Kill your darlings (and other dark edits)

Red pen on draftSometimes the secret to great creative work isn’t what you produce, but what you throw away or leave out. Think about cropping a photo. The role of white space in a clean design. Skylights or extra windows letting in more light.

And while it may seem counter-intuitive, similar strategies play a role in writing.

So if you’re struggling to get a concept onto the page in just the right way, the problem might not be what you need to add. Something already there may be holding you back. When you’re stuck or pushing your word limit, it may be time to go to the dark side of editing and look for stuff to cut. These “subtractive” strategies can add a lot to your copy.

Kill your darlings

“Darlings” are bits of writing you really love and just have to include somewhere. The witty phrase that makes you sound so clever. A conversation where your favorite character shines. That snappy smackdown of the cause or competitor you loathe most. Even experienced pros fall prey to them.

The trouble with darlings, unlike truly great ideas, is they just don’t seem to fit anywhere. They make you crazy as you bend over backward trying to include them where they don’t belong.

Signs you might be grappling with a darling include:

  • The idea came to you early in the writing process, before you thought the whole piece through.
  • Your darling doesn’t drive the reader toward your conclusion or call to action.
  • No one cares about your darling but you. (Sorry.)

“Killing” your darlings is the only cure. Can’t bear to hit the delete key? Cut and paste your darling into another document and save it for later. More likely you’ll forget about it, but you’ll get over it. It’s hard to kill darlings because we looooove them so. But the needs of effective words outweigh those of words that are just showing off.

Omit needless words

Rule 17 from Strunk and White’s The Elements of Style is perhaps the most famous maxim of that famous writer’s guide. And while E. B. White admitted “the huge task will never be accomplished,” it’s still the key to clear and concise copy.

In fact, it’s so tough to beat Strunk himself on this one that I won’t even try. Here’s rule 17 verbatim, which White called “fifty-nine words that could change the world”:

Vigorous writing is concise. A sentence should contain no unnecessary words, a paragraph no unnecessary sentences, for the same reason that a drawing should have no unnecessary lines and a machine no unnecessary parts. This requires not that the writer make all his sentences short, or that he avoid all detail and treat his subjects only in outline, but that every word tell.

Strunk goes on to slim down numerous examples, including cutting a paragraph down to a sentence with half the words. His biggest pet peeve is “the fact that”, which  “should be revised out of every sentence in which it occurs.”

The thumb test

This simple trick ties in with rule 17, though it applies equally to words, sentences, and even paragraphs. Not sure you need something? Try covering it with your thumb (or a sheet of paper, or whatever). If the remaining copy is just as good or better without the words you covered, they don’t belong there.

Like athletes, writers often need to “warm up.” So it’s a good practice to try the thumb test on the first few paragraphs of any given piece. Don’t be surprised if paragraph 4 turns out to be a much better introduction — it happens all the time.

Copy that fails the thumb test might work somewhere else in your piece, especially if it features relevant details. Just be willing to let it go if it isn’t necessary.

Breaking up isn’t hard to do

Jane Austen could get away with writing sentences 109 words long. She wasn’t competing with YouTube videos of adorable puppies. Your job is a bit tougher.

Shorter sentences make copy easier to read. Gurus differ, but holding most sentences to 20 words or less is a common guideline for marketing copy. Break longer sentences into smaller pieces if you can.

Just as designers use fonts and spacing, writers use punctuation, subheadings, sections, and chapters to shape the reader’s experience. In some cases, bullet lists can also be more effective than sentences or paragraphs packed with information. Tools that break copy up give readers visual “breathing room,” making them more likely to read to the end.


Deleting words can feel demoralizing, especially if you’ve worked hard to create them. But don’t let that stand in the way of writing great copy. Your draft is like the first chisel blows on a marble sculpture. It may look promising, but there’s still work to do. Editing is the process of smoothing and finishing the rough edges. Apply these rules mercilessly and take pride in the masterpiece that remains.

  Just write it

Document 1. Just write it.You sit in front of the blank screen. An endless sea of white, like the ice planet Hoth. If you could just write like Hemmingway — right now, please — life would be a lot less stressful.

You want the copy to be perfect — snappy, on target, compelling. But it’s soooooo hard. And the clock is ticking. And a million other things are clamoring for your attention.

If this situation sounds familiar, you’re not alone. Many writers — even seasoned professionals — struggle with getting a first draft on the page.

The solution? Stop caring about getting it right in one go. Just write.

The perfection problem

I’ve argued in the past that writer’s block is a myth, and I still believe it. But sometimes writers get in the way of their own success by focusing too much on knocking out a perfect draft right away.

This is different from not knowing what to write, because the “perfection problem” often shows up when you already know much of what you want to say. What messes you up is agonizing over what to say when, or how to say it in the first place. You’ve got all the background information crammed into your head, but don’t know what to do with it. It’s crazy-making.

Stop worrying and just write

There are a lot of details that make writing great. Don’t think about any of them when you’re writing a first draft. Don’t think about SEO, how many units you need to sell, how well the last promotion performed, or how soon the deadline is looming.

The only thing to worry about, if you need to worry now, is this: will the reader keep reading?

To answer that question, you need to know who are you writing for. Try to get into their head and think like they do. What will motivate them to take the action you want them to take?

With that in mind, do a brain dump. Write down everything you think you want to say, in whatever order it comes to mind. If it helps, you can make an outline first, or re-arrange everything later. What matters now is to get letters on the page. You can make everything perfect in subsequent drafts. That’s what they’re for.

Don’t start at the beginning

It’s tempting to try and nail the lead (the first headline or sentence) before you write anything else. Yes, it’s the first thing the reader sees. And yes, it’s the most important part of the copy, because if it doesn’t catch their attention, they’ll ignore everything else.

Unfortunately, the first thing you put on the page isn’t likely to be your best work. Most human brains start to “warm up” as they begin writing, making the words on the page more compelling after you knock out the first few paragraphs. Often it’s best to just start a brain dump, then go back and re-arrange things later.

In fact, it’s often more effective to think backwards, or to quote Stephen Covey, to “begin with the end in mind”. When writing, this means to focus on the response you want your writing to create, then figure out how to lead your reader to the same conclusion.

I once took this idea to extremes by writing the first draft of an entire direct mail promotion backwards. First I wrote the final call to action, then the second-to-last paragraph, and so on, finishing up with the lead. I don’t recommend doing this every day, but this type of thought process makes it easier to stay focused on where your writing needs to go next.

Don’t be afraid to cut stuff that doesn’t work completely. I often delete the first two or three paragraphs I write in a given session, or move them later in the piece. There’s no shame, and no one will ever know.

I won’t tell your readers. I promise. 😉

  Writer’s Block is a Myth

Writer's block is bad for pencils.You’ve heard the “writer’s block” story hundreds of times. Maybe you’ve even experienced it yourself. It usually goes something like this:

  1. Writer sits at desk to create amazing masterpiece.
  2. Nothing happens.
  3. Writer stares at a the wintery wasteland of a blank, white piece of paper/screen.
  4. Nothing happens.
  5. Agony/weeping/gnashing of teeth.
  6. Nothing happens.

There are few things more miserable for a writer than not knowing what words to put on a page, especially when there’s a deadline looming.

Yet despite its infamous reputation, “writer’s block” isn’t some wordsmith’s disorder that strikes without reason. In fact, it’s not what’s “causes” the block at all. It’s a symptom that appears when you haven’t done your pre-writing homework.

Writer’s block: fiction vs. reality

There’s a common misconception that writers just go into their lonely writer’s garrets, sit down, and start plopping words onto the page. This can work if you’re a fantasy novelist who practices “discovery writing,” but it’s a different story when it comes to marketing copy.

Writer’s block, then, is a sign that your brain needs you to do one or more of the following things before you hit the keyboard:

Listen to the client

What does your client want to communicate? If you’re working with someone who already has some marketing savvy, you’ll probably get a creative brief with background on the topic and some strategy guidelines. If not, you may need to ask the client for more details. Try to think like a member of the target audience when the client is filling you in. This will help you spot information the client may not have thought to provide because of their intimate familiarity with what they sell.

Identify the desired action

Every piece of marketing copy should focus on encouraging the reader to take one specific action. Download content. Request a consultation. Attend an event. Make a purchase. Make sure you know what it is before you write a single word.

Do research

Writer’s block sometimes strikes when you don’t know a key piece of information. For example, if you’re dealing with a very specialized or technical subject that you’re new to, you might need to learn about it before you can write about it. You’ll also want to learn as much as you can about the people you’re writing for. Who are your client’s buyers? What do they want and need? How do they talk? Do they think like your client, or do they have different motivations? The more you know about them, the more effectively you’ll be able to communicate your client’s message and encourage the action they want.


Another common cause of writer’s block is being overwhelmed with information. When this happens, your job is to get organized. First, figure out what you don’t need. Compare your material to the goals of the project, and set anything that isn’t relevant. Next, organize the remaining information in a logical order for the reader’s action journey. Stuff that attracts and excites their interest needs to appear first. Everything else should build on that, with each additional point of information guiding them one step closer to the desired action.

Low-tech solutions often work best here. I frequently tackle complicated projects by making 3×5 cards with summaries of all the key copy points. I spread them out on the table, move them around to find the most compelling flow of information, then gather them up into a stack and use them as my guide for the finished piece.


Still not sure where to begin? Try mapping things out in outline form. Once it makes sense there, you’ll literally have a roadmap that tells you exactly what to write. All you’ll need to do is add a little polish and detail.

If you’ve done the 3×5 card exercise described above, you’ve essentially built your outline already. Just pick up the stack and start at the top.

  Managing Multiple Writers

Rubber ducks in a rowHaving a writing partner who knows your business inside and out can be a great marketing asset. But what if you have more work than one writer can handle? Working with multiple writers makes the process a bit trickier, but it’s easy to manage if you have the right process in place.

Make consistency your goal

While your audience may not realize it, they expect to have the same experience every time they read something you publish. For example, if you’re serious one day and cracking jokes the next, your prospects might get confused or question your credibility.

The primary challenge when working with multiple writers, therefore, is to make sure you still “sound like you” no matter which member of your team does the writing. In fact, it’s more important for your writers to be consistent than it is for them to be clever, witty, or even brilliant. You can try to standardize your approach by having conversations with your writers, but it’s much better to have your expectations documented in writing.

Build a playbook

One of the best ways to keep multiple writers on the same page, as it were, is to set up a style guide or “playbook” that spells out what you’re looking for.

I’ll talk about what goes into a writing style guide in more detail in an upcoming post, but at a glance it should include:

  • Guidelines for the voice and tone of your brand, including who you’re writing for
  • Examples of good writing in your desired style
  • Writing examples that don’t fit your style
  • Specific words to use (or not use)
  • Any style or grammar practices you care about
  • A default stylebook for anything you haven’t covered, such as the Chicago Manual of Style or the AP Stylebook

Be generous with feedback

A good writer will eventually have an instinctive idea for how your brand should sound. It might even seem like he or she is reading your mind. Until they reach that level, the more feedback you can provide the better.

One of the most effective ways to give constructive feedback to multiple writers is to refer to the playbook, and to be as specific as possible. For example, you might suggest keywords that could be added to the copy, or indicate where the tone could be altered to emphasize the needs of a particular market segment. Don’t just say “this is wrong.” Be as specific as possible about what isn’t right, where relevant guidelines can be found in the playbook, and what could be changed to improve it.

As you give feedback, be open to the suggestions your writers come back with, especially if they work outside your organization. They may provide insights that hadn’t occurred to you. If they make sense, consider changing the playbook to accommodate them. If you’re not ready to go that far, try an A/B test to see which approach gets the best response.

  5 crisis management tips for freelancers

emergencyA few years ago, my wife Toni was working at a school that didn’t allow teachers to have mobile phones turned on during the workday. As a result, I was the one who got the call informing us that her father had died suddenly and unexpectedly.

I was juggling multiple projects at the time, one of which was on a tight deadline, but there was no question about what to do. I dropped everything immediately and made the half-hour drive to her school to break the news to her in person. The next day we were on the road to her hometown to support her family and attend the funeral.

Unforeseen crises like personal illness, accidents, natural disasters, and the deaths of friends and loved ones are a fact of life for any business owner, not just solopreneurs. And since our business model means we don’t get paid when we’re not working, even joyful events like births, marriages, holidays, and vacations can have a disruptive effect on our businesses.

Thankfully there are steps you can take to minimize the impact on your bottom line — before, during, and after a crisis:

1.    Build time for the unexpected into your schedule

Many freelancers and other business owners base time estimates on their peak productivity levels. For most of us, however, reality intervenes in some large or small way practically every day. Keeping a small amount of time each week unscheduled gives you the flexibility to put out minor fires before they turn into bigger problems.

2.    Schedule marketing in advance

Having a few weeks or months of material loaded into your marketing machine requires some prep work, but you’ll be glad you did it. My father-in-law’s death wasn’t the only time I’ve had to take an unscheduled leave of absence from my company, but my automated self-promotion pieces still published on schedule while I was away. Precautions like these help prevent your pipeline from drying up when you return to the office.

3.    Communicate when crisis strikes

Notify everyone who will be impacted by your absence as soon as possible, and be frank about what’s happening. Failing that, try to have a colleague, family member, or friend contact anyone you’re currently working with. It’s much better for you to give them as much time as possible to react to your situation than it is to disappear for a few days with no explanation until after the fact.

4.    Maintain a savings cushion

You’ve already heard this one if you saw Jim Krause’s presentation at HOW Design Live last year. Sock away 10% of your earnings to keep your business afloat — not just when crisis strikes, but to cover the occasional “famine” cycle. Six months’ expenses in the bank will help you sleep much easier at night.

5.    Remember: your real life comes first

It’s tempting to bend over backwards so your business goes on rolling in an emergency, but keep your priorities straight. I did a project launch call remotely a few days before the funeral, but only after I had confirmed I wouldn’t be needed for a short while that day. The rest of the time, I gave my full attention to my family’s needs.

All of my clients were very supportive and understanding during this time, and were quick to revise their timetables. Even my contacts at a company I had just started working with the previous week were sympathetic and accommodating. Good clients understand that this stuff happens to everyone — and could just as easily happen to them — so don’t be afraid to be straightforward about your situation.

  Give your email a power nap

Automator napEmail makes a lot of things easier for the modern freelancer, but it can also be a powerful distraction. Just like a ringing telephone, the “you’ve got mail” sound exerts a powerful Pavlovian influence, suggesting that your latest message is urgent — even if it’s not.

Recent updates to the Macintosh operating system are helping me to ignore email more easily by displaying quick preview windows when new messages come it. I can tell at a glance whether it’s an important client message that needs immediate attention or the latest “last chance” offer from LinkedIn (hmm…third one this month).

Even so there are times when I need to hunker down and write without distractions, which means turning the email monster off entirely. But there’s always that little voice asking “what if something really important come in?”

My current solution is an email “power nap,” assisted by a simple Automator workflow. My custom Mail Nap application sits on my desktop, ready to spring into action at a double-click. This handy little app shuts my email down, then reopens my mail application exactly one hour later. If I’m done with my deadline, I can check mail in peace. If not, I can make sure there are no emergencies and fire up the nap application again for another hour of focused productivity.

I’ve been testing this little helper for about three weeks now, and so far it’s working pretty well. I’m getting more done during “nap time” without stressing about missing anything major. After all, I’m only offline for an hour.

Want to try it for yourself? Here’s the basic Automator workflow I’m using (sorry PC users—this only works on Macs, but you can probably find something similar if you poke around a bit). You can customize it for a different mail application or a different amount of time, but the basic ideas are all here. When you’ve finished setting it up, just save it as an application to your desktop or wherever else you like.