The Power of Questioning Your Own Choices
We’ve all been there — standing at a crossroads, faced with an important decision, whether it’s something as trivial as what to eat for dinner or as major as changing careers. You ask yourself: “What should I do?” and often, the answer is quick, easy, and based on the first thought that pops into your mind.
But what if the answer isn’t always the best one? What if, instead of rushing into a decision, you paused for a moment and thought: “Wait a minute, what would the opposing side say?”
That’s where being your own Devil’s Advocate comes in.
What Does Being Your Own Devil’s Advocate Mean?
You’ve probably heard the term “Devil’s Advocate” before. It’s the person who deliberately takes an opposing view, often just for the sake of argument or to challenge a decision. In a debate, they push against popular opinion to help reveal hidden weaknesses in the argument.
But here’s the twist: Why leave that role for someone else? Why not challenge your own thoughts and ideas, question your own biases, and force yourself to look at every decision from both sides? When you step into the Devil’s Advocate role for yourself, you don’t just open up to more options, you also get the chance to see potential flaws in your thinking before making a decision.
A Simple Example from Everyday Life
Let’s say you’re standing in front of your closet, trying to pick something to wear for a big meeting or a casual gathering. You pull out that classic black dress (or whatever your “go-to” item is) and think, “This will do the job. I’m comfortable in this, and it’s safe.”
Now, here’s where the Devil’s Advocate part comes in. Instead of just accepting that decision, ask yourself:
“Is this really the best choice?”
“What am I trying to say with my outfit? What message am I sending?”
“Is there a bolder option that might make me feel more confident or aligned with the situation?”
By questioning the automatic decision, you might realize that wearing something a little more unconventional might make you feel more empowered and authentic — and could even open up new opportunities or connections at the meeting.
Why It’s Important in Bigger Decisions
While questioning what to wear may seem trivial, the same principle applies to bigger life choices — like deciding whether to take a new job, invest in a business venture, or change your daily habits.
Let’s take changing jobs as an example. Often, the immediate thought might be: “I don’t like my current job, and this new opportunity looks great. It’s a no-brainer!”
But when you put on the Devil’s Advocate hat, you ask the hard questions:
“Am I running away from something, or am I truly moving toward something better?”
“What are the long-term consequences of this decision?”
“Have I considered all the potential risks?”
This kind of self-questioning doesn’t just stop you from jumping into a decision impulsively — it helps you think critically and see all angles of a situation. It forces you to confront fears, biases, and assumptions you might have been too quick to overlook.
The Benefits of Playing Both Sides
When you’re your own Devil’s Advocate, you engage in a kind of mental sparring match. The goal isn’t to make yourself feel bad or doubt your judgment, but to uncover gaps in your logic and challenge yourself to come to a more informed conclusion.
Here are a few reasons why this works:
Avoiding Cognitive Biases: We all have biases — confirmation bias, emotional bias, and the like. Playing the Devil’s Advocate forces you to confront those biases head-on.
Building Stronger Arguments: By considering the opposite side, you’ll be better prepared to defend your position when someone else challenges you.
Making Better Decisions: You’ll weigh all options and consequences before jumping to conclusions, which leads to more well-rounded, thoughtful decisions.
A Personal Example of Being Your Own Devil’s Advocate
I remember a time when I was debating whether or not to start a new business. On one hand, it seemed like a fantastic opportunity. But I found myself quickly moving forward without really considering the obstacles or challenges I might face.
Then, I decided to play my own Devil’s Advocate. I listed all the potential downsides:
“What if it fails?”
“What if I don’t have the time or resources to devote?”
“What if I end up disappointed?”
By exploring those fears, I realized that my enthusiasm was clouding my judgment. I could then make a more informed decision, adjusting my plan, mitigating risks, and preparing for the obstacles ahead.
My Job Change Dilemma
A few years ago, I was offered a job with an impressive salary increase and the promise of growth. On the surface, it seemed like the perfect opportunity. I felt excited — but also nervous. At first, I thought about taking it immediately. But then I decided to play my own Devil’s Advocate. I asked myself:
“Why do I want this change?”
“Am I running away from something, or am I truly moving towards something better?”
“Have I considered all the possible challenges this change might bring?”
Instead of jumping into a decision, I took time to reflect and weigh the pros and cons. What I realized was that the new job was a shiny opportunity, but it wasn’t as aligned with my long-term goals as I thought. I ended up turning it down, and months later, I discovered that my original role was offering me the growth I needed, just at a slower pace. It’s a decision I’m thankful I questioned before rushing in.
Final Thoughts:
Being your own Devil’s Advocate isn’t about doubting yourself; it’s about empowering yourself. It’s about taking the time to ask the tough questions, challenge your assumptions, and step outside of your comfort zone.
The next time you’re about to make a decision, ask yourself: What would my Devil’s Advocate say?
The insights you gain could very well be the difference between a safe, short-term decision and a bold, game-changing move.
Remember, the power of self-questioning isn’t just about finding flaws; it’s about strengthening your vision and ensuring that you’re making choices that align with your deeper goals.
To be your best Advocate, improve your awareness. Read good books. Go through my book published yesterday “Let Them Talk” https://relinks.me/B0FGZHN5H6

“The next time you face a tough choice, step into your Devil’s Advocate role. Challenge your assumptions, weigh your options, and be more confident in your decision-making!”
Cheers!