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💡 The Big Idea: Clarity Comes From Asking Better Questions

Marc Champagne is a fascinating human.

He is the author of Personal Socrates (one of my favorite books), the host of the Behind the Human podcast, and a mental fitness strategist who studies the world’s top performers.

But before all that, he co-founded a journaling app called Kyo that grew to over 86 million users without any advertising. And then, one day, he decided it was time to shut it down and move on.

He tells the whole story in the book, but the detail I want to focus on for this newsletter is this:

At any point, we are one question away from a different life.

The Power of a Great Question

The right question asked at the right time has the power to completely change your life.

I experienced this when I made the decision to leave the day job last year. I was battling the fear of stepping out into the unknown and feeling the pressure to provide for my family.

But a simple clarifying question helped me go from a vague sense of uneasiness to clearly defining the dragons in my mind:

What’s the worst that could happen?

Talking through that question with my wife helped me realize that I had more options than I thought I did, which ultimately gave me the courage I needed to make the leap.

But there are other examples of great questions out there. Here are a few I like:

• What would it look like if this was easy? This questions from Ali Abdaal’s Feel Good Productivity book helps to reframe difficult things in a way that can make them seem fun.
• What am I optimizing for? We’re all optimizing for something. But if we don’t what it is, FOMO kicks in, and we feel we need to try to do it all. Recognizing what it is that is most important to us can make decision-making easy.
• What does this mean to ME? One of my favorite questions to ask when I’m reading non-fiction books. Just because someone has sold a bunch of copies doesn’t mean that the system they’re selling is right for the way I work. Asking this question helps me apply what’s helpful and discard what’s not.
• What would you do if you knew you couldn’t fail? This is one that I ask people during the LifeTheme cohort that my wife & I lead twice per year. This question is powerful because it forces you to dream bigger and consider things that require bravery and courage.
• What is the ONE thing that makes everything else easier or unnecessary? I quote this question from The One Thing a lot 😂 This question helps you identify the one thing that makes the greatest impact so you can focus on that.
• What would have to be true for X? We sometimes have trouble envisioning alternative scenarios. But by asking this question and starting with the assumption that things are inherently different, we can more easily identify the things that can help lead us toward that outcome.

Asking Questions & PKM

When most people think of personal knowledge management (PKM), they think about connecting information.

But I believe the key to PKM is asking questions.

Asking questions is an important part of any reflective process. And that regular reflection practice is essential if you want to keep information flowing into and out of your PKM system in a way that is in intentional alignment with your vision and your values.

Here’s a visual representation of how it fits into my PKM Stack framework that I teach in the Practical PKM cohort:

Reflection is the thing that keeps the train on the tracks. Without it, it’s easy to get pulled off course.

There are a couple of places I ask questions in my PKM workflows:

• My Daily Questions journaling
• My weekly planning
• My quarterly Personal Retreat process

The Personal Retreat is basically all about asking questions. I have a whole process I walk through in my Personal Retreat course, but I’ll share one of the more powerful pieces of it here before we wrap up 😉

Every time I do a personal retreat, I go through what I call a retrospective, where I end by asking 3 simple questions:

• What should I START doing?
• What should I STOP doing?
• What should I KEEP doing?

I simply add as many things as I can to these 3 lists during a 2-hour period, then choose what I want to take action on during my intention setting for the next quarter at the end of the Personal Retreat.

Every time I do a Personal Retreat, I force myself to pick at least one thing to stop doing.

This creates the margin required for me to say yes to things that are exciting to me without feeling overwhelmed.

How to Ask Better Questions

If you want to start asking better questions, here’s how to get started:

1. Make time to just think. In addition to the regular Personal Retreat I do every 90 days, I also schedule regular thinking time on my weekly plan. This protects the time and space to think about things without the pressure to be busy doing.
2. Start collecting questions. I tried a lot of different thinking time questions before I found some that clicked for me. You won’t really know which ones hit the mark though until you try them out.
3. Don’t force an answer. Give your brain time to unpack things. Richard Feynman famously had a collection of what he called his 12 favorite problems that he was regularly thinking about. The answers tend to come when you least expect them, so don’t try to force them in one 30-minute session.

Lastly, stick with it! It may take a little while to find a groove, but asking better questions is an acquired skill. You may struggle a bit at first, especially if you’ve inadvertently trained your brain to avoid things that make it uncomfortable.

Keep practicing, and you’ll find that when you learn to ask the right questions, the answers you’re after usually become clear.

😎 Something Cool: JournalCraft by TfT Hacker​

Obsidian is tailor-made for plain text nerds (like me ✋🏼) who love journaling. And if you’re looking to get started with journaling in Obsidian, TfT Hacker has a new resource called JournalCraft that can help you start asking better questions with a collection of templates and lessons.

While I do have my own journaling course and Obsidian-based journaling workflow, it’s very specific. It’s something that I’ve crafted and packaged over several years of journaling in Obsidian (my Daily Notes go back to January of 2020). But JournalCraft is different, in a very good way — it gives you some simple templates and LOTS of examples of how you might use them. The whole thing is packaged as an Obsidian vault, so it’s kind of an interactive product designed to help your journaling habit gain some traction.

The beauty of JournalCraft is in the simplicity IMHO. Both the information and the examples, I believe, will be incredibly useful for people who are new to journaling in Obsidian. It’s currently selling for $15, which I think is a great price for a resource like this. If you could use some help making a journaling habit in Obsidian stick, check this out.

📚 Book Notes: Personal Socrates by Marc Champagne

​Personal Socrates is a phenomenal book and easily the one that I gift most often (I’ve given away over 20 copies). While the 40+ character profiles are interesting, the real no-brainer value this book gives you is the accompanying questions. If you want to kickstart your ability to ask better questions, this book is a no-brainer.

If you want to download my notes from this book, click here. But I have to say, this one deserves a spot on your bookshelf 😉 It’s also a beautifully crafted book and comes in a hard case with a custom bookmark. There are a lot of little quality details (like showing how many pages are left in each chapter), so I highly recommend you get the print version if possible.

— Mike

P.S. A while back, I had the privilege of speaking to Marc when he came on the Focused podcast. This was one of my favorite episodes, and you can give it a listen here.