April 15, Shudder

Today my sympathies go to the front-lines-of-taxes warriors, the pawns in the front lines, the poor downtrodden schedule C individual businesses that have to pony up between now and midnight.

If you don’t know what I’m talking about, thank your lucky stars. And if you do, you have my condolences.

I’ve been there. All year as you collect on, say, consulting bills, you tell yourself that this year will be different, you’re going to put away the money you’ll need on April 15 to make the damn payments as required. Lots of knowing friends and family members remind you, throughout the year, that you’re not supposed to spend it all. And you know they’re right.

But the kids need shoes. And the mortgage has to be paid. And there’s always the hope you’ll get that big job in March to make it all right again.

But no, it doesn’t happen, and then comes April 15. I’ve been there:

• I’ve been in the long line of procrastinators and spendthrifts (no offense intended) waiting bumper to bumper to drop those envelopes into the drive-by mail slot just before midnight.
• I’ve been one of the ones scrambling for equity loans or whatever to make those payments.
• I’ve discovered, to my shock, that filing for an extension doesn’t mean you don’t have to pay until August 15; just that you don’t have to fill in the forms until then.
• And, perhaps the worst of the memory scars, dropping the form into the box with a check inside that is going to bounce if I don’t find more funds.

Boy, did I hate April 15.

So today I send you my sympathies if that’s where you are, and I celebrate all the years in which April 15 was a nightmare for me. The memories of trying to scramble serious money together at the last minute, with my heart in my throat and butterflies in my stomach, as I went through the Schedule C sole proprietor process of a single-person business plan consulting business that never managed to save enough money through the year to be able to pay what was owed on April 15.

I always tell people, do as I say, not as I did. When you’re living off variable consulting revenues, save a piece from every engagement, put it in a separate bank account, don’t ever think of it as yours. Hold it aside so you can pay your taxes as required on April 15.

So what I’m celebrating as well is that I no longer do it like that. Palo Alto Software finally grew up and 13 years ago hired our controller, bless her soul, who deals with our accountants and handles all of that in advance. They take money out of my checks and do the taxes, and on April 15 I’m just remembering hard times of the past, reliving them for blogging purposes only.