It’s Christmas Eve. I feel like handing out some gifts.

A few weeks ago, I invited people to send me their lists of films, books, or songs that speak to them about ambition. Then I asked a jury of Looking Closer Specialists to vote on the lists they found to be most inspired and interesting. I concealed the names in case they knew any of the players.

The vote is in. And the ambitious imaginations that produced the top five most popular lists will receive copies of the new book by The Chrysostom Society: Ambition, edited by Luci Shaw and Jeanne Murray Walker, and featuring an introduction by Scott Cairns.

Before I name the winners at the end of this post, I have a gift for everybody: a conversation with one of the writers who contributed to this book.

Brett LottI corresponded recently with my friend Bret Lott, the bestselling author of fourteen books, including Before We Get Started, The Hunt Club, Letters and Life: On Being a Writer, On Being a Christian. He is currently the nonfiction editor for Crazyhorse. His account of writing the novel Jewel — which led him all the way to an appearance on Oprah — is one of Ambition’s many memorable chapters.

I asked Bret several questions about Ambition and its challenging themes.

Overstreet: To whom would you recommend this book? Is it primarily for writers?

Lott: I’d say it’s for artists at large — ambition, in this day and age of Everyone Is a Superhero, gets a bum rap, as though it means stepping on the throat of someone else to get what you want. But an artist needs a kind of ambition in order to find the truest and best iteration of the work at hand, of the art itself; an artist also needs ambition to see to it that work gets the best venue, as it were, available. Artists have to be ambitious. And there’s nobody’s neck to stand on but your own.

Overstreet: How has your sense of ambition changed from the days before your first publication to now? Do you feel more or less ambitious?

Lott: I feel more ambitious than ever, but right alongside that ambition is the sense, because of how long I’ve been at this, of how hard it is to actually do this writing thing. I know more than ever my limitations, what I can’t do, but what I can’t do is what I want to do (I’m hearing Paul in Romans somewhere in here!), so it will be a matter of my ambition serving as the fuel I’ll need to attain that which I can’t right now.

One of my favorite quotes of all time, from John Berryman: “You should always be trying to write a poem you are unable to write, a poem you lack the technique, the language, the courage to achieve. Otherwise, you’re merely repeating yourself, going nowhere because that’s always easiest.” That’s ambition, and the only thing that will sustain you as a writer who continues to make art.

Overstreet: If you could write to your younger, pre-publication self about your ambitions, what would you want to communicate to that version of you? What do you wish you’d understood earlier?

Lott: It’s going to be a long haul. Gird your loins. This will be a path fraught with discouragement and a lack of vocabulary and moments — many of them — when you will fail. I’m just sayin’.

Overstreet: This is a time of megachurches, celebrity pastors, big-budget “Christian movies,” and controversial fusions of religion and politics. If you could draw our attention to one aspect of the Scriptures that could speak wisdom about ambition into this present cultural cacophony, what would that be?

Lott: Micah 6:8:

He has told you, O man, what is good;
And what does the Lord require of you
But to do justice, to love kindness,
And to walk humbly with your God?

Overstreet: Tell us about a specific ambition you’d still like to achieve.

Lott: I want to write a good sci-fi novel. Not one about the gizmos of the future, but one about real people with real concerns, who live in a future (with gizmos) I can’t yet see but which I hope to glimpse.

Overstreet: Do you have a particular role model when it comes to ambition?

Lott: Raymond Carver and Flannery O’Connor.

Carver wrote out of and through his own alcoholism, coming out the other side with a greater sense than ever before of both the fragility and the resilience of the human spirit. He was a writer when he was in the throes of alcoholism, but was an even better one afterward, when he could look back and, with empathy and conviction, write about what matters most: love.

O’Connor wrote most of her best work when she knew full well she was dying, and her ambition to write and to write well even in the face of her imminent death serves to this day as an example of how to finish well as an artist.

Overstreet: What are you most pleased about with this finished book?

Lott: The quality both of production and content. That sounds cliché, I know — hey, it looks good and reads well! But I place a great deal of value on how a book feels in my hand, its production value, its beauty. Nothing like a crummily printed book to turn me off, no matter the quality of its words. This one delivers on both fronts.

Overstreet: Is there a complementary book you’d recommend that readers pick up for further reading on this subject?

Lott: John Gardner’s On Becoming a Novelist might be the one I would suggest — though I think anyone who wants to make art ought to read this. The book isn’t about how to be a writer so much as it’s a compendium of who the writer is, a portrait of the mind necessary to accomplish writing a novel. In it there’s a line I quote a lot to let students know that this is all about risking things — about being risky, about trying what you cannot yet do. He writes, “A writer’s successes bring him more than praise, publication, or money: they also help him toward confidence. With each success, writers, like stunt riders and ballet dancers, learn to dare more.”

There’s also Richard Hugo’s The Triggering Town, in which he writes, “To write a poem you must have a streak of arrogance . . . . By arrogance I mean that when you are writing you must assume that the next thing you put down belongs not for reasons of logic, good sense, or narrative development, but because you put it there.” This is a terrific book for poets — and artists — who are making their way into the world of art.

With those thoughts on our minds, let’s turn now to some possible programming on the subject of ambition.

The winners of Looking Closer’s Ambition Contest, who will receive copies of Ambition to read in the new year, are…


…who recommended a three-movie marathon: 8 1/2, All About Eve, and Citizen Kane.

DeBruhl also had another film list place in the top 5: Whiplash, Black Swan, and Walk the Line. But we’re limiting the players to one prize, so for this second list he just earns extra bragging rights.


…who recommended a three-volume reading list: Jayber Crow, by Wendell Berry; My Name is Asher Lev, by Chaim Potok; and The Red and the Black, by Stendahl.


Stillion recommended movies: Citizen Kane, Julius Caesar, and The Peanuts Movie.

Orth made a playlist: “Fast Car,” by Tracy Chapman; “The Boxer,” by Simon and Garfunkel; and “Songwriter,” by Bill Mallonee.

Croft also made a playlist: “Opportunities (Let’s Make Lots of Money),” by Pet Shop Boys; “Over the Rainbow,” by Julie Garland; “The Impossible Dream,” by Andy Williams.

I’ll be asking them for mailing addresses so that I can send them this brand new book that will help them manage their own ambitions. I mean, I certainly wouldn’t want winning a contest to go to their heads and give them delusions of grandeur!

Thanks to all of you who sent in your lists. It was tough to pick winners.

Here’s an ambition for all of you: Have a merry Christmas!