How to succeed as a copywriter on Upwork

A guy named Nick Tubis interviewed me tonight for a product he’s making.

He actually hired me on the online freelance platform Upwork, to talk about how I became successful as a copywriter, on Upwork.

So Nick and I talked for an hour, and I gave him the full story of my Upwork experience so far.

In the end, he asked me, “Do you have one hack you would recommend to anyone getting started?”

I told him the truth:

Anybody can compete for any copywriting job on Upwork.

Ultimately, it doesn’t matter how much copywriting experience you have.

How much Upwork history you have.

What your background is.

All you do need are a few pieces of relevant previous work.

In fact, even one piece of relevant sample work can set you above the rest of the hungry crowd of freelancers crawling over each other to get a job.

Don’t believe me?

Let’s say a client just posted a job ad titled “Looking for 10-part email sequence to promote new supplement.”

My “application” for a job like this would simply be:

“I specialize in email marketing and I’ve written a lot about supplements.
Here are a few relevant samples:
sample1
sample2
sample3
Take a look, and if you like what you see, let’s talk in more detail.”

I regularly get 4-figure copywriting projects — and I even got Nick to pay me for talking about my Upwork expertise. And the stupid-simple template above is the only way I ever apply for a job.

“That’s great for you, John,” you might say. “But where am I supposed to get those relevant samples? Nobody’s hired me, so I can’t build a portfolio, and therefore nobody will hire me!”

Easy, friend.

You don’t need any previous paying clients to build a small but highly targeted portfolio.

Simply find a job you would like to get.

Then write a sample that’s very close to what they are looking for.

For example, in the hypothetical job I invented above, you would just write one email  promoting a supplement.

Slap this into your application, send it over to the client, and you’re off to the races.

Will it work every time? No. But if you do this every day, I would expect you would have a paying client by the end of the week.

By the way, even though I’ve had a lot of success on Upwork, I’m actively looking to move off the platform for various reasons.

That’s why, if you are interested in hiring me to do your copy, don’t  go to Upwork. Instead, get in touch with me here.

You should always judge a book by its cover

Former Smiths frontman Morrissey has a very polarizing public persona.

Unsurprisingly, he also has immensely devoted fans who have followed him for 30 years plus.

I read a Billboard Magazine interview with Morrissey today. It struck me how this interview is full to the gills of things anyone can copy to have a more dramatic public persona — and therefore a more devoted following.

Here are a few Morrissey lessons:

1. Agree and amplify

What’s the best way to respond when somebody accuses of you of something ugly? Agree and amplify the nasty fact, with humor and without bitterness or trying too hard.

BILLBOARD: “Feb. 20 marked the 30th anniversary of the release of the first Smiths album. How did you mark the occasion?”

MORRISSEY: “Is it only 30 years? It feels like 60.”

2. Use visual, colorful language

People’s brains work in pictures. So use visual language to make a point, and mix in surprising expressions and metaphors. (The good news is that this doesn’t have to be spontaneous. You can collect striking phrases, plan them ahead of time, and pull them out as needed.)

BILLBOARD: “It’s been reported that you’re now working on a novel. Is that true? If so, what are you writing about?”

MORRISSEY: “I can’t christen the baby until I at least see its head. It’s bad form, somehow.”

3. Surprise by inverting

Surprise shocks people into paying attention, and into remembering you. One way to surprise is simply to defy expectations. For example, when people expect you to be serious, be lighthearted. Focus on the trivial and irrelevant instead of the heavy and serious.

BILLBOARD: “In 2013, you endured a series of unfortunate maladies that forced you to cancel many tour dates. Are you still ill?”

MORRISSEY: “Well, I’m expected to see Easter. It was a bad year. I was in hospitals so frequently that the doctors were sick to death of me, and there’s nothing more ageing than lying in a hospital bed, trying to recover from hospital food. If your illness doesn’t kill you then the hospital food sees you off. That’s what it’s there for. Anyway, it was my time to go to pieces. Much overdue.”

4. Surprise by genuineness and sincerity

If you make a career of being tricky and irreverent, that becomes your norm. You can then surprise people further by taking a serious, no-nonsense stance on an issue — particularly one you find meaningful.

BILLBOARD: “You likened eating animals to pedophilia, a comparison some may find … extreme. Care to defend your point of view?”

MORRISSEY: “I don’t need to defend my own point of view. When you eat an animal you subject it to spiritual and physical rape, you eats its breasts … its rump … you cut off its genitals … whichever way you care to look at it, eating animals is violence at its most extreme.”

5. Have high standards

If something doesn’t meet your standards, you can simply ignore it. Another option is to dismiss it or mock it.

BILLBOARD: “Prince recently revealed that he’s an exceptional ping-pong player. What surprising, secret talent do you have?”

MORRISSEY: “I’m an exceptional ping-pong player.”

6. … And go back to surprising by inverting

Inverting the expected into the unexpected is a deep well you can go back to over and over.

BILLBOARD: “Lastly, what’s one piece of advice you wish someone had given you in 1984?”

MORRISSEY: “You should always judge a book by its cover.”

When infotaining emails fail

In 1975, the great copywriter Gary Bencivenga joined an upstart direct marketing agency.

They soon put out a gutsy ad in the Wall Street Journal to hunt for new clients. The headline ran:

“ANNOUNCING A DIRECT RESPONSE ADVERTISING AGENCY THAT WILL GUARANTEE TO OUTPULL YOUR BEST AD.”

There were only two catches:

1) You had to give Gary & co. creative freedom on the kind of ad to write — only legal and factual approval was asked for and allowed.

2) You actually needed better advertising. In Gary’s own words, “If we think your present advertising is excellent, we’ll tell you.”

I thought of this today because I’m looking over the wreckage of several email campaigns I wrote for a client over the past few months.

I put in serious work on these emails, and I thought I did a great job. When I handed them over to the client, he loved them. But apparently, they are underperforming what he was using earlier.

The thing is, I saw the earlier email sequences, and I was confident I could do better. They were dull and too heavy on the teaching, and I was going to make them intriguing and infotaining.

But that’s not enough.

What I should have asked for in addition to seeing the email copy is a breakdown of where the sales were coming from.

Were they all on day 0, and people weren’t even reading the emails?

Did sales trickle in as the relationship was established (which means that people actually liked reading the old emails)?

Was it all about the discounts (and was the copy largely irrelevant)?

Were the emails actually making any sales (the client hinted that they weren’t making any money through email marketing)?

Too late to ask now, because the client seems to have moved on to greener pastures.

However, going forward, I’ll insist on this sales info for two reasons:

1) It will help me decide whether I can in fact write emails that will do better. It’s not just about seeing the copy, but about finding out how that copy performs.

2) If I feel I can beat the emails, this info will give me useful clues about how to best do that.

Maybe obvious. But even old Gary above didn’t think to ask for the results in his gutsy ad — which makes me feel a bit better.

Bejako suffers from sirocco

“It’s a punishment in itself, the mind becomes exhausted, the joy of living seeps out through blurred eyes and darkened faces. You cannot even love yourself during sirocco, so how to make reasoned decisions about others!”
— Tereza Buconić Gović

Legend says that in medieval Dubrovnik, on the Croatian coast, a law decreed that no political decisions could ever be made during times of sirocco, a kind of nasty, hot, southerly wind that seems to disturb the mind.

Sirocco is happening right now, and I can seriously feel it. It’s hot and humid outside like it’s the middle of May. I’m not sleeping well, I’m tired, and my head hurts. I keep looking towards the horizon and hoping for a storm that will clear this evil wind away.

So what’s the point of this?

Well, sirocco.

It’s an interesting and clear concept. Plus I can tie it into a personal story.

In other words, it makes for a great opening for a bit of copy, most likely a sales email.

The thing is, these kinds of personal, clear, interesting concepts are lying around in plain sight, every day. They just need to be noticed and (most probably) written down — and then, when the time comes, used as a great idea to open an email with.

4 examples of shameless headline swiping

“Learning how to artfully swipe is probably the most important skill a copywriter can have.”
— Harlan Kilstein

I have a big swipe file of complete sales letters, but more than anything, I like to swipe headlines
After all, each headline is really an angle, a hook in itself. If you get the headline right, much of the copy writes itself.

My favorite source for headlines to swipe is not direct response copy
As I’ve mentioned before, I regularly go to Hacker News, a nerd bulletin board, and I pay attention to which general interest articles I click on. I write all these headlines down on an index card and put them in a growing stack under my pillow.

When it’s time to write copy, I go to my swiped headlines stack
And I force myself to write at least 10 or so headlines, using entirely different templates. Here are 4 such shamelessly swiped headlines, and the reasoning behind each:

1. Dog bites Trump -> The content is in the list

The original headline is brilliant, and it might seem that the second headline has nothing to do with it. But what’s really going on? The first headline is simply a modification of saying that’s popular among a specific audience (journalists: “Man bites dog”). Unfortunately, I couldn’t work the uber-clickable “Trump” into my own headline, but I could tweak an existing popular saying (direct marketers: “The money is in the list”).

2. Poland was shockingly liberal during 13th century -> Antibiotics can be shockingly good at causing weight gain

I’m not crazy about power words like “shocking” because they’re overused — every wannabe viral article or video is either “jaw-dropping”, “shocking”, or “epic”. That doesn’t mean that power words cannot or do not work, particularly if the rest of the headline is actually interesting in itself. In both the original headline and my own version, the headline was an interesting fact (rather than a screaming benefit) and the “shocking” power word increased curiosity a notch or two.

3. Why you will marry the wrong person -> Why your kraut will develop mold

Ok, this one is straightforward: Why [major unspoken fear of your target audience]. (My version was a subject line for an email promoting a home fermenting product.)

4. “Close to tears, he left at intermission”: How Stanley Kubrick upset Arthur C. Clarke -> “Almost fell over at how bad I looked”: Essential oil adverse reaction report

This is a good example of a headline template that I never see in direct response copy — a dramatic quote followed by a curiosity-baiting description of the content. Even though it’s not common for direct response, it must work, because similar headlines have sucked millions of people into reading articles.

The content is in the list

For the past week or so, I’ve been stuck writing about aromatherapy diffusers. This is for a book on essential oils I’m about to put out. (Diffusers are the little gadgets that you can use to disperse aromatic essential oils.)

Basically, I needed to write a review article. But I didn’t feel like summarizing thousands of online reviews for hundreds of separate diffusers. To make things worse, many of those reviews are either biased, paid for, or very incomplete. That’s not good enough — I only wanted to make top-notch recommendations to the people who will be reading my book.

So what to do? Well, I didn’t have a good plan, so I kept going back and forth. And back. And forth.

Fortunately, an idea hit me. I decided to write an email to my aromatherapy list, and ask for their experiences. I explained exactly what I was doing — putting together a list of diffusers that work well in practice, rather than just on paper. I explained the trouble with online reviews, and asked for personal feedback.

And to sweeten a deal, I offered a bribe. I’ve asked questions of my list before and the response hasn’t been overwhelming. So I took a page out of Ben Settle’s book, and offered something in exchange for getting people to take action (specifically, I promised them a free copy of my upcoming ebook once it’s finished).

The response has been great. I got lots of interesting feedback, including stuff I would never have found otherwise. Writing the section on diffusers suddenly became easy. I’ll also be able to use the same content (tweaked a bit) for an upcoming email, as well as for an article on my site.

And there have been some unexpected benefits as well.  I got more engagement from my list. I got some in-depth information, which makes it easier to imagine the people who read my emails as real persons instead of just email addresses. Plus I got more people interested in my book than I would have otherwise.

So to sum up:

The content is in the list. Whenever you are stuck for how to proceed with writing a piece of content, canvass your list. Ask for opinions on a specific question, or even better, ask for personal experiences on a specific topic. And give people something valuable in exchange for responding.

A subject line that’s good enough for Groucho Marx

“Mrs. Briggs… I’ve known your husband for many years, and what’s good enough for him is good enough for me.”

I’ve recently written several autoresponder sequences that culminate with a discount for the product on sale. However, it’s no good to just announce this in the subject line by saying “15% off coupon inside”.

Why not?

Because it’s boring.

Because everybody does it that way.

Because it only focuses on the hyper-buyers, and drives away everyone else.

Because with a little bit of work, it’s possible to get the same message across, while creating curiosity, building a relationship, and thereby actually increasing response.

So how do you do it? Here are a few ideas:

#1 Tease. Announce that you’ve got an incredible offer in the subject line, without saying explicitly what it is. Then carry this on throughout the email as long as possible without pissing the reader off. Example: “A free fermenting offer you probably can’t refuse”.

#2 Testimonial connection. Include a testimonial in the body of the email and find an entertaining way to tie into this in the subject line. Example: “A discount that will disappear like a late-night snack”.

#3 Pop culture reference. Find a movie, TV show, celebrity, PS4 game, whatever — and in some way tie it in to the offer (or don’t tie it in — it’s more important that it’s entertaining than that it ties in perfectly). Preferably, choose a bit of pop culture that won’t seem dated six months from now. Example: “A discount that’s good enough for Groucho Marx”.

The sink-or-swim sales letter close

Yesterday, I was finishing up a sales letter and I got to my least favorite part, the close.

That’s when you’ve made your offer, and now make one final big push to get the reader to buy. Many times, this is where sales letters reiterate all the benefits of the thing they are selling. Other times, they paint a bleak picture of how lonely and sad your life will be if you don’t buy.

I decided to do something different. I used an idea that I got from a sales letter from Ben Settle, which he included along with his monthly print newsletter several months ago. The sales letter was for a new $279 product for freelance copywriters that Ben was selling. it wrapped up with the following:

“It’s sink or swim around here to encourage implementation. So if you don’t think you can make your $279 back, simply don’t buy it. Otherwise, go here before April 1st to grab it for $100 off:”

Ben’s sales letter had a bunch of curiosity-soaked bullet points, but none of them pulled me in or made me consider buying. However, this one final statement almost made me get my credit card right away and order right away. Here’s why this close is so good:

1. It’s a challenge. This close doesn’t try to convince you. It doesn’t say “Just imagine how much richer you will be with this information!” It does just the opposite — it tries to dismiss you. To me at least, this was a challenge that I wanted to rise up to.

2. It creates vision. When I read this, I immediately asked myself, “Could I make $279 from this information?” And I then started imagining different scenarios where that could happen. This is what negotiation expert Jim Camp called creating vision in your adversary’s mind.

3. It’s different. Again, most other sales letters try to close you with high-pressure sales tactics. This makes Ben’s approach stand out, and it creates curiosity and intrigue.

4. It’s non-needy. Again, no high-pressure tactics here. This signals you don’t need the sale (as you genuinely don’t). Ironically, this will make it more likely for you to get the sale.

5. It repels the buyers you don’t want to have. “Repulsion marketing” is another cornerstone of Ben’s philosophy, and this sales letter close embodies it perfectly.

6. It’s about consumption. This close isn’t about being a dick (though it might sound like that to some). It’s about what’s good for you and for your prospects, something that Sean D’Souza calls an emphasis on consumption. In other words, if some prospects won’t get value out of what you’re selling, why would you sell it to them?

Now I’m sure this approach probably goes back many thousands of years, back to when the first copywriters etched their sales letters in wet clay tablets.

But if it has a name yet, I haven’t heard it. And so, in honor and memory of Ben’s sales letter, where I first saw it, I will call it the “sink-or-swim close” from now on.

Marketing heresy from the world’s greatest living copywriter

A while back, I was writing a sales letter for a probiotic and I was stuck for a headline.

The unique thing about this probiotic was that the strains it contained were proven effective in clinical studies (unlike just about every other supplement out there).

But that’s a really ugly, non-benefit-oriented feature to highlight in a headline.

So I borrowed a technique that I’d heard of in copywriting legend Gary Bencivenga’s farewell seminar. The resulting headline went something like this:

“Announcing a doctor-formulated probiotic that’s been clinically proven in controlled human studies to…”

And then it went on to list the 7 or 8 separate proven benefits that this probiotic was actually proven to deliver.

When I first heard of this headline technique, it seemed weak to me. After all, isn’t all good copywriting focused on a single, overriding idea? It certainly seems to be the conventional wisdom, and even I’ve done my part in propagating this.

And yet, here we have Gary Bencivenga, widely acknowledged as the greatest living copywriter, somebody who’s won control after control, and who’s been privy to the results of tens of millions of dollars worth of advertising tests, saying that you can have a headline that’s effectively trumpeting a half dozen separate benefits.

“Our *three* benefits are fear, surprise, and ruthless efficiency”

And Gary doesn’t stop there. I was just re-reading an interview he’s done with another famous copywriter, Clayton Makepeace, and I came across the following:

“I know this sounds like heresy, but I’d much rather have in a good direct mail package three or four or 10 good reasons to buy, than to have to sacrifice nine of them in favor of the one USP. The USP really can be misapplied to direct marketing where you have the luxury of closing the sale on the spot and can give one dominant reason to buy but also seven or eight other reasons. You don’t have to abide so religiously to a single Unique Selling Proposition.”

So what to make of all of this?

Maybe Gary understands copywriting at such a deep level that he can afford to break rules that apply to the rest of us.

Maybe he’s just stating in a slightly stronger form what many copywriters already do (“give one dominant reason to buy but also seven or eight other reasons”).

But maybe, just maybe, the current emphasis on “The One Big Idea” is a bit of a fad, and maybe there are other effective ways to create a successful direct marketing promotion.

Mother Theresa’s emotional manipulation advice

“If I look at the mass, I will never act. If I look at the one, I will.”
— Mother Theresa

One of the most valuable lessons I learned in the early years of my copywriting education came from Andre Chaperon’s Autoresponder Madness.

It didn’t have to do with autoresponders. It didn’t have to do with email. In fact, it was (and is) completely applicable to any kind of sales copywriting, and more broadly, to any kind of mass persuasion.

So what was the lesson?

It was how to understand your prospects on a deep level, and how develop empathy for the people you’re writing to.

I won’t give away Andre’s exact tactics for doing this, but his general approach is simply a ton of research. All of which culminates in a customer avatar.

This is not a demographic description. Instead, it’s a detailed story about a specific person who is facing the problems that you’re looking to solve.

I’ve found that creating such an avatar isn’t just a matter of getting better insight into the audience. There seems to be some kind of chemical switch in the brain that gets flipped when I’m writing to a specific person with a name and a face — versus to a vague, shapeless, and nameless mass.

It’s something I’ve also heard A-list copywriter David Deutsch describe as the “Hey Mitch” method. In other words, when David is writing copy, he (either literally or in his mind) says “Hey Mitch, here’s how to…” and then he goes into his sales pitch.

This process of calling out a specific name has the effect of exposing fine sounding but unconvincing phrases, which seemed fine just a minute ago. And it replaces them with natural words and ideas which are relevant to your audience.

Anyways, this name/face/avatar concreteness isn’t just for hypnotizing yourself into writing better copy.

In Made to Stick, Chip and Dan Heath tell a story of hospital staff who were subtly manipulated into caring about improving workflow. This is normally not a topic that staff would be enthusiastic about, but in this case they were shown a video from the perspective of a patient — coming into the hospital, being laid down on a gurney, waiting around, etc.

This concrete illustration got the hospital staff much more responsive and committed to helping improve the situation than if they had been barraged by statistics or facts about nameless patients.

This idea is summed up nicely in the quote by Mother Theresa up top (which I also first read in Made to Stick).

To wrap up: Concreteness, and looking at the individual, is powerful persuasion stuff on multiple levels. It helps you empathize with your audience, and therefore makes you more persuasive. At the same time, the same principle of being specific and concrete makes your audience more receptive to your ideas — again making you more persuasive.