Sylwia’s post — est. reading time: 9 minutes

There is no greater paradox in digital transformation than this: to secure the future, you must often dismantle what still functions. Legacy systems, structures, and revenue streams—those very assets that have delivered growth and predictability—can quietly become liabilities. Yet the impulse to preserve them is strong. After all, they work. They are stable. They still deliver returns. But therein lies the risk. Digital transformation is not about efficiency alone. It is about relevance. And nothing undermines future relevance like an unwillingness to let go of the past.

Across industries, organisations are waking up to the uncomfortable truth that transformation is not about layering new tools on top of old foundations. It is about making strategic choices to retire, replace, and reinvent. Not incrementally, but decisively. Yet that act—strategic sacrifice—is one of the hardest for leaders to make. It means cannibalising existing models, unpicking entrenched workflows, and challenging the metrics that once defined success. It demands courage and clarity, especially when legacy still pays the bills.

Why Functional Legacy Is Still Risky

Legacy systems are not inherently flawed. In fact, many continue to perform reliably. Core banking systems process transactions without fail. Manufacturing ERPs coordinate supply chains to the hour. On-premise CRMs still manage customer records. But the question is not whether these systems work—it’s whether they serve the future. In an environment shaped by speed, data, and customer experience, legacy systems often inhibit more than they enable.

They lack flexibility. They resist integration. They absorb disproportionate maintenance costs. And most crucially, they codify outdated assumptions about how the business should operate. When transformation efforts are forced to accommodate legacy constraints, innovation is reduced to workaround. And transformation becomes a facade—an app layer over an unchangeable core.

Moreover, legacy lives beyond technology. It lurks in reporting structures, incentive schemes, and decision-making hierarchies. A legacy mindset resists experimentation, prizes predictability, and favours optimisation over reinvention. These cultural artefacts can be even harder to uproot than old code—but no less essential to confront.

Case in Point: The Strategic Sacrifice Imperative

Consider the case of a global media platform that once led the market in physical distribution. For years, it generated consistent revenue from mail-order content. But anticipating the shift to digital, leadership chose to deprioritise its profitable arm and invest aggressively in streaming. This wasn’t a reaction to declining sales—it was a proactive decision to kill a healthy part of the business in service of a more scalable, sustainable future. The short-term cost was real: lost margins, stakeholder backlash, and internal uncertainty. But the long-term benefit was market leadership in a digital-first model that its competitors failed to match.

Contrast that with the fate of traditional rivals who clung to their legacy. Despite possessing brand recognition and infrastructure, they were unable—or unwilling—to sacrifice immediate gain for enduring transformation. They optimised what had worked before and were ultimately outpaced by newcomers who had no legacy to protect. The lesson? Digital transformation rewards strategic risk, not sentimental attachment.

Why Leaders Struggle to Let Go

Executives face immense pressure to sustain quarterly performance. Legacy systems are often deeply entwined with revenue targets, performance bonuses, and shareholder expectations. Sunsetting them can appear reckless, especially when they still deliver. This creates a behavioural trap: deferring transformation until the pain becomes undeniable. But by the time legacy systems truly break, it’s often too late to recover competitive ground.

There is also emotional attachment. Teams have built careers around legacy platforms. Leaders feel loyalty to the models they helped scale. And internal narratives develop around what can’t be touched—because “that’s how we’ve always done it.” These stories are comforting, but they are also corrosive. They anchor organisations to a past that no longer fits the market.

Change also carries visibility. Killing a functioning system feels riskier than maintaining one. It draws attention, demands justification, and often triggers resistance. But the greater risk lies in invisibility—watching relevance slip away, one incremental delay at a time.

Letting Go Is Not Destruction—It’s Curation

To be clear, transformation does not mean abandoning everything that came before. It means curating what to preserve, what to evolve, and what to retire. It’s a disciplined process of subtraction—not recklessness, but refinement. And it starts with a clear articulation of future strategy. If legacy does not enable the future vision, it must be interrogated. Does it scale? Does it integrate? Does it accelerate? If not, it belongs on the exit path.

Some systems can be modernised incrementally—replatformed, containerised, wrapped with APIs. Others require wholesale replacement. But every organisation must map its legacy landscape not just in technical terms, but strategic terms. Where does legacy create friction? Where does it limit experimentation? Where does it lock in cost? The answers to these questions reveal more than a system inventory—they reveal transformation priorities.

Funding the Future Without Starving the Present

One of the hardest parts of killing legacy is funding what comes next. Transformation requires investment: in new platforms, capabilities, and people. Yet legacy consumes budget, talent, and operational focus. Leaders must find a way to dual-track: sustain the core while funding the edge. This is not easy—but it is possible. It requires ruthless prioritisation, a shift in investment horizons, and cross-functional alignment around what matters most.

Some organisations adopt “two-speed IT” models, where innovation units are separated from legacy teams. Others pursue phased migration, gradually shifting workloads to cloud-native platforms. The key is intentionality. Left unattended, legacy will grow roots. Managed actively, it can be pruned—and the future funded.

The Cultural Shift: From Ownership to Obsolescence

Legacy is not just a technical burden. It is a cultural one. Transformation requires shifting attitudes towards ownership, permanence, and control. In the legacy world, systems were designed to last decades. In the digital world, longevity is measured in adaptability. Leaders must normalise the idea that some platforms—and the practices tied to them—have expiration dates. This means incentivising outcomes over process, fluidity over hierarchy, and progress over preservation.

Crucially, this cultural work cannot be delegated to IT alone. It requires cross-functional alignment: HR redefining career paths, finance rethinking cost models, compliance embracing iterative change. Everyone must move beyond legacy—not just the codebase, but the mindset that built it.

When to Kill: Criteria for Letting Go

So when should a legacy system, process, or model be retired? There are no universal rules—but there are indicators:

• When integration costs exceed business value.
• When security risks outweigh platform familiarity.
• When customer experience suffers due to latency, rigidity, or inaccessibility.
• When teams circumvent the system to get work done.
• When the system can’t support future innovation goals.

In these cases, clinging to legacy is not cautious—it’s costly.

The Endgame: Creating Legacy on Purpose

Ironically, the companies that succeed in transformation are those that create their own legacy. They make hard calls early. They build platforms designed for flexibility. They scale with discipline. And they leave behind models that others study, admire, and emulate. Their legacy is not in the systems they preserved—but in the decisions they dared to make when they still had a choice.

So ask yourself: What are we protecting that no longer serves us—and are we willing to let it go before it lets go of us?