🌳 10 Powerful Stoic Questions to Change Your Life

💭 Quote of the Week

Just like that perfect Spotify playlist can shape your mood, your thoughts shape your life. Marcus Aurelius figured this out 2,000 years ago: the thoughts you keep on repeat become the soundtrack of your decisions, reactions, and life satisfaction.

And here's the thing - your thoughts are only as good as the questions you ask yourself. Let me show you why...

💡 Stoic Lesson of The Week

Picture this: You're staring at your ceiling at 3 AM, mind spinning with "what-ifs" and "should-haves." Your thoughts are a tangled mess of work stress, relationship drama, and that embarrassing thing you said at a meeting three years ago. (Just me?)

Here's what the Stoics figured out that took modern psychologists millions of dollars to confirm: The quality of your life often comes down to the quality of your questions. Not the answers - the questions themselves.

Think about it. When you're spiraling about a work problem, asking "Why does this always happen to me?" leads to very different places than "What can I learn from this?"

The silver lining? You can upgrade your mindset and life with better questions—questions that can be like finding a compass when you’re lost in the woods.

Change your questions → Change your life.

📖 How to Actually Use This

Anxiety & Overwhelm Questions

Instead of asking these common questions:

• Why does this always happen to me?

• What if everything goes wrong?

• How can I control this situation?

Ask these better (Stoic) questions:

1. “What's the opportunity here that I'm not seeing yet?" (The Marcus Aurelius special)

2. "Will this matter in a year? A month? A week?" (Marcus Aurelius's zoom-out technique)

3. "What is actually within my control and what can I let go of?" (Epictetus's favorite question - the guy who stayed philosophical even as a slave)

Decision-Making Questions

Instead of asking these common questions:

• What if I make the wrong choice?

• What will others think?

• How can I be 100% sure?

Ask these better (Stoic) questions:

4. "What's the worst that could actually happen - and could I handle it?" (Seneca's fear-buster)

5. "What would I do if reputation didn't matter?" (Cato's clarity question)

6. "What would the wisest person I know do here?" (Seneca's mentor method)

Dealing With People Questions

Instead of asking these common questions:

• Why are they like this?

• How can I change them?

• Don't they realize they're wrong?

Ask these better (Stoic) questions:

7. "What about their behavior is actually harming me?" (Hint: usually nothing)

8. "What virtue can I practice in this situation?" (Turn annoying people into growth opportunities)

9. "What if they're actually doing the best they can with what they know?" (The Stoic empathy hack)

The Ultimate Daily Question

10. "How can I make today a masterpiece within my control?" (This one's my personal favorite - it combines action with acceptance)

11. Bonus question: "What would this look like if it were easy?” (This one has saved me countless hours of my life)

Try This Now: The 2-Minute Question Upgrade

1. Think of the question that's been spinning in your head lately. You know the one…

2. Look at your current question. Is it a "why me?" question, a "what if" spiral, a "how do I control" question?

3. Find its upgrade from the list above. For example:

   • "Why does this keep happening?" becomes "What's the opportunity here?"

   • "What if I fail?" becomes "What's the worst that could actually happen - and could I handle it?"

   • "How do I fix them?" becomes "What virtue can I practice here?"

4. Now, try your new question out loud. Yeah, actually say it. Notice how your body feels different when you ask the better question. That's not woo-woo stuff - that's your nervous system recognizing a path forward.

Bonus points: Set a timer for 2 minutes and write your answer to the new question. Even if you don't solve everything, you'll be thinking about it like a Stoic instead of spiraling like a stressed-out squirrel.

📖 Story Time

Picture Rome, 165 AD. Marcus Aurelius, the most powerful man in the world, is sitting in his war tent near the German frontier. His army is fighting a pandemic. His most trusted general just betrayed him. And now a particularly difficult senator is trying to undermine him back in Rome.

Most emperors would have been asking: "How quickly can I have this guy eliminated?" (Previous emperors had killed for way less.)

Instead, Marcus pulled out his journal and wrote something fascinating. Instead of plotting revenge, he asked himself: "How is this making me a better emperor? What virtue can I practice here?"

The result? Not only did he handle the situation with legendary calm, but that same senator eventually became one of his strongest allies. Not because Marcus tried to change him, but because better questions led to better responses. The same senator later wrote that it was Marcus's unexpected patience that transformed their relationship.

🤔 Takeaway

Your mind is like Google - you'll always get results that match your search terms.

Upgrade your questions, and you automatically upgrade the results.

Your Weekend Challenge: Catch yourself asking a weak question (you will). Immediately swap it for its stronger version from the list above. Do this for 24 hours. Watch what changes.

Question to Ponder: What's one common question I keep asking myself that I’m ready to upgrade?

🔗 Interesting Reads & Listens

• The Art and Science of Asking Better Questions (Shane Parrish)

• An oldie but a goodie: 17 Questions That Changed My Life (Full pdf from Tim Ferriss or a brief summary)

• Tactics and Strategies for a 2025 Reboot—Essentialism and Greg McKeown (Tim Ferriss Podcast)