What 30 Years of Copywriting Taught Me That No Book Covers

The Lessons Nobody Writes Down

There is a particular kind of knowledge that accumulates only through years. Not the kind you find in copywriting books, and not the kind you pick up from a weekend workshop or an online course. It is the knowledge that forms slowly, through thousands of projects, hundreds of failures, decades of testing, and the quiet accumulation of patterns that only become visible after you have been doing this long enough to see them repeat.

I have been a direct-response copywriter for more than thirty years. I have written for Apple UK, IBM, Microsoft, and Citibank. I have worked across health supplements, financial services, SaaS, e-commerce, and information products. I wrote the campaign for Belron/Safelite that generated $523 million in tracked sales over nine years. And I have survived every cycle of "copywriting is dead" that the industry has produced — from the death of newspapers to the death of direct mail to the supposed death of everything at the hands of artificial intelligence.

What follows is not a chronological memoir. It is a collection of hard-won lessons — the things I wish someone had told me at the start, and the things that no one could have told me because they only make sense after you have lived them. These are the principles that shaped how I think about the craft, the business, and the future of turning words into revenue.

Research Is the Job. The Writing Is the Easy Part.

This is the lesson I would tattoo on the forehead of every copywriter starting their career, if they would let me.

When most people imagine a copywriter at work, they picture someone staring at a blank screen, searching for the perfect phrase. That image is almost entirely wrong. In my experience — across every niche, every format, every client — the writing phase accounts for perhaps 20% of the total effort. The other 80% is research.

Before I write a word of a sales page or VSL script, I immerse myself in the prospect's world. I read customer reviews — not the five-star reviews, but the three-star ones, where people explain exactly what they hoped for and exactly how they were disappointed. I read forum threads. I study support tickets. I interview customers, sometimes for hours. I analyse competing products, not to copy their messaging, but to understand what the market has already heard and become immune to.

The Belron/Safelite campaign is the clearest illustration of this principle. Five previous copywriters had failed to produce a campaign that met performance targets. They were all competent writers. Their copy was clean, professional, and logically structured. But they had all started from the same flawed assumption — that windshield replacement was a convenience decision. The research I conducted revealed something entirely different: the real driver was safety. That single insight, which came from deep research rather than clever writing, was worth $523 million.

This is the lesson that separates the copywriters who earn modest fees from the ones who command premiums and deliver outsized results. Your research ceiling is your results ceiling. No amount of writerly talent can compensate for a shallow understanding of the person you are writing to.

The Best Copywriters Are the Best Listeners

There is a romantic notion that great copywriters are great wordsmiths — people with an unusual facility for language who can craft sentences that sparkle and persuade through sheer eloquence. After thirty years, I can tell you that this notion is almost completely backwards.

The best copywriters I have known — and the best version of myself, on the projects where I have done my finest work — are not distinguished by writing talent. They are distinguished by listening ability. Specifically, the ability to hear what an audience is actually saying when they describe their problems, their fears, their frustrations, and their desires.

When I write email sequences or long-form sales copy, the most powerful phrases in the final piece are almost never my own invention. They are the prospect's words, reflected back to them. When you write in the language your audience actually uses — not the language you think sounds persuasive, not the language your client uses internally — you create an uncanny sense of connection. The reader feels understood. And a reader who feels understood is a reader who trusts you enough to buy.

This is what Gary Halbert understood instinctively. It is what Eugene Schwartz codified in his work on market awareness. And it is what I have found to be true in every single market I have worked in, without exception.

The practical discipline is straightforward: before you write, listen. Read customer reviews obsessively. Study Reddit threads, Facebook groups, Amazon reviews, and support forums. Pay attention to the specific words people use — not the polished version, but the raw, unfiltered version. Those words are worth more than any copywriting formula ever devised.

Copy That Impresses Copywriters vs. Copy That Sells

Early in my career, I wanted to write copy that other copywriters would admire. I wanted the clever metaphor, the unexpected turn of phrase, the headline that made people say "I wish I had written that." This desire nearly ruined me.

The copy that impresses other copywriters and the copy that actually converts are rarely the same thing. Sometimes they overlap. Most of the time, they do not. The cleverest headline I ever wrote tested poorly. The plainest, most direct headline I almost discarded outperformed it by 340%.

This is a painful lesson because it attacks your ego. Every writer wants to be admired for their craft. But direct-response copywriting is not a literary pursuit. It is a revenue discipline. The only opinion that matters is the one expressed through the prospect's behaviour — did they click, did they buy, did they convert?

“The day I stopped trying to write copy that impressed other copywriters was the day my results started compounding. Cleverness is the enemy of clarity, and clarity is what sells.”

This does not mean good writing is irrelevant. Clear, well-structured, rhythmically sound prose outperforms clunky writing consistently. But the kind of writing skill that matters in direct response is not the kind that wins literary prizes. It is the kind that removes friction between the reader and the action you want them to take. It is invisible craft — the reader does not notice the writing because the writing is not calling attention to itself. They notice only that they understand, they believe, and they want to act.

If you are studying the work of famous copywriters, pay less attention to the lines that dazzle you and more attention to the structural choices that guided the reader from attention to desire to action. That architecture is where the money lives.

Why I Stopped Chasing Awards and Started Chasing Results

In the early part of my career, working with companies like Apple UK and IBM, I existed in an environment where creative awards mattered. Award-winning campaigns opened doors. They impressed creative directors. They filled portfolios.

Then I transitioned to direct response. And the currency changed overnight.

In direct response, no one asks about your awards. They ask about your numbers. What conversion rate did that sales page achieve? What was the return on ad spend for that VSL? How much revenue did that email sequence generate in its first 90 days? These are the only questions that matter, and they cannot be answered with a trophy.

This shift was liberating. It removed subjectivity from the equation entirely. The copy either works or it does not. The metrics tell the truth. There is no committee of judges deciding whether your work is clever enough. There is only the market, voting with its wallet.

I have found that the copywriters who produce the biggest results — the ones whose work drives the kind of numbers that justify premium rates — are almost universally people who made this same shift at some point. They stopped optimising for peer approval and started optimising for prospect action. The distinction sounds small. The impact is enormous.

The Compounding Value of a Swipe File

I started building my swipe file in the early 1990s. Physical clippings at first — newspaper ads, direct mail pieces, magazine tear-sheets. Then digital files as the industry shifted online. Three decades later, that collection is one of the most valuable assets I own.

But not for the reason most people assume.

Early on, a swipe file is useful for borrowing techniques. You see a headline structure that works, and you adapt it. You see an opening hook that grabs attention, and you model it. That is legitimate and valuable. But after thirty years, the swipe file transforms into something more powerful: a pattern recognition engine.

When you have studied thousands of successful campaigns across dozens of markets and every major medium — print, mail, radio, television, web, email, video — you begin to see the structural patterns that repeat. The same persuasion architectures appear in a 1960s direct mail piece and a 2025 VSL. The same emotional triggers drive action in health supplements and financial services. The same headline frameworks produce results in every decade.

This pattern recognition is what allows experienced copywriters to look at a new brief and immediately sense the angle, the structure, and the emotional driver that will work. It is not intuition. It is thirty years of accumulated data, processed unconsciously. And it is the reason that experience compounds in this profession in a way that very few other skills do.

If you are early in your career, start your swipe file today. If you have been doing this for years, revisit your collection regularly. The patterns are there. They just take time to see.

Why Direct Response Survives Every Death Prediction

I have been declared obsolete more times than I can count.

In the 1990s, the internet was supposed to kill direct mail and the copywriters who depended on it. In the 2000s, social media was supposed to make traditional advertising — and the persuasion-based copy that powered it — irrelevant. In the 2010s, content marketing was supposed to replace sales-driven copywriting with "value-first" approaches that were somehow going to generate revenue without ever directly asking for the sale. And now, in 2026, AI is supposedly replacing copywriters entirely.

Here is what actually happened each time: direct response adapted, and demand for the best practitioners increased.

Direct response survived because it is not a medium. It is a discipline rooted in human psychology. The principles that made a 1950s direct mail piece effective — deep understanding of the prospect, emotional precision, clear articulation of the offer, a compelling reason to act now — are the same principles that make a 2026 VSL effective. The delivery mechanism changes. The human wiring does not.

Every "death of" prediction confuses the carrier with the cargo. Newspapers died, but the principles of headline writing transferred directly to digital. Direct mail contracted, but its persuasion architecture became the foundation of email marketing and sales funnels. And AI is currently transforming how copy is produced, but it is not transforming what makes copy persuasive. The cargo — the understanding of human motivation — remains the same.

This is why I tell younger copywriters to study the fundamentals relentlessly. The classics — Schwartz, Halbert, Caples, Ogilvy — are not historical curiosities. They are operating manuals for human persuasion that happen to have been written in a different era. The principles are permanent. Only the applications change.

Strategic Thinking: The One Skill That Matters Most

If I could keep only one skill from thirty years and surrender the rest, I would keep strategic thinking without hesitation.

Writing skill gets you to competent. Strategic thinking gets you to exceptional. The difference between a campaign that generates $50,000 and one that generates $5 million is almost never the quality of the prose. It is the quality of the strategic decisions made before the prose was written.

Which audience segment are you targeting? What level of market awareness are they at? Which emotional driver will move them? What is the unique mechanism that differentiates this offer from everything else they have seen? How does the persuasion sequence build from attention to desire to action? What objections must be overcome, and in what order?

These are strategic questions, not writing questions. And they determine the ceiling of every campaign.

I learned this gradually, but the lesson crystallised during my work on the Belron campaign. The five copywriters who failed before me were not bad writers. Their copy was technically proficient. But they made a strategic error — targeting the wrong emotional driver. The moment the strategy shifted from convenience to safety, the results transformed. The writing stayed roughly the same in quality. The strategy was what changed everything.

“After thirty years, I am more convinced than ever that what separates a $5,000 copywriter from a $50,000 copywriter is not writing ability — it is the ability to think strategically before writing a single word.”

If you want to increase the value of your copywriting, do not take another writing course. Study strategy. Study positioning. Study market analysis. Study the decision architecture that determines what to say before you decide how to say it.

What Fortune 500 Companies Teach That Small Clients Do Not

My years writing for Apple UK, IBM, Microsoft, and Citibank were not the most profitable of my career. They were the most educational.

Fortune 500 companies operate under constraints that force you to develop disciplines most freelance copywriters never acquire. Every claim must survive legal review. Every message must align with brand standards that were developed by teams of people smarter than you. Every piece of copy must work within a system — it is not a standalone artefact but a component of a larger machine.

These constraints felt limiting at the time. In retrospect, they were the best training I have ever received.

The legal review process taught me that defensible claims are more persuasive than unsubstantiated ones — because readers can sense the difference, even if they cannot articulate why. The brand alignment requirement taught me that consistency builds trust over time in ways that individual campaigns cannot. And the systems thinking taught me that a sales page is never just a sales page — it is one step in a journey that includes everything the prospect has seen before and everything they will see after.

Working with smaller clients can teach hustle, speed, and resourcefulness. But Fortune 500 work teaches rigour, precision, and the discipline of getting it right because the stakes of getting it wrong are measured in millions. Both experiences are valuable. But if I had to choose one foundation for a career, I would choose the one that teaches you to think before you write.

Why the Best Campaigns Come From the Worst Briefs

This is one of the most counterintuitive lessons I have learned, and it took me at least fifteen years to fully understand it.

The best campaign I have ever written — the $523 million Belron campaign — came from a brief that five other copywriters had already failed to crack. The obvious angles had been exhausted. The conventional approach was a dead end. There was nothing in the brief that pointed toward the winning strategy. I had to abandon the brief entirely and conduct my own research from scratch.

That pattern has repeated dozens of times throughout my career. A client hands me a brief that is either maddeningly vague or frustratingly prescriptive in the wrong direction. My initial reaction is annoyance. And then, almost every time, the work that emerges from that frustration is stronger than the work that comes from a perfectly polished brief.

The reason is simple: a bad brief forces you to think for yourself. A good brief can become a trap — it gives you the illusion that the strategic work has been done, when in reality the client's assumptions may be wrong. When the brief is obviously inadequate, you have no choice but to go deep. You conduct your own research. You form your own hypotheses. You approach the problem with fresh eyes rather than accepting someone else's framing.

I am not suggesting that briefs do not matter. They do. But I have learned to be suspicious of the brief that feels too complete, too tidy, too confident in its assumptions. The brief that leaves room for the copywriter to discover something is almost always the one that produces the breakthrough.

How AI Changed My Process but Not My Principles

I have been integrating AI into my copywriting workflow since the tools became capable enough to be useful, and I want to be direct about what I have found.

AI has changed my process significantly. Research that used to take days now takes hours. Competitive analysis that required manual reading of dozens of pages is now accelerated enormously. Headline brainstorming, angle exploration, and variation testing have all been compressed. I produce more work, faster, at the same or higher quality than before AI.

But AI has not changed my principles at all.

The strategic thinking that determines what to say — which audience to target, which emotional driver to leverage, which persuasion architecture to build — remains entirely human. The emotional precision that makes copy resonate at a visceral level remains entirely human. The ability to read a market, sense the unspoken fears and desires, and craft a message that feels like a personal conversation — that remains entirely human.

What AI does brilliantly is accelerate the mechanical phases. What it cannot do is replace the judgement, intuition, and strategic depth that thirty years of experience provide. I use AI the way a master carpenter uses a power saw: the tool is dramatically faster than the hand tool it replaced, but the carpenter still decides what to build and where to cut.

The copywriters who will thrive in the coming decade are the ones who integrate AI into a strategic workflow — using it as a force multiplier for their expertise, not as a substitute for it. The ones who will struggle are those who mistake AI's speed for AI's competence, and who confuse generating words with creating persuasion.

The Thread That Ties It All Together

If I step back and look at these lessons as a whole, a single theme emerges: copywriting is not about writing. It never was.

Copywriting is about understanding human beings — what they fear, what they desire, what they believe, and what moves them to act. The writing is merely the vehicle for that understanding. It is the delivery mechanism, not the payload.

This is why direct response has survived every technological disruption for more than a century. This is why a swipe file from the 1960s still contains relevant principles. This is why AI can accelerate the process but cannot replace the practitioner. The technology changes. The delivery mechanisms change. The human psychology that drives every purchase, every click, every conversion — that stays remarkably constant.

After thirty years, I am more certain of this than I was at the start: the copywriter's real job is not to write well. It is to understand deeply. Everything else follows from that.

What Comes Next

I am not done learning. Three decades in, the craft still surprises me. Markets shift. New channels emerge. AI reshapes the landscape. But the fundamentals — research, empathy, strategy, clarity, accountability — remain exactly where they have always been: at the centre of everything that works.

If you are building a campaign and you want it built on thirty years of these lessons — not theory, but tested, proven, revenue-generating practice — I would be glad to hear from you. Whether it is a VSL, a sales page, an email sequence, or a complete funnel strategy, the principles are the same. And they work.

If you are a copywriter early in your journey, I hope something in these lessons saves you time. Study the classics. Build your swipe file. Listen more than you write. And measure everything — because in this profession, the numbers are the only truth.

Thirty years taught me that the best copywriting is not the most impressive. It is the most human. Start there, and the rest will follow.