Irony: How Companies Fight to Preserve Their Legacy and Lose Everything

In business, no matter the market or the products and services offered, relevance is fleeting, and complacency is dangerous. Let me share the story of a once-thriving company—a cautionary tale that serves as a reminder for all of us.

This company had everything going for it: a high-end, customizable product designed to meet the unique needs of large corporations, backed by robust, internally built technology and exceptional implementation and service. For years, it was a key player in its market, winning over thought leaders and securing highly referenceable customers. This success also fostered a loyal base of employees—some drawn by the company’s appealing work-life balance, and many on the technical side who relished being the heroes, customizing the product to meet each customer’s specific needs.

But over time, the landscape shifted. The market evolved. New competitors emerged, offering innovative solutions with self-service capabilities that allowed customers to configure the product independently, without assistance, and at a lower cost. These competitors introduced fresh methods that resonated with the market’s changing needs. Yet, the company stood still. Why? Because everyone was getting what they thought they wanted—the status quo felt comfortable and familiar.

But complacency has a price. Eventually, the company’s shareholders voiced their concerns. They sought the value of a product company, not a services and consulting company. The market had moved forward, and the company, clinging to its past successes, had not. What once made the company great had become its greatest vulnerability, highlighting the irony of success: without adaptation, even the strongest companies can lose their way.

I've learned that in business, nostalgia can be our worst enemy.

It’s easy to get stuck in what used to work and ignore the changes happening around us. As I often say, "In business, standing still is not a strategy; it's a slow surrender." Instead of adapting, this company doubled down on what had always worked before, falling into what I describe as the "default strategy" trap—continuing without a deliberate plan to evolve. It ended up catering to a shrinking group of laggards in niche sectors—customers who clung to the old ways just as the company did. The glory days of explosive growth were over, and the business was stuck in the past, while the rest of the world moved forward.

Recognizing this, new leadership stepped in with a clear-eyed vision for the future: modernize the technology stack, overhaul the product lineup, and completely revamp the go-to-market strategy. The goal was to reclaim the company's place at the forefront of the industry. But I've come to realize that the hardest battles are fought not in the market, but within the walls of the company itself. As I often remind myself, “Change is inevitable, but growth is optional.” The toughest part of transformation is not about outmaneuvering the market—it’s about overcoming internal resistance.

Resistance came swiftly and fiercely. Longtime employees, nostalgic for the golden years, viewed the proposed changes as a threat to their legacy. Middle management, comfortable in their routines, feared losing their influence. The culture, deeply ingrained and slow to evolve, pushed back against every new idea and every attempt to disrupt the status quo. It reminded me of Niccolò Machiavelli’s famous observation: “It must be considered that there is nothing more difficult to carry out, nor more doubtful of success, nor more dangerous to handle, than to initiate a new order of things. For the reformer has enemies in all those who profit by the old order, and only lukewarm defenders in all those who would profit by the new order.”

The internal resistance slowed the opportunity to succeed with all new products and processes. Decisions that should have been simple became complex. Plans were watered down, compromises were made, and the momentum of the initial vision began to dissipate. Many would literally 'grin' and 'ignore' the changes just doing what they always did, a process affectionately known as 'grinf*cking'. The company missed opportunities to lean into the changes that give it back control of its own destiny, all while competitors continued to innovate and capture the market.

Consider Kodak, a brand synonymous with photography for over a century. When digital cameras began to gain traction, Kodak, with its deep roots in film, was slow to pivot. Despite having the technology and the know-how to lead the digital revolution, the company hesitated. It clung to its legacy products and the comfort of familiar markets. By the time Kodak finally embraced digital fully, it was too late—the competition had already seized the advantage.

Or take Blockbuster, which once dominated the video rental industry. When Netflix introduced a new business model based on mail-order DVDs and later streaming, Blockbuster had the chance to acquire Netflix early on but chose not to, convinced that its brick-and-mortar stores would always be the preferred option for customers. That miscalculation proved fatal, as Blockbuster’s refusal to embrace the change ultimately led to its downfall.

Another example that comes to mind is BlackBerry in the technology industry. BlackBerry once dominated the smartphone market with its secure email service and iconic keyboard phones. But as consumer preferences shifted towards touchscreen smartphones with robust app ecosystems, BlackBerry clung to its physical keyboard and failed to adapt quickly enough to the changing landscape. They were confident that their business users would continue to value the security and functionality of BlackBerry devices, but the company missed the broader trend of mobile computing and app-driven user experiences. By the time BlackBerry tried to pivot and release touchscreen devices and a new operating system, it was too late—the market had already moved on, and Apple and Android had seized the lion's share.

Reflecting on these examples, I’m reminded of something I often say: "You need to know when to say no. Not every opportunity is worth pursuing if it takes you off course." In our story, the new leadership's efforts, despite being well-intentioned and rooted in a solid strategy, ultimately fell short due to the unrelenting resistance from within. And so, instead of seizing the moment to reinvent itself, the company languished. With progress stymied, the only viable path left was to sell to private investors. What followed was predictable: cost-cutting measures, restructuring, and layoffs.

The irony is palpable.

Those who fought hardest to keep things the way they were didn’t get what they wanted. The layoffs and restructuring upended the very stability they were trying to preserve. The market had changed, customer expectations had evolved, and the company, once a leader, was no longer relevant. By resisting change, they squandered their one real opportunity to control their own destiny.

This story is a powerful reminder that in today’s business landscape, you’re either moving forward or falling behind. Standing still isn’t an option. Change is difficult. It challenges us, disrupts our routines, and forces us to confront the unknown. But resisting change is not a strategy—it’s a slow surrender. The market won’t wait, and neither will your competitors.

Adaptation and innovation are not just options; they are necessities. You never have it figured out and you can now just phone it in. Whether it’s updating your technology, refining your product, or redefining your go-to-market strategy, the ability to pivot is crucial. One thing I always remind myself is, “Different beats better.” Sometimes, it's not about being the best at what you used to do, but about being unique in what you’re going to do next. Don’t let nostalgia for the past rob you of the future. Embrace the discomfort. Seize the opportunity to reinvent.

Because the cost of resisting change isn’t just irrelevance; it’s the loss of the one thing you can control: your own destiny. ??

#Leadership #ChangeManagement #Innovation #AdaptOrDie #BusinessStrategy