than reactive changes that feel inflicted upon you.

Ben Thompson, writer of Stratechery, one of my favorite technology analysis publications, wrote about the value of retelling those early moments: Culture is not something that begets success, rather, it is a product of it. All companies start with the espoused beliefs and values of their founder(s), but until those beliefs and values are proven correct and successful they are open to debate and change. If, though, they lead to real sustained success, then those values and beliefs slip from the conscious to the unconscious, and it is this transformation that allows companies to maintain the “secret sauce” that drove their initial success even as they scale. The founder no longer needs to espouse his or her beliefs and values to the ten thousandth employee; every single person already in the company will do just that, in every decision they make, big or small.

Credit is a noisy and misappropriated currency. Without truthful attribution, the forces driving performance in a team become apathetic and ultimately resentful.