For twenty years, I worked as a contract technical writer in New York City. Most contracts began with a 3- or 6-month term but were extended.

I worked at about two dozen different companies and organizations. And I collected some “strange but true” experiences.

These stories are true. …

Are you new to technical writing and want to advance your career? This list might save you some unnecessary frustration and aggravation.

Find the tone patronizing or condescending?

It shouldn’t be, especially if you understand one thing. These 11 items reflect issues I personally experienced when I began my career…

1) Focusing on a Full-Time Position

We all know the ideal partner doesn’t exist, that life does not follow a Disney script, but many of us persist in the illusion that a perfect partner-for-life is out there somewhere.

Likewise, we often persist in believing that a perfect full-time position awaits…



This is my take on a nearly 10-year-old post, “​Top 10 Most Frequently Asked Questions,” (About Technical Writing) by Tom Johnson. Most of what Tom says in his original post is valid today.

His blog, I’d Rather Be Writing, is the most visited blog by a technical…

Not all technical writers understand contracting. Some have always worked as employees. They’ve never had to review a contract or even understand what goes into one. Even if they’ve hired contractors, they’ve encountered only a slice of the contracting lifecycle.

The following is based on my 20 years as a…

This has been revised to remove some of the harder edges without softening the meaning. Hope you enjoy. -- Bobby

Who am I?

As a long-time contract technical writer in New York City, I’ve interviewed about 70 times. When I began, I had no clue what questions to ask.

Back in 2000, the (contract) game was slower. The process, simpler. …

New to Upwork? This article shows you how to avoid the traps on Upwork and make money writing

PS: A hands-on, real world technical writing course. Jump on the wait list:

Upwork is the largest freelance community in the world. Like any enormous community, it has its pitfalls. Why does Upwork get a bad rap among writers? One of the main reasons is that writers new to…

PS: A hands-on, real world technical writing course. Jump on the wait list:

If you want to become a technical writer, or you are a new technical writer, this article might help. You could crack open a grammar book and feel childish. Or, you can use this grammar refresher…

Bobby B Kennedy

Tech Writer for > 20 years. Founder, Become a Technical Writer ( A hands-on, real-world technical writing course.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store