The Insider’s Guide to Becoming a (Contract) Technical Writer

Mister Technical Writer
11 min readApr 26, 2021


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. Now is a good time to grab a new contract as a technical writer!

Which locations are best?

It’s no secret that big cities tend to pay better but this is especially true in contracting.

The same job in New York City might pay 20% less in Central New Jersey and 30% less in Northeast Pennsylvania.

So, if you want to earn the most, consider moving to (or close to) a big city.

Your resume as a contract technical writer

“Technical Writer” should be your title or objective — the largest font on your resume. It’s highly unlikely your resume will be noticed if it doesn’t carry this title.

Make it good!

We’re writers. Our resumes should be highly polished (as we used to say about our boots in the army). If I see typos on resumes, they’re tossed. It’s that simple. The same for poor phrasing.

My advice:

  • Raid your sofa. Check under your bed and dresser. Find that money someplace and hire a professional. A good resume writer will ask you clarifying questions that will extract more from your experience than you thought possible.

If you really can’t afford a pro, then:

  • Print it out and read it aloud to yourself. Share it with a few close friends and ask for their honest feedback. What impression do you create?
  • Send it to staffing agencies and ask them for their opinion. They employ people who are constantly updating resumes.

Your Portfolio as a contract technical writer

Back in the day, my portfolio was a black binder. I could always email a few samples to win an interview. Then during the interview, I’d pull out my massive black binder and ask them if they wanted to review my work.

Indeed, they did. That binder got heads nodding and often won me contracts.

Today, an online portfolio is essential for contract technical writers. On a basic level, it tends to reinforce the fact that you are who you say you are. You can also send links by email to your portfolio pieces.


Most work as a technical writer is covered by an N.D.A. (non-disclosure agreement). You’re not supposed to share, and you shouldn’t. However, you can “anonymize” content by removing any identifying information from a document. Alternatively, some polished portfolios contain pictures of key pages that are scannable but not readable. If you have the design skills to do this, I’d suggest you do.

Working with job boards

Numbers Game? You’ve heard it called a numbers game. It’s true.

By creating a system and sticking to it regularly, you can depersonalize the experience, and not hurt as much when you’re rejected for a role.

Passive (search agents) and active searching

Job board search agents notify you when a job is posted. Agents can be focused on your location or specific niche (“Denver Technical Writer” or “Software Technical Writer”).

Active searches

Log in on a regular basis and search actively as well; set aside time for a focused and proactive search for interesting roles. If in the process, you find a new keyword, create a new agent. (You can also remove an agent if it’s not producing results.)

In the US, your resume should be posted on boards like


Other boards:

  • (their Slack board; channel: #Job-Posts-Only).


While you’re waiting for a contract, you can find work on

Before you yell “Heck no!” because of what you’ve heard, maybe you can take a closer look.

There are good contracts on Upwork but before you respond to job postings, sign up for Danny’s email list at Danny is an “Upwork Jedi” and can teach you how to succeed where so many fail.

About staffing agencies

Staffing agencies face a cutthroat business environment. The emergence of international outsourcing over the past 20 years has made them direct competitors with domestic firms. They represent not only US Citizens and Visa holders but also Visa eligible applicants at highly competitive rates. Some of these are billion-dollar firms with huge operating budgets. It’s a “dog-eat-dog” industry.

Further, the business models of staffing agencies must assume that most applicants they carefully select for their end clients do not get hired. They can spend hours finding, interviewing, and vetting references only to face repeated failures to win contracts.

Some companies do not require staffing agencies to be on a select list of “approved vendors.” This means a dozen staffing firms or more could be presenting resumes for a specific position. Therefore, you’re likely to see multiple emails about the same position. Confusing, right?

Some “boutique” agencies with fancy offices and huge marketing budgets (i.e., massive overheads) enjoy 40% margins on the hourly wages of their contractors. In other words, they bill the end client $100 and pay you $60

Most margins are much less. However, don’t worry about what they’re taking home. Worry about what you’re taking home.

They look after themselves first

I think a lot of people new to staffing agencies really believe that they care about your welfare.

Companies are made up of people. A company is not a person.

It’s important to understand that no matter how nice individuals can seem, most staffing agencies don’t give a hoot about your well-being. They’re just looking for someone to make them stand out. They’re looking to make a profit.

I have met a few exceptions but they’re invariably senior people in smaller firms who enjoy a lot of latitude over business decisions.

Emails from staffing agencies

Most initial interactions with staffing agencies happen via email. If you do happen to get a phone call, it’s usually immediately after they’ve sent you a JD (job description). If they haven’t, ask them nicely “Could you please send me the job description?”

Reading subject lines

Beware flowery adjectives!

Look at the adjectives shaded in red above. Urgent; Exciting; Immediate etc… usually mean the recruiter is trying to get you to open their email, nothing more. (Other common openings: Interviewing Now; Needed ASAP.)

Think about it: What’s a non-immediate job opportunity? I haven’t seen many of them.

The descriptions in green tend to be free of hype.

Lesson: Beware the first word or two in a subject line.

The email body

Look for terms like “Rate Confirmation” or “Right to Represent.”

Larger end clients want the last four digits of your Social Security Number or your month/day of birth so they can track you in their system. This helps them avoid duplicate submissions from multiple firms (which means they must reject a candidate).

How to respond?

Sometimes they’ll mention the hourly range. Sometimes they say, “it’s flexible” or “it’s market rate,” but mostly they’ll display a number or a range.

If they don’t provide a rate clue on their first email, I’ll send a nice reply like:

Hi Tom,

Thanks! This looks like a great fit. Before we discuss the specifics further, would you by any chance have a ballpark wage?

Magic Terms:

Look out for the following magic terms:

* EXCLUSIVE: This means they’re the only firm presenting candidates. Much less competition for them and you. You may be one of three or four candidates.

* BACKFILL: Someone is leaving a contract prematurely due to illness or childbirth and the position IS needed urgently. These are typically fast-moving positions. You won’t be waiting days by the phone to hear if you’ve been hired or not.

Say yes when you mean maybe

Anytime a requirement (“req” in their lingo) is released to multiple agencies, there’s a mad scramble to “lock-in” commitments from applicants to avoid poaching or duplicate submissions.

Must you commit to a rate if you’ve agreed to it in your email response? If you don’t agree to their proposed rate upfront (or they to your higher rate), your resume is not presented. It’s that simple.

I’ve found that most contracts have some flexibility in the rate. If it’s close to my desired rate, I’ll say yes. If it’s not close, I’ll tell them what my rate is.

Then, I’ll wait till after the interview to ask for more.

Of course, no staffing company wants to hear that.

“You agreed to the rate, didn’t you?” they’ll say.

“Yes, but that was before I knew the scope. The scope in the interview was greater than the scope in the job description sent to me.”

How could they argue with that?

I’ve found most agencies will pay you more rather than lose the contract to a competitor. Will you be invited to the Christmas party at year’s end? Maybe not.

But you’ll have the additional money to throw your own party.

If you like the job and do well, you could be there for a long time and that money will add up. You always want to get the best rate possible.

One dollar more per hour over two years becomes a lot of money!

Low-ball offers

If you see a very low rate, ask nicely if they have any flexibility at all on the rate. Some will. Some won’t.

You can say “Good luck with it” and move on.

I’ve seen hourly rates that are not much higher than the minimum wage. I don’t know how they do it. And I don’t care.

I‘ve never accepted low-ball wages as a contract technical writer.

Don’t do it, even if it’s your first position. You’ll resent the job and yourself for underselling yourself.

Quick quiz:

How does a lost dollar easily become thousands of dollars lost?


When you accept a lower rate than you could otherwise get, and then remain on the contract for two years. Do the numbers. A dollar can cost you dearly over the length of the contract.

Also, staffing agencies do not give you raises unless they think you’re ready to jump to another opportunity. Raises in contracting are extremely rare. Staffing agencies have their revenue forecasts over the next umpteen months, and they’re loathe to adjust them downward for one contactor.

No duplicate submissions

Do not agree to be represented by more than one recruiter for the same job.

The client will reject you even if you’re the best fit because they won’t want to deal with two competing agencies fighting over you.

Asking the best questions

Some of the best questions to ask staffing agencies:

* Is this an exclusive contract for your firm?

* Have you worked with the end client before?

* Can you tell me about the end client?

* Do you have staff on board already? (If so, are they attached to this project?)

* What’s the hiring manager like?

* What are the other candidates (my competitors) like?

About job descriptions

Know the joke about the Christmas fruit cake?

“The worst Christmas gift is fruitcake,” cracked the comedian Johnny Carson. “There is only one fruitcake in the entire world, and people keep sending it to each other, year after year.”

That applies to many job descriptions as well. It seems like companies have one template, and they just keep reusing it year after year after year.

If what you’re reading sounds like jargony gobbledygook, that’s because it IS!

Ignore the gook and read the requirements. They’re typically bullets.

If you fit 40% of the bullets, apply. Too many people wait to match 80% of the requirements and they miss out.

Job descriptions are often like a description of our ideal partners. They don’t exist. Neither does the candidate who’s going to fit an excessively detailed job description.

About contracts

Contracts include the hourly rate, payment terms, confidentiality protections, and a non-disclosure agreement between you and the staffing agency. The end client has nothing to do with your contract.

Less than two years after starting as a Technical Writer, I formed an S Corp. I invested in a lawyer who gave me outstanding advice about contracts.

He was expensive, so I learned how to do it. I also learned that I had every right to disagree with a term and cross it out or amend it before signing.

My advice:

* Pay for a lawyer when starting out.

* Don’t hesitate to change the contract. At this point, everyone wants you on board.

* Most don’t request a change because most don’t read contracts. Then they find out they’re required to give four week’s written notice to terminate the contract but they can be fired at any time!

* PS: I insisted on equal terms regarding termination. Many contracts today state: “either party may terminate this at any time.”

Tax status

Companies use staffing agencies to avoid the burdens of issues like taxes, benefits, and legal matters (like disciplinary actions). The last thing they want is for you to be confused for an employee or anything more than a temporary worker.

For this reason, a W2 tax status, where you are an “employee” of the staffing agency, is prevalent today.

A few years back you’d often be offered a choice. You could work “1099” as an independent contractor, and the staffing agency would take their cut and give you the rest. You’d get a higher hourly rate, but you’d be responsible for taxes and benefits.

Don’t worry about the following!

Unresponsive recruiters

Even after they genuflect before you, throw roses at your feet and swear on their mother’s life not to ignore you, they go ahead and forget to update you on your status, especially if you were passed over for the job.

Try not to personalize this. Play the numbers. They do!

The margins your agency makes on your wages

I’ll never forget the department manager calling me into her office just before Christmas one year. This was a global media company in a tower overlooking Central Park.

“Bobby, these invoices seem a little off. Take a look at this.”

Without hesitation, I looked at her finger on the display. I couldn’t believe my eyes. There was the hourly rate they were billed. It was a LOT more than I received.

I became rattled about it and struggled to regain my focus. I did the math. It was a 40% margin! The steam poured out of my ears.

Then on the subway ride home, I had a flash of insight. Yes, it was a huge margin; it had to be the biggest in over 10 years. However, my hourly was the largest, too.

I worked for a “preferred vendor” with a fancy office and reps who looked like models and delivered bagel breakfasts every other Friday. I learned that this was how this global media giant and agency wanted to do things, and it wasn’t my business. I was a beneficiary too.


Many staffing agencies offer benefits. You can ask them before your interview. Especially in the United States, their health insurance might be a lot more affordable and higher quality than what you can get as an individual. Ask!



Mister Technical Writer

Bobby B. Kennedy. Tech Writer for > 22 years. Founder, Become a Technical Writer ( A hands-on, real-world technical writing course.