Courtney C.W. Guerra has been writing her Dear Businesslady column since 2014, first on The Toast and now on the financial advice site The Billfold. She is the author of Is This Working?: The Businesslady’s Guide to Getting What You Want from Your Career (April 2017, Adams Media, a division of Simon & Schuster). Starting out with experience in food service, retail, and data entry—plus a joint BA in English and visual arts—she proceeded to build her resume through a series of administrative positions, both corporate and nonprofit. She’s spent most of her career as a writer and editor supporting humanities research at the University of Chicago. Read our interview with the lovely Courtney below…
What motivated and inspired you to start your own business?
In my day job (working with faculty on applications for research funding) I’m constantly giving advice—and editing. At some point I started thinking that I might be able to use those same skills to help coach like-minded people on their career decisions, and I pitched a column to The Toast (RIP). It took off, and here we are!
Tell us about your business.
When giving advice, I see my role as a kind of “life editor”: I’m offering feedback based on an external perspective. In the column, I’m answering specific questions, and I love having the chance to address particular problems that readers are dealing with. I used that experience when writing my book IS THIS WORKING?, compiling a list of common workplace issues and sharing my insights on how to navigate them.
Are you currently running any promos/contests/giveaways that you would like our readers to know about?
Nope, but I’m always on the hunt for new questions to answer for my column! Send ’em my way: DearBusinesslady@gmail.com.
Where is your business based?
I work remotely, so this is a complicated question! I live in Syracuse, NY, but my job is in Chicago—I do a lot of traveling back and forth between both cities (supplemented with pleasure trips to a variety of other places).
What were the first few steps you took to get your business up and running?
My first columns introduced people to my voice and viewpoint. I had to think about how to frame my suggestions in a general way, so that they’d be helpful to people who didn’t share my exact same background.
What has been the most effective way of raising awareness of your business and getting new customers?
Since I started preparing for the release of Is This Working?, I’ve gotten a lot more active on social media. The book also means that I’m no longer anonymous, which—while slightly scary at first!—has been really great in the long run: now that my colleagues know about my secret identity, they’ve all been really supportive (and willing to spread the word that I’m a resource for work advice).
What have been your biggest challenges so far?
I think most first-time authors have some trepidation about actually completing their manuscripts on time. I certainly did, at least initially—but by the time I was finished, I was something like 6k over the target word count!
How did you overcome these challenges?
While I wasn’t thrilled to hear “you need to cut a huge amount of text from your book,” I saw it as a test of my editorial skills. In the end, I managed to shave away all the superfluous text, without sacrificing personality and style, and there’s no question that the book is better for it.
How do you keep motivated through difficult times?
I take my role as Dear Businesslady seriously: when people write to me, I feel a sense of duty to offer them useful, compassionate advice. If I’m not in the right mindset to work on a column, I remind myself that someone else is depending on me, and that’s usually enough to propel me forward.
I also like to remember that bad moods, anxiety, writer’s block—these are all temporary conditions. They’re not fun to experience, but they’ll subside eventually, and you’ll have renewed motivation once they’re gone. It’s sort of like when you’re finally healthy again after suffering from a cold—your basic baseline suddenly feels like a remarkable gift (“Wow, I can breathe through my nose again! Amazing!”). You can use that to your advantage.
How do you distinguish yourself from your competitors?
There are a lot of advice columnists out there—I should know, I read a lot of them regularly!—and I think there’s room for all of our voices. My own style is more expansive/comprehensive than others (especially in the “work advice” realm), and I try to infuse my writing with humor whenever possible.
For the book, I was going for something that would feel friendly and approachable to 20-somethings, but also remain relevant and useful for people further along in their careers. It’s not about dictating: “Do This, Don’t Do That”; instead, I explain the cause/effect relationships that someone might consider before making professional decisions. With some snark and silliness sprinkled throughout.
What is the best advice you have received recently?
I’m always finding life lessons in my own experiences. I had a situation recently in my “real job” where I let myself get overburdened and ended up finishing a project at the last minute, with predictably less-than-ideal results. When I was trying to figure out how to avoid repeating the same mistake, I realized: when you’re on the edge of burnout, your ability to care about quality can get compromised.
Work/life balance is one of my favorite issues to discuss, but that aspect hadn’t quite connected with me. It’s one more reason to set limits on how much you take on. If you don’t, your output—and, in the long term, your reputation—will suffer.
What advice would you give to other entrepreneurs?
To any aspiring writers: find an outlet and WRITE. I wouldn’t be in this position if I hadn’t submitted that initial pitch. (I’ve also been rejected plenty of times too, so don’t let that discourage you when it inevitably happens.)
As a kind of middle point between these two suggestions, I’d encourage anyone—not just writers—to be open and receptive to feedback. It’s discouraging to hear, “Hey, this thing you worked hard on isn’t as good as it could be,” and I’m sympathetic to that, but criticism is how you learn to do better. If you have a negative emotional reaction in the moment, that’s fine (as long as you’re responding professionally, obviously!). However: you need to revisit the project after you’ve set those feelings aside in order to actually grow.
What is your favorite business tool or resource?
Since my business is writing, I’m obsessed with the Chicago Manual of Style. I have free access through my work, and if I ever switch jobs, I’m going to have to pay for a subscription. There’s no better resource for answering esoteric grammar questions. But for anyone who’s not enough of a pedant to pay for CMoS lookup privileges, Mignon Fogerty’s Quick and Dirty Tips site is a good free alternative.
What is a good article or book you have read recently?
I love Roxane Gay’s Bad Feminist. Her essays are thought-provoking, funny, heartbreaking, informative—sometimes all at the same time.
On the professional front—and in honor of the fact that we just celebrated #EqualPayDay—this Forbes piece by Lisa Gates is a great script for negotiating a higher salary.
What are you currently learning about for your business or looking for help with?
Now that Is This Working? is finished and out in the world, I’m just trying to get it in readers’ hands. I’m really proud of how it turned out—I think people will find that it’s a lot more entertaining than a lot of books in the same category.
What are your goals for the next few months and how are you striving to achieve them?
I want to continue getting the word out about the book—which means scheduling readings and talks, doing interviews like these, etc. I have a background in improv and sketch comedy so I’m weirdly comfortable with public speaking, and I’d love to connect one-on-one with folks seeking career guidance. If anyone’s interested in booking me for an event, they should get in touch!
What social media outlets do you use? List them below.
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