True Confessions of a Freelance Copywriter: The Undercover Letter

Yeah, okay. So, this is going to be about copywriting (for the most part) because that's what a) I am and b) my head is wrapped around right now.
It truly is an obsession.

Hope Springs Eternal or The Dreamer's Disease

Now, I call Columbus, OH my home but I've done the majority of writing outside Columbus and a very large chunk of that majority was outside the O-H. This was never my intention and it has certainly had its share of downsides (upsides, too) but it never left me downtrodden. Being the eternal optimist that I am, I believed that these opportunities in ad markets great and small would allow me to return home to C-Bus and lead me to greater things when I returned. I still believe this but keeping the faith requires heavy hustle and a Poppins-style bag of tricks.

Hustle and Show

The hustle, though time-consuming and sometimes monotonous, is automatic at this point but the bag of tricks is something else entirely. I'm a big fan of the undercover letter, or the cover letter that isn't. For newbies and oldbies, it's one of the most important gate-busting items in a creative's arsenal. Sure, it's who you know more times than not but what happens when you don't know anyone? Nothing, if you don't have an undercover letter to show. This is one I wrote awhile back that connected me with some great people and decent opportunities (and vice/versa):

I’m the idea man.
All day long, I plan and plan and plan.
I’ve got an idea for everything-
because everything is wrong.

The above hubristic claim is something I wrote down in a notebook YEARS ago.

They were intended to be lyrics to a Beatle-esque song that borrowed more from Apples in Stereo than it did from the Apple Corp. legends (in mono).

The song, the band and the concept never saw the light of day.
Alas, I wasn’t meant to be the Midwest’s less profound, but sunnier answer to Elliott Smith.
I was however meant to be in advertising and take my appreciation for great ideas to strange, new and interesting places both physical and metaphysical.

I was meant to be an advertising copywriter.

As an ad copywriter, I don the guise of the Idea Man and create great advertising.

I look forward to finding an agency that is the perfect fit.

I look forward to working at an agency that gets it right.

I’m the idea man.
All day long, I plan and plan and plan.
I’ve got an idea for everything-
because everything is wrong.

Is it trying too hard to be hip? Definitely.
Does it reek of self-importance? Absolutely.
And scream a certain brand of idealistic B.S.? Maybe.
Did it generate a favorable response? Yes!

And that's it my friend. That's all anyone could ever hope for or want.
An interesting cover letter that says something - anything - can be the difference between an interview and a generic form email.
Remember, there are various forms and levels of interesting. Just know your audience.
Interesting is good. Offensive -not so much.
It's risky business and there are no guarantees but if you wanted safe, you wouldn't be in this business.

The Spartan Copywriter

Roots in Rural America

My parents always questioned who (I know it’s whom but I refuse to be that guy)
I obtained my creative side from.
I say it was a mix of both blended with only child universalities and pop culture obsession contributing heavily to the cause, but my dad was a big influence.
He has a great talent for telling stories and jokes and he does it with such economy; making the joke or story his own by shaving it down considerably. He attributes “being Spartan with his words” due to the way he was brought up. Which is to say, being raised by his grandparents – two Silent Generation saints – in rural Southern Ohio.

Resisting Writer Tendencies

As a copywriter, I adapt Dad’s method to avoid copy clutter, redundancy and increase recall. Don’t get me wrong though, I love words and yes, sometimes I’m tempted to incorporate certain literary devices or add a choice nomenclatural gem to a staid piece of collateral – after all, writers have their writer tendencies – but I resist, employ the “less is more” aesthetic and become The Spartan Copywriter.

Long Form ≠ Long Winded

We all know quantity doesn’t equal quality and if you can sum up what you want to say in a couple of paragraphs or a sentence – do it.
Unfortunately, I’ve encountered resistance in the past with this philosophy and have even, at times, been asked to expand at the request of the powers.
This counterintuitive action is usually taken out of fear.
Ex: “If a client is billed for copywriting, then by golly, they’re going to get their money’s worth.” Sigh.
The truth is (and I think most advertising professionals would agree) the client’s copy needs are best served with effective on-target messaging that the audience will actually read (read: short copy). Sure, it may affect the layout slightly or be the difference between a font size or two but it can really be the difference between greatly increasing product/service name recall and your value with the client.

Blame it on John: An introduction of sorts

This thing is going to shake, shimmy and shape-shift into a hundred different variations of itself a million times over, but for now, it’s this one thing and this is the first post.



Too often, we place too much emphasis on living in the now and make umpteen attempts to forget the past. Moving on is healthy.

Progress is paramount for success, right?

Well, this writer is a healthy time traveler and nearly five years in, I still draw strength and inspiration from the past.


I struggled and suffered for a long time to make it, going here, there and everywhere but mostly, nowhere at all. Now, I'm here with some sense of permanency.

For one person or for everyone, I offer this: the first philosophy-defining, buzz-catching letter from a hungry dreamer.



"Blame it on my relentless optimism or blame it on John Lennon and if you blame John, blame Elvis, Chuck Berry and Robert Johnson too. It's all their fault. I'm a dreamer and my own career-oriented American dream is to be a copywriter. They tried to tell me I was an artist so they sent me to art school. While there, my love for advertising began to manifest into this enormous obsession with ad ideas both written and visual. I was coming up with more ideas than there were allocated projects and was rapidly filling my college ruled notebooks with these ideas. Questions started to arise: "Are you a designer or a copywriter? Thanks to steadfast determination, I appeased the powers that be, finished a well-rounded portfolio and completed school (five months early). I've talked to a few copywriters since beginning the pre-requisite network-o-rama and it seems I'm cut from the same mold. Rather than being Salinger and Hawthorne it was more Starsky and Hutch. I am young though and in this field, not as experienced as most would like.

At the most, I’ve gotten my feet wet.

I will tell you that whatever I lack in experience I make up for in sheer will and the desire to prove the doubters wrong.

Like I have so many times before."