The Ten Commandments for Successfully Working With a Freelancer

I love freelancers.

That probably isn’t surprising, considering I am one.

I also love the clients who hire them. Most freelancer-client relationships begin with good intentions on both sides: the client needs help, the freelancer has skills that can make life easier, and everyone is genuinely hoping this will become one of those magical working relationships where things simply get done. And sometimes it does.

But freelancers and employees are not interchangeable. The expectations that work beautifully with one can create frustration with the other. Most problems I’ve seen don’t come from bad people or bad intentions. They come from unclear expectations about availability, ownership, communication, scope, and what exactly you’re paying for.

So, in the interest of peaceful collaboration, healthy boundaries, successful projects, and freelancers everywhere continuing to answer their emails without developing a nervous twitch, I offer you:

I. Thou Shalt Remember: Thy Freelancer Is Not Thy Employee

Your freelancer works for themselves. That means they choose the hours, schedule, and rhythm that allow them to do their best work.

If you need someone online from 9 to 5, available every Tuesday afternoon, or poised at their desk precisely when you need them, congratulations: you may be looking for an employee.

A freelancer can absolutely be dependable without being continuously available.

II. Thou Shalt Not Expect Thy Freelancer to Love Thy Business More Than Thou Dost

A great freelancer can care deeply about your business. They may celebrate your wins, worry about your systems, notice things you haven’t noticed, and occasionally lie awake thinking, “There has GOT to be a better way to do that.”

But they will never care about your business quite as much as you do. Nor should they.

It is your livelihood, your vision, your risk, and possibly the thing you’ve been thinking about since 3:14 this morning.

Expecting a freelancer to carry the same emotional ownership is unreasonable.

Expecting them to care, do excellent work, and take their responsibilities seriously? Completely fair.

III. Thou Shalt Ask Before Thou Delegatest

Before dropping a project into your freelancer’s lap with the cheerful words, “Whenever you get a chance,” ask whether they actually have a chance.

Freelancers usually have multiple clients, competing deadlines, and carefully arranged workloads. Knowing their bandwidth before assigning work isn’t excessive politeness. It’s how projects get completed well.

A simple, “Do you have room for this?” can prevent a surprising amount of chaos.

IV. Thou Shalt Purchase Thine Own Dang Tools

If your business needs software, a subscription, a platform, an app, or some strange little piece of technology that only your company uses, that tool belongs to your business.

Please purchase it.

Then give your freelancer access.

Your freelancer should not be maintaining an ever-growing collection of $29/month subscriptions because seven different clients each decided they desperately needed something.

Thou shalt own thine own software stack.

V. Thou Shalt Give Projects, Not Attempt to Manufacture an Employee From Afar

Freelancers often thrive when they’re given ownership of a project, outcome, or defined area of responsibility.

“Please build this workflow.”

“Please organize this system.”

“Please create this campaign.”

“Please figure out why this process keeps breaking.”

Excellent.

“Please sit nearby digitally all day in case I suddenly think of something.”

Less excellent.

If what you really need is someone consistently performing a tightly defined set of daily operational duties on your schedule, again: you may not be looking for a freelancer.

VI. Thou Shalt Allow Thy Freelancer to Leave the Village Occasionally

Freelancers take holidays.

They take vacations.

They have families, appointments, lives, and occasionally the audacity to go somewhere without Wi-Fi.

They should communicate planned absences reasonably. But they are not automatically responsible for making certain your entire operation is perfectly tucked into bed with a glass of water before they leave.

If one person being unavailable for several days sends your business into crisis, the issue may not be the vacation.

It may be the system.

VII. Thou Shalt Remember That Other Clients Also Exist

If your freelancer isn’t available to you, that does not necessarily mean she’s drinking coffee on the porch wondering what to do with herself.

She may be building someone else’s workflow, troubleshooting a scheduling disaster, writing copy, fixing a CRM, untangling an automation, sitting in a client meeting, answering twelve emails, or trying to determine why something that worked perfectly yesterday has suddenly decided it no longer believes in technology.

Freelancers juggle more than most clients ever see. That’s part of the job. Your project matters. It just isn’t the only project.

VIII. Thou Shalt Not Expect Thy Freelancer to Own an Entire Haberdashery

A good freelancer wears a lot of hats.

Possibly an alarming number of hats.

But she does not own the hat store.

There will be things she doesn’t know how to do, platforms she hasn’t used, and skills she hasn’t yet developed. That’s normal. What matters is whether she’s willing and able to learn.

And if you’d like her to learn something specifically because your business needs it, expect to pay for that learning time.

You aren’t just paying for the finished task. You’re paying for someone who is expanding her expertise so she can solve a problem for you—and probably solve it much faster the next time.

Skill development has value. Even when YouTube is involved.

IX. Thou Shalt Remember: Thy Freelancer Is Not Karnac the Magnificent

Your freelancer cannot interpret smoke signals, vague emails, mysterious Slack messages, or instructions that begin with, “You know that thing we talked about?”

Say what you mean.

Ask the question.

Make the request.

Tell her what outcome you want.

And when she asks a follow-up question, please answer it.

Clear communication saves time, money, frustration, and several unnecessary rounds of detective work.

Also—and I say this with love—consider rereading your email before hitting Send. Sometimes the problem is not that your freelancer misunderstood you. Sometimes the email was written during turbulence.

X. Thou Shalt Cease Thy Search for the $20-an-Hour Unicorn

Every job posting seems to want one.

A rockstar.

A unicorn.

A ninja.

Someone who can write copy, build websites, manage projects, configure automations, run a CRM, edit video, create graphics, answer phones, understand HIPAA, troubleshoot Zapier, develop strategy, manage your calendar, and somehow also “have a great attitude.”

These people do exist. They are experienced. They are efficient. They are busy. And they are usually not cheap.

A broad skill set represents years of learning, experimenting, failing, fixing, practicing, and figuring things out.

You may look at a task and think, “I could do that.”

You might be right.

But the better question is: How long would it take you?

A skilled freelancer may complete in an hour what would take you half a day because she has done some version of it fifty times before. That efficiency is not evidence that the work was easy. It is evidence that she knows what she’s doing.

Stay in your lane.

Respect hers.

And for the love of all things freelance, please stop asking unicorns to work for pony prices.