If you bring in a freelancer, chances are you’ve got:
- A specific need.
- Something tactical.
- Something that needs to get done now.
But you don’t need a full team, just someone who knows how to do the work. So you find a specialist, hand it off.
That logic makes sense, and when it’s done right, it works really well. The expectation—whether it’s said out loud or not—is simple: hand it off, and it gets handled.
Sometimes, that’s exactly what happens. But sometimes there’s a gap between what you expected and what it takes to make it work.
At first, it feels like progress. You’ve got help, work is moving, and there’s finally some momentum. Then, things start to slow down. Not dramatically, but just enough to notice.
You’re checking in more than you expected. Clarifying things you thought were already clear.
Getting work back that’s close, just not quite there.
So you adjust it, send feedback, and you try again.
A few weeks later, you’re still in it. The same conversations, same revisions, and same sense that you’re working harder than you should be to get this across the finish line.
And here’s the part that’s hard to pin down: Nothing is obviously broken, but it’s not working either.
What’s actually happening
Most people assume this is a talent issue, and sometimes it is. Sometimes you simply hired the wrong person. That happens.
But more often than people expect, that’s not the real problem. What looks like “needing too much direction” usually isn’t that. It’s a lack of context.
They don’t know:
- What’s been tried
- What matters most
- What “good” actually looks like here
So they ask more questions, pause, or they take a shot and miss. From the outside, it feels slow. From their side, it’s just incomplete information. What’s actually happening is simpler, and harder to see:
Everyone is doing their best inside something that isn’t set up to work.
The freelancer is trying to deliver. The internal team is trying to guide. Projects are moving forward. But there’s no structure holding it together. There’s no clear throughline, shared context, or person connecting all the dots.
So the work gets done, just not in a way that builds. t’s like trying to run a relay race where no one agrees on where the baton gets passed. Everyone’s running hard. They’re talented, trained, and capable.
But the handoffs are messy, and that’s where you lose.
The model problem
This is where it gets uncomfortable, because the issue isn’t just execution. It’s the model itself.
Most mid-market companies are running marketing in a way that looks reasonable on the surface:
- Hire specialists as needed
- Keep costs flexible
- Plug in talent where there’s a gap
That approach makes sense until you realize what it assumes: the pieces will connect and guide themselves. They don’t. And unless there are layers of experienced leadership shaping, guiding, and aligning the work, the system starts rewarding the wrong things: Activity over progress, output over alignment, and speed over cohesion
So even good people end up miscast. The right person, doing the right kind of work, but working inside a model that makes it harder than it should be.
Where the cost shows up
The hidden cost doesn’t show up all at once, or in obvious ways. It shows up in:
- Rebriefing work that should have been clear.
- Revisiting decisions that should have stuck.
- Reworking things that were already “done.”
This is supposed to be efficient. Flexible. Cost-effective. But that only works if the work actually works.
Because you’re not paying for the work once. You’re paying for it:
- Again when it needs to be redone
- Again when priorities shift
- Starting over. Again.
It shows up in resets.
- Switching freelancers
- Rethinking direction
- Starting over. Again.
It shows up in time, but not just time spent doing the work. It’s time spent:
- Managing
- Clarifying
- Chasing
- Fixing
And eventually, it shows up as something else:
Freelancer fatigue.
You probably don’t call it that, but you feel it, and it’s real. You’ve tried a few people, made some progress, but nothing has really clicked. At some point, the question shifts from “Who should we hire?” to: “Why does this keep happening?”
A different way to look at it
It’s easy to keep focusing on the pieces, like finding better talent, giving clearer direction, and managing it more closely. Sometimes that helps, but it doesn’t fix the underlying issue. Because this was never just about the pieces. It’s about what they’re being plugged into.
The shift
When the structure changes, everything changes:
- Work starts to connect.
- Decisions stick.
- Momentum builds instead of resetting.
Good freelancers become easier to work with, strong contributors actually look strong, and weak links become obvious (and fixable).
Not because people suddenly got better. But because the system finally supports them.
One thing to leave you with
You might have a great team or a great freelancer. They might be working hard. And it can still feel harder than it should.
For a long time, we’ve said:
The marketing model is broken for the mid-market.
Not because the people aren’t capable. Because the way the work gets assembled and managed makes it harder than it should be.
And that’s where the real cost lives.
