Why Some Challenges Can’t Be Solved with a Checklist
In life, work, and relationships, not all problems are created equal. Some can be solved with enough time, effort, and organization. Others shift under our feet the moment we think we’ve found an answer. Recognizing the difference between complicated, complex, and wicked problems helps us respond with the right mindset and strategy instead of relying on brute force or wishful thinking.
Complicated Problems: Many Steps, Clear Solutions
A complicated problem is one that takes multiple steps or processes to solve—but each of those steps is knowable. Think of building a jet engine, filing your taxes, or following a workout plan. There’s a right way to do it, and experts can teach you the process.
Complicated problems reward precision and discipline. They can often be solved with checklists, standard operating procedures, or best practices. When something is complicated, what you need most is expertise and persistence.
Examples:
- Repairing an engine
- Completing a PhD program
- Managing a detailed financial audit
The key insight: Complicated doesn’t mean impossible—it means methodical.
Complex Problems: The Overlap of Many Complicated Ones
A complex problem arises when multiple complicated problems interact, overlap, and influence one another. It’s no longer just about following steps—it’s about navigating the dynamic relationships between systems.
Think of running a business, leading a team through change, or maintaining family harmony while balancing health, career, and personal growth. Each of these areas may have solvable parts, but together they form an unpredictable whole.
Complex problems demand adaptability, systems thinking, and emotional intelligence. They require you to respond, not react—to observe patterns, test small interventions, and learn continuously.
Examples:
- Leading an organization through cultural change
- Managing chronic stress while caring for others
- Coordinating disaster relief across multiple agencies
The key insight: Complexity can’t be conquered—it can only be managed.
Wicked Problems: When Every Solution Creates New Problems
A wicked problem can be either complicated or complex—but what makes it “wicked” is that every attempted solution spawns new issues.
You don’t “fix” wicked problems. You engage with them. Each attempt to resolve one aspect reveals hidden tensions or creates ripple effects elsewhere.
Social issues, mental health systems, and global challenges like combatting terrorism, stopping narcotics trafficking or preventing veteran suicide are wicked because their “solutions” inevitably produce unintended consequences.
Wicked problems demand humility, collaboration, and persistence. They require both analytical skill and emotional regulation—the ability to stay engaged without being overwhelmed.
Examples:
- Reforming healthcare or education
- Addressing poverty or addiction
- Healing generational trauma
The key insight: Wicked problems don’t have solutions—they have evolutions.
Applying This Framework to Your Life and Work
Recognizing what type of problem you’re facing changes your approach:
- Complicated: Follow a plan.
- Complex: Adapt the plan as the system shifts.
- Wicked: Work the problem, knowing the “answer” will change over time.
When you misclassify a problem, frustration follows. You can’t checklist your way through grief, or improvise your way through an aircraft inspection. Matching the problem to the right mental model helps you respond with clarity and control.
The Mental Fitness Connection
From a Mission-Focused Mental Fitness perspective, this framework trains two vital skills:
- Cognitive flexibility – the ability to shift strategies as the nature of the problem evolves.
- Emotional regulation – the ability to stay calm and engaged when outcomes are uncertain.
Understanding which kind of problem you’re facing isn’t just a matter of strategy—it helps generate mental readiness.
Related Reading from the Archive
- The OODA Loop and Emotional Regulation
Explores how observation, orientation, decision, and action can stabilize your thinking in dynamic or high-stress environments. - Reframing Failure as Feedback
Discusses how shifting your mindset from “problem” to “process” transforms how you approach complex and uncertain situations. - Stress, Systems, and the Self
Examines how mental, physical, and social systems interact — a key insight for understanding complex problems - Mission-Focused Mental Fitness
Outlines a framework for building psychological adaptability and emotional discipline in the face of unpredictable challenges. - The Power of Pause
Explores how intentional stillness can help you navigate complexity without overreacting or overcorrecting. - Organizing Your Self-Care
Connects the Eisenhower Matrix and VA Whole Health model to help prioritize what truly matters amid competing demands.
Thanks for Reading
If you’re looking for practical tools to build resilience, mental clarity, and physical well-being, you’re in the right place. Tactics Total Wellness is based in Charleston, South Carolina, and I write weekly about mindset, performance, and integrated living for veterans, first responders, and high performers across the Low Country.
👉 You can explore more insights at www.tacticstotalwellness.com/blog
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