On my wedding day.
Signing escrow papers.
Buying a German sports car.
Buying a German Sheperd.
Having children (still asking).
I think the fact that I'm a freelancer just puts me in more situations where it becomes a reasonable question to ask.
For example, I find myself asking it right after I get the phone call or email inquiring about my availability. Again when I hear their reaction to my day rate. Yet again after I cave and let them negotiate my day rate down - usually in tandem with, "What the f% was I thinking?"
Regardless of the account, even if it's something I want to work on, when I hear what it is the question comes up again.
It's always top of mind when I hear who they want me to work with, whether I've worked with that person before or not.
And if the office is a hellish, brain-deadening, soul-killing commute to a foreign and frightening land, for example Orange County, I ask myself the question on the crawl in.
Then, just before I enter the brick building, designer warehouse, high-rise tower, faux-hip loft, converted fire station, hotel or craftsman house where the offices are located, I pause for a tentative moment outside, look at the doorway I'm about to go through, and ask it again.
But here's the thing: the question itself is a cruel tease. Because it can't be answered until you're actually there.
Of course by no means does that imply everyone won't try to answer it for you. But it's really one of those questions, like, "How much of this can I take?" "Is it worth the pain?" and "Is Super Shuttle hiring?", that only you can answer for yourself.
If I'm being honest with myself, and if you know anything about me you know that's something I hate doing, I have to say the answer I almost always arrive at is "something great".
I wonder if you asked yourself the question before you started reading this post.
It's okay. I don't need to know the answer.