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 technical writing contractor in the New York City region. For this reason, this article is US-centric. However, I suspect practices are similar in Canada.

Remote during covid

COVID has boosted remote opportunities. More companies are hiring more contractors from remote locations. …

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 over 20 years ago. I suspect they’re relevant to nearly all technical writing roles, no matter the industry.

1) Be genuinely helpful

Strive to be friendly and helpful (to those above and below you). This doesn’t mean you relax your boundaries and become a doormat.

Tech writing is a support role. So be supportive!

2) Just listen (at least for the first month on the job)

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. But new technical writers today seem as clueless about contract technical writing as I was (over 20 years ago).

I hope this article helps technical writers navigate the often confusing, complex, and lightning-fast world of contract technical writing.

Signing that first contract!

How to ask these questions

You want to ask these questions in a natural manner, ideally on the phone, or by email (in an email thread). Not rat-a-tat-tat machine-gun style…

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 Upwork fail to navigate its hazards. This article hopes to help you avoid those hazards and earn more money.

She’s a smart searcher

1. Search Smartly

It might be obvious, but match your search to your goals. If you’re getting started, and looking to build a portfolio, then choose “Entry level” jobs. If you’re experienced, choose “Expert.”…

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. It might provide some needed clarity and help improve your writing.

One acronym that has been key in my technical writing career is “SVO.”

This also refreshing…


SVO = “Subject Verb Object” is the basic sentence structure for English. It is the only sentence structure you must know as a technical writer.


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

Upwork is good at some things and not so good at other things.

If you’re looking for the top rate anyone in your field can earn, then you’ll likely be very disappointed. Upwork takes a 20% fee on your earnings.


  • If you’re building out your portfolio, it might be your best option.
  • If you’re moonlighting and taking odd jobs that fit your schedule, Upwork can pay well.

In fact, I recently contracted to complete a user guide for $1500.00. It seemed a perfect fit for…

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

If you can write fairly well, chances are you can become a technical writer. The following shows you how can create your first user manual.


The following assumes you can write in clear, simple sentences. Even if you’re still learning to write well, you can use the following free tools to improve your writing:

  • MS Word’s Spelling and Grammar Checker
  • Hemingway app (
  • Grammarly (
  • Voice dictation (use your computer’s native voice dictation application).

1 Define Your Audience

You might not know at the start, but that’s OK. The…

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

After working 20 years in the New York City region, I’ve identified 7 personality traits of a good technical writer. They:

Waldemar Brandt Unsplash
  • Write and edit well
  • Learn quickly and holistically
  • Speak well and often (but not too often)
  • Enjoy learning about technology
  • Perform independent research
  • Operate well in a support role (not the center of attention) and
  • Take pride in refining their craft.

Many people are shocked to hear that getting started as a technical writer does NOT require technical knowledge. Sounds like a contradiction, right? There’s a very good reason for the confusion.

Bobby B Kennedy

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

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