12-3-2025

Overthinking: The Art of Creating Problems That Don’t Exist

Why Waiting for the 'Right' Decision is Holding You Back, and What to Do Instead

Written by Tana Plewes
5 minute read

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Creativity thrives on missteps and imperfections—a truth beautifully articulated by Ed Catmull of Pixar. Yet, overthinking hijacks this process, turning creativity into a battlefield of self-doubt and hesitation.

The Perfectionism Trap

Overthinking is often perfectionism in disguise. It’s the fear of looking bad masquerading as an obsessive pursuit of doing things right. It’s an invisible prison we build around ourselves. A survival mechanism to avoid criticism and judgment. And it’s everywhere. No one is immune—not you, not me. The difference is that some recognize its grip and break free faster than others.

The root of the problem? Faulty standards of success. We’ve been conditioned to measure achievement through a distorted lens, trapping us in cycles of avoidance and stagnation. It’s time to shatter these illusions, liberate ourselves, and take bold action. Right here, right now.

Lean Into Discomfort

Stepping into the unknown is uncomfortable, but that’s where possibility lives. Fear of ruffling feathers or saying the wrong thing is the enemy of progress. So what if people disagree? So what if you challenge the status quo? Your willingness to take action might just be the catalyst someone else needs to move forward.

The goal isn’t to make the perfect decision—it’s to have a decision-making framework that keeps you in motion. Progress doesn’t come from having all the answers; it comes from choosing the next right action and committing to it.

Overthinking in Family Businesses: A Unique Challenge

Family businesses, with their deep personal ties and history, are especially vulnerable to the paralysis of overthinking. Here’s why they matter:

  1. Agility Over Bureaucracy – With fewer than 250 employees, family businesses have the agility to create cultures of trust, transparency, and innovation.

  2. People Over Profits – These businesses are deeply woven into the fabric of their communities, proving that business isn’t just about money—it’s about impact.

  3. Collective Power – Family businesses make up 98% of employer businesses in Canada, meaning their collective influence on the economy is immense.

  4. No Room for Politics – Decision-making is centralized, and there’s no safety net for bad choices—owners must act decisively.

  5. Relationships Are the Lifeblood – When trust erodes, families fracture. Ignoring problems only escalates them. Addressing them head-on is the only path to sustainable success.

The Choice Point: Where Action Happens

One of the most damaging mistakes family business owners make is failing to recognize when they’ve reached a critical decision point. It’s not about having the “right” answer—it’s about making a choice and taking deliberate action. Here’s a common scenario:

The Underperforming Employee Dilemma

You have a team member who’s disengaged. Mistakes pile up, customers are frustrated, and resources are wasted. The person might be a longtime friend, the boss's relative, or someone going through tough personal issues. What do you do?

Ignoring the problem isn’t an option. But too often, decision-makers hesitate, waiting for a perfect solution. Instead, they lean on their top performers to compensate for the poor performance. These are the 20% carrying 80% of the workload. It’s a temporary fix that breeds resentment and burnout. Meanwhile, the real problem—lack of decisive action—remains unresolved.

When decision-makers avoid tough choices, a culture of complacency takes root. Problems spread like weeds, and disengagement becomes contagious. The longer inaction persists, the more complex and costly the problem becomes.

The Growth Opportunity in Discomfort

If you find yourself stuck at a choice point, consider this: the discomfort you feel is your invitation to grow. Business isn’t about having all the answers—it’s about navigating uncertainty with confidence. The moment you stop trying to be right and start making moves, you shift the trajectory of your business.

Here’s the key: You’ll either achieve your goal or learn exactly what you need to adjust. Both outcomes move you forward.

Decision-Making in Business: No One “Right” Way

Effective decision-making isn’t about avoiding mistakes. It’s about building a trusted network, seeking the right expertise, and acting with conviction. Consulting only with internal teams that share your blind spots leads to stagnation. External advisors—mentors, financial experts, and lawyers—can help broaden your perspective and unlock better solutions.

Transformational Listening: The Missing Link

Most people listen to confirm what they already know. Transformational listening involves setting aside personal biases and truly hearing new perspectives. It’s about:

  • Seeing the world through someone else’s lens.

  • Being willing to sit with discomfort.

  • Allowing space for unexpected insights.

This is where breakthroughs happen. If you’re clinging to certainty, you’re shutting out possibility.

Are You Ready to Break Free?

Growth isn’t for the faint of heart. The decision to challenge your own patterns isn’t easy, but it’s necessary. Here’s how you’ll know if you’re truly ready:

  • If you believe you have all the answers—you’re not ready.

  • If you rely only on your inner circle’s perspective—you’re not ready.

  • If you see yourself as powerless—you’re not ready.

  • If you talk about values but don’t live by them—you’re not ready.

  • If resentment clouds your ability to engage openly—you’re not ready.

Want to know where your business stands? Take our Free Quiz to find out how well you're positioned for growth and resilience.

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