Better Know a Speaker: Katie Gilbert

Katie Gilbert

Katie Gilbert is a Chicago-based freelance writer focused on the economy, investing, social issues, and the many places where they overlap. Her work has appeared in Al Jazeera America, The Atlantic, Forbes, Psychology Today, Institutional Investor, and elsewhere. She taught journalism for three years as an adjunct professor at Manhattanville College in Purchase, New York. She will be a part of the “Breaking into Newspaper and Magazine Writing” panel at CWC 2015.


What does a day of work look like for you? What’s your process?

As a freelancer, I’ve had a lot of flexibility to play with the shape of my workdays over the past eight years. Through trial and plenty of error, I’ve learned a few things:

Sticking to structured work-only time (within traditional business hours) allows me to stick just as strictly to non-working time. If I get lazy about this, it doesn’t tend to lead to secretly gratifying Netflix binges, but to many more hours than necessary in front of the computer, half-working. I have an app on my laptop called Anti-Social that blocks access for a given number of hours to my favorite/most-reviled time-suck sites. I also pay for membership at the Writers Workspace in Andersonville, where I can tuck into a cubicle and get much more done in an hour than I can manage in three hours at home.

That said, I don’t deprive myself. Several hours of productive writing time in the morning earns an hour (or more) to make myself a nice lunch and take a stroll. Writers aren’t machines! We need breaks. I’m more serious now than I’ve ever been about laboring to keep weekends–or some two-day combo each week–work-free.

At the end of each day, I take stock of where I spent my time and plot out a plan for the next day. I use OfficeTime to track where my hours went, and Todoist to manage my to-do list. (I’m forever indebted to this Skillshare class on productivity for introducing me to Todoist and several other tools and techniques that I’ve integrated into my workday.)

What has been the biggest help (a piece of advice, a mentor, a particular residency) for your career?

The most important advice I’ve received about freelancing, or any type of writing endeavor: Don’t try to do it alone. I believed for too long that I had everything I needed on my person and in my laptop to build a thriving freelancing career, and I did okay, but I’ve done so much better since I’ve acknowledged the importance of a writerly community. Writing is hard, and contrary to mythology, no successful writer makes it happen all by herself. We need to commiserate, we need to trade edits, we need to share leads on gigs, we need to discuss what we’re reading, we need to give advice on wrangling tardy checks, and we need to be inspired by one another.

Why attend the Chicago Writers Conference?

See above. Get out there and meet some of the other people doing what you do. If you don’t have business cards yet, go to and get some made. Make it a goal to give out a certain number (10? 35?) over the course of the conference. You may get a writing gig out of it, or ever better, you may get a new writing buddy with whom you can swap tricks of the trade over drinks.

Have you registered for CWC 2015? What are you waiting for? For bimonthly updates, subscribe to our newsletter. Looking for tips, book recommendations, fun articles, and inspirational quotes? Like us on Facebook and follow us on Twitter!