Timeless Advice from Frank Chimero

Our sense of time is all out of whack. When people link to older blog posts and articles, they’ll maybe call it ‘timeless’ or say some other inane thing like, ‘Old, but good!’ Two years old isn’t old! A two-year-old can’t even wipe his own ass.

Let me let you in on a little secret: if you are hearing about something old, it is almost certainly good. Why? Because nobody wants to talk about shitty old stuff, but lots of people still talk about shitty new stuff, because they are still trying to figure out if it is shitty or not. The past wasn’t better, we just forgot about all the shitty shit.”

Frank Chimero


These thoughts are good. I appreciate the way Frank pulls back the curtain, reminds me what’s behind this movie studio western town set: same old human stuff… fear, greed and the slight possibility of a connection.

Even that word “connection” is a facade: something we can say right now, something with a sense of meaning that won’t feel too cheap, but not something an actual writer would say. And not something we’ll say in anymore in 20 years.

What would Hemingway say as a replacement? Maybe he’d say, “fear, greed and the remote chance of a fuck, maybe even love.” I’m not very well read. I don’t know.

This article is good and you should read it if you’re in a self-important industry like “interactive design” or “design” or “business.” Hopefully it’ll bring a little more “fucking” and less “connecting” into your work.

David Ogilvy’s Copywriting Process

In April 19, 1955 David Ogilvy wrote this to a Mr. Ray Calt. It outlines his process for copywriting an ad. It’s refreshing and human and I’m grateful for this honest look into his thoughts about work. (source)


Dear Mr. Calt:

On March 22nd you wrote to me asking for some notes on my work habits as a copywriter. They are appalling, as you are about to see:

  1. I have never written an advertisement in the office. Too many interruptions. I do all my writing at home.

  2. I spend a long time studying the precedents. I look at every advertisement which has appeared for competing products during the past 20 years.

  3. I am helpless without research material—and the more “motivational” the better.

  4. I write out a definition of the problem and a statement of the purpose which I wish the campaign to achieve. Then I go no further until the statement and its principles have been accepted by the client.

  5. Before actually writing the copy, I write down every concievable fact and selling idea. Then I get them organized and relate them to research and the copy platform.

  6. Then I write the headline. As a matter of fact I try to write 20 alternative headlines for every advertisement. And I never select the final headline without asking the opinion of other people in the agency. In some cases I seek the help of the research department and get them to do a split-run on a battery of headlines.

  7. At this point I can no longer postpone the actual copy. So I go home and sit down at my desk. I find myself entirely without ideas. I get bad-tempered. If my wife comes into the room I growl at her. (This has gotten worse since I gave up smoking.)

  8. I am terrified of producing a lousy advertisement. This causes me to throw away the first 20 attempts.

  9. If all else fails, I drink half a bottle of rum and play a Handel oratorio on the gramophone. This generally produces an uncontrollable gush of copy.

  10. The next morning I get up early and edit the gush.

  11. Then I take the train to New York and my secretary types a draft. (I cannot type, which is very inconvenient.)

  12. I am a lousy copywriter, but I am a good editor. So I go to work editing my own draft. After four or five editings, it looks good enough to show to the client. If the client changes the copy, I get angry—because I took a lot of trouble writing it, and what I wrote I wrote on purpose.

Altogether it is a slow and laborious business. I understand that some copywriters have much greater facility.

Yours sincerely,

D.O.

Here’s some more writing tips on this site, and for all you freelancers out there (or wannabe freelancers), here’s a big ol’ guide about how to become a freelance writer.

Trent Walton’s Advice for New-ish Designers

“Do whatever you can to set the bar really high. Find people who are better than you and follow them. Develop your taste. Develop a goal for where you want to be and if your skills aren’t there yet, that’s totally okay. I think that knowing what good is and being able to strive for it is key because then you’ll be willing to do whatever it takes to connect the dots. Find what you love about your field and focus on that and the details will take care of themselves.”

Trent Walton

How Louis C.K. Does so Much

“I learned that sharks sleep parts of their brain, like rolling blackouts; they can’t fall asleep because they can’t stop moving or they’ll suffocate. So they sleep sections of their brain at a time. So I do kind of a version of that, where I shut down brain centers. I literally tell myself, ‘Don’t logistically problem-solve for the next three hours, but you can talk to folks.’ Driving my kid home from school — ‘don’t think about all the professional things you have to do.’”

Louis C.K.

Stephen King on Two Kinds of Novelists

“I think novelists come in two types, and that includes the sort of fledgling novelist I was by 1970. Those who are bound for the more literary or “serious” side of the job examine every possible subject in light of this question: What would writing this sort of story mean to me? Those whose destiny (or ka, if you like) is to include the writing of popular novels are apt to ask a very different one: What would writing this sort of story mean to others? The “serious” novelist is looking for answers and keys to the self; the “popular” novelist is looking for an audience. Both kinds of writer are equally selfish. I’ve known a good many, and will set my watch and warrant upon it.”

Stephen King, intro to The Gunslinger

Aim For The Medium Chill (Not The Big Chill)

“There will always be a More and Better just beyond our reach, no matter how high we climb. We could always have a little more money and a few more choices. But as we see it, we don’t need to work harder to get more money to have more choices because we already made our choice. We chose our family and our friends and our place. Like any life ours comes with trade-offs, but on balance it’s a good life, we’ve already got it, and we’re damn well going to enjoy it.”

The Medium Chill


I liked this article. It put these thoughts in the right order… not too cute, not too brash.

It’s a struggle for me to walk this line between ambition — the call to a better me, a higher thing — and what we know is the stuff of happiness — being in the now, being grateful for what you have, focusing on relationships.

I struggle to not put “settling” in that last bit. It feels a bit like settling. “Settling” feels a bit like giving up.

So I like the way this guy makes The Medium Chill feel a little less like giving up.

A while ago I had an existential crisis. Like, literally in the park with my son on a shitty Portland day while I recorded an audio note about how nothing matters and I should just become a janitor and stop trying so hard.

I thought through the muck and landed on this as my new mandate: make some people’s lives better in small but meaningful ways.

That’s my medium chill mandate.