The teams most at risk aren’t the ones struggling — they’re the ones who just won. The moment success locks in, something shifts: teams stop questioning, adapting, and taking smart risks. And that’s exactly when they start losing. They optimise relentlessly, fine-tuning their proven recipe until it’s so specialised, so efficient, so tightly honed that they are completely unprepared when the rules of the game inevitably change.

Your biggest threat isn’t the competitor you’ve got your eye on — it’s the quiet force of your own past wins holding you in place.

Welcome to The Success Trap. Let’s talk about how good teams get stuck, how to avoid it, and, if you’re already there — how to find your escape velocity and break free.

Why Repeating Success is Riskier Than You Think

When teams find a winning formula, their instinct is to repeat it. After all, success feels good, and repeating what works feels safe. But every repetition hardens the process, reduces flexibility, and quietly introduces rigidity as muscle memory takes over. Instead of exploring new opportunities, teams become locked into extracting more and more value from the same old formula — until their advantage disappears.

And that’s when they fall into the Happy Path Trap.

Teams that relentlessly optimise around what already works naturally start refining only the smooth and predictable parts of the experience. They unconsciously design for the ideal customer journey, ironing out known friction points while ignoring edge cases and outliers. This approach feels efficient, but it’s also blinding. Real customers aren’t ideal, and their journeys aren’t frictionless.

By focusing too narrowly on what’s working, teams overlook the messy, frustrating, imperfect parts of the experience. Yet those friction points are where innovation hides. The uncomfortable, inconvenient complaints that don’t fit neatly into the current model are often the first signals of a shift in customer needs. Your most vocal, unhappy customers might actually be pointing you toward your next breakthrough.

Success creates habits, and habits create inertia. Optimising exclusively around the happy path ensures you’ll miss the problems—and opportunities—that lie just off the beaten track.

Key Insights:

• Success makes the status quo feel rational — even inevitable.
• Past success creates internal advocates who defend the existing approach, even when better options appear.
• Teams start optimising for certainty instead of adaptability — and that’s when innovation dies.

Why Success Creates Blind Spots

When success arrives, it doesn’t just reward — it distracts. Teams start drinking their own Kool-Aid, convinced that what worked yesterday will surely keep working tomorrow. They stop scanning the horizon for threats or opportunities, assuming they’ve cracked the code. It’s human nature: the brain craves certainty, and success provides precisely that.

But certainty is a seductive illusion. Teams that assume today’s winning strategy guarantees tomorrow’s results become blind to subtle but crucial shifts — in customer behaviour, the market, technology, or even their own business. They see what they want to see — and dismiss anything that challenges their proven model. Before they know it, protectionism becomes their strategy.

This is how Facebook initially dismissed Snapchat’s disappearing messages, how Instagram resisted short-form video until TikTok reshaped the landscape, and how your team might be quietly overlooking the next big shift — until it’s too late.

The Metrics Trap

Successful teams often become prisoners of their metrics. They assume that what made them successful in the past will keep defining success indefinitely. But data quickly becomes a crutch instead of a tool. They obsess over the wrong signals, measuring what was important before, not what’s important now.

The result? They’re blind to disruption precisely because they’re looking at outdated dashboards. They literally can’t see the shift happening — until it rolls right over them.

Past success is the enemy of curiosity. It whispers, “Don’t look over there — you’ve already figured this out.” But the truth is, the more confident you feel, the less clearly you see. And clarity is exactly what you need when the rules start to change.

The Slow Death of Adaptability: How Good Teams Become Static

The danger of the Success Trap isn’t dramatic or loud — it’s insidiously subtle. Good teams rarely get stuck overnight. Instead, success slowly turns dynamic teams static, step by cautious step:

Efficiency Becomes the Only Goal

Good teams naturally want to improve. They obsessively pursue efficiency, streamlining and trimming every corner of their proven process. But when efficiency takes priority over adaptability, the team becomes rigid. Suddenly, change feels expensive and even threatening.

Past Success Becomes Sacred

Yesterday’s winning strategy transforms into dogma. Instead of continually re-examining their approach, teams elevate past success to untouchable status. Questions or challenges become unwelcome disruptions rather than essential conversations.

Identity Anchoring deepens this problem. Successful teams don’t just become attached to their methods — they become emotionally invested in their identity as “the team that built Product X” or “the team known for Strategy Y.” Changing the approach feels like changing who they are, triggering intense emotional resistance and defensiveness. Identity Anchoring subtly transforms adaptability into betrayal, making even minor pivots feel like profound threats.

They Optimise for Scale, Not Adaptability

As companies grow and become more successful, they typically optimise for scale rather than adaptability. They build repeatable processes, reduce variability, and standardise everything from decision-making to technology. On paper, this looks smart. But scaling a process designed for yesterday’s market doesn’t help you adapt to tomorrow’s disruption. The more rigidly optimised a team becomes, the harder it is to change course quickly when the world inevitably shifts.

They Stop Taking Calculated Risks

Success makes people cautious. Good teams stop taking calculated risks and begin favouring guaranteed results — low-risk wins over high-impact bets. They retreat into core innovation, refining and optimising what already works while avoiding riskier adjacent or disruptive innovation.

• Core Innovation feels safe. Improving an existing feature, making a process more efficient, or tweaking pricing.
• Adjacent Innovation is riskier. It involves expanding into a related market, applying existing capabilities in a new way, or shifting into an emerging customer segment.
• Disruptive Innovation is the boldest. It challenges the status quo, often making the team’s current model obsolete.

Most teams default to Core Innovation because it feels rational. But over time, playing it safe turns them into incumbents defending a shrinking advantage while someone else redefines the game.

When Teams Stop Innovating and Hope Someone Else Will

When teams stop taking calculated risks, they often outsource innovation by default. The assumption emerges that if radical change is needed, someone else will handle it — a specialised innovation team, an external consultant, or even a competitor. By the time they realise they’re lagging, it’s often too late.

Instead of building innovation into their core operating model, teams treat it like an isolated function. This creates two problems:

1. Innovation silos. When only one group is responsible for breakthrough ideas, the rest of the organisation becomes passive.
2. Risk aversion creeps in. The broader team becomes focused on sustaining success, not redefining it — reinforcing the Success Trap.

When innovation isn’t owned by everyone, it becomes just another initiative — one that can be postponed, de-prioritised, or ignored altogether.

The Cultural Rot That Follows

When teams avoid hard choices, culture fills the gap — often in ways that make things worse. Two silent killers emerge:

• Hero Culture: When recurring problems arise, the quickest fix is often to call in a trusted hero—someone who swoops in and saves the day. While this may feel efficient in the moment, heroics mask deeper systemic issues. Teams stop focusing on prevention and build workarounds instead. Over time, organisations optimise for those who can solve crises the fastest, not those who can prevent them from happening in the first place.
• Favourites Culture: Success can also create invisible hierarchies. Teams begin rewarding those most visible in past wins rather than those driving actual progress. Familiarity replaces meritocracy, and real accountability disappears. Over time, this undermines trust — the foundation of true innovation and continuous improvement.

Static teams feel secure right until the moment they’re suddenly obsolete. Their comfort zone becomes a danger zone.

Sidebar: The Hidden Biases That Keep Good Teams Stuck

Good teams don’t just drift into the Success Trap — they’re actively pushed there by their own minds. To escape the trap, you first need to recognise the subtle, invisible biases holding you in place:

• Confirmation Bias: Once we believe something works, we only see evidence that supports our decision — and ignore anything contradictory.
• Status Quo Bias: Humans naturally prefer what we already know. We resist change, even if logically, we understand it’s necessary.
• Loss Aversion: We feel losses more painfully than we enjoy equivalent gains, so the fear of losing what we’ve built makes us excessively cautious.
• Survivorship Bias: We look at past success stories (the winners) and assume their methods were correct — overlooking countless teams who used the same methods but failed.
• Sunk Cost Fallacy: We invest more resources into past decisions because we hate abandoning something we’ve already invested effort into—even when it’s no longer working.

These biases aren’t just theories—they shape your choices, culture, and future. Simply recognising them weakens their hold and creates space to think differently, act boldly, and finally break free of the Success Trap.

How to Escape the Success Trap

Getting trapped by success is easy — escaping it is a tough challenge. But it’s not impossible. If your team is feeling stuck, or if you’re suspiciously comfortable with the way things are going, it might be time to shake things up. Let's take a look at how…

Kill Your Darlings (Before They Kill You)

The thing that made you successful yesterday could be the very thing holding you back today. Learn to challenge your sacred cows regularly. Great teams aren’t afraid to retire products, features, or processes — even successful ones — if they no longer align with customer needs or market shifts.

Make Questioning the Norm, Not the Exception

Celebrate curiosity as loudly as you celebrate execution. Encourage your team to ask uncomfortable questions continually:

• “Is this still working?”
• “What assumptions are we making?” and the hardest of all,
• “If we started fresh today, would we build it this way?”

Balance Efficiency with Slack

Efficiency is excellent until it isn’t. Teams need slack — capacity deliberately reserved for exploration and innovation. You're too busy to spot new opportunities if you’re constantly running at 100% capacity. Build in deliberate slack. Keep a percentage of your effort free to explore new ideas, technologies, or markets.

Innovation Thrives in Imperfect Systems

Perfectly optimised systems rarely produce breakthroughs. In fact, some degree of friction, redundancy, or even inefficiency actually creates fertile ground for innovation. When teams face imperfect processes or unexpected problems, they’re forced to think creatively, find novel solutions, or even wholly reinvent the approach. Don’t obsess over perfection; leave room for a little chaos — because that’s often where fresh ideas and true innovation emerge.

Interview Your Churning Customers — Not Just Your Fans

Most teams obsess over their happiest customers, who keep buying, engaging, and validating what’s already working. But your biggest insights aren’t hiding in glowing feedback — they’re in the customers who left.

Churned customers reveal where reality diverges from your assumptions. They show you:

• Where friction points exist that you’ve ignored.
• What emerging alternatives are pulling them away.
• What new needs is your product failing to meet.

By regularly interviewing customers who left, you escape the Success Trap by confronting honest, unfiltered feedback — not just the safe, comfortable data that reinforces past decisions.

The harsh truth? The answers you don’t want to hear are exactly the ones you need!

Actively Listen Out for Weak Signals

The future rarely announces itself loudly. It comes through subtle whispers — unexpected user feedback, small market shifts, quiet product complaints, and strange behaviours in your data. Listen carefully. Weak signals are often early warnings or opportunities, easily missed by teams fixating on past successes.

Regularly Reevaluate Your “Success Metrics.”

Metrics reinforce behaviour. The metrics that brought you success in the past might not serve you in the future. Challenge them regularly, and ask: “Are we measuring the right things or just the comfortable things?”

Escaping the Success Trap isn’t about avoiding wins but never settling for past victories. It’s about staying alert, adaptable, and always ready to move forward, even if it means stepping away from something you once loved.

Leadership Re-positioning — The Vulnerability Practice

If teams are going to escape the Success Trap, leaders must go first. Breaking free from past success isn’t just a tactical shift — it’s an emotional and cultural one. People need permission to question what’s working, and that starts right at the top.

• Model Intellectual Flexibility. The best leaders openly admit when an old approach no longer serves the team. They don’t just allow debate — they initiate it. They signal that evolving a strategy isn’t failure; it’s leadership in action.
• Create Rituals for Abandoning Successful Approaches. Teams hold retrospectives on failures, but what about when something that worked is no longer the right approach? High-performing teams formalise a process for consciously letting go of once-successful strategies, products, or processes.
• Celebrate “Productive Failures.” Not all failures are the same. Some reveal new insights, expose flawed assumptions, or lead to unexpected breakthroughs. Leaders who reward learning over ego create environments where teams don’t cling to past wins just to feel safe.

The best teams don’t just permit change — they practice it. If success has made you rigid, the fastest way out isn’t another framework or efficiency tool. It’s leadership that embraces uncertainty, rewards adaptation and isn’t afraid to move on.

Closing: The Success Paradox

Winning can become a burden if you’re not careful. Good teams don’t just survive success — they leverage it. They understand that past wins are temporary, not permanent permission to coast.

The paradox of success is that it shrinks your field of vision. When you’re winning, it’s easy to forget that innovation rarely comes from the core — it emerges at the edges. It’s the places you aren’t looking, the quiet corners of your customer base, or the subtle shifts happening outside your industry that often hold clues about what’s next. Great teams know this and intentionally look beyond their familiar boundaries for inspiration.

This is why horizon planning matters. It’s not just strategic jargon — it’s creating deliberate space in your plans and calendars for discovery. The only way to escape the gravitational pull of your current success is to step back, look outward, and allocate time and resources to experiment beyond the immediate payoff. If innovation isn’t explicitly part of your planning, it won’t happen by accident.

Remember, good teams never settle into their victories. They challenge them, disrupt them, and sometimes even dismantle them intentionally. Because they know the truth that static teams don’t survive: either you evolve, or the market evolves without you.

Stay uncomfortable, keep learning, and never confuse a winning streak with permanent advantage.

Have you ever witnessed a team ensnared by their own success? What is the most prevalent bias you’ve observed that hinders teams? Please leave a comment—I would be keen to hear your thoughts.

Escaping the Success Trap — And What To Read Next

Breaking free from the Success Trap isn’t just about recognising the problem — it’s about taking action before it’s too late. But this is just one of the hidden costs of success; there are two more that I have written about previously:

• In The Success Delusion: Why Teams Stop Thinking Once They Ship, I explored how teams declare victory too soon — mistaking short-term engagement spikes for long-term success, and why that mindset kills growth.
• In The Success Tax: Why Teams Overpay for Bad Ideas (And How to Stop), I explored why teams waste millions — not because they lack good ideas, but because they commit too soon. ‘Deciders’ blindly invest without testing, while ‘Seekers’ validate before scaling, avoiding the hidden ‘Success Tax’ that comes from refusing to quit when they should.

If this post resonated with you, go deeper with those two pieces — understanding why teams get stuck is the first step to ensuring you don’t stay there.