In the book and on this website, I frequently talk about the need to “contemplate” the question that you are working with. But what does that actually mean?
Your first instinct is probably to think harder, make a pros-and-cons list with a spreadsheet, or ask friends for advice. Those things can help, but sometimes the hardest questions need something different. They need contemplation.
What Is Contemplation, Really?
Contemplation sounds fancy or mystical, but it’s actually pretty straightforward: it’s the practice of sitting (or sleeping) with a difficult question without rushing to answer it.
Think of the difference between gulping down your coffee on the way out the door versus actually tasting it. Contemplation is like that, but for thinking. You’re not frantically searching for the answer. There is no deadline. You’re giving the question space to reveal things you hadn’t noticed before.
This matters because hard questions are usually hard for a reason. They involve competing values, uncertain outcomes, or parts of ourselves we don’t fully understand yet. A quick decision may work for simple problems, but complex ones need time to unfold.
Regular thinking often runs in circles, like a gerbil on a spinning wheel. You rehash the same arguments, feel the same anxiety, and end up where you started. Contemplation is more patient. It’s less about effort and more about creating the right conditions for insight to emerge from within.
It’s about recognizing when you’re not being honest with yourself. We all have blind spots and assumptions we wish were true. Reflecting helps you notice these instead of just avoiding them.
A Simple Process to Get Started
You don’t need to be a philosopher or meditate for hours. Here’s a practical approach:
Step 1: Write down your question clearly. Not “What should I do about my career?” but “Should I accept this specific job offer, and if not, what am I really looking for?” The act of writing forces precision.
Step 2: Set aside 15-20 minutes of uninterrupted time. No phone, no distractions. You can sit quietly, go for a walk (my favorite), or find whatever setting helps you think. Do this regularly—maybe three times a week. This is “You” time.
Step 3: Ask yourself honest questions about the question. This is where it gets interesting. Instead of trying to answer your big question directly, ask things like:
- What am I assuming is true here?
- What am I afraid of in this situation?
- If I could give advice to a friend with this exact problem, what would I say?
- What would the opposite choice look like, and why does that scare or attract me?
- What do the key words in my question actually mean? (For example, what does “success” or “right” or “fair” really mean to me?)
Step 4: Notice what comes up without judging it. You might feel resistance, discover fears you didn’t know you had, or realize your question isn’t actually about what you thought it was about. That’s all useful information.
Step 5: Let it sit. After your contemplation session, let your mind rest. Don’t force conclusions. Often insights come later—while you’re doing dishes, waiting at a traffic light, or falling asleep.
Step 6: Return to it. Come back in a few days and see if your thinking has shifted. Write down what’s changed. Over several sessions, patterns will emerge.
Some of your questions won’t have clear answers. Life is full of situations where uncertainty is unavoidable. That’s okay. Contemplation isn’t about reaching perfect certainty; it’s about developing a deeper understanding of yourself and your situation. When you finally do choose, you’ll know you took the question seriously.
That kind of clarity is worth the time it takes to find it.
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