I don’t think many copywriters see the trend that’s been taking place in the freelance market for the past few years now.

But I do know that it’s not slowing down.

What I’ve noticed is that there’s a new paradigm in how freelance copywriters and clients are going to HAVE to work together going forward, if they’re both going to have successful businesses.

And it runs quite contrary to the old model that’s been working for almost a hundred years.

How It Used To Be

From what I can tell from all the old Gary Halbert newsletters and copywriting books of yesteryear, things were a bit different for freelance copywriters.

A business owner created a product or a book or an offer. You wrote a sales letter (sometimes a space ad). And the business owner would take your letter and mail it 10 million times if it worked.

If it didn’t work you might tweak it and test new angles until it did work.

Then, you’d collect a nice royalty check every month for years (on top of your big fat upfront fee).

The business owner would be happy as they could keep mailing this asset week after week after week and profit.

This Model Is Dead

The gold old days are over.

The whole “writer’s lifestyle” – where you can spend all day at the beach while the postman stuffs your mailbox full of royalty checks is gone.

The internet changed that.

And things will never be the same.

Now, you don’t just have one kind of project.

From what all the old timers say… sales letters used to be king. And structurally, depending on market awareness levels, they weren’t too structurally far off from a space ad.

This was pretty much all you had to write back then.

Now, businesses don’t just need sales letters or space ads.

They need a ton of things written:

  • Emails
  • Sales letters
  • Facebook ads
  • Squeeze pages
  • Order pages
  • Upsell pages
  • Cross-sell pages
  • Downsell pages
  • Thank you pages
  • Youtube ads
  • Explainer scripts
  • Video scripts
  • Webinar scripts
  • Product launch sequences
  • Social media posts
  • Blog posts
  • Tweets
  • In-product copy
  • Package inserts
  • Direct mail pieces
  • Radio Ads
  • Podcast ad rolls
  • Teaser copy for every piece of content
  • Articles
  • Whitepapers
  • Slide decks
  • Messenger bot campaigns
  • Funnels
  • Strategy outlines
  • SEO stuff
  • Ebooks
  • Product descriptions
  • Etc…

Sure, some of this stuff might have been around back in the day. But thanks to the internet, there’s an EXPLOSION of copy needed to run a business.

Which is a good thing.

But it’s a bad thing if you’re a writer who thinks you can start your career off just writing sales letters right out of the gate.

It’s going to be a tough battle.

And sure, there are people who survive doing that.

But there’s a new model for achieving success in this game if you want to not only survive… but thrive.

How To Win The Game

When I was a school teacher, the biggest obstacle for me escaping my job was not having enough consistent client work to replace my salary.

Sure, some people just burn the lifeboats, cross their fingers and hope for the best.

But I was planning on getting married.

I was planning on buying a house.

I wasn’t willing to put my life on hold and “wing it” on my own.

I wasn’t willing to eliminate my main source of cash flow until I knew I could match and/or exceed it.

I knew that I had to find a consistent source of income for my freelance copywriting business before I could successfully make the jump.

I knew the only way I’d win the game figuring out this whole “recurring revenue” thing in my freelance copywriting business.

Rule #1 Of Freelance Copywriting Success

The first rule of investing is “don’t lose money.”

The second rule is see Rule #1.

For freelancers, the first rule is “keep the money coming in.”

There’s nothing worse than being needy and having to whore yourself out to try to get a gig just to pay the bills.

Clients can smell neediness.

This sixth sense is ingrained in all of us.

We can sense when the person we’re talking to needs something more than we do.

And when we sense this, we know we have leverage.

This is why so many freelancers settle for cheaper rates or give up all of their power in a client negotiation.


It all comes down to need.

Your level of success as a freelancer is inversely correlated with your levels of need.

The less you need, the more you can get.

And the more you need, the harder it is to get what you want.

The best way to eliminate need:

Keep the cash coming in.

Month after month.

More and more.

Build up the war chest.

Build up the F.U. money.

When you don’t NEED anything, freelance copywriting is the most fun job in the world.

When you have all of your financial worries taken care of, you can take on whatever clients you want, doing whatever kind of gigs you want, at whatever price you want.

The New Paradigm For A Successful Working Relationship Between Freelancers And Business Owners

I don’t think you’re going to find a lot of success in this game if you’re (A) starting from 0 and you’re (B) trying to get by just doing one-off jobs.

And there’s a good reason why.

You see, when you first start out in this game, you’re brand new.

No experience.

No samples.

No confidence.

No clients.

No testimonials.

No self-worth.

No nothing.

And within the first twelve months, most copywriters expect they’ll be making $10,000/month.

Kind of laughable, really.

You see here’s how it goes in real life:

You decide you want to do something >>> you find a mentor/master who can show you how it’s done >>> you begin your apprenticeship and soak up all of your mentor/master’s knowledge >>> you spend a long time practicing your craft and eventually become proficient (going from 0% to ~80%) >>> you become a journeyman and work to go from 80% proficiency to 90-95% proficiency >>> you decide to open your own shop (or go freelance) and do your own thing. You are now the master/mentor.

But here’s how most people try to go about the whole freelance copywriting thing:

Decide you want to do something >>> read a bunch of books >>> immediately try to get clients with no experience or samples or practice >>> get frustrated when you’re not hitting your goals.

See what’s missing from the second path?

There’s no apprenticeship.

There’s no period of time where you’re learning how it’s done.

There’s no period of time when you’re getting your reps in.

There’s no feedback loop…

It’s All About The Reps

The only reason I am where I am today is because I knew that I sucked horribly, and the only way I was ever going to get better was to get a lot of reps.

I knew my first 10 sales letters would be god awful.

I knew my first 100+ emails would probably be cringeworthy to read.

I knew I wasn’t good when I started.

And I knew I’d have to fail a lot until I GOT good.

So, what I decided to do was just accelerate this whole process.

I decide to book myself solid with every crappy job I could find. I took free gigs. I took gigs from embarrassingly low prices. I took gigs in every niche I could just so I could start failing and fail faster.

Now, here’s what I learned:

My stuff actually wasn’t terrible.

Turns out, if your client has a good product and a good list, it’s kind of hard to completely screw up the copy. Unless you really try.

And I also learned that after doing every kind of project a few times, I got really good at it.

But I still needed to accelerate things even faster.

So I started seeking out…

The Holy Grail Of Freelance Copywriting Gigs

If you’re going to survive as a freelance writer you need some form of stability.

You cannot live the rest of your life wondering where the next check is going to come from.

I mean, yes… in the grand scheme of things, we all do to some point – even employees have this worry.

But if you’re starting from zero every month and literally have no clue what’s going to happen to your income over the next 30 days, you’re in for a rough life, my friend.

The ultimate form of stability, security and freedom for freelance copywriters are retainer gigs.

And the moment you get your first retainer, the moment you realize you’re going to be getting a check every month and you can shift more focus to mastering your craft… that’s the day your life is going to change forever.

Discipline Equals Freedom

Some copywriters are scared of working with only one or two companies on a retainer basis.

It smells suspiciously of a J.O.B.

I understand the concern.

But I think getting a retainer is the most freeing thing you can do for your copywriting career.

Instead of worrying about the next client, you just get up every day and write.

When you’ve done all your work, you’re done.

You have the freedom to do what you want.

One of my favorite podcasts is Jocko Podcast.

Jocko Willink’s famous mantra is Discipline Equals Freedom.

By having the discipline to do the hard stuff, you can enjoy a greater sense of freedom in your own life.

It’s a deep idea that I’m not going to get too into the weeds with here.

But it’s completely applicable to becoming a freelance copywriter.

You need the discipline (and the opportunity) to write every single day.

Copywriters Are People Who Write Copy Every Day And Get Paid For It. If You’re Not Doing Those Two Things, You’re Not A Copywriter.

I think a lot of people want to get into copywriting because of the freedom aspect of it.

They want to not be at a 9-to-5.

I understand that desire more than anyone.

But I think what a lot of guys and gals don’t realize is that if you’re going to do this, you’re going to have to work.

You’re going to have to write every single day.

You’re going to have to study effective advertisements every single day.

You’re going to never be able to turn your brain off, and you’re just going to have to be OK with that.

I think young writers get enamored in the lifestyle and the glitz and the glamour of the digital nomad lifestyle… and the Ferarris in people’s youtube videos and all that stuff.

But the life of a writer isn’t always a glamorous one.

You gotta write – a lot.

Every day.

You’re going to write some good stuff.

And then you’re going to wake up the next day and write some absolute dogshit.

You’re going to have campaigns that bomb.

You’re going to have deals that fall through.

You’re going to get your hopes up and have your dreams crushed soon after.

You’re going to have to put your ass in that god damned chair every single day and produce, whether you feel like it or not.

Copywriters write copy.

Copywriters get paid to write copy.

Those are the only two pre-requisites for making this work, but you need to learn how to make both of those things happen.

The #1 way I’ve found to (1) ensure that I’m writing every single day and improving my skills by having my stuff ACTUALLY TESTED and (2) ensure that I’m getting paid for this is by getting retainer gigs.

What A Successful Freelance Copywriter Looks Like In 2018 And Beyond

A successful freelance copywriter in this day and age is going to have at least one retainer.

They’re going to choose one, two, maybe even three companies that they form a deep, lasting relationship with.

They’re going to do this because they understand that to become the top in their field, they need a ton of tested reps.

They know they’ll benefit from writing with a feedback loop between their ads and their market.

They know they don’t want to spend half the month doing research for a new client every single month.

They know that they’re going to be more than just the guy or gal who writes words on paper for a business owner. They’re going to treat their client’s business like it’s their own.

They’re going to nurture their clients business and think critically about all parts of a campaign and the overall marketing strategy.

They’re going to focus all of their energy into creating the best possible result for that client… and they’re not going to worry about where the next check is coming from because they know if they do an effective job for this small handful of clients… they’ll never have to worry about money again.

This is how you win the game.

The game has changed.

It’s never going to be like it once was.

You’re going to have to adapt what you’re doing, or you’re going to be left behind.

Or worse… you’re going to have to find a new career.

How To Get On The Path To Success

Seeking out deep relationships with a handful of clients is the best way to become a world-class copywriter.

In my mind, it’s the only way to achieve any kind of long-term success in this game.

If that’s your goal, I’d like to invite you to join my email list and sign up for my free course, How To Land Your First Four-Figure Copywriting Retainer Deal below…

10 thoughts on “The New Model For Freelance Copywriting Success In 2018 (And Beyond)”

  1. Pingback: An Open Letter To An A-List Copywriter (From The Guy You Lambasted In Your Last Email) - The Email Copywriter

  2. Dude, Chris, great job laying this out in detail. I’ve passed it along to a few people, especially some younger folks who’ve been asking questions about the biz (including how to get more traction).

  3. Pingback: Round II: Recap Of My “Closed Door” Discussion With The A-List Copywriter - The Email Copywriter

  4. This is great Chris, just stumbled upon your site today and read a few of your blog posts. You’re killin it.

    Already signed up for your course, but an in-line opt-in form at the end of the article could be helpful for others!

  5. Great blog, I actually read every single word! I didn’t think I was even capable of that anymore.

    As a newbie freelance copywriter I found this very insightful. Thanks for the tips 🙂

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