My 10 Go-To Reflection Questions (and Where I Found Them)
For 500 days in a row, I’ve written 500 words of Morning Pages. If you’ve never heard of Morning Pages, it’s a fancy way to say journaling. Every morning, I type out anything and everything that’s on my mind.
Most mornings are brain dumps to clear my head and get on with the day. But I sometimes like to reflect on specific questions. Over the years, I’ve found there are 10 questions that help me reflect or work through any problem.
If you’re interested, I’ve aggregated each of these questions into a nicely formatted template. If you drop your email in the box at the bottom, I’ll shoot it your way.
1. How am I complicit in creating the conditions I say I don’t want?
This question is a staple for me. On the first Sunday of every month, I’ll sit down and truthfully answer this question.
This question helps me identify where my actions aren’t matching my words. I’ll often say I want to do things a certain way on paper, but then fail to do them that way. By answering this question, I can see where I’m lying to myself.
This question comes from Episode #373 of the Tim Ferriss Show with professional coach Jerry Colonna. This episode is loaded with questions and ideas that will leave you more reflective and curious.
2. Where am I feeling the Resistance?
Every Monday morning, I ask myself this question. If you’ve never heard of the Resistance, you should read Stephen Pressfield’s The War of Art today. It’s the most influential book on my productivity and motivation I’ve ever read.
What elicits the Resistance? Any act that rejects immediate gratification in favor of long-term growth, health, or integrity. Or, expressed another way, any act that derives from our higher nature instead of our lower. Any of these will elicit Resistance.
You can check out my notes on The War of Art here.
3. What would I do to make today horrible?
This question leverages the Inversion Principle. Avoiding poor decisions is easier than making the right ones. So instead of thinking of everything I want to do that day, I think of everything I could do to make today horrible. Then I just avoid doing those.
4. Where am I making things more complex than they need to be?
I sometimes make simple things more complex than they need to be. Overcomplication creates billion-dollar industries. But most solutions are simple and deserve no more than a tweet’s worth of text.
For a deep dive into why we overcomplicate things (and how to stop doing so), check out this deep dive blog post.
5. What would this look like if it were easy?
This is the first of three questions I found in Tim Ferriss’ blog post 17 Questions That Changed My Life.
This question assumes the answer to my problem is easy. I then think of all the ways that might be true. Working backwards this way always shakes up my perspective, leading to new insights.
6. What if I did the opposite in every area?
I sometimes get stuck in my default way of doing things. To refresh my outlook, I’ll think about what would happen if I started doing everything opposite of how I currently am.
For example, I recently went 13 weeks on the Carnivore Diet, just to see what happened. So I asked the question - “What would happen if I went Vegan for 13 weeks?”
I don’t plan on doing so, but the answers I came up with were more interesting than I thought they’d be.
7. If I could only work for four hours this week, what would I work on?
I occasionally feel overwhelmed with too many things. This question helps me identify the highest leverage thing I can work on. It also leverages Parkinson’s Law, adding a creative constraint to better target my attention.
8. How could I achieve my 10-year goals in six months?
This question is the most fun to answer. On the first Saturday of every month, I’ll give it a whirl.
Thinking in extremes helps to wash away any self-imposed limitations. The answers are usually unrealistic. But there have been plenty of times where this change in mindset lead to some insightful ideas.
9. How would the type of person I want to become handle this?
When faced with a big decision or problem, I ask myself this question to look for a bolder response. Thinking about the best way I could possibly handle something sets a high bar for action.
This question comes from a blog post from one of my favorite writers, David Cain. It’s called How to Get Out of a Rut in 20 Minutes and is filled with even more reflection questions.
10. What would I do if it was impossible for me to fail?
Fear of failure is one of the most common self-imposed limitations. Eliminating failure as an option and sincerely asking “what would I do now?” helps me think bigger and bolder.
Now it’s your turn
I’ve aggregated these questions into a nicely formatted template that you can copy and fill out yourself. If you’re interested, I’ll email it to you along with a few other of my favorite reflection resources. Just fill out this template below.