Asking Questions That Scare You: A Path to Growth

Asking questions can be daunting.

Not the polite, everyday questions like, “How are you?” or “What time does the meeting start?”—but the big, uncomfortable questions that challenge us to step into uncertainty.

These are the questions that hold the power to unlock new opportunities, deepen relationships, and spark personal growth.

Yet, they’re often the ones we avoid. Why? Because they scare us.

The Fear Factor

I’ve always been someone who thrives on meaningful conversations.

But even for me, asking scary questions hasn’t always been easy. I remember vividly the first time I asked a question that terrified me.

Asking questions that scare us isn’t easy, but it’s essential. The fear of rejection, judgment, or failure often looms large.

Yet, on the other side of that fear lies growth, clarity, and sometimes even life-changing revelations.

Why Scary Questions Matter

Growth happens outside our comfort zones. My own journey of connecting with others and sharing my thoughts online started because I dared to ask questions like, “What if I posted consistently?” and “Could I turn these interactions into a meaningful business?” When we avoid difficult questions, we also avoid opportunities to learn and evolve. Consider these examples:

In Relationships: Asking, “How do you really feel about us?” can lead to deeper understanding or necessary clarity.
In Careers: Asking, “What skills do I need to move to the next level?” can open doors to mentorship and advancement.
In Life: Asking, “What if I pursued my dream?” might push you toward the life you’ve always envisioned.

Scary questions often hold the keys to answers that can reshape our trajectories. Avoiding them only keeps us stuck.

A quote I love:

"How big would you dream, if you knew you couldn’t fail."

Common Types of Scary Questions

Personal Development Questions: These challenge our self-perception and push us to grow. For example, “What am I doing wrong?” or “How can I improve?”
Relationship Questions: These questions make us vulnerable but are crucial for connection. Examples include, “What do you need from me?” or “How do you feel about this situation?”
Career Questions: Often tied to our professional aspirations, these include, “Can I have a raise?” or “What’s holding me back from promotion?”
Big Life Questions: These touch on our deepest desires and fears. For instance, “What if I started my own business?” or “Am I truly happy?”

Strategies to Overcome the Fear

If these questions scare you, you’re not alone. Here are strategies to help you face them with confidence:

Reframe the Outcome: Instead of fearing rejection, see it as redirection or an opportunity to learn. Even a “no” can provide clarity.
Prepare Yourself: Think through the question and its possible answers. Practice how you’ll ask and be ready for different outcomes.
Focus on the Reward: Visualize the positive change or insight that could come from asking the question.
Start Small: Build your courage by asking progressively challenging questions. Start with ones that feel slightly uncomfortable and work your way up.

A Question That Changed Everything

One of the scariest questions I’ve ever asked came at a pivotal moment in my life. It reminded me of the countless conversations I had with strangers during my LinkedIn journey. When I was considering a major career change, I doubted my abilities. I reached out to a mentor and asked, “Do you think I’m ready?” Their response wasn’t just encouraging; it also came with constructive advice that reshaped my approach. That one question didn’t just give me the confidence to move forward—it also gave me the tools to succeed.

Your Turn: Ask the Question

What’s one question you’ve been avoiding? Maybe it’s a conversation with your boss, a heartfelt discussion with a loved one, or a moment of self-reflection. Write it down. Then, challenge yourself to ask it within the next week. Don’t overthink it—just take the leap.

Scary questions are scary for a reason: they matter. They force us to confront our fears, open ourselves up to vulnerability, and take risks. But they also hold the potential to transform our lives.

So, what’s the question you need to ask?

@HarryGbc

P.S.: Day 8 of writing on article dot app

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