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

by Scott Belsky

Those seeking a linear journey with less instability can still be successful, but they often struggle to create anything new.

You feel lost and then you find a new direction; you make progress and then you stumble.

As a manager, I sought to hire people who were seeking a journey rather than a particular outcome. The more immersed I became in the start-up world, the more I wanted to operate without sensationalism. When the journey feels gritty and real, your potential becomes more tangible.

The middle is seldom recounted and all blends together in a blur of exhaustion. We’re left with shallow versions of the truth, edited for egos and sound bites. Success is misattributed to the moments we wish to remember rather than those we choose to forget.

there are so many moments along the way that keep you going. You just need to endure the lows and optimize everything that works.

you cannot travel the path until you have become the path yourself.

the “lost years,” because Behance’s progress felt excruciatingly slow, and we learned everything the hard way. I’m surprised we survived.

The line between a big win and failure is thin.

As you craft your team’s culture, lower the bar for how you define a “win.”

Don’t seek positive feedback or celebrate fake wins at the expense of hard truths.

State the facts clearly and honestly—Don’t try to say that you needed to clean up performance issues or that the company is better off without the people that you so painstakingly hired. It is what it is and it’s important that everyone knows you know that.

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.

Accept the burden of processing uncertainty.

we’ll often cut corners or ignore real issues in order to stem our fear of the unknown.

Fight resistance with a commitment to suffering.

tolerance and commitment to enduring the fight against the self-doubt and gut-wrenching hardships that real life and society will throw at you.

By avoiding conflict, we don’t smooth out the rough edges of our ideas and plans.

Hardship brings your team together and equips you to endure for the long haul.

The upheaval of ordinary life causes a group of people to overlook their differences and unite around common causes.

We think about providing that kind of emotional support to our friends. . . . But we can also do it at work. And it makes us closer to the people we work with. And I think it builds a much stronger organization.”

“The impediment to action advances action. What stands in the way becomes the way.” Indeed, the frictions we encounter help us find a better way so long as we face them.

Teams need to be reminded where they are and what progress they are making. As a leader, you are your team’s window.

More important, you are a storyteller. Your job is to make history more interesting and relevant when retold than when it happened.

As you summarize your team’s exhaustive work and struggles over the months or years that have passed, conjure up the perspective that excites you the most, and then share

“From the very beginning, we’ve wanted people that really believe in the mission. If you have FOMO [“fear of missing out”], go elsewhere. We are impacting lives of people and transforming health care.

it was a matter of our first path being wrong, never our mission being wrong.

By luring new employees with your mission, as opposed to flashy titles or the best compensation package, you’ll build a more durable team that is willing to try different paths to achieve the mission they signed up for.

Leave every conversation with energy.

People want resolution, and they want the confidence and motivation that comes along with a clear plan.

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.

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

Your team needs energy transfusions, especially in the middle miles when circumstances feel dire and there is no end in sight.

It’s more important to be collaborative than to be correct.

You need to do your fucking job.

“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,”

The only “sustainable competitive advantage” in business is self-awareness.

During great moments, we are liable to have an inflated sense of self. We believe we are right more often than we actually are.

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.

Self-awareness means being permeable. An undeniable theme among founders I’ve worked with is that the less defensive they are, the more potential they have.

Those who are able to openly absorb and selectively integrate what they hear consistently outperform those who are impermeable to suggestion.

deeply admire founders and designers I have worked with who seek ...

Discussing your flaws invites others to do the same.

Attribute your wins to those around you, and be the first to take responsibility for losses.

Nobody remembers, or is inspired by, anything that fits

The pressure to conform stems from the natural desire to be understood. But what you gain in relatability by latching onto an existing model, you lose in free-range innovation.

“Learn to say ‘fuck you’ to the world once in a while.” Do your thing.

In tough moments when your prospects feel grim and hope is fading, your mind will only make it worse. You’ll begin to question your ideas and tell yourself that you’re not qualified and that your team isn’t good enough. You’ll become your own worst enemy and you’ll stop believing in your own plan and abilities. When this happens, what you need is 20 milligrams of OBECALP. Stat.

Imagine, for a moment, that all your self-doubts are simply a function of society’s immune system, designed to extinguish nonconforming actions. You’re questioning yourself because you’re doing something different and society is trying to stop you—your body is trying to reject the thing that is taking it out of its comfy homeostasis. There can be only so much innovation and change in a world that runs on consistency and people falling in line.

Remind yourself that progress is vision paired ...