The Smartass Manifesto

I’m a smartass. That’s my brand. I might as well admit it.

What does that mean?

It means that in any given situation — meeting, client interaction, blog post, reaction to news, Facebook post, romantic date — my mind immediately tries to find a unique, snarky, counterintuitive take. The ultimate smartass remark, intended to get your attention and also, to make you think.

Ask anyone I’ve worked with. You can’t be around me without experiencing it. It’s not always fun, but it’s always interesting.

It’s why, when the Wall Street Journal asked me to describe the experience of the new Scrabble GO app, I told them “It’s like being inside the small intestine of a unicorn that just ate a bunch of rainbow Skittles.” Now those words are actually in the paper with my name attached to it. See? Smartass.

Let’s get a few things straight. One, I actually am smart, as least as far as books and school and stuff like that. Two, I don’t like to go along with the crowd — if they all go right, I’ll won’t just go left, I’ll go off in some odd direction. And three, I like to crack jokes and get attention. Put that all together and you end up with a smartass.

It’s sort of amazing that I could actually have a career with an attitude like that, but I figured out after a little while that I had to be careful with it — and to use my powers to actually try to help the companies I worked for do something useful.

Principles of the Smartass Manifesto

When I was young — and talking back to one of parents, I’m sure — my father once told me “Nobody likes a smartass.” He’s right. It’s a dangerous way to live your life. But he implied that I had a choice.

You choice is not to be a smartass or not to be one . . . your choice is, if you are one, what are you going to do about it?

It strikes me that if you’re reading this, perhaps I can help you. If you are an incorrigible smartass, there are ways to be one that will destroy you, and ways that will allow you to live a good and interesting life.

These are the ten fundamental principles of the successful smartass. Please take them to heart. Good luck with this — and if it doesn’t work, don’t sue me, it’s all on you.

1 Your job is to contribute

If you are reading this, the lord has gifted you with an active mind, creativity, and a quick wit.

You must use your gifts for good, not for evil.

Don’t be a smartass for yourself. Be a smartass for the good of the team. If you can keep actual objectives in mind, you can contribute a lot. That includes remarks that make people think (assuming your workplace is one that values actual thinking).

2 Pay attention to context

Any good smartass is constantly aware of context. That means what happened two minutes ago; what happened a year ago; how people think; who is sensitive and who is not; whether people are happy, sad or frustrated; and how much smartass tolerance people have. You have to be very alert to see and integrate all that into a remark in the moment. If you’re not paying attention, then you’ll be perceived, not as a smartass, but as a jerk — and jerks don’t last long.

3 Don’t be “pro” or “con” — find a third way

Going along with the crowd is boring. Don’t just do that — smartasses don’t go along.

Going contrary to the crowd is tedious, too — because then you’re just a contrarian.

The smartass looks for a unique path, untrodden by others. Do that, and you might find something unique, not just to say, but to contribute. And at least it’s won’t be boring.

4 Snark upwards, never downwards

Smartasses aren’t mean. You’re not there to hurt people. That’s why it makes no sense to pick on the little guy. He’s just trying to get along.

No, the target for a smartass is somebody in power. The corporate stooge who makes no sense. The person who just mouthed off about platitudes for ten minutes.

This is, of course, very dangerous. People in power don’t like to be poked fun at. That’s why you need to be clever about it. Point out the flaws in ideas, not people. And calibrate — stop if you’re about to lose your job (unless this is the moment when you’ve decided to leave that job, of course).

5 This is not a vendetta

Smartassiness is about love, not hate. You don’t turn it on the same person repeatedly as a weapon. That gets tedious, and if there’s one thing a smartass shouldn’t be, it’s tedious.

6 Be deeper than one remark

If your job is to provoke thinking, what happens when you do?

What happens when the person next to you says “Wait a minute, what if he’s right? What did you actually mean by that?”

Unless you can answer that question, you’d better hand back your laminated smartass certification card.

You’re quick-witted. Use that quick wit to go a little deeper. Then people will start thinking and talking. And your reputation will be as a person who stirs the pot, not just a joker.

7 Learn to apologize

You’re going to go over the line. It happens.

If you hurt somebody, apologize soon after, with clear knowledge of what you did wrong, abjectly, and quickly.

A smartass who can’t apologize won’t last long, because while people can tolerate a hurtful mistake, they can’t tolerate somebody who won’t own up to it.

8 Work hard

You still have a job. That’s because you put in the work. That’s what earns you the respect to get to be a smartass once in a while.

Smartasses who don’t work hard end up thrown out on their (smart) ass. That’s only fair.

9 Marry someone tolerant who laughs a lot

If someone doesn’t appreciate your smartass qualities, you’re not going to have a very happy relationship.

Don’t turn your wit against your lover — at least not very often. A person with a sense of humor can take a joke, but not being repeatedly made fun of.

If your partner is going to be any fun, they’ll poke fun at you, too. You’d better learn to take it as well as you give it. If you can do this, there are a lot of smiles ahead for you. If not, expect a bunch of suffering, guilt, and shame. Not what you ought to be looking for in a relationship.

10 Enjoy everything

You’ll win some. The smartass learns to see the irony in what goes wrong even when things are going right.

You’ll lose some. The smartass can see the irony in the losing, not just the hurt. It’s a decent coping mechanism.

You’ll see stuff nobody else would even think of. That makes life fun and interesting.

You’ll always be looking for something new to do, to say, to think, to understand, to ridicule. That’s an endless quest. And one that’s worth pursuing forever.

It’s a fascinating way to live your life, being a smartass. Own up to it. And learn to do it right.