In It, On It, All In: Rethinking the Leadership Pendulum

One of the most common leadership mantras I’ve heard—especially as businesses scale—is that leaders must “get out of the weeds” and “work on the business, not in it.”

It’s well-intentioned advice. And in many ways, it’s necessary. Leaders can’t afford to be consumed by the day-to-day forever. Someone has to think about the bigger picture, the systems, the long-term strategy. Someone has to work on the business.

But somewhere along the way, this idea hardened into a binary. As if working on the business and working in the business are two opposite ends of a spectrum—and as you grow, you’re supposed to permanently migrate toward one.

I believed this for a long time. I saw “working in the business” as something you eventually outgrow, like training wheels or entry-level tasks. At World 50, as I took on more responsibility and the company scaled from a scrappy team of 40 to a global organization, I made conscious moves to step away from the day-to-day—to work on the business full time.

But in the years that followed—especially during moments of transition, turbulence and growth—I started to question that decision. And eventually, I reversed it.

Today, I see it differently. The best leaders don’t graduate out of the business—they undulate between periods of immersion and elevation. They go deep, then surface. They observe, then engage. They listen, then shape. They don’t choose between working in the business or on it. They do both—just not at the same time.

The best leaders don’t graduate out of the business, they undulate between periods of immersion and elevation.

This is the story of how my thinking on this has evolved—through my time at World 50, through building The 601 Group, and through some of the most important leadership transitions of my career. It’s also a proposal for a new model of leadership—one we’re embedding into the DNA of our company as we grow.

Because I no longer believe this is a style choice. I believe it’s a strategic imperative.

The Early Years: Building While Doing

When I joined World 50, we were a company of fewer than 40 people. There were no neatly drawn lines between functions, no layers of management, no org chart hierarchy to speak of. Everyone was building the business while doing the work. We didn’t talk about “working in” versus “working on” the business. We were too busy doing both.

I was launching new communities, onboarding members, leading calls, building relationships, crafting summit conversation guides, solving problems in real time—and at the same time, helping shape strategy, improve processes and think about how to scale. My role was part builder, part operator, part architect. But that wasn’t unique to me. That was the culture. We all wore multiple hats, and we wore them fast.

It was messy. It was chaotic. It was thrilling. And it worked—because we were close to the product, close to the customer and close to each other. You didn’t need a dashboard or a report to know how things were going—you felt it, every day.

You didn’t need a dashboard or a report to know how things were going—you felt it, every day.

Looking back, those early years were the foundation for everything that followed. They taught me how valuable proximity is. How many of the best insights come from being embedded in the work. And how strategy, when disconnected from experience, tends to drift.

But they also planted the seed for a false belief: that one day, to be a “real leader,” you’d need to take a step back and stop doing the work entirely. That eventually, you’d earn the right to focus only on the blueprint—not the bricks.

That day would come later. And I would follow that path. But it would take years, and a few wrong turns, to realize that stepping back isn’t always progress. Sometimes, it’s distance disguised as growth.

Scaling Up: The Need for Separation

As World 50 grew, so did the complexity of our business—and the demands of leadership began to shift.

By 2019, I was a senior Group Leader, overseeing a large portfolio of communities and leading two of our most active groups: Supply Chain 50 and Innovating 50. It was a rewarding and deeply engaging period—I was still in the work every day, hosting calls, shaping content, building relationships with members. But I was also beginning to feel the strain of context switching. The bigger the portfolio became, the harder it was to do both: run great communities and step back to lead and help scale the organization.

That year, I made a conscious decision. If I was going to lead at a higher level, I needed to spend more of my time working on the business—not just in it. I had to zoom out, build systems, mentor other leaders and create the conditions for scale.

It wasn’t about checking out—it was about leveling up. I wanted to help architect the next phase of World 50’s growth. I wanted to take what I had learned from being in the business and apply it more broadly. And I believed that doing so required a shift in time, attention and energy.

It wasn’t about checking out—it was about leveling up.

The next year validated that shift. In 2020, I was promoted to lead all Group Leaders and oversee the performance and direction of every community across the company. My scope expanded significantly—across teams, geographies and newly acquired businesses. I slowly transitioned out of day-to-day community leadership and into a full-time focus on leading the team and scaling the business.

And it made sense. We were growing fast. We were integrating three acquisitions. We were building new functions, new systems and new processes. We needed people thinking across the enterprise—and I was one of them.

But in making that shift, something else started to happen. Slowly, quietly, and almost invisibly at first: I became just a little bit farther from the work. A little bit farther from the customer. A little bit farther from the reality of what it felt like to be on the front lines.

I didn’t notice it at first. But it would come into sharp focus a few years later.

Going All In On the Business

By 2021, I was fully out of the day-to-day. I had handed off my last active community and stepped entirely into a leadership role focused on managing the team, evolving our playbook and supporting growth across the company. I was, in every way, working on the business.

And for a time, it felt right. The business was scaling rapidly, and my calendar reflected it. One-on-ones with every Group Leader. Strategic planning sessions. Internal projects and initiatives. Integration meetings across newly acquired businesses. Working sessions with our CEO and functional heads.

There was no shortage of problems to solve—and I loved that part of the job. I enjoy thinking structurally, coaching leaders, connecting dots across teams and working on long-term improvements that create leverage across the entire business.

But over time, I began to sense a widening gap between our strategies and the real experience of the team and our members. Some decisions felt a little too theoretical. Some priorities sounded right in a presentation but didn’t hold up under the weight of reality.

Some priorities sounded right in a presentation but didn’t hold up under the weight of reality.

I started to notice that fewer people around the table were spending any meaningful time inside the core product of our business—our member communities.

This drift was no one’s fault. It’s a common outcome of scale. As companies grow, leaders tend to rise further away from the work. Proximity gives way to process. Strategy gives way to abstraction. Feedback becomes secondhand.

But something about it didn’t sit right. Because if we were going to keep growing while staying true to what made us great—if we wanted to keep delivering real value to our members—we couldn’t afford to lead by assumption.

If we wanted to keep delivering real value to our members, we couldn’t afford to lead by assumption.

And so, in late 2024, I made a decision that surprised a few people.

I raised my hand to take over Supply Chain 50 again—not just as an advisor or executive sponsor, but as the active Group Leader.

I wanted to get back inside the work. To feel it again. To understand firsthand how our model was evolving, what members were experiencing, what pressures the team was under and how the expectations around us were changing. I didn’t just want to support from a distance—I wanted to stand in the trenches.

Back in the Trenches

Stepping back into the day-to-day as the active Group Leader of Supply Chain 50 was one of the most clarifying decisions I’ve ever made.

At first, it felt a bit like returning to an old house—you remember the layout, but everything’s slightly changed. The cadence of calls, the expectations of members, the internal tools and systems—it had all evolved. But what hadn’t changed was the core of the work: understanding what our members are dealing with, delivering value in every interaction and earning trust moment by moment, relationship by relationship.

And it didn’t take long to realize how much I had missed.

I had missed the adrenaline of a high-stakes call. The nuance in a member’s voice when they said something was “fine” but meant the opposite. The behind-the-scenes text threads with team members solving a problem minutes before going live. The granular decisions that never make it to a strategy deck but shape the member experience in ways that matter deeply.

The granular decisions that never make it to a strategy deck but shape the member experience in ways that matter deeply.

And I had missed the insight that only comes from proximity.

Being back in it reminded me that some of the most important things can’t be delegated or abstracted. You have to feel them. You have to hear them. You have to live them. That’s how you stay close to the truth.

The timing wasn’t accidental. We were navigating new leadership, evolving member expectations and increased internal pressure. Our team needed stability—and someone who truly understood the demands of the role, not in theory, but in practice. I wanted to be that person. Not just to help guide others, but to re-immerse myself in what it meant to serve our members with excellence.

And this experience forced me to confront something I hadn’t expected: the tension I’d long carried between working in the business and working on it wasn’t just about time—it was about identity.

I had once seen being in the business as a step backward. Now I saw it as a step deeper.

That realization changed everything.

The Realization: It’s Not Balance, It’s Rhythm

For most of my career, I thought the goal was to find the right balance between working in the business and working on it.

But this past year taught me something different.

It’s not about balance—it’s about rhythm.

Balance implies simultaneity, that you can hold both roles equally and at once. But the truth is, when you’re deep in the day-to-day—running calls, leading teams, responding to the immediacy of what’s in front of you—your time and mindspace are consumed. There’s not enough slack for strategy. And when you’re fully focused on the strategic, organizational or financial architecture of the business, you start to lose contact with the texture of the work and the truth of the customer.

Balance implies simultaneity. Rhythm implies intentionality.

Trying to “balance” both doesn’t create strength. It creates dilution.

What works better is something more intentional: undulation.

The best leaders I’ve watched—and the moments when I’ve been at my best—weren’t defined by constantly doing both at the same time. They were marked by a deliberate rhythm. Periods of diving deep into the work, followed by periods of surfacing to reflect, systematize and shape the path forward.

This isn’t a random back-and-forth. It’s not reactive. It’s rhythmic. Purposeful. Done with awareness and intentionality.

This was the mindset shift I needed. I had been thinking in terms of career progression—as if working in the business was something you eventually graduated out of. But that model assumes that growth is linear. That leadership is a ladder.

It’s not. Leadership, in its best form, is a pendulum. You swing into the business to gain clarity, credibility and insight—and then swing back out to apply what you’ve learned at scale. Then, when the conditions call for it, you dive back in again.

The key isn’t to live in one place or the other. The key is to keep moving.

The mistake is thinking you have to pick a side. The power comes from knowing when—and why—to shift.

Case Studies: Leaders Who Undulate

One of the great privileges of my career has been the opportunity to learn from extraordinary leaders—both directly and from afar.

Over the past decade, I’ve become obsessed with studying how great businesses are built. I read founding stories, biographies and memoirs. I listen to long-form interviews and podcast deep dives—Acquired, Founders, The Knowledge Project and others. I pay attention to the details behind the headlines: not just what a leader built, but how they built it. What they paid attention to. When they stepped in. When they pulled back.

And again and again, I see the same pattern emerge. The most effective, enduring builders—especially in moments of crisis, scale or transformation—don’t just lead from the outside. They dive back in. They switch modes. They immerse themselves in the work when it matters most.

Here are six of the clearest examples:

Elon Musk: Sleeping on the Factory Floor

During the chaotic “production hell” of Tesla’s Model 3 rollout, Musk didn’t just direct solutions from a distance—he moved into the factory. Literally. He slept on the floor, worked beside engineers and diagnosed bottlenecks in real time. It wasn’t performative. It was practical.

This hands-on leadership helped him identify constraints that weren’t being surfaced in reports, and it reset the tone across the organization.

No one was too senior to solve problems. When the stakes were highest, Musk wasn’t reviewing PowerPoints, he was fixing robots.

Lesson: When the business is broken, no amount of dashboard management will save you. You have to walk the floor.

Steve Jobs: Back to the Whiteboard

When Jobs returned to Apple in 1997, the company was on the brink. His first move wasn’t just to restructure the executive team—it was to dive headfirst into product. He slashed the bloated product line, sat in on design sessions and worked closely with teams to shape the iMac, iPod and eventually the iPhone.

Jobs was a master strategist, but his strategic clarity came from proximity to product and customer.

He didn’t just set the vision, he embedded himself in the details to ensure the execution matched the ambition.

Lesson: If you want to build something great, you have to live close to the work—not just talk about it.

Howard Schultz: Return to the Barista Line

In 2008, after stepping down as CEO, Schultz returned to lead Starbucks during a period of flatlining sales and cultural drift. His response? He shut down more than 7,000 stores for barista re-training. He visited locations personally. He worked to reignite the passion for the craft of coffee—and the experience of the brand.

Schultz didn’t need to do this for appearances. He did it because he believed that Starbucks’ strength wasn’t in strategy decks—it was in the everyday moments between baristas and customers.

Lesson: Sometimes, the best turnaround strategy is to go back to the front lines and remember what made the business great in the first place.

Anne Mulcahy: Listening Before Leading at Xerox

Before taking the CEO role at Xerox in 2001, Mulcahy didn’t start with a plan—she started with questions. She spent months visiting employees, listening to their frustrations, asking what was broken. She didn’t delegate this. She did it herself.

By the time she stepped into the top role, she knew what was happening—not from secondhand summaries but from the voices of the people doing the work.

Lesson: If you want to lead transformation, start by walking the floor and asking better questions.

Sam Walton: The Relentless Store Walker

Few leaders embodied the undulating model better than Sam Walton. Even after building a national retail empire, he never stopped visiting stores. He talked to cashiers. Took photos of displays. Rode in delivery trucks. Compared prices. Jotted down notes in spiral notebooks.

He didn’t see this as micromanagement—he saw it as insight. The frontline was where the truth lived.

Lesson: If you’re too important to walk the floor, you’re too distant to lead well.

Herb Kelleher: Culture in the Cockpit and on the Tarmac

Herb Kelleher, founder and longtime CEO of Southwest Airlines, was famous not just for building an iconic low-cost airline, but for doing it while remaining deeply embedded in the culture of the company.

He didn’t just visit airports—he loaded bags. He didn’t just send thank-you notes—he wrote thousands of them by hand. He believed that culture was not a memo, but a daily practice.

Kelleher’s presence wasn’t just symbolic, it was operational.

Lesson: Culture isn’t a slogan. It’s what leaders reinforce by where they choose to spend their time.

These stories reinforce what I’ve come to believe: the best leaders know when to dive in and when to step back. They don’t confuse elevation with detachment. They don’t see being “in the business” as a demotion. They see it as essential.

And as we build The 601 Group, this isn’t just something I admire from afar. It’s something we’re putting into practice.

The 601 Group Blueprint: Embedding the Model

At The 601 Group, we’re still in the early chapters of our story. But already, we’re thinking hard about what kind of company we want to become—not just in what we build, but in how we lead.

From the very beginning, we’ve been intentional about creating an organization where excellence in operations and strategy coexist. Where no one is above the details, but no one is buried in them forever. Where leaders have the permission—and the expectation—to undulate between working in and on the business, depending on what the moment requires.

This is something our core leadership team—Gina, Suzie, Anna, Jeremy, and myself—talk about regularly. We’re building a business that requires care at every level: immersive guest experiences, creative product development, high-quality operations and scalable systems. That means sometimes we’re hands-on in a class, walking the floor or solving a real-time problem. Other times, we’re focused on hiring, refining brand standards, developing training models or mapping out multi-market expansion.

We’re not trying to live in both places at once. We’re trying to build a rhythm.

And just as important, we’re trying to normalize that rhythm for the leaders who will come after us.

One of the cultural foundations we want to establish is that leadership at The 601 Group doesn’t mean detachment. It doesn’t mean sitting in a back office. It means being present. It means staying close to the product, the customer and the team—but also knowing when to step back, reflect and build systems that scale.

We’re already seeing how powerful this can be. The leaders closest to the work are generating some of our best ideas. And when we step in periodically, not to micromanage but to reconnect, we return with clearer insight and stronger strategy.

As we grow—from one location to many, from a local brand to a national one—we’ll inevitably add layers, teams and distance. But the goal isn’t to eliminate that distance entirely. The goal is to shorten the time it takes to close the gap—by building a culture where leaders know when to get close again.

If we get this right, we won’t just build a great company. We’ll build a company that stays great, no matter how big it gets.

For now, I continue to balance my role at World 50 with my contributions to The 601 Group. But as we look toward the future—and as I one day make a full transition into this business—I want to be sure this cultural foundation is already set in stone.

And that realization—about rhythm, immersion and timing—has me reflecting again on my current chapter at World 50. Leading Supply Chain 50 has been one of the most rewarding and energizing roles I’ve ever held. But I’m beginning to feel the early signals that it may soon be time to undulate back again—to shift from being in the business to working on it. Not because I’m stepping away, but because stepping back might allow me to support the team, the members and the company in new and necessary ways.

Conclusion: The Pendulum Is the Point

If there’s one thing this journey has taught me, it’s that there is no perfect ratio. No tidy formula. No leadership chart that tells you when to switch gears.

You learn the rhythm by living it.

You make the shift when you feel disconnected from the customer—or when the team needs clarity and you’re buried too deep to see the path ahead. You move back in when the details matter most, and you zoom back out when systems, scale and structure require your attention.

The goal isn’t to escape the pendulum. The goal is to ride it with intention.

Looking back, I can see where I held onto the wrong assumption for too long. I believed that growth meant graduation. That the measure of success was how far you could distance yourself from the work. But I’ve come to see things differently.

Now, I believe that the best leaders move in cycles. They immerse to understand. They ascend to design. They return to re-anchor. They repeat.

And when organizations make space for this kind of leadership—when they embed it into their culture—it becomes a powerful engine for truth, clarity and long-term excellence.

At World 50, at The 601 Group, and in whatever I build next, that’s the kind of leadership I want to model. That’s the kind of rhythm I want to live.

Because the truth is, the pendulum doesn’t pull you away from leadership, it brings you closer to it.

And that’s the work.

To stay close enough to the action to hear the signal, but far enough above it to see the pattern.

To serve the team by being in the trenches and by charting the course ahead.

To lead not by picking a lane, but by knowing when to change lanes altogether.

That’s the model we’re building. That’s the leader I want to be. And that’s the rhythm I hope carries us forward.

Until next time!

- Mike