top of page

What I learnt about freelancing by managing other freelancers.

Issue #005 • It’s both welcoming and brutal — it’s up to you.

Handwritten Text Closeup
French Literature
Abstract Art Collage

I’ve been freelancing for most of my adult life. I was pretty sure I had it figured out: how to price, how to pitch, how to communicate, how to deliver. Until recently, in my role as a Freelance Content Strategist, I started managing other freelancers, contractors, and content agencies for the first time.


I was shocked by the extremes of the freelance spectrum. I was both overcharged for low-quality work and undercharged for top-notch work during my first week. After a few weeks of managing other freelancers, I have pretty much figured out what to look for in terms of getting the job done.


So, this is my advice for every aspiring freelance strategist.


On what to do.


But more importantly, what not to do.


1. Lead yourself by owning your results


If you’ve secured a bigger project, especially one that will be needing over several weeks, you should own the responsibility to update the Project Manager with results. I highly suggest you schedule weekly or at least biweekly check-ins that you use to update the client on the project’s progress.


In most cases, a short email update is enough.


You’d be surprised how much value this simple update has for your client. The Project Manager can use it to update their boss and it takes the hassle of reaching out to you off their plate. By leading yourself, you show that you care about the outcome and are eager to be an asset to the project.


2. Be transparent with pricing


I was shocked at how much of a thing this is. If a prospect asks you for a quote, be as specific as you possibly can. They won't hire you if you aren’t, or try to avoid the question altogether. You become an estimable cost by ensuring that your invoices are on point with what you discussed beforehand.


Pricing is the main point where you establish trust.


And it’s something that is extremely valuable in today’s competitive cycles. By the way, if you’re faced with a client who doesn’t ask you about quotes when sending a new project your way, I believe you should still respond with a quote to avoid later discussions and lead with transparency.


3. Don’t take gigs you aren’t skilled for


I’m currently facing this problem with an agency that agreed to a big gig and has now realized they may be lacking the skills. This is extremely frustrating. The project is getting increasingly delayed, and I’m spending a ton of time communicating with the agency and quick-fixing problems.


The project cost is skyrocketing every week.


This is a bad experience for both parties.


Decline projects you don’t have the skills for.


I know it sucks to pass on good business. But you’ll save yourself and the client a lot of hassle. In general, say no if you lack the skills or if you lack the time. If you overestimate your abilities and realize it, communicate this with your client to give them the possibility to plan for potential delays.


4. You own your contract


I was hard-pressed to know how many freelancers start working without contracts or don’t seem to care about the details. If you are one, you may as well be ready to get burned. Especially if you’re working with creative deliverables, it’s important you make the ownership part clear from day one.


Will the client get all rights to your work?


Do they receive it once your invoice is paid?


Or when the project starts?


How many revisions can you make?


Or how much time will you be spending?


It makes sense to take the time to develop a contract that is personalized to your needs. If you’re working with a bigger client that has standard procedures for dealing with freelancers, you can ask for them to add points to their contract and make sure the scope of your work is clarified at best.


More than everything else, wait for a clear go.


This actually surprised me the most when I started working with freelancers. More than one of them started working on a project before a contract was mutually signed, a brief was specified, or pricing was agreed on. This can go really, really wrong, not only for the client but for the freelancer as well.


If you don’t wait for a clear go, you may end up not getting paid, working with an unclear brief, and wasting a lot of time. Plus, your client may feel you’re not trustworthy if you assume you can start a project without their clear consent. Make sure you put the signatures before starting any work.


5. Demand a proper brief


Freelancing is not a guessing game. Sadly, many Project Managers don’t understand what a good brief is. This is due to the fact that they’re busy, they’re ‘in’ the product, and they often don’t understand the production process a freelancer goes through. This isn’t always a red flag though.


You need to guide your client towards the brief you need.


I suggest you ask clear questions, going through a checklist of things you need to know in order to start production. It also helps to ask for additional material that already exists: product demos, FAQs, and client cases. If you’re missing essential information to get started, make this clear to your client.


Being a freelancer is not that hard


Most clients understand we’re all humans and that there will be mistakes, delays, and conflicts. What matters is that your behavior can be estimated. When I work with a freelancer, it’s usually due to time or budget constraints. This means being easy to manage is one of your top USPs as a freelancer.


And what’s the easiest to manage?


Consistency.


I want to have a feeling for when I can expect an answer from you, how available you are for calls, and if you communicate well in writing or are better dealt with on a call. All of this is easy to estimate if you are consistent. This industry demands just as much interpersonal skills as core domain skills.

Subscribe to Read. Write. Repeat.

bottom of page