Why Fear of Failure Blocks Career Growth: Breaking Through Your Comfort Zone
"I'm afraid to take on bigger challenges because I don't want to fail."
This confession came from Shane during our recent coaching session. As a rockstar program manager for several years, Shane had mastered his craft. Every project under his leadership succeeded, and he had refined his delivery methodology to a science.
His meticulous attention to detail, consistent follow-through, and ability to anticipate risks had become his professional signature. This consistent excellence propelled his career forward quickly.
But now he faced a new hurdle.
"I had a performance management conversation with my manager recently and he told me that he wants to assign me much more complex projects. I'm nervous, I want to do a good job but this will be very different from what I'm used to. I don't want to drop the ball," Shane shared
While I understood Shane's concerns, his manager's advice was exactly right.
Once you've mastered your current role, advancement requires demonstrating capability at the next level—which inevitably means tackling increased complexity and scope.
This is the natural progression in any career path: mastery at one level becomes the foundation for growth at the next.
Regardless of natural progression cycles, Shane’s apprehension is completely valid, especially when you care deeply about maintaining high performance.
The fear of failing at something new after establishing a reputation for excellence creates a powerful psychological barrier. But as we talked more, it became clear that Shane was focusing on the wrong thing.
He had already proven his ability to perform excellently. Now, instead of worrying about potential failure, it was time to scale his past success.
Three Challenges of Complexity
If you find yourself in Shane's position with an opportunity to take on bigger challenges, here's how you can prepare to handle increased complexity successfully:
1. Complexity Comes With Ambiguity
No matter your role or project type, stepping up means strengthening your ability to make high-quality decisions without having every detail available.
Ambiguity is uncomfortable because it removes the certainty we crave when making important decisions.
In Shane's case, his previous projects had clear parameters and well-defined success metrics. Moving to more complex initiatives meant entering territory where some elements would remain undefined, even as work progressed. This creates decision-making anxiety that can paralyze even the most capable professionals.
To develop your ability to navigate ambiguity effectively:
Gather as much information as possible: Be thorough in your information collection, but recognize that you'll never have 100% of the data.
Use available details to map out different scenarios: Practice "if-then" thinking. What might happen if you proceed with option A versus option B? What contingencies could you prepare for each path?
Identify patterns in the current circumstances: Look for similarities to previous situations you've successfully navigated. What principles or approaches worked then that might apply now?
Develop a framework for decision-making under uncertainty: Create a personal approach to evaluating options when information is limited. This might include weighted criteria, minimum thresholds for proceeding, or key questions that must be answered.
This approach improves your critical thinking abilities and helps you navigate the ambiguity that accompanies more complex work.
Over time, you'll become more comfortable making decisions with incomplete information—a hallmark of senior leadership.
2. Complexity Comes With Uncertainty
While ambiguity relates to lack of information in the present, uncertainty deals with our inability to predict the future. Managing risk feels manageable when you can predict potential issues. However, solving complex problems demands adaptability when facing the unknown.
For Shane, his previous projects followed predictable patterns where risks could be identified and mitigated in advance. More complex work introduces elements that cannot be foreseen, requiring a different mindset and approach.
Instead of trying to avoid uncertainty:
Mentally prepare yourself to enter situations without knowing exactly what to expect: Accept from the beginning that unpredictable elements will emerge.
Embrace learning and course correction as you go: View your initial approach as a starting point, not a fixed path. Build in regular checkpoints to assess and adjust.
Acknowledge upfront that pivoting will likely be necessary: Communicate to stakeholders and team members that adaptability is part of the plan, not a sign of poor planning.
Develop comfort with saying "I don't know yet, but here's how we'll figure it out": This transparent approach builds more trust than false certainty.
Create feedback loops that capture emerging information quickly: Design systems that bring new information to light promptly so you can adapt accordingly.
We're much more amenable to change when we anticipate it, even without knowing the specific details. Face new complexities accepting that there are "unknown unknowns," and become comfortable with this reality. This mindset shift turns uncertainty from a threat into an expected part of the process.
3. Complexity Comes With Doubt
Complex projects and initiatives often fail not because of insufficient technical capability, but due to lack of consensus and buy-in among key stakeholders or within the project team. As complexity increases, so does the diversity of perspectives on how to proceed.
For Shane, moving to more complex projects meant engaging with more stakeholders, navigating competing priorities, and building alignment across a broader spectrum of interests. This environment naturally breeds doubt—in yourself and others.
When stepping into something new and complex:
Create and maintain alignment on a common goal and vision: Repeatedly reinforce the ultimate objective, especially when challenges arise. This shared purpose provides an anchor amid uncertainty.
Be mindful of how you express doubt, particularly from positions of influence: Your team will look to you for cues about how to respond to challenges. Express concerns constructively, paired with potential solutions or next steps.
Develop rituals for rebuilding momentum after setbacks: Have specific approaches ready for when doubt threatens progress. This might include refocusing on recent wins, clarifying immediate next steps, or reconnecting with the project's purpose.
Distinguish between productive and unproductive doubt: Learn to recognize when doubt is highlighting legitimate issues versus when it's simply resistance to change or discomfort with uncertainty.
Remember that your uncertainties can reverberate across the team: Be strategic about which concerns you share broadly versus those you process with select individuals or mentors.
Effective leaders acknowledge the reality of doubt while preventing it from derailing progress. They create psychological safety for team members to express concerns while maintaining the momentum needed to move forward.
Embracing Growth Beyond Comfort
I worked with Shane to analyze his default responses to these three challenges so he could become aware of his tendencies and shift his approach as needed.
This self-awareness is crucial—our automatic responses under pressure often revert to patterns that served us in the past but may not be effective at higher levels of complexity.
We explored these questions:
When I don't have all the information I need, how do I typically react—do I freeze, overanalyze, or take action?
How comfortable am I making decisions without perfect clarity, and what enables me to move forward?
In what situations do I tend to seek reassurance from others, and when do I trust my own judgment?
How often do I revisit and adjust my decisions based on new information?
What signals tell me that I need to step back and recalibrate versus push forward?
Through this assessment, Shane identified that he hesitates to move forward without consensus and feels most confident when everyone is aligned. This preference for alignment is a strength in many contexts, but at higher levels of complexity, complete consensus becomes increasingly difficult to achieve.
For his success in more complex projects, building consensus will be crucial to help him feel supported. Additionally, he'll need to trust his own judgment more based on available information and observed patterns, even when complete consensus isn't possible.
Final Thoughts
Complexity should never be a reason to remain within your comfort zone—no one wants to be a master of average. You can only progress by taking on new challenges to develop new skills and learn valuable lessons.
The reality is that career advancement requires demonstrating capability at the next level before you're promoted to it.
This creates an inherent tension: you need to operate beyond your current role's parameters while still fulfilling your existing responsibilities. It's uncomfortable by design.
But the path to advancement in any area of life isn't avoiding failure; it's embracing the growth that comes from navigating complexity.
By acknowledging the ambiguity, uncertainty, and doubt that accompany complex work—and developing strategies to address them—you position yourself to excel at higher levels of responsibility.
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