Things You Should Know About Working With Freelancers

Most (/all) freelancers didn’t start out because they were drawn to contracts, invoicing systems, and quarterly tax estimates. We started because we found something we loved doing, something we were strangely good at, and something we needed to share with the world.

Creativity is at the core of this path. And to do it sustainably, we had to learn business as a survival skill. That means that the business side may look different from what you’re used to with larger teams and corporations.

So if you’re coming from a structured environment with legal and HR departments and locked-in SOPs, be aware:

• Freelancers each run their business differently.

• There’s no universal playbook.

• We’re often adapting on the fly.

If something seems unclear, ask your freelancer directly and honestly. They will appreciate you taking the time to communicate openly — especially if you’re in a niche they haven’t worked in before.

That sounds like… a really difficult business relationship, right? Wouldn’t it be better to hire the huge marketing agency (who makes the same type of content over and over and over again)?

That might tick the box for you. But the trade-off is in truly original work that can’t be mass-produced.

When you work with a freelancer, you’re not getting a templated productized service that’s churned out in bulk. You’re getting a customized creative partnership. Granted, it requires more work from you than entering a prompt into a generative AI engine — because you’re working with a real human being putting their soul into something that’s made just for you.

The upside — it’s human, original, and made with care. And that shows in the final product.

“The work will always be received in the same spirit with which it was created.”

I can’t remember who said that but it feels appropriate to include here.

Also — because freelancers aren’t bogged down by internal politics or corporate red tape, we have more creative freedom — and that shows up in the work.

You’re hiring our artistic originality. If someone’s work resonates with you, it’s probably because it carries a creative voice you can’t find anywhere else.

You’ll get their style — unless you specifically ask for something different. And if you do need something that matches your brand’s exact aesthetic, here’s what helps:

• Don’t just tell your freelancer what you want in words — show them with visual examples.

• Use multiple examples and explain what you liked about each.

• Doing this before work even begins keeps the creative back-and-forth to a minimum and helps your freelancer create something that aligns with your vision and their strengths.

Just like in any good collaboration, the clearer the shared vision, the better the outcome — in terms of aesthetics, overall net happiness, and in meaningful results for your brand (i.e., increased revenue, trust with your customer base, reputation in your community).

When you work with a freelancer — if they’re a good one — you’re working with someone who’s doing it not for money or notoriety, but for the love of the game.

Us freelancers care deeply about what we’re making, and we want you to care about it too.