How to Critique Someone’s Writing

As a person who makes my living with words, I’m regularly asked to read people’s writing and give feedback. A business plan. A resume. Website copy. A grad school application essay. A profile for an online dating site.

I usually say some variation of yes to the request. But giving feedback is complex. Sometimes the person really wants me re-write the piece, not just give feedback, which makes me feel uncomfortable. People are also vulnerable when they ask for feedback. So I have learned to tread the line between honesty and brutality.

Writers aren’t the only ones who are asked to give this kind of feedback. Everyone gets to play editor from time to time. As friends look for jobs, they need help with resumes and cover letters; children ask for help with essays and papers; bosses and colleagues need to know if a speech or report is up to snuff.

When I’m asked to give feedback, I try to follow the following few ground rules. These guidelines have helped me to be honest yet mindful of people’s feelings. They have also set up some useful boundaries and to create the best environment for helping people.

1. All feedback should include something constructive. When I started teaching seminars for The OpEd Project, the advice I got for reviewing student work was to start with two positive pieces of feedback because people hear constructive/critical feedback better after positive engagement is established. This is probably because of the negativity bias, a psychological phenomenon which causes people to place more emphasis on negative experiences rather than positive ones. {Read the rest at Yahoo!}


Transforming Art Into a More Lucrative Career Choice

Aiming to end the notion that “starving” and “artist” are necessarily linked, some artists have begun to figure out ways to make art and money at the same time.


Getting on a non-profit board

Can I kvell for a few moments? One of my star students, Pamela Ryckman, just got a story published in the Financial Times about how to get onto a nonprofit board. She came up with the story idea in class and the minute she showed me the pitch, it was clear the piece would find a home.

I met Pamela when she wrote this profile about me for a local downtown paper, The Villager. After writing the article, Pamela decided to take my class. Then my poker buddy Paul introduced her to an editor at the FT. How’s that for good karma?


Getting your first byline

A friend just asked me how she can start publishing her articles in newspapers and magazines. Since many people have come to me for advice about this, I’ve decided to answer her via a blog post so that it can help others as well. Below are the questions I’m most commonly asked.

How does the process work? In most cases, proposing an article for publication goes something like this. You have an idea for an article. You identify the publication you want to write for. You write a pitch letter (also called a query letter), trying to get the editor interested in your idea. You find the email address for an appropriate editor. (For magazines,, is a terrific site for locating editorial email addresses. For newspapers, you can usually find email addresses on the company website or by calling the switchboard.) And then you email your pitch letter and pray for a response. Note what is missing from this description; you do not send the whole article. How you write the article will vary based on what the editor asks for after reading your pitch.

Does it always work like that? Pretty much, except when you’ve written a personal essay or an Op-Ed. In those instances, you should write the whole piece and send it in, following the publication’s writers’ guidelines. Writers’ guidelines are exactly what they sound like, guidelines for how the publication wants freelancers to behave. Often, the guidelines are available on a publication’s home page, or by contacting the publication and asking for a copy. These days, the best information on what publications are looking for is on’s “How to Pitch” series. You can also read writers’ guidelines for a lot of publications at Both and Mediabistro charge an annual subscription fee. I use Mediabistro ($49 per year.)

How much work should I do when writing my pitch letter?
In the beginning, writing that pitch letter will feel as challenging as writing the article itself. This is normal. A good pitch letter should grab the reader from the start and it should answer these three questions — why this idea? why this writer? why now? Click here to read the pitch letter I used for the first story I wrote for The New York Times. And click here to read the finished article (note that they begin exactly the same way; that is not an accident.) I got the assignment even though I had no prior clips, probably because I answered those three questions.

What do I do after emailing the pitch? How should I follow up and how many times?
One of the hardest things about freelance writing is that many of your pitches won’t be answered. That doesn’t mean the pitches are bad. It mostly means that the editor hasn’t even read your email. Editors are drowning in email, much of it from colleagues and writers they already know. So it is hard to get their attention. Which is why your pitch should have an intriguing subject header (and mention that it’s a pitch.) Often, it takes a little nudging — an email or a phone call — to get an answer. And often, even with a little nudging you might not get an answer. I usually give it three tries in some combination of email and phone calls before I give up and send the pitch somewhere else.

Some of the books I have tell me to use regular mail. Should I ever pitch by regular mail?
If you have any books that say that, they are out of date. Never pitch by regular mail. (One exception might be for obscure literary journals, but the overwhelming majority newspapers and magazines conduct all business by email today.)

What should I expect when/if the editor replies?
You’ll probably have a conversation or email exchange about how long the piece should be, when it will be due, and how much you’ll be paid. The editor will then likely send you a contract. If she remembers. (I’ve written many articles where the contract only shows up after the article has been published.)

What are some ways to break into a publication if you’re unknown?
At the beginning, you’ll do better pitching ideas in your areas of expertise. If you don’t have any published articles (a.k.a. “clips”), but you are the go-to person for pet-training tips, vegan restaurants, or nudist colonies, then start pitching articles about pet-training, vegan restaurants, and nudist colonies. Your expertise will help. Trade publications (publications that serve a professional community) are easier to break into than consumer publications (the glossies you see on the newsstand). Online versions of consumer publications are often easier to break into than the print version of glossies. Community newspapers and publications distributed for free are always looking for content. As are many web sites. Alumni magazines are also a great place to get started. Of course, with any of these outlets, if you know someone and can get an introduction, use the connection!

How much do publications pay for articles?
Pay rates for freelance submissions haven’t gone up in decades. The “standard” for years has been a dollar a word, but many publications (especially newspapers) don’t pay more than .50 a word. Glossy mags can pay more than $2.00 a word, but I know very few veteran freelancers who are earning more than $1 a word on a regular basis. Many publications don’t pay at all. At the beginning, don’t write for the money. Write for the experience. Eventually, if you’re good, you’ll start to get paid. Meantime, you’ll hone your skills.

Note to any publicists reading this:

Now that I’m on the receiving end of lots of pitches for my “Shifting Careers” column, I’m noticing that the same principles of successful pitching apply for publicists as for freelance journalists. I’m not sure if all media folks would agree, but I am partial to pitches that show someone has read my prior columns and has customized the pitch letter to appeal to my interests. It helps if it is an idea I haven’t heard before or a new take on an old idea. Following up once or twice is nice. Any more than that starts to feel stalky. I seldom write an article based on a press release, though I do read them.

Keep in mind that this is a pretty basic overview. Once you start writing and publishing articles, you’ll hit a whole new set of issues. I’ll tackle some more advanced questions in another blog post.

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Denver wrap-up

I’ve just spent a few days in Denver, where I’m happy to report that the low humidity does wonders for those of us prone to the hair frizzies. In other news, Denver was also home to a some very slash-receptive audiences and even a spot on local tv, so that’s always nice.

Here’s the link to my appearance on the Denver morning news.
(I’m told this will expire in 30 days so please watch soon!)

On Wednesday, Carol Ross, a career coach who specializes in Boundary Crossers, interviewed me for the Northwestern University Alumni Club. Carol’s work is very innovative and she has an excellent blog worth a visit. And last night, I organized a salon called “The Secret Lives of Writers” through the Lighthouse Writers Workshop, which is hosting a great two-week LitFest. If you’re anywhere near Denver and interested in writing, get yourself over to the Lighthouse site and sign up for some workshops and panels. More information on that here.

The New York Law Journal covered my book today in this article, “Lawyers Find Bliss in Pursuing Alternate Careers” (not sure if the registration will let you in, but if it doesn’t, I’ll see if I can post it to my website.) This is shaping up to a pretty perfect Friday! I’m now turning off the computer and getting ready for a walk in Washington park with my old friend Jen before hopping on the plane.

** Carol Ross also blogged about her interview with me. You can read it here.


Take a Class, Tweak Your Career – (

When I left the law to pursue freelance writing, I debated going for a masters degree in journalism. But then I took a few adult education classes and realized that for my goals, it wasn’t necessary to go back to grad school. It also didn’t make much sense to me to invest tens of thousands of dollars for a career where I’d be earning substantially less than my salary as a lawyer. I’m now a huge fan of these kinds of classes. This week, my online column for the New York Times, Shifting Careers, is about why these classes are often all you need for a dramatic career shift.


Two NYC seminars taught by friends

BOOK PUBLICITY TELESMINAR with Stephanie Gunning (5/10)

Stephanie Gunning is offering a FREE teleseminar on the secrets of successful book promotion. She’ll be interviewing Brian Feinblum, of publicity firm Planned Television Arts, and they promise to spill the beans on:

* Pitches that impress radio & tv producers
* Elements of kick-ass electronic press kits
* The ooh-la-la factor in press releases
* The ins and outs (and merits) of local tours
* Easy approaches to in-print journalists

Date: Thursday, May 10
Time: 8 PM (ET), 5 PM (PT)
Cost: $0
How to register: Follow instructions at
Any questions, contact Stephanie Gunning –

EXTREME SUCCESS SEMINAR with Karen Salmansohn (5/21)

May 21st/Soho House.

According to Salmansohn, “You don’t need to work longer hours — just ballsier hours.” In this seminar, Salmansohn will give pointers on “how to become your balliest, most successful self” — from her empowering book, BALLSY: WAYS TO SCORE EXTREME SUCCESS.

How to register: Sign up at paypal at Salmansohn’s site —
Location: Soho House @ 9th Avenue, between 13th/14th St.
Time: 7-8:30pm
Cost: $35 PER PERSON
Any questions contact Karen Salmansohn —


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