Collaboration with Charity Singleton Craig: What Made It Work?

I thought it would be interesting to ask Charity some questions about our collaboration together. So I would like to start by asking you: What were some of the biggest challenges that you feel we ran across during our collaboration?


The Challenges

Charity: I would like to say there were no challenges, but actually there were a few challenges that I think we handled well.

All of them, I think, stemmed around our communication with each other. I think in various ways, you and I had different preferences for how we communicated, when we communicated, and the type of information that needed to be communicated.

I think over the course of working through this project—and we’ve collaborated on other things as well—that we have had to come to an agreement about which things we need to talk about and which things could wait. I think that we have, over time… those change. Those change from project to project. They change from week to week, actually, depending on what’s going on in our lives.


The Joys

Ann: That’s good. Now, let’s balance that out and talk about the joys, because I don’t want people to be afraid of collaboration. I’m hoping that we can model one way that has worked well. What are some of the joys that you’ve experienced from collaborating with me in particular? But feel free to talk about other collaboration projects you’ve had.

Charity: Great. I think collaboration is very appealing to me, and it has been for quite some time, I think for several reasons.

One is that when we collaborate, we provide more perspectives for the end reader. And I think having multiple perspectives, especially for a book like On Being a Writer, is very helpful to people because there’s not really one way to do it. And even if each of us had written a book, I think it would be received differently because people would be comparing their own experience to one. Being able to compare it to multiple experiences, I think, has been very helpful for readers.

I also think that I’ve learned a lot, and the writing that came out of me for this project is different than if I had done it by myself. So doing it together actually produced different kinds of writing, I think, because I would see what you would write. And then also just as our relationship grew and developed, my writing life grew and developed, and so the content ended up being a different product in the end.


Would You Do It Again?

Ann: That’s good. Would you do it all over again if you had the opportunity?

Charity: Yes.

Ann: Good answer. With you, too. All right.

Thanks for collaborating with me on this podcast and sharing these thoughts with our listening audience. And if you let me know if you have any other interesting ideas, maybe we can collaborate again.

Charity Singleton Craig and Ann Kroeker coauthors of On Being a Writer

Charity: Sounds great. Thank you.


Ann: Well, one reason Charity and I wrote the book was to invest in other people and encourage them in their writing lives. So we both hope that your writing life flourishes.


A Quick Reflection for You:

Collaboration isn’t always easy—communication styles differ, priorities shift. But when you work through those challenges together, you create something richer than either of you could alone. Multiple perspectives. New writing. Growth.

If you’re thinking about collaborating with someone, don’t let the challenges scare you off. Just keep talking. Keep adjusting. And enjoy what emerges.

  • What challenges did you face when you collaborated on a creative project and how did you work through them?
  • Have your collaboration projects been filled with enough joy to balance out the challenges?
  • Would you collaborate again? If so, what would you do differently? If not…why not?

9 thoughts on “Collaboration with Charity Singleton Craig: What Made It Work?”

  1. My most recent, and much smaller-scale, collaboration was when I had four friends over for tea and toast and poetry and we all wrote a poem together. It was fun, and we played nicely with each other. The stakes were low. I know at least a couple of them would like to do that again.

    The thing that comes most strongly to mind isn’t about writing. It was about the roughly 10 years I was in a band. Lots of collaboration there, with more than one person. There were frustrations and there were joys, and all of us in the founding five maintained friendships after we’d parted ways musically. I think we’d do it again. Charity is right, communication can be the biggest challenge.

    I have some collaborations coming up, so I’ll keep that in mind as we navigate new territory.

    THIS collaboration, by the way, you two talking — I hope you had as much fun making it as I did listening to it.

    1. Some great examples, from the recent tea, toast and poetry gathering, to the music, to your upcoming collaborations. Thanks for sharing your work! And I agree with Charity’s observations, that communication was key, and we had different needs and desires for what we felt was necessary. I’m glad she brought that up. I think others could find disagreements in artistic approaches or content tension. It just happened that most of ours came in *how* we were working. Staying attentive to tension and addressing it early will be key to a healthy partnership.

      We did have fun, and it didn’t take much time to record. The videos we were working on took a lot more time–they won’t be ready for a week or so, but you see the podcast is already live!

    1. Look what I can do. Behind the scenes, in an editing mode, I can make you say things you never said (though I won’t) and I can take away commas you never intended (which I did).

  2. I’m thoroughly enjoying your podcasts, Ann, and I’ve been anxious to respond to this one, but two full days of traveling, four days celebrating Christmas and birthdays with my son and his family in Louisiana added to the bookend days of preparing to travel and recovering from travel have prevented me from doing so until now. For three years, a writer friend, Robbi, and I collaborated on a project that she conceived. It was eventually self-published earlier this year, and we both learned much in the process. The concept was Robbi’s. She wanted to use my photography, but she also wanted me to work closely with her in writing the prose. It was a huge learning curve for both of us as we determined what artistic elements were important to each of us, learned when and when not to compromise, and practiced giving and receiving much grace in the process.

    1. Patricia, thank you for this generous and thoughtful reply. I love learning about collaborations, and it sounds like you both learned how to play well together, respecting each person’s contribution and offering grace through compromise where needed. As you heard in Charity’s responses, communication was key, so that we could get our ideas and preferences out on the table for discussion and to make decisions. I’m glad your work with Robbi went well. Where’s your project?

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Ann Kroeker, Writing Coach

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