“Short and sweet.” It’s a cliché. It’s also a condition which everything from wedding vows to Academy Awards acceptance speeches should strive to be. To a copywriter, headlines are the supreme articulation of shortness + sweetness. That said, the quest for the right headline is almost never short or sweet. It’s long. It’s painful. It’s the copywriter’s crucible.

Some just think of the process as headline writing—the scribbling out of a small batch of lines and picking the winner. Others practice a more formal approach to finding the ideal headline. It’s known as the “100 Headlines.” It goes like this: you need a headline. Ideally, it will be a headline that can raise a brand’s sales by double-digit percentages and define it through future decades using fewer words than you find on a Surgeon General’s Warning. For this, you will need to write 100. Then junk 99 of them.

If you went to ad school then you know the 100 Headlines as the process popularized by Luke Sullivan, but immortalized by Sally Hogshead (She would want me to point out that yes, it is her real name). Hogshead’s “800 Headlines” were for BMW Motorcycles. Her agency needed eight ads. You might say, “Well, it’s easy to sell motorcycles to men.” And it is. But, writing copy that defines a company like BMW when you’re simply a junior copywriter—not so easy. So, why 100? Why not scribble out 10–15, hand ‘em off and jump back on Facebook?

Because your first 15 are usually junk. And so are your first 30, 40 and sometimes 50. Like rock music, greatness doesn’t even become possible until the mid-50s.

Let’s say I am writing headlines for a car insurance company. Chances are they aren’t my insurance provider; I’ve never been to their office; and I am unable to tell their policies from those of their competitors. Odds are good that my first shot at a headline will not make its CEO invite me over for dinner. Indeed, Hogshead wrote those 800 without so much as ever revving a motorcycle—let alone a BMW. Let’s choose an everyman’s car insurance company and go with State Farm. In just over one minute, here are five headlines:

- Life happens fast. State Farm happens faster.

- You’ve been there for others. Now let us be there for you.

- Some auto insurers claim to have your back. We’ve got your front too.

- Take some of the risk out of turning the key.

- It’s funny to think that such a small piece of plastic can cover so much ground.

Bleh. Blah. Yuck. People turn mountains into gravel looking for diamonds scarcely bigger than a pencil eraser. It’s a lot of work for such a little thing. In the process: people die, limbs are lost, and countries tumble into civil war. All of this when we have labs making diamonds so stunning that no one except an expert can tell them from the genuine article. So why not get by with imitations? Why do so much for so little? Because it’s a diamond, and people have gotten divorced for much less. And most headlines suck. Next time, write 100. It won’t be short. It won’t be sweet. But if you survive, your boss and your client will thank you. They might even invite you over for dinner.