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How Ukraine Defied History

2025 August 24
by Greg Satell

I still remember feeling a bit awed when I first arrived in Ukraine in 2002. I had already spent five years in the region, so I was no stranger to Eastern Europe or to post-communist societies. Yet Kyiv was different. It was much larger than other regional capitals, like Warsaw, Prague, or Budapest, and it carried an air of what felt like destiny.

Still, Ukraine was a cynical place. Corruption was endemic. There was little civic discourse, and almost no appetite for political or social mobilization. The prevailing attitude was, “Nothing will ever change, so why bother thinking about it? Just do your job, take care of your family, and maybe save enough for a decent vacation every now and then.”

Today, Ukraine has been utterly transformed to an extent very few thought possible. And it’s worth looking back to understand how it underwent such a profound shift. Because if change can happen in Ukraine, where everything once seemed so completely hopeless, then there is no limit to how we can impact the world. That is something truly worth exploring.

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If You’re Serious About Change, You Need To Make These 3 Mindset Shifts

2025 August 17
by Greg Satell

People become leaders by first becoming effective managers. They create cohesion and consensus among their team. They maintain an atmosphere of predictability so everybody knows what to expect and focus on executing a plan with excellence. That’s how you consistently deliver value to customers, partners and other stakeholders.

But when you are pursuing change, none of those things will help you. When something is new, untried and untested, you can’t expect an immediate consensus to form around it. You can’t expect predictability either, but need to embrace uncertainty. Instead of focusing on execution, you need to explore and find new answers through some trial and error.

That’s one of the things that makes transformation so hard. You need to mode shift away from what’s made you successful up to this point and do things differently. That requires you not only to change actions, but to adopt new mindsets. It is these mindset shifts that many of the leaders I work with find most challenging. Here are three of the most important.
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Happy 16th Birthday Digital Tonto!

2025 August 10
by Greg Satell

Much of what this blog has become was born in the winter of 2004 on Independence Square in Kyiv. It was there, with the uncertainty and confusion of the Orange Revolution swirling around us, that we stood shivering in the cold. We didn’t know what would become of us, or of Ukraine, or of anything, except that we hoped for something better.

I’ve spent much of the ensuing two decades trying to make sense of what happened during those days. Why were those in power so powerless to shape events? What was that energy that seemed to cascade through the crowds? How does a status quo that seemed so entrenched for so long, then seem to disappear in an instant?

I found some answers, wrote articles and books about them. But new questions continue to emerge, especially now that we appear to be at an inflection point and a confluence of forces are pushing us toward a major realignment. So I’m still trying to figure it all out and writing about it. I’m glad you’ve chosen to join me. Here are my favorite articles from the past year:

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It’s Good to Learn From Your Mistakes. It’s Better to Learn From Someone Else’s.

2025 August 3
by Greg Satell

When people talk about Steve Jobs, they usually focus on his triumphant return to Apple. The company was on the brink of collapse. Jobs came back and lead one of the greatest corporate turnarounds in history. Under his leadership, Apple created iconic products and became the most valuable company in the world.

Yet we rarely hear much about his years in the wilderness, especially his failures at NeXT Computer.  It was the missteps there, like poor product-market fit and lack of software development, that informed his later successes. You can’t fully understand Jobs’ success unless you follow the entire journey, stumbles and all.

I get the same feeling every time I see a protest march. People often look back at the 1963 March on Washington as a model for change. But there have been roughly 300 marches on Washington, and that’s the only notable success. If we want to drive real change—in business, activism, or anywhere else—we need to study not just the rare wins, but all the failures too.

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The Experts Aren’t the Problem. It’s How You’re Listening to Them

2025 July 27
by Greg Satell

It’s become increasingly common for people to justify wacky ideas—ranging from Holocaust denial to miracle cures—by claiming that they are doing their own research. Originally coined by conspiracy theorist Bill Cooper in the 1990s, the phrase has become a rallying call for those who seek alternatives to mainstream expertise.

Yet doing your own research is much harder than it would first appear. As Leonard Read pointed out in his classic essay, I, Pencil, even an object as simple as a pencil requires expertise in everything from mining, chemistry, logistics and myriad other things to produce it. It is far too complex for any single person to do it by themselves.

Pencils are far less complicated than most things we have to make decisions about. Anybody can, of course, access papers in scientific journals and see what they have to say, but unless you’re an expert you will be unable to evaluate the validity of the materials and methods used to carry out the research. To benefit from expertise, you need to learn how to listen critically.

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When You Fail To Forge Shared Values, Your Vision Will Fail Too

2025 July 20
by Greg Satell

In 2016, in the wake of Donald Trump’s election as President of the United States, Teresa Shook, an Indiana lawyer who had retired to Hawaii, posted a simple message on Facebook: “We have to march.” Within hours, her post went viral and what began as a single voice quickly snowballed into a nationwide call to action.

An experienced activist, Vanessa Wruble, began organizing a formal effort that included fashion designer Bob Bland and recruited three prominent activists of color, Carmen Perez, Linda Sarsour, and Tamika Mallory, to serve as co-chairs. They wanted to address the “whiteness problem” and build a more diverse, representative coalition.

Tensions soon flared. The women of color were wary of being tokenized, while some of the white organizers didn’t appreciate being lectured about their “blind spots.”  For a time, they managed to paper over these divisions, but it was only a matter of time before the movement unraveled and, despite a well attended march, the women failed to further their cause.

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3 Stupid Things Leaders Often Think

2025 July 13
by Greg Satell

Leaders begin their role with the best of intentions. No one starts out by thinking, “I want to make everyone’s lives miserable and undermine their performance.” Yet, we know many do just that. Most are thrust into the role, with very little training or development, because they were good at something else or there was simply a hole to be filled.

In Good Boss, Bad Boss, organizational psychologist Bob Sutton writes, “Devoting relentless attention to doing one good thing after another—however small—is the only path I know to becoming and remaining a great boss” and that’s good advice. But before you can become a great boss, you first need to stop being a bad one.

The first step? Letting go of the beliefs that undermine your leadership effectiveness. While nobody sets out to adopt counterproductive ideas, certain myths creep in over time and shape decision-making.  These misconceptions lead to poor actions that harm both leaders and their teams. Here are three of the most common stupid things to watch out for:

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When You Feel The Urge To Create A Conflict, Create A Dilemma Instead

2025 July 6
by Greg Satell

On February 12th, 2004, at the direction of San Francisco Mayor Gavin Newsom and in defiance of California Law, city officials began issuing marriage licenses to same-sex couples in what would come to be known as the Winter of Love.  Coming just in time for Valentines Day, it captured the imagination of the LGBTQ community.

Yet the backlash was swift. Within weeks, President Bush called for a constitutional amendment declaring that marriage can only be between a man and a woman.  Conservative groups swung into action and in 2008 were successful in placing Proposition 8, a law so harsh that many believe that it paved the way for marriage rights.

Saul Alinsky warned that every revolution inspires a counterrevolution. Out instinct is to try to silence dissent, but that will always backfire. There is a better way. Rather than try to overpower those that oppose your idea, you can create a dilemma that forces them to discredit themselves. By inciting a crackdown, that’s exactly what Newsom’s ploy did.

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The End of History All Over Again…

2025 June 29
by Greg Satell

When I was living in Moscow in 2003, I couldn’t help thinking, “This must be what Weimar Germany felt like. These people don’t know that they lost the Cold War. They think their leaders betrayed them and surrendered. They will try to dominate again.” At the time, I wondered if I was being a bit alarmist. Today, it’s clear that I was not.

I had come to Moscow with the perspective of having spent more than 6 years in the region, most of it in Poland, where the country was rapidly modernizing and westernizing. The fall of the Soviet Union was seen as unambiguously positive there. In Moscow though, you could deeply feel its sense of loss of imperial identity and its visceral desire to restore its national pride.

It seemed, as Francis Fukuyama famously wrote, like the end of history. The conflict between communism and capitalism had come to an abrupt end. Just one model remained. But, as Fukuyama also noted—and as I saw firsthand in Moscow—the human urge to assert identity remained. What we were witnessing wasn’t an end, but the beginning of a major realignment.

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Why You Should Beware The Action Trap

2025 June 22
by Greg Satell

My friend Jessica Kriegel often warns leaders about the action trap, the mistaken belief that if we just do something we’ll get results. We’re conditioned to have a bias for action, to do something rather than nothing. Yet actions without a sound strategy are doomed to fail. We need to avoid the trap of doing stuff just to make ourselves feel better. Action is no substitute for discipline.

The truth is that good ideas fail all of the time for all kinds of reasons. The status quo always has inertia on its side and never yields its power gracefully. There are also cultural norms and rituals that are rarely obvious. And beneath the surface, there are always unseen obstacles that can derail even the best-intended efforts.

Until you identify, analyze and understand exactly what your actions are targeted at, you’re just wasting time and resources. Even worse, as you lurch from one failed action to another, you create stress, erode trust and fuel change fatigue, making future actions even less likely to succeed. Smart leaders learn to avoid this cycle. Here’s how they do that effectively.

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