Real talk: freelance/contract writing

Someone in the Write the Docs Slack was asking about things to consider as she pondered transitioning to a freelance/contract technical writing career, and I have Thoughts to share:

Benefits and administrative overhead

Freelance/contract typically means 1099, which means no benefits - no insurance, no matching 401(k), no PTO, and you do your own tax withholding and paying. These things have a real dollar value, so it’s worthwhile to consider what your rate needs to be to make up for the cost of losing those benefits.

Additionally, taking care of these tasks require a lot of administrative overhead that eats into your working time, especially when you’re just starting out and figuring stuff out. So if you want to work a 40-hour week, you may end up working 45-50 hours for a while as you spin up on new knowledge and processes.


You have to be good at selling yourself and your services. This can feel unnatural at first for some people, and if you’re someone who doesn’t like doing that, you may not enjoy the process. You will likely spend a lot of time when starting out figuring out how you want to position yourself, tweaking website/resume copy to appeal to the clients you want, how to screen for clients that are likely to respond to your particular style/skills, etc.

When I first started freelancing, I spent anywhere from 10-20 hours weekly looking for/applying for projects, on top of any hours I was actually working. YMMV, obviously.

Work availability

In terms of working on things you’re passionate about… when you’re doing freelance/contract work, you may not always get that luxury. It’s very feast-or-famine. You may have a lot of work availability at once, or you may have months where you don’t have any projects going on. When you haven’t had anything in the pipeline for a while, you may be more likely to go after projects that don’t excite you just to have some income.

Making your own schedule

Re: making your own schedule: freelance offers some flexibility, but especially if you’re doing contract work, the client may expect you to work a regular 9-5 just like you were a corporate worker. In a lot of contract gigs, you’re expected to behave/function like a company employee, report on-site during regular hours, etc. - so it’s kind of like being an employee without the benefits, and typically on a temporary timeframe. If you’re doing a project-based gig vs. a contract, you may have a little more flexibility in making your own schedule, but there are also fewer of those.

Pitfalls of the freelance/contract world

There are serious pitfalls possible in the freelance/contract world. There are clients who slow-pay, or never pay at all. (The latter has only happened once to me, but I have had clients drag out billing for months; I’ve fired a few clients for this reason.) I’ve landed gigs, only to have them get canceled at the last minute, and then I have nothing to replace them. Exactly twice, I’ve gotten into a gig, only to find out that the client’s expectations were completely unreasonable and the gig wasn’t going to work out. Bail early in those situations, and I’ve learned to better screen my clients to make sure we’re aligned before starting a project.

Screening clients

First and foremost, I look for a client who either has a strong idea of what they want, or is open to letting me lead the process as the expert; someone who doesn’t know what they want but wants too much control can be an issue. I look for how reasonable their expectations are. Is their project far too vast to accomplish in their stated timeframe? Are they in love with a specific toolchain that isn’t well-suited to their project? Are they flexible in their approach? I start with general questions and then follow up with specifics based on their answers to get a feel for how it would be to work with them, and whether I think what I can deliver will align with their expectations.

In terms of slow-pay and no-pay clients, I look for level of professionalism. Are they an established company, a startup, or someone with a side project? Do they ask for a W-9? Do they have other vendors? How wide is their online scope? If it’s a pretty big company that regularly works with vendors, they probably already have a fixed contract they use and they’ll ask for a W-9 (in the US anyway), and you can probably rely on them to pay - although it may be slow. The issues I’ve had have been with smaller companies, companies that re-org or individuals with side gigs, so I’m a bit more wary about those.

Contract pitfalls

As a freelance/contractor, you typically will not own rights to the work you produce. If it’s public, you may be able to point a future employer at it, but if it’s proprietary, you will not be able to show your work to future employers. This can become a major bummer when you’re hunting your next project/gig - I’ve done some awesome work I can’t show people because the IP belongs to the client. I even wrote a blog post about it a few months ago.

Beware of contracts that generically state that work you do/writing you produce while working for X becomes the property of X. I’ve seen really generic clauses that could apply to work you do outside of the client’s contract while you’re also contracting for the client. The most recent contract I signed had language specific to the work I produce for the client belongs to the client, and work I produce outside of client work is 100% mine, and I’ll be ripping off that language for every future contract.

(Also, when contracting, typically the employer provides the contract; you may get to suggest changes, but usually it’s a pretty fixed thing. If you’re doing stuff on a project basis, or more casual work you pick up from word-of-mouth or off something like a Craigslist, you may have to provide a contract.)

Finally, there’s legal liability. There’s one client I worked with that had language in the contract that said any legal liability for the content I created was my responsibility. i.e. if someone got injured following my directions, I was legally liable, not the company publishing/providing the content. Don’t sign those contracts. You do not want to assume legal liability for some jackass out there who injures himself using a hammer - or a more complex, dangerous power tool.

Where to hunt for freelance/contract work

This has changed for me over the years. Back in the day, I did a lot of work on Elance, which then became oDesk… I don’t know what it is now. I’m also very public about being a writer/tech writer, and have had work come to me from my personal network.

Over time, I got a stable pool of clients, and those clients would recommend me when people they know needed a writer, so I stopped going out looking for work because so much was coming to me. That was probably 2-3 years after I started freelancing.

More recently, I spent two years in a full-time gig, and then took some time off, so I only recently (this year) spun up the work hunt engine again. This time, I’ve found my engagements via Slack. I’ve applied for a lot of things on job hunting sites - LinkedIn, Indeed, Dice, ZipRecruiter, WeWorkRemotely, and have had mixed results with those. I got a couple of offers but they couldn’t meet my rate requirement, but I also got a lot of screening interviews where I never heard back from a hiring manager.

It helps to have strong samples, and be able to speak authoritatively to process; I’m currently working on an open source project in my free time, so I can show examples of my API work when my current engagements finish.

Finally, YMMV but there’s a freelance developer on a Slack where I’m a member, and he routinely posts queries he gets from his Craigslist ads (developer offering services) when he doesn’t have the bandwidth to do them himself, so there may be some traction there; I’m not sure.