On Writing

The End of Optimism (and Good Riddance!)

That deadline is fine! My schedule is wide open! The only thing on my calendar is my kidney transplant.

Writers may have a reputation for being cantankerous loners with drinking problems, but that characterization is not true at all. In my experience, most of you out there are cheery, charming optimists!

Did I just describe you? How lovely! Now, knock it off. That optimism of yours will ruin your career.

Alright, I’m exaggerating, but I would recommend that you adjust your optimism in one particular area: Stop Overpromising.

An optimist often thinks he or she can do more than what is realistically possible. As a magazine editor, I see this type of person all the time.

“Do you think you can have a draft to me in two weeks?” I ask.

“Absolutely!” the writer tells me. And she seriously believes it, too.

But in that moment of certainty, Ms. Optimist forgot to consider (or mention) that she has a sick, aging mother who needs tending; two children at home for summer vacation; another writing assignment she hasn’t exactly started yet; and a full time job that requires her to, you know, work full time.

We can all guess how this story ends. Two weeks come and go and my grubby little hands are empty. In fact, Ms. Optimist hasn’t even started the assignment. Now she’s filled with anxiety, guilt, and self-loathing – which is awful. Then she calls me up and grovels for an extension – which I find awful.

She apologizes upwards and downwards and sideways. Then she goes on about her personal problems – the sick mother, the two kids underfoot, and the other freelance job (that she also hasn’t finished) – begging me to take into consideration the very same things she failed to take into consideration when we agreed upon the deadline two weeks ago. It is not her finest moment.

See what optimism will get you?

So! May I humbly suggest a dash of pessimism?

Allow me to explain: I’m reasonably good at managing my time, so when I think a writing job will take me two weeks to complete, it often does. But, hey, it doesn’t always. Things happen. Who knows what’s waiting for me around the next corner? So when I think a job will take me two weeks, I ask the editor for three (or even four if I can get away with it). I might hear a little sigh of disappointment when I ask for the extra time, but I know that disappointment will later be replaced with delight when I submit my story ahead of deadline.

Full disclosure: I have never been hired by a sea turtle – but if I had, he’d be as happy as this.

Better yet, when my story comes in early, it looks as if I made an extra special effort to make the editor’s life easier. My reputation as Mr. Reliable is duly earned and I play well with others!

It’s easy to look good when you keep your promises under control.

Disney theme parks are especially good at practicing the art of underpromising. When you’re on line for a ride, you will see signs letting you know how much longer you’ll need to wait. Disney World’s wonderful little secret, however, is that when you reach the “30-Minute Wait” sign, you’ll never have to wait 30 minutes. You’ll be on Dumbo’s back in fewer than 15 – and you’ll be happy as a clam because the wait wasn’t nearly as long as you had expected. There’s a reason why Disney World is called “The Happiest Place On Earth.”

Not Disney World.

Now, imagine how happy Disney World would be if the sign said “30 Minute Wait” but you had to wait an hour. You would be livid. The editor whose deadline you missed might be similarly so.

Now I’m gonna tell you my little secret: As a magazine editor, missed deadlines don’t trouble me very much. Some people who don’t know me very well think it’s because I’m an easygoing fella, but, trust me, that’s not the reason. I’m untroubled because I’m a pessimist.

In other words, when I asked that cheery, charming, optimistic writer to get me a story in two weeks, I knew I wasn’t going to need if for another four.