This is a truncated version of the EFA Chicagoland Chapter News. If you would like to read the full e-newsletter, visit the archive, where you can also subscribe to have it delivered to your inbox monthly.


  • Change Delayed. The IRS rule change requiring third-party payers like Venmo and PayPal to issue 1099-Ks for those paid at least $600 through their services has been delayed by one year. The extra time is intended to reduce confusion and the “ginormous” burden the threshold change caused.
  • Book Books. Is reading more books on your to-do list? If you like books about books, the Chartered Institute of Editing and Proofreading suggests 10 of 2022’s best.
  • Loss Aversion. Want to form a new habit? Whatever your goal, services like stickK and Beeminder may help you meet it by backing up your intentions with cold hard cash. You set a goal and if you don’t meet it, the money you put up is lost or donated to your most (or least) favorite cause.


Important Dates for 2023

A new year means remembering to put important dates on your calendar, which includes the due dates of self-employed estimated taxes. For 2023, those dates and respective earnings periods are:

  • Jan. 17. Final payment of your 2022 estimated taxes due on earnings from Sept. 1 to Dec. 31, 2022
  • April 18. First payment of your 2023 taxes due on earnings from Jan. 1 to March 31
  • June 15. Taxes due on earnings from April 1 to May 31
  • Sept. 15. Taxes due on earnings from June 1 to Aug. 31
  • Jan. 15, 2024. Taxes due on earnings from Sept. 1 to Dec. 31, or for the full year ahead

For other important SE tax information, see the IRS Small Business and Self-Employed Tax Center. And if you haven’t done it yet, now is also the time to update the copyright date on your website.

New Year, New Skills, New You?

Who says you can’t teach an old freelancer new tricks? Well…no one, probably, but the following resources from your fellow freelancers may help you learn something new:

  • Charge What You’re Worth [free]. Inkblot Editing’s nine-part course promises to give “you actionable ways to find your ideal freelance rates, say goodbye to the hustle, and build a profitable business that energizes you.”
  • How to Mark Up PDFs [£79]. This self-paced, eight-module course from Denise Cowle “focuses on using the tools in Adobe Reader DC to mark up a document effectively and efficiently.”
  • Yearly Reflections 2022-2023 [free]. Sophie Playle of Liminal Pages offers a free PDF workbook for freelance editors to reflect on how their business went in 2022, and to then use insights to direct the year ahead. The workbook prompts you to review your work for the past year, consider your clients, take a close look at your money mindset, and strategize marketing and networking for 2023.

Free 8-Part Retirement Program Begins Jan. 24

Ready to get your retirement ducks in a row? You’re in luck: The Museum of American Finance will present a free eight-part Retirement A to Z series from Jan. 24 to March 14.

“These programs are designed to introduce you to the many possible sources of retirement income and resources…[and] provide participants with the information needed to help them secure their finances for the future,” the museum writes.

Programs include:

The webinars are produced in partnership with the New York Public Library Thomas Yoseloff Business Center.


By Amy Spungen

  • The Writers’ Co-op. Have you ever given up midway through a project and dumped a client who proved impossible to deal with? I did, just last year. So have hosts Wudan Yan and Jenni Gritters, who discuss when to walk and when to stay in “To Bail or Not to Bail.” They explain how to know when you’ve had enough so you can navigate this very tricky client situation. (Dec. 19. 2022)
  • Deliberate Freelancer. Melanie Padgett Powers explains how to “Evaluate—and Expand or Fire—Your Clients for a Strong 2023.” Similar to the section on goal-setting in the free Yearly Reflections workbook described above, she suggests ranking your clients and then using the best as guideposts for setting client priorities going forward. As always, Padgett Powers is straightforward in evaluating her own successes and failures as she reviews the past year. (Dec. 8, 2022)
  • The Editing Podcast. In case you need a reminder of its importance, Louise Harnby and Denise Cowle discuss “Editorial Humility: Who’s the Boss of the Book?“ in this brief but illuminating episode. Perhaps most helpful are their suggestions for working with anxious authors and explaining the “why” of our edits. (I’m pretty sure you already know that the author is boss of their book.) (Dec. 7, 2022)


For nationwide (and some worldwide) media- and publishing-related conferences, classes, webinars, and other events of interest to self-employed editorial freelancers, see the Media Types Omnicalendar.