Alas, it’s not really the kind of prize one can look forward to, because it doesn’t go to a person.

No, the Phrase of the Year prize goes to the phrase itself.

And winning generally has to do with how useful a particular phrase is in resolving something in the business on the pirate ship that causes me stress, resentment, duress, or costs me insane amounts of money.

The 2009 winner.

Ah, 2009. Some of you probably remember the Phrase of the Year.

That was the year of working with a large staff crew, and no sense of what they were actually doing. Not knowing how to be a captain.

Lots of tossing and turning and waking up in the middle of the night wondering.

And then not wanting to nag but not knowing how to ask-without-nagging, and not being able to stand the not knowing.

The phrase of the year turned out to be:

Hey, can I get a progress report on this, please?

Clean, clear, not obnoxious, and something to say before the point of being pissed off about something not being done. An excellent Phrase of the Year.

So good that I didn’t even need to use it in 2010.

I was completely ready to be all “Hey, progress report?” in 2010. But I didn’t need to.

It was as if the essence of that magical phrase had already permeated the culture of the ship to such an extent that it had rendered itself unnecessary.

For one thing, we stopped having a crew. It’s just me and the First Mate piloting the ship, with some strategic helper mice who function as advisors.

And we replaced the disastrous $600/month bookkeeper with one who is competent. And cares. At $80/month. Huh.

I was totally ready and in position to ask for progress reports, but she reports in all the time — with enthusiasm and with bright, curious, useful questions. So I haven’t had the chance.

The 2010 Phrase of the Year also turned out to be about progress reports, though.

Mine.

My biggest screw-ups this year involved not sharing with other people where I was in my own process.

Even though I’m on permanent email sabbatical, we get hundreds and hundreds of questions requests each week. And there are always some that the First Mate doesn’t know what to do with.

He brings them to Drunk Pirate Council, and then I sit with them.

But I really sit with them. I meditate on them and brain-dance on them, and I think about how it fits with the culture of what we do here.

This takes time. And most of the uncomfortable situations and misunderstandings that happened this year came from not telling people that this is what was happening.

Here’s the 2010 Phrase of the Year:

Havi’s going to take some time to meditate on this, and we will get you an answer as soon as we have it. 🙂

Classic example of a time this was really needed.

A woman wrote asking if she could apply to the Week of Biggification retreat and not stay with us at the hotel, and what the cost of that might be.

To me, this was a culture question. And a useful one:

What is the culture of this shared experience, and how much of it is directly a part of being fully immersed in a very specific and other-worldly environment, eating together, having spontaneous strategy-and-silliness sessions in the late hours…?

So I had to think about group dynamics, about different ways it might work, unanticipated problems or challenges that might come up as a result.

I was curious. We mapped out options. We hired two different consultants, thinking this may well come up again, and I’d like to have a strategy for how it might work.

But we forgot to tell the Asker of the Useful Question what we were doing, so she was left hanging.

Not okay.

By the time we got back to her, she was feeling annoyed and frustrated.

And after having spent nine hours and $750 trying to come up with plans for how it could work, I didn’t have it in me to put in more time trying to explain that we hadn’t actually been blowing her off.

Even though she deserved a fair and loving response, and a clear apology. I am so sorry. It wasn’t fair. I screwed up.

My hope is that 2010 Phrase of the Year is going to help me with situations like this.

We can let people know where we are with their questions.

And that more time involved in putting together a response doesn’t mean that we care less. It means that we care more. Maybe we can share more about the process too.

I already have the Phrase of the Year for 2011.

Which is kind of hilarious because the year hasn’t started yet.

But I know what it’s going to be.

That’s a terrific idea! Why don’t you do that?

Instead of spending this year feeling anxious and overwhelmed every time someone makes a suggestion for another fabulous thing I could do, we’re going to skip that part.

Instead, we’ll go straight into encouraging other people to make those beautiful things happen. And be happy for them. And help where we can.

Turning pain into knowledge.

Sometimes when I think back on various Phrases of the Year, it’s hard not to think of all the hurt.

The misunderstandings, the pain, the missed connections. The ways that I screwed up. The residual frustration about all the ways that other people … weren’t able to be the people I wanted them to be, which is not their fault.

All that time spent being annoyed about how hard it is when you can’t get milk from a stone. My focus was in the wrong place.

But here’s what the Phrase of the Year reminds me to do:

I am allowed to have my grief and my pain. And I can also look at all that agony and remember that it’s business school tuition.

Instead of a diploma, I can just frame the Phrase of the Year and put it on my wall. And look forward to the next one, because it will be unbelievably useful.

Raising a toast.

To all the wonderful, helpful, sovereign phrases of 2011 that are still to come.

May they find us swiftly, with ease and grace.

And may there be lots of toast.

And comment zen for today.

We all have our stuff. We’re all working on our stuff. It’s a process.

We let people have their own experience, and we don’t give unsolicited advice.

Celebrating the Phrase of the Year with me is welcome. Drinks! And add some phrases of your own if you like. The more the merrier.

Love to all the commenter mice, the Beloved Lurkers and everyone who reads.