A Stack of Questions I Really Like
Hard questions + the time to chew on them = a proper differentiator. Because nearly no one else actually does this.
If you’re holding time every Friday or Sunday or whenever to reflect, I’d recommend building a stack of questions you can pull from. I have dozens on index cards and I'll grab one or two at random each session. It's helpful and makes the whole reflection thing way more manageable. I never search for the "right" card for the moment, but the random prompt I pick usually ends up shaping my week anyway. It just sort of works out.
Here are some that might help you get started - some are my own and others are pulled from places like Seth’s Blog and James Clear and FS:
Think of your best potential customer (should be a real person). Why would they pay 3x more for the thing you’re building than they pay to solve the problem now?
What aspect of your work is hardest to copy? How can you do more of that?
What are you still working on that has already peaked? Is it time to let go and try a different approach?
Exploration is how you discover what works. Persistence is how you make the most of what already works. What does your situation require? More exploration or more persistence?
What would your best customer pay $3,000 for? If $3,000 doesn’t sound like a preposterous amount, pick a number that does.
Great businesses come from the combination of unlikely things. What are you doing that’s “unlikely,” or something competitors wouldn’t/couldn’t think of or do?
What got you most excited this past week? How can you do more of it next week?
How can you make this all more fun?
What are you currently avoiding? What’s a way to make progress on that thing in the next 5 minutes?
Which of your current habits is least aligned with the type of person you hope to become?
Bruce Lee on pushing yourself: “Don’t fear failure. Not failure, but low aim, is the crime. In great attempts it is glorious even to fail.” Are you aiming high enough?
What’s already working? Can you do it more?