Hey Freelancer! Get that money.
So I want creatives to get paid. I want us to live off the work we love to create. I want these talented fuckers — maybe just like you — to quit that hospitality job, that retail job, that corporate BS life and do what’s inside your heart.
And after over a decade running creative production studios and hiring and mentoring hundreds and hundreds of creatives, I can see 2 clear paths to making money with your craft:
Being a freelance warrior
Running your agency filled with other creative warriors
That’s 2 paths. There are more, and nuances to different applications. But if we’re talking creative business, these are the ways I have found creatives can make a steady career and income.
For myself, I’ve done the freelance life as a musician and creative consultant, but the majority of my career has been growing agencies and hiring photographers, retouchers, videographers, editors, writers, graphic designers, musicians, stylists — and everything around that photo and video production world.
I know people can get paid for this because a) I’ve made a great living from it, and b) I have been blessed to be able to pay people to work in this space. In fact, last I checked, I had paid over 10 million dollars to creatives. That’s awesome.
So if you’re thinking where to take your career, I want to help break down in this video some of the pros and cons of one of those 2 main options.
Again, this is just all from my experience. Try and watch with an open mind, and it will be your task to apply it to your chosen field. You could be a fashion designer, or a tattoo artist, or even a freaking hair stylist — whatever the path, I’m pretty sure some degree of this applies if you are creative enough to apply it.
So first up is the freelancer life.
You’ve got your tools, your creative medium, you’ve spent the time honing your skills, and you’re now at the level where you’re ready to get paid — or possibly have been paid a bit for odd bits and pieces. Awesome!
If you’re a freelancer now looking to get even more work, or better work, this might help as well.
The world of freelance can be a tumultuous one — but also very rewarding.
The pros include:
You can make a lot of cash
You can dictate when and where you work
Time and freedom is yours to control
There could be a great variety of work you can do
You can be spontaneous and adventurous
The cons include:
Instability in cash flow — you can make no cash
Lack of security
Having to sell yourself and find new jobs
Like I said before, I’ve hired a lot of freelancers over the years.
I’m going to share with you now my observations from seeing what freelancers get the most work, get the best pay, and are most requested by clients.
You might be surprised by the answer.
I’ll start by saying this — I think as a freelancer, your main sources of income will be either an agency (like the one I own) or independent brands/companies, etc.
Either way, the following tips run true.
Here’s the kicker:
The best freelancers I’ve ever seen — the ones that crushed all the others — were almost never the best at their craft.
They were average to slightly above-average creatives.
But they worked. And they made a lot of money.
How?
Because they had exceptional people skills.
Which, as a creative — and if you know any creatives — is generally a scarce resource among us, am I right?
There are obvious exceptions. My best video editor doesn’t need to talk to people, so people skills are redundant. His work is incredible, and he is trustworthy and reliable.
BUT — if that editor had a toxic character or an attitude with the team, I’d get rid of him regardless of skill. So there’s that.
And what do I mean by people skills?
Well, they have charisma.
They ask questions.
They appear interested and invested.
They can influence people and have an infectious positive energy.
They make people feel good.
I’m telling you, that means the world to clients.
Does the quality of the work have to be high? Sure.
But I’d argue the quality of the person needs to be higher first.
For example, I’ve had incredibly talented photographers get given no work because of their attitude, ego, or even just bland personality — while average photographers make absolute bank.
The good news is — I 100% see it as a learned skill.
Like any creative medium, you might suck at first — but the more you practice, the less you seem to suck.
Pick up Dale Carnegie’s book How to Win Friends and Influence People to get started.
An adjacent note to that: Look good. Show up right. Look the part as a creative professional.
It’s a shallow, cruel, aesthetic world. That’s the reality of it.
People want to work with good-looking people.
Now — you might not be a supermodel. I’m definitely not.
But if you work out, and you’re healthy and confident, then the aura you hold yourself in will be something attractive to clients.
Sorry if that offends anyone — but these are just my observations.
Fit people get more work than unfit people.
And I know plenty of businesses that see your body as a reflection of you.
Think about the traits needed to have a healthy body:
Do you have impulse control?
Are you disciplined?
Are you committed and consistent?
Are you confident?
Do you even like yourself?
Are you ruled by emotion?
Do you only do things when you feel like it?
These are all assumptions that are made.
Another big thing I’ve noticed with top working creatives:
They take on working with a company as if it were their own.
They’re not just a freelancer — they become a representative of that company.
They audibly support the company.
They align with its values.
They believe in the owners and what they’re doing.
And they become champions for that company.
I’m telling you — this is a superpower if you can master it.
Yes, your clients are your clients. There’s an exchange of value — you work, they give you money.
But if they can tell that you are rooting for them to win, and you believe in them?
That money will keep flowing.
In fact, I’m going to repeat that because it’s so important:
If someone feels that you believe in them and their mission, they’ll have you around as much as possible.
Lastly — be available and communicate fast.
Think about this: there is usually someone whose job it is to book freelancers.
Make their life easy. No-brainer, right?
My booking coordinators have a list of 20 photographers they can call for a job. Guess who gets the first call?
The photographer who replies the fastest and locks something in — so they can move on with the rest of their day.
It’s never the person with the most experience or the most industry awards.
So everything fast. Reply fast. React fast.
Time is our greatest resource.
Use it to your advantage.
Success loves speed.
Speaking of time — I’m going to wrap this up.
Because hey, I have real businesses to run. This isn’t my gig. This isn’t how I make money.
But these are a few tips I thought I’d share that you probably don’t hear all the time.
I’ll break down the agency side in another video.
Because truthfully — you freelancers have a special place in my heart.
You’re like the wandering Ronin — living on your own terms, fighting, never knowing where the next meal will come from...
But you back yourself.
And that — I think — is badass.
Keep creating.
Keep evolving.
And create the life you want — on your terms.
