Bossman threw me in the deep end this morning. The conversation went something like this:

Bossman: BTW, you’re leading the training this afternoon, OK?
Internal me: EEEEEEEEEEEE! Um. OK?
Actual me: Sure, I can do that.
Bossman: Great. You’ll also be doing one tomorrow.
Internal me: In for a penny, in for a pound! Also, EEEEEEEEE!
Actual me: You bet, Bossman!

It went fine. I felt wobbly on a few things, but he was there to steady the boat. And he felt I did well enough to do another one tomorrow and a really, really solo one next week. So I said to him that he can throw me into any deep end, and I’d figure out how to swim. And that’s true.

If you wait until you’re ready to [insert the thing you’re thinking about doing here], you’ll never do it. Amen, brother. Everyone into the pool!

Planning’s always good, but if you need to have everything in place before you can be ready, it’s going to be tough to move forward with anything. If you feel completely unprepared, that’s quite another thing. But there’s some threshold where you have to be OK with cannonballing in (so that life, – or, yaknow, your boss – doesn’t just toss you in either way). The Chief Operating Officer at our company submitted an op-ed in the Computer Business Review a while back that talked about promotion dynamics. If a promotion opportunity becomes available, a woman will only pursue it if she feels 100% prepared, whereas a man will pursue it if he feels 60% prepared.

I’ve been thinking about that statistic for a while. I have kids-of-friends who don’t want to apply to a job because they don’t have the whole list of requirements. I have peers who don’t want to go to Italy (or wherever) until their house is paid off. There’s a point, through, when continuing to plan means refusing to enact the plans. There’s only so much you can read about the art of the Louvre before you need to get your ass to Paris.

This morning, when Bossman asked me if I thought I was ready to present, I could have said yes. I could have said no. Both of them might have been what I believed. But I asked him if he thought I was ready. Without hesitation, he said that he thought I was. So I thought I was, too. Bossman gave me the extra nudge of confidence that I needed to believe in myself. That right there is the sign of a good leader.

This Lent, may I help others discover their confidence, as my boss did for me. May I have faith to step forward, even when I can’t see the whole path.