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

by Scott Belsky

You survive the middle by enduring the valleys, and you thrive by optimizing the peaks.

No matter what it is you’re trying to create or transform, the myth of a successful journey is that it starts with the excitement of an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line.

IT’S NOT ABOUT THE START AND FINISH, IT’S ABOUT THE JOURNEY IN BETWEEN.

The start is romantic. We love talking about it because it is inspiring without the complication of substance and strife. Conception is an adrenaline rush fueled by grandiose visions paired with naivety. You’re inspired by a destination and have no idea how you’ll get there. The solution in your mind’s eye is rose colored. You don’t yet know how the cards are stacked against you.

Influenced by the famous Thomas Edison quote, “Genius is 1 percent inspiration and 99 percent perspiration,” 99U is dedicated to the execution of ideas rather than the ideas themselves.

Persevering long enough to transform vision into reality was harder than I ever thought it would be;

I felt the weight of every decision, and the careers of those who quit their jobs to join me, on my shoulders. My shoulders alone.

When I think back to those lost years, I recall a constant somber loneliness, a suffering from the feeling that nobody else could relate. The struggle was further compounded by the optimism I had to exude to my team and potential customers and partners.

Monica Mehta, author of The Entrepreneurial Instinct, studies the role of brain chemistry in entrepreneurship.

Alternatively, “Each time we fail, the brain is drained of dopamine, making it not only hard to concentrate but also difficult to learn from what went wrong.”

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.

While important to celebrate and manufacture wins early on, make sure they’re not fake wins.

What should you celebrate? Progress and impact.

Only by learning to tolerate uncertainty can we allow processes to play out and experiments to unfold.

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.

starting a company is a roller coaster of suffering. You need to be comfortable with hearing ‘no’ over and over and not let that destroy your will.

Studies show that when companies provided assistance programs that offer financial support and time off when employees faced unexpected adversity (such as if their home was damaged by a natural disaster or a relative fell sick), “it actually paid dividends in that people felt like they belong now to a more caring company,”

Teams need to be reminded where they are and what progress they are making. As a leader, you are your team’s window. You need to call out and describe the landmarks that you pass along the way, constantly reinforce the terrain you have already covered, and prepare folks for the map ahead.

Storytellers make the past relevant to the future, even when it is dry and irrelevant.

how do you manage such a setback when it happens? As Anne recalls, the team was so bought into the mission that they were largely undeterred. “The more passionate you are about the cause, the less hard it is,” she explains. “When you have so much conviction that you’re doing the right thing, you see such a challenge as part of the process rather than a road block. We were used to people not understanding us or not liking us, so our attitude was always ‘We need to prove it to them’ versus ‘What are we doing wrong?’ With enough conviction, you can cut through ambiguity.”

was a matter of our first path being wrong, never our mission being wrong. We wavered only on how we were going to get there but not the endpoint.”

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. But still, your perspective during the most difficult

When distractions and drama arise, acknowledge them, and then recontextualize them so that the suffering pales in comparison to...

Despite the circumstances and solemn sense of many of these meetings, David had a way of leaving every meeting on a high note. He would acknowledge the challenges before us while reminding each team why their work was important and what success would eventually look like. Even after painful meetings that lasted multiple hours without any sense of closure, David still managed to bring it together at the end in a way where we all left with energy—something along the lines of, “Hey, I know this is rough and we’ve got some serious work to do, but I also know we’ve got a good plan and the right people,” and adding something funny and uplifting at the end.

Your job is to be an energy giver rather than taker, which is common among founders and leaders I admire. Chief among them is Jon Steinberg, the former president of BuzzFeed who went on to found the news media network Cheddar. Those who know Jon will attest that he is a force of nature. Every team pep talk is an infusion of energy and insight about why the “old model” of cable news is wrong and why Cheddar is the pioneer for the future of the industry. If an idea from his team is great, he’ll turn the company on a dime to make it happen. Having served on Jon’s board, I have witnessed firsthand how he motivates his team, board members, and clients. The common theme across interactions with Jon is that he’s all-in, all the time.

When Dunkin’ Donuts became a big Cheddar client, Jon started wearing Dunkin’ apparel, catering every meeting with Dunkin’ Donuts and coffee, and sharing weekend shots of his family at Dunkin’ on Instagram. What better way to infuse energy into a partnership and send a clear message ...

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

Whenever I needed to force myself to take action that would be painful in the short term but was for the greater good, I would whisper to myself, “Scott, do your fucking job.”

The hopelessness you’re feeling is a common phase that precedes progress; we often feel the weakest just before our immune response kicks in.

In her late twenties, Angela Duckworth quit her job as a management consultant to teach middle school math in New York City. She observed that students’ success was determined by their effort more than anything else.

In 2016, she wrote Grit: The Power of Passion and Perseverance

“Grit is having stamina. Grit is sticking with your future, day in, day out, not just for the week, not just for the month, but for years, and working really hard to make that future a reality. Grit is living life like it’s a marathon, not a sprint,” Duckworth said in her 2013 TED talk.

It sounds like a normal process in retrospect, but spending months if not years pursuing one path and then hitting the reset button can exhaust and demoralize a team. But Tony felt that, so long as you’re gaining confidence in the opportunity and absorbing the lessons learned, you have a renewable energy source.

“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.

The trick is to separate the hardship from what you’re learning. If you’re learning that your assumptions were wrong—that customers don’t want your product or that you’re building the wrong thing—then you should ask yourself: 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.

If you’ve lost conviction but refuse to change course because of what you’ve already invested or achieved, then you’re officially doing things for the wrong reason.

One of my friends who worked at Apple for a number of years recalled Steve Jobs’s ability to change his mind on the turn of a dime when a better solution was presented—he didn’t get stuck with an operating mode just because it had been one that was working. He had famously strong opinions, but he was also able to detach from them. In this way, Steve was the embodiment of the famous advice to have “strong opinions, weakly held.” Only by letting go are you able to truly attempt a new perspective of your venture before you quit.

In her decision to sell her business, she focused on the three constituencies she served—shareholders, employees, and clients—and led a process that proved successful for everyone involved. Alexa sold her company, LearnVest, to Northwestern Mutual on a Wednesday for a reported $350 million and then went into labor on Sunday.

As you encounter such periods in your own career, compartmentalize each drama individually and remind yourself on the horrible days that tomorrow will be better. Compartmentalizing doesn’t mean burying or denying the emotional toll; it means facing one challenge at a time and using each one to provide more perspective for dealing with the others.

Storms have the habit of feeling like their own little worlds, even though they’re just weather patterns and they move on.

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.

Insecurity work puts you at ease, but it doesn’t actually get anything done.

When you spend 30 minutes going down a rabbit hole to answer a particular question, be sure to ask yourself, “Why is this question important and how is the answer actionable?” If the answer is just self-assuring but not actionable, it is likely insecurity work.

If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When you feel lost in ambiguity, ask a different question.

The Muse, which now serves fifty million users, more than 65 percent of whom are women.

Kathryn’s story is a common one. 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.

In a talk he gave at the Aspen Institute in 2009, Amazon founder Jeff Bezos, legendary for his long-term vision, reiterated this point. “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.” To sustain yourself over this time, you can’t look for accolades, and you can’t rely on being understood. Playing the long game is a test of your fortitude, your ability to persevere, and just how genuine your interests are.

There are so many people in the world with ideas to transform industries and build iconic brands. But very few people can stay loyal to a strategy long enough for their vision to materialize. 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.

Seemingly quick wins have deep roots. You need to set up and provide measures for your team to help them endure long periods of doubt, ambiguity, and being misunderstood. Being able to extend your team’s hunger and drive over a long period of time is the ultimate form of patience.

Great teams gain their strength and resilience while toiling their way through the valleys, not just from relishing the view from the peaks. And yet start-ups lose people when the tough challenges come up.