The gap between where you are and where you want to be can be closed with just one learnable skill.

I figured that out during night shifts as a security manager — no control, no real money, just time to kill. So I taught myself direct response copywriting, and built the skill that bought my freedom.

I went from writing $25 articles to working with the biggest brands in my industry, writing funnels that generated over $25M in sales, and becoming top 1% in my field.

I write about the thinking, ideation and systems behind the work and my interests: 

How to be more autonomous, more persuasive, and more discerning about what you do and what you spend your time on - for greater leverage in life.

If I wanted to go from $0 to $100k as a freelancer in 12 months, here's what I'd do now (FULL PLAN BELOW):

1. Identify valuable companies that spit cash.

- No startups
- No independent coaches/solopreneurs, etc
- Companies doing over $5 million are a nice place to start



2. Identify a PROBLEM tied closely to their SALES PROCESS.  Examples:

- If I'm a graphic designer, for B2C I'd want to focus on creating "offer mockups" and checkout page graphics that invite the sale. OR I'd go high-ticket B2B and create beautiful sales presentations for their sales teams.

- If I'm a video editor I'm creating direct response Facebook ads and VSLs all day long.

- If I'm a copywriter, direct response marketing campaigns would be the only thing I'd remotely consider.



3. I'd connect with every freelancer I could find and offer them a referral cut.

- Warm intros mean I can command higher pricing to absorb the costs
- Warm intros mean I can close deals at a faster cadence
- Paid referrals keep incentivising freelancers to send me MORE work (the relationship is an asset that compounds, unlike a cold email shot).



4. I'd charge middlin' fees for rapid turnarounds - I wouldn't settle for rock-bottom prices just because I'm new.

If I'm new starting at $0, I can't compete on track record & reputation.
So it would be difficult to charge high fees.  Howevere, I wouldn't race to the bottom of the Upwork slush pile, either...

I'd simply charge "medium" industry prices by outworking my competition and marking up the work based on SPEED of delivery.  

And I'd go overboard on customer service/great communication.



5. I wouldn't target even monthly income spreads.

If we say $100k a year is $8,333/mo, earning $8,333 in my first month is unrealistic.

I'd simply target the amount over a YEAR, and let the later months in the year compound.

You make more money when you start extending your time horizons, and stop wanting everything to happen for you in the space of a week or a month.



Job done, I think.

Anything you'd do differently?

Cain Smith

Copywriter & Marketing Consultant | $25M+ in revenue generated | Writing about autonomy, strategy & one-person leverage

13 unreasonably simple habits that made me too expensive to hire in-house (even for a $200k Head of Copy job offer) :

1. No Zoom before 2pm - and batch all calls to Tuesday/Thursday afternoons. Mornings are for thinking and writing, not yapping.

2. Minimise "Manager" time and protect your "Maker" time like it pays your rent/mortgage (because it does).

3. Never start work without at least 50% of your fee upfront. Cash flow your business, always.

4. Stop saying "let me check my calendar." You already know if you want to do it. "I don't have availability" is a complete sentence.

5. Keep auditing your clients.  If one is becoming unprofitable, they have to go (it's nothing personal, it's business.  They'd say the same to you).

6. Kill your fluffy website.  Your passion isn't a differentiator.  Clients just care if you can make them money - lead with results.

7. Never allow a client to train you to be their employee.  All tasks/time management/focus allocation is done according to YOUR plan.

8. Keep raising your rates regularly, in line with demand and experience.  Never stay still.  Inflation/the economy doesn't (well the UK is stagnant, but that's a different story).

9. Never compete on price. 

10. Talk about your achievements more.  It ain't braggin' if ya done it - no one (apart from maybe your spouse) will promote you relentlessly and grow your reputation for you.

11. Keep talking about your goals.  Show them you have no interest in being "tamed" - you have big ambitions too.

12. Hang out with people who charge more than you. If you're the highest earner in your freelance group chat, you're in the wrong chat.

13. Get comfortable being unhireable. If companies keep trying to persuade you to join them on long-term retainers after working with you, and it just doesn't appeal to you... you're winning. They can't afford you. That's the point.

I write sales copy for a living, for 8 and 9 figure companies - I've sold MILLIONS of dollars of products.  And I always hate it when I see copywriters comparing copy to great novels & fiction.

They're almost NOTHING alike.  There are way too many fundamental differences for a valid comparison.

Writing direct response copy for a living changed my mentality around writing forever.

The stuff I write now?  I'd have HATED to read this stuff in my 20's.

The conversational tone, the logical sequence of beliefs, all the proof and "spoon-feeding"...

I'd have called it "bad writing."

And it IS bad writing, to an extent... 

If your goal is to write novels or poetry.

You see, the beauty and ecstasy of fiction prose is that it demands a lot of the reader.

The reader has to join the dots, fill in some blanks, explore some unoccupied spaces.

But with direct response copy - that's too much effort and energy for the reader to expend.

If I leave you with blank spaces to fill in... I've lost you.  You'll end up confused.  

And you'll go away and buy from someone else - someone who put in the extra work and joined all the dots for you.

Of course, some "purists" will resist this idea.

"But the reader will only buy if they FEEL like it's THEIR idea..."

Yes.  

But that doesn't mean you start writing sparse, minimalist prose and leaving them to figure everything out for themselves.

The reader can only form an idea - an idea strong enough to lead them to the sale - if they have all the information they need to arrive at that conclusion.  Even if you're dealing with a sophisticated audience and you deliberately add some friction - applications, "grabbers", paradoxical questions that force people to think and engage etc - all you're doing is greasing the sales chute for that particular type of buyer.

My take:

There are little bits & bobs of inspiration we can pluck from our favourite authors...

But if you want to get good at SALES COPY, don't waste much time studying novelists and poets.

Honestly - you'll learn more form the publishing house than the authors themselves...

By studying how the book is SOLD.

I hit 9k followers this week - but I first started posting in 2020! (I spent over 2 years not posting at all).  So what have I learned from this SLOW growth?


- Hate to say it, but volume and consistency matters.   

If you're not top of mind, you're not top of mind.  You knew that already though. Going AWOL for 2 years? Not good for post views and follower growth.



- Having a purpose is essential.

My LinkedIn strategy is - if copywriters, freelancers & creators are NOT subscribing to my email list, I have NO purpose being on here.  I post purely to attract email subscribers.  This can slow your growth down, because...



- Shitposting will get you more views and more followers.

Possibly even more email subscribers, too (although I'm sceptical of that).  But it will generally bring lower-quality people into your circle.  No thanks.  And it goes against my principles too, because I like to be an organised, purpose-driven kinda bloke.  Which brings me to...



- Posting without purpose is pointless (and immature)

I see loads of "professional" adults logging into apps on their phones and doom-scrolling and gossiping - the same kind of ultra-low quality, low-IQ behaviour they criticise their kids for.  And I could be just as easily zombified, if I didn't proactively fight against it. I write my posts in Buffer and schedule them, I check comments 1-2x per day - I'm in and out fast.  I have more important business to attend to.  Again, this slows growth.  But it keeps me intentional and deliberate and true to myself.  I just concentrate on writing good quality content off the platform.  And something I've learned about that is...



- Hooks are everything.  Well, 80% of everything, at least.  Like that bloke Ogilvy said.

Considering I'm a direct response copywriter, I was appallingly slow at figuring this out.  But every post on LinkedIn really is essentially a "cold ad."  You may have some regular followers, but you need to treat this as "cold traffic copywriting" - it's different to email.  



- Ultimately, though, I think the algorithm shapes audiences' tastes - audiences don't shape the algorithm.  

If you don't believe this (or rather, don't WANT to believe it) just look at how the mainstream press operates.  You see what they want you to see, hear what they want you to hear.  A "zeitgeist" is generally manufactured - the fastest-growing creators are the ones surfing trends the LinkedIn algorithmic gods have decided to reward this month.  So if you prefer to just write content YOU'D like to see (my approach) just accept slower growth as the trade-off.

 - - - - - - - - - - - - - - - - - - - 

If this post smells like "grim determination" and nothing more - trust your nostrils.

I don't really like LinkedIn at all, to be honest - in fact, I just I don't like social media.  I prefer email.

If you prefer email, too - and you'd like to hear from me in your inbox - you can sign up here:

www.cainsmith.com

As far back in my freelancing life as I can remember, I always wanted to be a direct response copywriter.

I used to read sales letters by Clayton Makepeace and admire his storycraft, his energy, the muscularity of his copy...

Hear stories of Eugene Schwartz making a fortune, living on Park Avenue, curating a fine art collection in his penthouse apartment...

Read about the copywriters who got flown to client offices, treated like rock stars, given equity & royalty deals that paid out YEARS after the work was done.

I used to read these stories and think to myself:

"It's always these guys.  You never hear about any blog post-writing legends!"

And at the time, that's what I was mainly doing. Writing blog posts.

I was only getting around $260 per post, give or take...

But in truth, my disappointment WASN'T just about the lack of money.

I had, after all, heard about some blog post writers earning 6 figures -  writing more specialist content, mainly for B2B tech companies.

The thing is... this work never appealed to me.  It always looked so dry & boring.

And let's be honest... no one ever TALKS about these people, do they?

No one really wants to DO what these people are DOING.

There just seems to be an unspoken understanding:

This stuff - 6 figures or not - just ISN'T the Super Bowl of our craft.

But direct response copywriting is.  The proof is all around you.

The greats everyone refers to - the copywriters people are TRULY inspired by - always seem to be direct response copywriters:

- Halbert
- Bencivenga
- Ogilvy
- Gossage
- Hopkins

And me? 

I wanted the excitement, too. The glamour. The challenge.  The power and the glory.

Being able to say: "I wrote a promo that sold over a million dollars worth of product."

Working with businesses your HEROES worked with.

And most importantly — knowing your work actually MATTERS...

That it drives revenue. That companies' offers succeed or fail based on what YOU write.

THAT'S the truly fulfilling side of this business.

So if you're a copywriter who's always felt curious about direct response, but felt intimidated by it or confused by it...

Don't allow yourself to be so easily disheartened.

The barrier to entry isn't as high as you think. 

And the opportunity is bigger than it's ever been.

In fact, this Sunday, I'm sending out a blueprint to my email subscribers on where I see demand & opportunity in the direct response landscape right now...

The skills required, the niches and products that are hot, the stuff that's changed from the 90s and crucially—the stuff that's remained the same.

Personally, I think there's a real shortage of practical, relevant and CURRENT intel like this.

Especially from people still actively writing at the top end of the market.

I'm trying to bridge that gap.

So if you're at all curious and interested...

The email goes out this Sunday, 1st March.

Subscribe here to get it:

www.cainsmith.com

Stories sell — and I sell $25k+ copywriting projects to clients by telling them TWO types of stories...

I give names to both of them.  And the first type of story I call "Performance."

These stories reveal the nitty-gritty of what I do.

They're highly tactical...

And they include case study wins & deep-dive insights into my "Hows" and "Whats."

Founders and CMOs LOVE this kind of content. Because a lot of the time, they can implement the advice quickly and get an almost immediate uplift in results.

"Performance" talk is also advanced stuff - it shows you're a serious operator who knows your stuff.  And for this reason it differentiates you...

Because anyone can write generic fluff, after all.

Then there's the second type of story...

I call these stories "Perspectives."

This is content where I reveal the depth and texture of my character...

My philosophy towards business, success, and life in general.

My Perspectives are sometimes so deep, they resonate strongly with my clients on an emotional level.

- "Performance" shows my clients what kind of a copywriter/marketer I am.
- "Perspective" content shows my clients what kind of a man I am.

When you're charging premium prices...

And essentially entering into mini-partnerships with clients on projects...

BOTH of these things are vitally important.

I've worked in-house at some THE biggest companies in DR - & helped an ecom brand grow from $900k/mo-$3m/mo. So some people think it's strange I'm going it alone as a freelancer...

- Why not stick around in the machine and become a Publisher for the one of the big boys?

- Why not stay with the ecom brand and become CMO, maybe sweat out some phantom equity and work towards a huge exit?

- Why not just write in-house and take larger and larger stakes in what you write - you could end up making even more money this way?

All of those paths are no doubt highly rewarding.

And the people who commit to them and succeed - I salute you.

But I see the path I'm taking as a freelancer as absolutely no less successful.

- Cash flow-wise, I make more money than most Publishers and CMOs (feels good in the "here and now", at least)

- My positioning and "outward" reputation (as opposed to in-house, where you're kept under wraps) has opened up options for me.  I get lots of opportunity, which buffers risk.

- I get flexibility and "schedule freedom" that I value more than anything else in business.

- All of this can be channelled towards some larger, equity-building venture at any point in the future if I choose.  I haven't "lost out" on any of these opps.


Lots of assumptions get made about why talented people choose to be "just" freelancers.

But I think many of the people making these judgements need to look at THEIR models holistically - their income, their time & schedule freedom, their relationships/network and optionality - and ask themselves if their path is actually ANY better.

The answer to that question could be uncomfortable for them to hear.

I have 5 cunning client vetting questions that help me decide whether a project is a "Hell yeah" or a "Christ, no..."

1. What budgets & scale have your media buying team handled in the past?

For a direct response copywriter at least, this is probably the most important question on logistics.

I could write the world's greatest promo - but if the media buying team aren't good, your promo is getting seen about as much as a typical organic LinkedIn post!

Ergo...

I don't make much money, no matter how well I actually perform.


2. Who will be reviewing my work and to what extent? 

This is a Big Boy question. I'm not being territorial.

In most projects, I'm used to three stakeholders reviewing my work:

- The copy chief/publisher/founder
- The "guru" whose voice the promo is in
- Compliance/legal team

I want to make sure we have expectations around a streamlined and efficient review process set - before we even agree a deal.

If I don't like the process, the deal isn't happening.


3. How do you typically manage the process of split-testing and optimisation - and who is charge of that role? 

This question can achieve several things.

If you want to, you could upsell them on optimisation/CRO work if they don't have anyone who does that.

And if they DO have an optimisation team, it gives you the opportunity to ask deeper questions about their performance and track record - just like the media buying question.  Business is a team sport - your copy can't succeed in a vacuum.


4. What else have you got in the pipeline?

This is probably the most difficult question to ask on this list, because it sounds so nosey!

But I'm trying to get a feel for the business's larger, longer-term goals here - beyond the immediate project in question.

Yes, knowing this intel can obviously get you upsell and/or future opportunities.

But mainly, it shows me how THIS project fits into the wider strategy - and by reading between the lines,  what success looks like for the client - without asking that cringey, cliched "If I could wave a magic wand for your business right now...." question.  You'll learn more.  They'll tell you the truth, rather than what they want you to believe.


5. What is your experience paying royalties to copywriters & how does this process work? 

I only work on a royalty basis now so this is a crucial question for me.

But if you're new to royalties/inexperienced with them, it's still a great question to ask.

It does three things:

A) It anchors expectations (the implication here is that you EXPECT royalties, even though you haven't explicitly said so).
B) You find out whether they pay royalties or not, and
C) If they do, they tell you how the process works (so you don't have to lead it)

- - - - - - - - - - - - - - - - -

Adapt these to suit your industry/discipline - I hope they serve you well.

Retainer work can turn you into someone else's bitch if you're not careful...

Done badly, they can lead to:

- Similar duties & obligations of an employee, with
- NONE of the protections and perks.

I found myself working in a couple of bad retainer agreements in the past until I rediscovered my plums.

Here a few pointers on what to avoid in retainer arrangements:

- Meetings/huddles/calls unless absolutely necessary 

Any meetings you do attend need to be strictly focused on the work you're producing. You're NOT a part of their team so you don't attend "team meetings."  Your team is YOU.

- No "open-ended" retainer relationships.

They need to have a specified start & end time (3 months is a good sweet spot) with clearly defined deliverables.

- No Slack chat open door.

By all means, join their Slack channels but treat these like meetings.
Essential comms only (I treat Slack exctly the same as email - I check it 1-2x per day, switch notifications off, and don't reply ad-hoc requests the way an employee would).

Remember, they're not going to pay into your pension or handle your tax obligations for you or pay you sick pay or vacation leave...

As a freelancer, you're in the business of YOU.

You help grow clients' businesses so you can grow YOURS...

The #1 objective is always to grow YOURS.


If you like this kind of stuff, subscribe to my emails here:
www.cainsmith.com

This week I'm breaking down what I learned from Arnold Schwarzenneger about becoming a better copywriter & feeelancer - there'll be 4 actionable takeaways you can use for your business.

A little freelancer quirk I've noticed - top 5% freelancers don't tend to have websites.

Usually this boils down to an "Account-Based Marketing" approach:

- They attract the best opportunities by working with the best clients in their field
- They get to know these clients "in the shadows" - at events, in emails and WhatsApp chats, from warm introductions provided by other industry players
- They negotiate the best deals from a place of trust built via an "underground reputation".

I'm not crapping on websites per se.  If I felt I needed one, I'd have one.

I used to have one in the past but there was no strategy behind having it - I just thought I needed it as some kind of "business card."

Now, I work with the biggest brands in my field and we just chat and make deals over emails and WhatsApp voicenotes and brief Zoom calls.  

Yes, even the "cold" ones.

They don't opt into my email list so they can get the "Top 5 VSL Tactics Info Publishers Are Deploying Right Now!"

That would attract a totally different kind of client...

One I'd only be interested in atrracting if I was going for lower-ticket, higher-volume work.
It's all horses for courses.

However, I DO have a landing page (still not a website!) for a different enterprise - nothing to do with clients.

It's for freelancers and creators who want to become hard to underpay, even harder to replace, and impossible to control.

If you like the sound of it, you can join me here:

www.cainsmith.com

Copywriters - let's share cool, hidden, secret resources with each other...

THE CHALLENGE: You have to reveal ONE book/film/training/resource/anything that's made you a better copywriter... 

AND IT'S GOT TO BE OFF THE BEATEN TRACK.

Here's the basic governing rule:

NO Captain Obvious stuff alllowed.

Don't come at us with Eugene Schwartz or Gary Halbert or Joe Sugarman or Claude Hopkins or David Ogilvy or... you get the idea.

It must be an "off the beaten track" recommendation - a real hidden gem.

I'll give you mine.  It's a book (my copy is an ebook):

- Secrets of Successful Direct Mail by Dick Benson.

The backstory:

I originally got this book as free bonus when I bought Brian Kurtz's Overdeliver book back in 2021 (a gem of a book, too).

I didn't even read it at first - Brian gave away a gazillion bonuses with that book offer.  And Dick's book was just one of them.

But I finally read it last year - after it had squatted untouched in my Google Drive for nearly 5 years.

I was blown away.  This is like a field manual for serious direct response marketers.

Dick is the greatest list/offer man of all time.

He wasn't a copywriter - although he could spot great copy from a thousand paces.

This ebook is chock full of case studies from Dick's 40+ year career - that's all it is.  

Case study after case study after case study.

Which offers worked on which lists.  Which offers didn't work.  Price tests, payment terms, guarantees, publication formats, headline split tests...

206 pages of gold.

The vast majority of this will work in modern-day digital marketing, too (I recently structured a winning offer for a client modelled off one of Dick's winning case studies).

You're welcome , you're welcome, you're welcome.

What's your favourite hidden gem?

Share it here.

I've never once written a strong first draft of anything.  Not once in 8 years of writing professionally.

And I write 5,000 words or more of sales copy a week, for some of the biggest direct response brands in the world.

All of my best writing starts as something I’m genuinely embarrassed by at the end of Day One. 

Disjointed thinking, weak transitions, misplaced sections, arguments that started earnestly but went nowhere…

Even with all my research and planning and scaffolding - the first drafts always stink.
But I've learned something about that shitty first draft over the years, and it’s this:

IT’S THE PROCESS.

You’ve just got to let that first draft parade around on the page, as it is, warts and all, everything hanging out.

Your imagination is an exhibitionist…

You can put some clothes on it later.  Just let it be free for a while.

I’d bet good money on the writers who find writing HARD— at every level, in every discipline, copywriters, coaches, consultants, founders writing their own content — aren't struggling because they're bad thinkers.

I’d guess it feels painful because they're editing while they write - letting the inner critic jump in way too early.

And to be fair, the internal critic is a useful person sometimes.

But they belong in a separate office…

They shouldn't be hovering over your shoulder while you're giving birth to an idea, telling you how to handle it better.

The first draft has one job:

Get the thinking out of your head and onto the page — all of it, in whatever shape it arrives in. 

That's it. 

It doesn't need to be good… it just needs to exist.

The rest of your good writing will be down to good editing… 

And editing is a completely different job, done at a completely different time, by a slightly different version of you.

For  more philosophical musings such as this, go here:

www.cainsmith.com

How much money should freelancers invest into coaching, courses & communities? 10% of your revenue? More?

I don't divvy up my investment by percentage or amount.  There's never a set number.

I invest in these assets in seasons...

And currently, I'm in low season.

Prior t this, I was a member of a mastermind for about 7 or 8 months.

I got the knowledge I needed, and then I moved on - staying in it would have only been a distraction. 

Sometimes I'm in these programs almost purely for connections (if the size of my "luck surface area" in my network is the bottleneck of my growth).

Other times I'm in it for education - i.e. there's specific knowledge I'm seeking, and I want to unlock it.

In these "knowledge-seeking" seasons I can be very aggressive with my investment...

I'll throw the kitchen sink at a problem to solve it.

If, on the other hand, I KNOW what I'm doing...

I have a plan, I've devised a process, I trust it...

And now it's just a matter of patience & execution, blocking & tackling... just chipping away at the objective at hand...

I don't join or study anything else. And I stay "locked in."

My advice:

1) Be very focused on what you've chosen to learn - avoid broad, random, "scattergun" education.  It feels productive, but it isn't.

2) Bias yourself towards action. Get just enough education to perform - then DO.

3) Don't muck around with ANY other learning/skill development until you've solved the constraint in your development.  Otherwise you're avoiding solving problems - and you're being a procrastinator.

This rubric for skill development might not be to everyone's taste.

But it's definitely served me well.

And I think it's a pretty good way of seizing advantage of opportunities:

First, you identify an opportunity.

Next, you figure out what you need to do to take advantage of it.

Then you attack it.

- - - - - - - - - - - - - - - - - - -

If you enjoy stuff like this, you might enjoy my emails.  

I'm sending a "state of the union" address on the opportunities I see in direct response to my email ist this Sunday, 1st March...

And I'd argue that taking this approach to learning (as I've outlined in this post) and combining it with the knowledge you'll get from this week's email will compound the value.

Sign up here:

www.cainsmith.com

P.S. I don't republish my emails anywhere else yet...

So if you don't sign up before Sunday 2pm EST, you'll miss it.

The best freelancers I know think about client selection the way VCs think about deals...

Not every deal gets funded.  Not every pitch gets a meeting. 

And the deals that DO get close consideration aren't just scrutinised on the basis of the idea...

The infrastructure surrounding it is put under the microscope, too.

And this is the way I approach clients & projects.

When a new client approaches me - I'm interested in the the brief.  Sure. 

But what I'm actually evaluating is whether this business can deploy what I give them.

It's wise to see mental bandwidth as your balance sheet.  And every project you take is a capital allocation decision. 

You're deploying your most finite resource — focused, expert thinking — and you want a return on that investment.

Which means some clients are good investments...and some clients - well, they just AREN'T.

These are a couple of the green flags I look for before I commit my bandwidth:

- A media buying team that knows what it's doing. . 
- A business with a strong ability to create outsized value in the market. 

 A $3M company and a $40M company are not the same client, even if they're in the same niche and paying the same fee. The upside on the second is categorically different.

A VC doesn't fund a brilliant founder with no route to market. 

So I won't write for a brilliant offer that doesn't have strong distribution to the right audience. 

I've passed on projects that looked great on paper for exactly this reason — and never regretted it.

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