A Good Question > A Perfect Answer
Three questions that might mess with your defaults—in a useful way
Hey there,
This week’s Winning Weekly breaks form.
No advice or “try this.” Just some questions meant to sit with you longer than any checklist would.
Questions help us make discoveries. They get us unstuck. They can sneak past the part of our brains that wants to keep doing what it’s always done even if we are dissatisfied with it.
So pause, think, and maybe pivot.
The Cost of Competence
Have you ever found yourself excelling at something—and quietly resenting it?
A lot of people assume that if you’re good at it, it must be your thing.
But what if competence is a trap—and the better you are, the harder it is to leave? What could you do?
Winning the Wrong Game
Have you ever won something, only to feel… weirdly empty?
Most people spend their lives optimizing for the rules they were handed.
But what do you do if you feel like you’ve been winning the wrong game?
Constraints
Have you ever caught yourself saying, “I can’t”—and then realized no one’s actually stopping you?
A lot of people confuse routine with reality.
But what if the constraints you’ve accepted weren’t as limiting as initially thought? How could you get creative?
If one of these questions nudged something loose, I’d love to hear from you about which one. Just hit reply.
Or better yet—forward this email to someone who could use some thought starters to start making changes. It might be the nudge they didn’t know they needed.
Thank you for reading and wishing you a successful week.
Warmly,
Scott Henderson