
A friend posted a short video this week asking about the “when” of things. When do you act? When do you wait? When do you pivot?
I just turned 60, so that probably changed how I heard his questions.
I can’t think of many important decisions where I thought, I’m completely ready for this. And I’m increasingly convinced we have readiness backward.
It’s easy to imagine that first we’ll prepare, then gain confidence, our uncertainty will disappear, and finally we’ll be ready to take action.
Life doesn’t always work that way.
Sometimes, the only way to gain confidence in something is to do it. The doing becomes part of the preparation. It creates clarity we can’t get from thinking alone.
Does that mean we should always move first and prepare later?
Nothing is that simple.
Preparation and thinking are important. But past a certain point, more analysis is just another excuse for waiting.
The harder part of these “when” questions may be determining our level of commitment.
Being ready isn’t the same as being casually willing to try. It means I’ve prepared as well as I reasonably can, accepted that I may still be uncomfortable, and decided that uncertainty no longer gets the deciding vote.
But if I’m not willing to bring the commitment required to see something through, I shouldn’t start.
Turning 60 is a reminder that our time is finite, whether we think much about it or not. Every decision to wait is also a decision about how we’ll spend that precious time.
I have no idea what the next decade will bring. The best parts of my first six were mostly unpredictable.
There’ll be more opportunities, more decisions, more things worth building. Also, more uncertainty, doubt, and hesitation.
Wisdom isn’t knowing exactly what to do, or precisely when to do it.
It’s recognizing when we’ve thought enough, prepared enough, listened enough, prayed enough, and waited enough.
Then committing to move.
Photo by Gennady Zakharin on Unsplash – Sometimes we have to start moving before the path makes sense.

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