I landed at the O’Hare International Airport in Chicago with a few ideas, a memoir, and an allergy the aircraft ventilation gave me (forgot my pills, shame on me). I got through customs, took the Blue line downtown, arrived at my apartment, and used the rest of that Sunday to decompress after travel. The next day, I was ready to start.

I came to the office and went straight into a short, fairly informal planning meeting. It was just me and Joost. I led the product side while he was the team lead, yet with no team at that point. I shared my ideas. Immediately, it was clear we couldn’t finish either of them. At least not without help from other offices. We had to figure out how to make this team succeed.

In my previous company I built and managed a team of sixty engineers and product managers. It was different here. I came, inherited a team, got vague problems to solve, and a huge org to thrash. I doubted if I could ever build a successful product here. An offer to set up a new team overseas looked like a good chance to claim agency.

A month later, I flew to New York and came back to Chicago with a problem: the key components of our solution were owned by other teams in Europe. We couldn’t influence their roadmap but were completely dependent on them. Then an engineering lead in Amsterdam texted us with an initiative. My immediate thought: they want to turn us into a support team. Fragmented focus. No creativity. Just technical work. I spoke with Joost. We crafted a plan. Yes, we can handle this one thing. But it cannot become routine. That day I realized how fragile focus is.

Finally, I came to Joost with the personalized checkout product. He was concerned.

“We shouldn’t take this,” he said. “We don’t have enough people and don’t know anything about building AI products. I’m worried.”

“Don’t worry. We will figure it out,” I replied.

I knew this was the right product, the right opportunity. We didn’t know exactly how to do it, but that was precisely the point.

Forming

After speaking with customers, it was clear we can’t only deliver conversion improvements. We also need to report on the results, show them in a dashboard. An engineering team back in Amsterdam had bandwidth. But we decided to take another route.

I called an engineer in São Paulo, Brazil. Smart guy who worked with us on some minor projects before. He had the right skills, knowledge, but importantly he was a great fit for the team. Great character, willing to build new products, eager to learn. He was open to moving to Chicago.

Teams with bandwidth, right competences (on paper), and able to start working right away seem to be easy wins. Look how I solved the resource gap! Just a few reshuffles. But sheer availability never guarantees performance.

We didn’t, and couldn’t, hire the whole team straight off the bet. Value wasn’t clear but more importantly, the problem wasn’t clear. As we talked to customers, ran experiments, and relentlessly iterated, we unfolded the problem and formed a team around it.

I’d been thinking about this wrong until I read Team Topologies. Teams must be aligned with the value they should deliver, not grouped by expertise.

A self-sustained team needs to trade the benefits from the economy of scale for fast communication. And that’s on purpose.

When building novel solutions, reporting lines often kill communication. A data engineer discovers a technical gap, she leans toward a backend engineer. They might pull in a few other teammates. They discuss. They disagree. And eventually they resolve the issue. All in less than 30 minutes without touching calendars. If you’re in an unknown territory, those things happen daily. Now, imagine the data people are in another team.

We moved the guy from Brazil because he completed our team. But we only did it once it was inevitable, avoiding hiring for the bench. On his first day, he could add value.

You can never understand the problem fully from the get go. Keep the team intentionally small. Remove handoffs even at the expense of efficiency. Keep reframing the problem and reforming the team accordingly.

Focusing

When I was describing all the great things my team was working on, my manager stopped me mid-sentence.

“This is all great. But what’s the most important thing right now?” he asked.

What he meant was where the leverage points lie. Every complex system has them. The pieces that either make it or break it. Finding them is key for your team’s focus. How do you decide what’s worth solving right now?

From Gary Keller’s The One Thing, I got a practical tool to return my team to what matters. He calls it the Focusing Question and it goes like this: What’s the ONE thing I can do such that by doing it everything else will be easier or unnecessary?

Writing next year’s strategy, I was asking myself: What must a product bring to make a real difference in this company? I went on around the company, asking people from commercial teams, leadership, or engineering.

Eventually, I came to specific numbers. Revenue increase, impact on customer stickiness, and the most valuable customer cohort. That was my north star. No abstract metric. A very specific outcome that anyone from the board to the last engineer could understand.

In my team, it sparked the kind of conversations I didn’t hear before. During planning sessions, teammates started prioritizing experiments and initiatives against the outcome. They were asking: Does this initiative have the capacity to substantially contribute to our goal? The north star metric acted as a limit. The team didn’t need me or anyone else to kill their darlings. Ruthlessly, they did it themselves.

Driving

It was Friday evening, one engineer was finishing a feature we agreed to deliver that week. A few details were still missing. But he promised to share a demo with our colleague in Amsterdam. So, he pushed overtime.

“I promised to finish it so I have to finish it,” he told me.

It was around 7 PM, Chicago time. Amsterdam folks were fast asleep. No one overseas actually cared about the Friday delivery. The guy did it because the excitement of the work drove him.

Frankly, most managers care about their team’s motivation about as much as a two-year-old about their parents’ blood pressure.

Wondering how to get people motivated, I read the works of Robert Ryan, Edward Deci, and Teresa Amabile. They studied human motivation for decades. I found it’s about the right conditions. Their research explained what happened that Friday evening.

He knew exactly what had to be done. It was challenging but he had the right skills. The next step, recording a demo and posting in a Slack channel, was a meaningful milestone. The next week we mentioned the story during our standup and thanked him for his effort.

Becoming

Months after I came to Chicago, standing by my desk, I looked around. Three teammates were whiteboarding data pipelines. The data scientist was showing our latest experiment’s results to Joost. The designer was clarifying the user experience to an engineer.

Everything felt right. For this I had joined this company. This team. This culture. But a few months earlier, none of this existed.

We started with no team, no roadmap, no plan, and no product. Later, we launched a global product in a company processing over 1 trillion euros a year. That day, by the desk, watching my team’s creative flow, I wasn’t doubting my presence.

That day I became a chaos pilot.

Are you trying to do the same thing inside an org that wasn’t built for it?

You’re in the right place.

I once spoke with a CEO running one of the region’s biggest movie sites. Let’s call him Bart. Users were rating films, writing reviews, and he was selling ads. The traffic was insane. Bart wanted to do something new. The ad business didn’t feel sustainable. Maybe subscriptions. Maybe original content. Maybe new markets.

I suggested we do discovery — analyze his business, customers, and opportunities. Figure out his strengths, weaknesses, and where we could actually build something.

Bart’s response?

“Ideas won’t take you any time. I’m not paying you for ideas. You get an idea when you wake up fresh, take a shower, stare at the sun.”

The discussion was brutal. Right then, I knew there’s no business with this guy. That response told me everything. That sentence told me everything. Maybe he was brilliant at selling ads and building his site. But he had no clue how innovation actually works.

Bart’s not alone. Most people think creativity is a flash of inspiration. An idea that hits you in the shower.

It’s a lie.

Or is it? Aren’t shower ideas the heart of creativity?

Yes, but those aha! moments come after long stretches of exploration and deep work. An idea isn’t a lightning bolt. It’s a raindrop. You need hundreds before it starts raining.

Research has confirmed this for decades. In 1957, Paul Christensen was the first to study the relationship between quality and quantity of ideas. He asked participants to generate ideas for plot titles and unusual situations, giving them 12 to 16 minutes. Every two minutes they drew a line to mark the time period. The finding was clear: creativity increased as time passed. Later studies kept confirming and expanding on this. Brian Lucas and Loran Nordgren asked students to generate thematic ideas for Thanksgiving for 10 minutes, then predict how many more they could generate in another 10 minutes. Students underestimated their abilities to generate more ideas by around 50%, predicting they would create ten more ideas in additional ten minutes while actually generating on average 15. And those later ideas were more original!

The pattern holds: more ideas lead to more creative outcomes. And despite what you might expect, quality doesn’t drop with quantity. Your later ideas are usually better, bolder, more creative. Early ideas, on the other hand, tend to be more conformist. Teams often aren’t creative simply because they generate too few ideas.

So what about the shower? There is something to it. The shower helps you break the pattern. It resets your brain. You don’t focus on anything specific for a moment. As physicist Frank Offner said: “If you have a problem, don’t sit down and try to solve it.” When you stop staring at one thing, your brain starts connecting dots in new ways. But those connections only happen after you’ve already put in the hours. Without that groundwork, you can shower for weeks and get nothing.

Quentin Tarantino followed this creative routine while writing Inglourious Basterds: Start around 10:30. Write till 6. Then hit the pool. Hanging out in the pool, ideas started showing up. His mind wandered. He’d think critically about the day’s work, then climb out and jotted down notes for tomorrow. The same principle applies when you’re stuck on a puzzle. You walk away, come back, and suddenly see the solution. You had to forget the wrong approach first. That’s what stepping away does. It helps you forget the dead ends.

Jihae Shin and Adam Grant studied how procrastination helps creativity. Seems backwards, right? Procrastination kills performance. How could it help? When you only execute, you rush in. You’re in operational mode. But when you let yourself get distracted (not hours of TikTok, but genuine mental breaks) you might spot unconventional paths. There’s a sweet spot. Moderate procrastinators are 40% more creative than people who never procrastinate, and 33% more creative than chronic procrastinators. Taking time to think, switching contexts, seeing new angles. But creativity isn’t magic. You still need persistence, resilience, and passion. Without those, you never ship.

Here’s what this means for your team: ideas aren’t lightning bolts, despite what Bart believed. Teams building innovative products need to generate and test many ideas. They need to persist beyond what feels productive. And they need to switch focus regularly to refresh their perspective and escape dead ends.

Creativity takes time. Your team’s ideas need to go both deep and wide.

The sun came through the window. I woke up around seven o’clock. My kids and wife were still sleeping, which is unusual for this hour. It was the holiday vibes, I guess. I looked out of the window and saw a castle ruin on the opposite side of the lake. The sky was blue with a few clouds, and the lake was mirroring the green shores and the castle tower. It was a beautiful morning on the west coast of Ireland.

It was the sixth day of our road trip. We drove, found a place to stay in the afternoon, stayed overnight, and hit the road again. That night we found a lovely bed & breakfast by Carrigafoyle Castle. The view from the window, Celtic music in the background, a pair of lamas behind a fence. It wasn’t just the beautiful nature, but also the culture. Ireland, being a relatively small country at the periphery of Europe, has an edge in creative culture.

With the population only five million, Ireland gave the world writers, actors, musicians, influenced cuisine and lifestyle of many more people. Samuel Beckett or James Joyce in literature. U2 or The Cranberries in music. Cillian Murphy or Colin Ferrell in acting.

How come the cultural impact is so distinct? Why is it that the country is so creative relative to its population?

The more I was thinking about that, the more I began to realize the same is true for any creative endeavor. Country, business, personal. So… what did Ireland do differently?

Constraints

Before we landed in Dublin, we were expecting different vibes. “You’re gonna love the city, it’s so beautiful,” people said. I don’t know why but I thought it would be somewhat similar to British cities. I mean… It would make sense, right? The two countries are right next to each other, they share big parts of history, they speak the same language. Look closer and you see they are very different.

If the two countries were restaurants, the UK would be fine dining and Ireland would be a pub.

Great Britain effectively ruled over Ireland for over a century. Irish people were second class citizens within the monarchy. They had formal representation in the British government but it was exactly as I said… just formal. It was the poorer periphery of a prospering kingdom. Everything escalated with the Great Famine in the mid-19th century when over two million people fled the country and around one million died of hunger.

The unrest of the unsettling century made it clear the people couldn’t make it through economic power. They didn’t control the country nor could they easily produce and export new products. Art became their refuge. Shortly after the Great Famine, Oscar Wilde was born in Dublin. Then, later James Joyce or Samuel Beckett. Those authors transformed the national trauma into relatable characters and witty stories about search for identity and belonging when exiling far from home. Readers fell in love with the profundity.

Irish people prove that constraints are in fact an enabler. Limits force us to try new ways which we wouldn’t otherwise think of. Ireland succeeded in the arts because they occupied a unique position. Part of the English-speaking world but never really at the center of it. Intimacy, the “smallness” of life’s experience, was combined with the breadth of the audience they could reach. Being cultural outsiders made them legends.

Connection

Countless times during the trip, I had chats that surprised me. A lady working on a gas station helped with the coffee machine or a random guy asked whether you wanted to take a picture because he saw you having a nice picnic with a family in a park. They would crack jokes and wouldn’t stick to transactional core for the conversation but rather showed actual interest in you.

As the country’s history unfolded, Ireland either didn’t have a formal government or another power governed the land. For the most part there was no such thing as an official narrative. Societies work like big organisms because they share the same values. Often grounded in religion. Those values are enforced by law. But if you remove the authority… Values seek another place to go.

Irish stories spread orally. In social gatherings. In pubs. People preserved their culture over centuries by simply sharing it over a pint or good meal. Writers iterated on their stories with their peers. Musicians played in countless pubs and bars to test the audience’s response to their new songs. It reveals something crucial about creativity: it must be grounded in the reality of the lived experience of the audience.

Irish artists were bouncing ideas off of their “test audience.” And it helped them in two ways: they got feedback and they spread the ideas.

C.S. Lewis, born in Belfast, brought the Irish storytelling habits to British literature. Together with J.R.R.Tolkien and a few other writers, they met every Tuesday in an Oxford pub called The Eagle and Child. They sat around a table in the corner and discussed their work. This unofficial club was called the Inklings. And because they were willing to socialize their ideas, they gave the world the beautiful stories of The Lord of the Rings and The Chronicles of Narnia.

Irish creators understood that you must socialize ideas early. Talk about your work. Show it to the people. Then, continue working, incorporating their feedback. The audience didn’t control the work. But listening to the audience made it better.

Courage

Once during breakfast, an older lady approached me. She asked about my kids and we started chatting. Coming from New York state, she came to Europe for a few-month-long road trip. It turned out she had Irish ancestry. And she was very proud of that.

Ireland reminds me of the United States. It’s no coincidence. Do you remember the famine in the mid-nineteenth century and two millions of Irish people fleeing the country? Around a million ended up in America. Seeking new lives, they settled in the United States. But they didn’t just escape. They brought their heritage and they came to build.

Half a century after the famine, a young man named Michael Collins helped to change the course of the country. He started as a revolutionary and soldier who played a key role in the establishment of the Irish state in the 1920s. He had the courage to stand up for what he believed in, but he was not just a protest voice.

When the separation from the United Kingdom was actually taking place, Collins stepped into politics and became deeply involved in negotiating the treaty itself. And politics, unlike revolution, is about compromise. Part of that compromise was the separation of Northern Ireland from the rest of Ireland.

That decision turned him into a black sheep among many of his own people.

He was eventually shot at the age of 31, but what makes him such an important figure is not only that he stood against the system. It is that he had the courage to do what many activists never do: help build a new system, even at the expense of his own reputation and ultimately his life.

The old lady’s ancestors left the country, built new life in the United States, and made her proud of her heritage. I feel like there was a piece of Collins in her ancestors as well. They had the courage to cross the ocean and didn’t do it with their head bowed down. They had the courage to leave, but they also had the courage to create. Somewhere I’ve heard someone describe this trait as being a “fuck-off guy.” Impossible to intimidate. That edge, that willingness to stand alone, feels deeply Irish to me.

…

Irish people struggled through years of occupation, wars, social unrest, and millions of people fleeing the country. You would expect a traumatized and broken nation. Instead, whenever you hear Celtic music or recognize elements of it in modern music, you immediately know where it comes from. When you read Irish authors, you identify with the urge to self-identify, living far from home.

Years ago, I was sitting on the floor of my apartment in Prague, getting ready for an investor pitch I had the next day. I was nervous. But I knew I wanted to build, not just… be. Finding a way around my own limits and surrounding myself with the right team, I pulled it off. Was it a great success? Not really. But I learned a ton about myself and what it takes to be creative. Because long before I came to Ireland, I wanted to find Michael Collins. I wanted to stand alone, but also build something. I wanted to be the fuck-off guy.

It’s the dream, right? A sea of senior PMs, each owning “big strategic initiatives,” working hand-in-hand with leadership. No hierarchy. No bureaucracy. Just freedom.

Except… There’s a catch.

Watching teams rise, stall, and quietly burn out, I’ve noticed something. And I want to alert you to my findings. When you flatten the structure, you don’t remove the work of management. You just hide it.

The Myth of Middle Management

In big companies, middle managers often don’t manage people. They manage information.

Who knows what. Who should know what. Who forgot to tell someone something.

It’s messy, repetitive, sometimes absurd, but it’s also what keeps an organization moving in the same direction.

Now, imagine AI taking over that role. It’s already trying. We’ve got AIs writing emails (the kind you’d rather have another AI summarize for you), updating dashboards, and “distributing context” across teams. The promise? Information flows perfectly. No middle managers needed.

Sounds elegant. Almost utopian.

Until you realize that when you remove the people who carry context, you also remove the people who care about it.

What Actually Happens When You Go Flat

You end up creating an organization for senior PMs only.

You eliminate paths for growth because when everyone’s a “lead,” the only way to move is sideways. Or the highway.

You drain domain knowledge over time because your top people move on and you have no juniors to train.

You raise the risk of burnout because without clear support structures, autonomy starts feeling a lot like isolation.

And worst of all, you erase the one competitive advantage humans still have over machines:

The ability to care.

The Void Behind the Title

I’m not saying we need more layers. Nobody wants that.

But when you remove a title, you also remove the work behind that title. And unless someone deliberately fills that void, the team starts to drift.

Flat doesn’t mean leaderless.

It just means the leadership work gets redistributed, usually to the people least equipped or least willing to carry it.

Leave the Team Better Than You Found It

There’s an old Scout’s rule in coding: always leave the code cleaner than you found it.

Maybe leaders should do the same… with teams.

Because if you flatten everything so much that nobody’s left to shape, grow, or protect the people doing the work, you’re not building a stronger system. You’re just erasing the parts of it that make it human.

A group of cunning con artists is constantly spotting new marks. Mickey Bricks Stone is the head of the crew, the mastermind. His crew is a blend of unique skills: Albert Stroller, the seasoned grifter; Ash Three-Socks Morgan, the team’s tech genius; and the newbies in the team, the Kennedy siblings, Emma and Sean.

Carlton Wood and Harry Fielding, two greedy traders with intellectual property rights, crossed their path. These men tricked a trusting man into a deal where he lost control over the cutting-edge security technology he created. Despair led the man to suicide. Mickey’s crew decided to take revenge.

The stolen invention? A theft-preventing security device for art galleries. Wood and Fielding closed a lucrative deal with an art gallery in London but lost an advertising agency due to Wood’s volatile temper. That was the opportunity for Mickey’s team. Pretending to be PR experts, they tricked Wood and Fielding into a very risky PR move: “With our technology, insurance is obsolete. The painting is theft-proof.”

Wood and Fielding agreed. The con was on.

Now, it’s easy. They just need to steal the painting, let Wood and Fielding pay the finder’s fee, and disappear with the money. Ash is the tech guy. He gets them anywhere, even into a secured gallery to steal an unstealable painting.

But not this time.

The system is really good.

They can’t steal it.

“Just get us in,” Mickey said. “I’ll handle the rest.”

Days later, in the early morning, Wood and Fielding got an unpleasant call from the gallery.

“The painting is gone!”

But how? Wasn’t it impossible to steal it?

Here’s where creativity and strategy come in. There’s a technique called "What if." You can use it for problem-solving, too. Start by defining the rules.

The rules of this con?

The security system stays, no theft insurance, and they must steal the painting to claim the reward.

Once you have the rules, you ask, “What if…?”

What if they don’t steal the painting?

The last step is “Imagine if.” Visualize a scenario where this could work.

They don’t move the painting. But they need to make it look like it was stolen. No need to have the painting in their hands, just an empty wall in the gallery.

What if we build a fake wall in front of the wall with the painting? The gallery thought it was stolen, but it never left.

Next time you face a seemingly impossible challenge with your team, try to think of the fake wall. And ask yourselves, “What if…?

Coincidentally, a short movie, Cars Toons, had been planned for release at the same time. Their computing capacity couldn’t handle both projects simultaneously.

Greg Brandeau, the senior VP of system technology, had two choices: spend $2 million on new computers or delay Cars Toons. With time running out and pressure mounting, he turned to Ed Catmull, Pixar’s co-founder and CEO.

“I don’t see how we’re going to get out of this mess,” he said. “Ed will have to make a decision.”

Catmull listened without a word, then asked a few questions and shared his view: “We don’t have $2 million for new computers.”

Brandeau expected this answer. “Then, do we delay Up or Cars Toons?”

“Neither,” said Catmull. “We need both done on schedule. See if you can figure something out.”

Brandeau returned to his team, desperate.

After seemingly endless discussions, someone suggested, “Can we borrow Disney’s computers and use them here?”

Disney had acquired Pixar a few years before, but the two companies did not share their resources. Disney had its HQ in Burbank, and Pixar was still in Emeryville, almost a full day’s drive away.

“Insane!”

But they did it anyway.

The team trucked 250 of Disney’s RenderFarm computers and rendered both movies in time for the release date.

There are two kinds of decisions: either-or and both-and. Either-or means compromise. Both-and means combining the best of all options. Catmull refused either-or. Spending an extra $2 million or delaying the release date were two bad options. He pushed for the best solution.

Quick decisions may speed up the process, but they lead to mediocrity. The real challenge and excitement in creative work lie in holding conflicting ideas and combining them in a novel way.

Decisiveness is overrated.