I’m going to do something I’ve never done before, pretty soon. I’m really nervous about it, too.

I’m meeting with an accountant.

This is something it might’ve made sense to do a bit earlier in my freelancing career, but it’s hard to justify the cost of an accountant when you’re not actually making very much money. (Or so I told myself, anyway.) Now I’m in need of a lot of guidance and the guilt is weighing me down. Plus—having never been to an accountant before—I have no idea how this will go; how he’ll view my conduct and my mistakes.

I’m not Catholic, but what I envision for this meeting in my mind’s eye looks an awful lot like every movie scene involving a confessional that I can remember. “Bless me, Mr. CPA, for I have sinned. I have not made quarterly tax payments. I did not allocate the proper amount of money for my retirement fund. And I haven’t been to the dentist for a while, either. What? Oh, sorry… I got carried away there.”

When I first started freelancing, it was towards the end of the year. My (paltry) freelance income for those few months didn’t really impact my taxes.

My first full year of freelancing, I did okay. I mean, I think for my first year it was a perfectly respectable income. Uncle Sam felt differently, which was ultimately good news for me; once I factored in all of my deductions, I didn’t owe anything.

2007, though, was the turning point. The good news? I made a living wage this year. That’s really exciting until I remember that I haven’t paid a dime in taxes yet. *ulp* And as if that wasn’t going to complicate things enough, I also got married, moved, and have owned two houses for half the year.

That sound you just heard in the distance was my copy of TurboTax spontaneously combusting.

Going to an accountant will be good. He’ll help us get things figured out for this year’s taxes, and we’ll determine what I should be doing about estimated payments moving forward. (I’m “excused” this year because I didn’t owe last year, and as long as I pay up in April, that’s fine with the government. But next year I could face stiff penalties if I don’t pay quarterly, and that’s in addition to all of the crying I’ll have to do when it’s time to pay.) Maybe we’ll do some retirement planning. We’ll finally have that talk about whether or not I should incorporate.

It’s gonna be good. All good. I’m lucky to have been successful enough to have these problems.

Please remind me that I said this when the accountant tells me how much money I owe, because my very rudimentary math tells me I am going to be very, very sad come next April.