Compelling Content in 4 Easy Steps: Read At Your Own Risk!
The writing I’m most proud of has never been published. It’s never been Liked, Tweeted or Stumbled Upon. Few have ever read it, yet I consider it my most compelling work.

It’s not a blog post, e-book or autobiographical novel (though I’ve written all three).

It’s an essay that I wrote from my grandfather’s perspective… during and after my grandmother’s funeral.

I wrote the essay in my college dorm, in one sitting, with tears pouring down my face. One minute, I wasn’t writing; the next, I’d been writing for hours. For a brief period, I entered into my grandfather’s grief. Though I’d not yet met my husband, I could feel a small portion of what it must be like to lose the love of your life.

That small portion devastated me… and it brought my writing to life.

The secret of this essay, my most compelling content, my best work? Connection. And that’s what you’re striving for as a writer. Writing great, connective content lays the foundation for your site’s success.

How do you foster this deep connection with your audience?

1. Write about the things that make you human (the things that humble you).

Your moments of vulnerability, the things you’ve done that both scare you and shape you? Those are the stories you need to write.

It’s no coincidence that my post on smashing my brother’s guitar sees significant traffic. It’s no surprise that readers keep returning to posts like Jon Morrow’s On Dying, Mothers, And Fighting For Your Ideals, Ash Ambirge’s The 67 Emotions Of Online Success, and Niall Doherty’s My Biggest Secret.

What do these posts have in common? All are deeply personal, yet they aren’t about sharing private details simply for the sake of it. They are about writers humbling themselves and telling their truths so that readers are empowered to do the same.

To write a post like that, you need two things: a sense for what your compelling story is, and a critical eye to discern how it can help your readers.

Not sure what your story is? Write the one you’re afraid to tell. In the words of Rainer Maria Rilke, “Our deepest fears are like dragons guarding our deepest treasures.”

Next, think creatively about how your story could serve your readers. I struggled with the thought of telling the I-smashed-my-brother’s-guitar story with my kind, caring (presumably non-instrument-smashing) readers… until I realized that it could form the first in a series of posts on ‘Owning Your Anger’.

2. Write about the things that are (almost) too painful to share. Tell the truth.

For example…

Here’s the thing about my grandmother’s death: though I loved her, I didn’t know her. Not really. We didn’t connect when I was young, and we didn’t connect when I was older, either.

It’s sad, but it’s the truth.

As I recall, this lack of connection had something to do with a poem I wrote about her being too busy. In all fairness, my grandmother had seven children, a myriad of grandchildren and a lot of baking to do for the holidays. Even so, I longed for her company, not her cooking. I reached out to her, and she wasn’t available. So I poured my feelings into a poem, which went something like, “Can’t she spare a moment/To talk and listen to me?”

In all innocence, I shared the poem with her, thinking that my truth would help us to connect. I was maybe seven or eight, too young to realize that brutal honesty might not be the best place to start.

Needless to say, it did not go over well.

This incident sent an unfortunate message to my childhood self: don’t tell the whole truth in your writing. Don’t upset the grown-ups. When you did that, it made your grandmother feel bad.

As a writer, you probably have a similar experience locked in the dark corners of your psyche. Somehow, somewhere, someone told you that telling your truth was a bad idea. That telling your story would get you in trouble.

Maybe it was true then, but it most likely isn’t true now.

Now, you’ve got to tell your truth. (If you need a boost to get started, I recommend the Cowardly Lion crash-course in courage.)

3. Identify, identify… and then identify some more.

Oddly enough, I feel as though I got to know my grandmother when I wrote about her from my grandfather’s perspective. When I looked through my grandfather’s eyes, I saw my grandmother anew. Instead of seeing a busy woman with a sink full of dishes, I saw a beloved wife. I saw the woman my grandfather loved for over fifty years. It was my identification with my grandfather that allowed this; I wrote the essay for him, to him, as him.

This is your mission as a writer: to identify with your readers. To share your story, and in doing so help your readers see their struggles and heartbreaks in a new light. As Anne Lamott writes in Operating Instructions:

“…the job of a writer is not to get up and say [to the troops], ‘Tomorrow, in battle, most of you will die…’ Instead, a writer must entertain the troops the night before….the best way to entertain the troops is to tell stories, and the ones that they seem to like best are ones about themselves.”

4. Empathize (bridge the divide).

Last Thanksgiving, my grandfather was laid to rest beside my grandmother. In the years before his death, I built the kind of friendship with him that I longed to have with my grandmother. My essay sparked a connection, and somehow, that terrible time brought us closer together.

That’s your task as a writer: to be an alchemist. To take loss and pain and turn it into work that benefits others. To feel what your readers feel, and show them that they’re not alone.

Your work will deepen as your compassion deepens. In response to my essay, my grandfather wrote: “Your insight as to what must have been going on in my mind at that emotional time was remarkably accurate….I [give] you an A+.”

I’d found a way to empathize with my grandfather, and the result was writing magic.

In my essay, my grandfather quotes a verse by poet John Ashbery. This line seems particularly resonant now, after his death: “The factories are all lit up/The chime goes unheard./We are together at last, though far apart.”

Whatever brings us together though we are far apart…that’s what’s worth sharing. That’s what you need to be writing about. That’s what makes content compelling. And that, my friend, is the only guide to great copy I’ll ever need.

Caroline McGraw is a L'Arche Program Director who writes about 'helping you find meaning in your most challenging relationships' at A Wish Come Clear. Her (free) ebook, “Your Creed Of Care: How To Dig For Treasure In People (Without Getting Buried Alive)” is now available at her website.


  1. […] Today’s Post: Read At Your Own Risk: 4 Devastating Steps To Your Most Compelling Content […]

  2. Joe says:

    Caroline, this is
    an excellent post. These subjects are imperative if you are to, as you said,
    bring your writing to a deeper level. My grandparents, who are both gone now,
    are often the centerpiece of my posts. They taught me so much about life and how
    to relate, that I think it would be a mistake not to make the attempt to pass it
    on. My best writing now (and my future content) always seems to hinge on a
    memory that won’t fade. Reading your post, the images are vivid. I can see your
    grandmother doing her dishes at the sink, not quite aware of the little girl
    needing her attention.


    I was fortunate to
    have a great relationship with my grandmother, and I feel for you because yours
    remained undeveloped. But as readers, we reap the benefits of this through your
    “compelling” writing. Lucky us!

  3. Mark Harai says:

    Hi Caroline – this is such an inspiring post, moving actually. 

    Thank you for sharing them… Anyone can become a more effective writer with this perspective.


  4. Wow. And after further reflection I will say wow again. That’s what all writers need to understand. A great great post.

  5. This is beautiful Caroline. It really IS a guide to great copy! Worth bookmarking for my blog file and well worth retweeting!
    Thanks for sharing.
    (Hi Danny!)

  6. Jana Quinn says:

    Stunning post, Caroline. As a theatre major in college, I often inhabited the “shoes” of others in exercises just like the one you did with your grandfather’s letter. I think being able to have that vulnerability in front of an audience has informed my writing immensely and made my voice stronger than ever.

    The part about empathizing, I think, is wonderful. I believe that just identifying a customer or colleague’s problem is not enough; you must really show them that you can feel their pain, even if you’ve never been in the same situation.

    Thank you for the very moving post.

  7. Marlee Ward says:

    Hi Caroline,
    Great work here. It’s a tall order that reaps huge rewards, but I think it’s easier said than done. I’m still working towards that point of vulnerability in my work. That said, I’ve found that it’s when I go the deepest that I get the greatest response. Thanks for this!

  8. Donna says:

    Wow! Well done! And magic it is.

  9. Anonymous says:

    Outstanding post.  I’ll be thinking about this the next time I sit down to write.  Thank you.

  10. Jk Allen says:

    Hi Caroline – great read. 

    I’ve found it to be not only a source of great ideas but also of closure, to write about topics that “are almost too painful to share”. Recently I did a post where I shared a pretty scary event in my life that included a fire, attempted murder and prison. Writing that really helped me flush out the life lessons that I took from that event. And, it was a great way to share something very personal from my life. Nicely written Caroline!

    Hey Danny and Peter – thanks for hosting this!

  11. Benny Hsu says:

    Great post. Writing from the heart and keeping in mind how it will benefit the readers. Will keep that in mind for future posts.

  12. I really like the human elements of this, Caroline. It’s not only the driving force behind the social media revolution, it’s a huge hallmark of the evolution of our species, as a result of real time talk. (which I’m highly psyched about) Super post. Really Super Post. 

  13. Wow, Caroline! What a powerful post. I loved what you had to say about identifying with your readers or your audience. I can definitely feel that sometimes I am trying too hard to provide a lesson or provide value of some kind that I may lose my ability to identify with my audience or my readers may be feeling, thinking, seeing or even saying. You’ve got me thinking Caroline! I love it when I can read something like this and leave some serious thoughts. Thanks for sharing your perspective here on FirePole! 

    • No problem, Hector! I know just what you mean ~ that feeling of “trying too hard” and forgetting to identify with your readers as you write. I get the sense that we’ll always come up against that feeling…but that we can keep returning to the stories that move + shape us, and gain perspective + clarity to move forward.
      Thank you for your comment + affirmation!

    • No problem, Hector! I know just what you mean ~ that feeling of “trying too hard” and forgetting to identify with your readers as you write. I get the sense that we’ll always come up against that feeling…but that we can keep returning to the stories that move + shape us, and gain perspective + clarity to move forward.
      Thank you for your comment + affirmation!

  14. Stacey says:

    Thanks so much for this post, Caroline! It’s a shining testament to the value of telling a personal story that makes for compelling content and valuable lessons.

  15. […] … their power to change their circumstances and improve their lives. He always thought I had a compelling story to tell, and he always treated my brother Willie as a valued member of the family. He used to say […]

  16. Cheoy Lee says:

    Well * definitely* practice what you preach in your own writing – while telling us to write empathetically, you rite incredibly so. For all the dry, unoriginal “writing advice” I’ve seen out there, this is the best.

  17. […] others skip right to the end for conclusions and calls to action. Some prefer emails to be more intimate and personalized while others like lists and […]

  18. […] first order of business was to get some compelling content on my Right Mix Marketing site. I had been on the fence about going to Blog World LA, which was […]

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