How a Follow-Up Email Landed Me a Freelance Writing Client Worth $450+ Per Article

frustrated writer


It’s frustrating, isn’t it?

Life as a struggling freelancer is hard enough.

You send out pitch after pitch, scrambling to get a hold on the writing markets. Squeezing your fingers into every little crack you come across, praying it’ll be the handhold you can use to hoist yourself into the future.

And then you come across a job posted by THAT client.

You know the one I’m talking about. Your dream client.

The big fish.

“This is the one,” you tell yourself. “If I can just get through to this ONE guy, I can free up some financial breathing room, get some experience under my belt, and before you know it I’ll be writing for Copyblogger and beating off new clients with a stick.”

No more Ramen for dinner.

No more feeling embarrassed when you tell someone what you do for a “living,” knowing you’re not really making a living at all.

No more wondering if you’re the laughing stock of the family dinners. Like the awkward uncle constantly trying to sell his nephews and nieces on the multi-level marketing scheme he’s been duped by.

This one is different. The guy even said right there in the ad what he’s willing to pay, and it’s nothing to sneeze at either.

So you jump into your email account and you pull the trigger.

Off goes your query into the ether.

And the Worst Part About Pitching Dream Clients Begins

waiting clock
Yep, the waiting game.

You wait…

And you wait…

And you wait…

But you never hear anything back.


And doesn’t that just suck the motivation right out of you? You try not to count on anything too much in this game, but hey, we’re all human, right? And when your pitch doesn’t even warrant a reply, it…stings.

And sometimes, just sometimes, you can’t help but wonder if there’s some way to salvage the pitch that fell short.

Maybe you could have pleaded a better case. Maybe you should have sent better examples. Or maybe your timing was just off.
I went through such a freelance writer crisis a couple weeks ago, and against my usual prospecting policy, I went ahead and sent a follow-up.

And landed a client who is now paying me $450 and more per article.

The highest rate I’ve earned yet.

From a client I almost let get away…

How to Send Pitches Without Going Insane
Before I explain how I did it, let me explain my usual rule or there’s a risk I’ll send you down a dark path. Whether you start out in low-end content markets, where marketing your writing services is a numbers game, or higher-end markets, the best policy is to set and forget.

Once you send off your pitches, you’re done; you don’t wait around or go chasing after the client, tugging on their pant leg and crying out for “just one chance.”

For one, chasing after uninterested clients positions you as a desperate writer rather than someone who dropped them a line to see if you’d be a good fit. This kind of desperation not only diminishes your value in the eyes of the prospect but weakens your negotiating leverage.

It’s always best to hide it when you need a client more than they need you. On top of that, chasing after clients who don’t respond to queries can do a number on your mindset. It comes from a scarcity perspective. And once you cross over that line, you’re playing a losing game.

Each writing pitch becomes a plea for help. Each email a cast into barren waters that you don’t actually expect to garner any bites. It’s typically best to spend that time sending out pitches to new prospects.

Just move on – that’s my motto.

Why I Shredded Up the Rule Book and Threw it in the Trash

Shredded Paper


All the above aside, I’m just as human as you are.

I hadn’t done any proper marketing in a long time, and my biggest client, a national insurance giant that was ordering fifteen $105 blog pieces per month for a year and a half, suddenly stopped ordering.

Poof – gone, just like that…

It was time to pick up some more work…fast.

I spotted this particular client on a job board during a frenzied bidding spree. He was calling for writers that could write intelligently about online marketing, he was offering $0.30 per word for 1500-word articles, and he appeared to have a lot of work.

I knew I was qualified for the job.

“Man, if I can land this one…” I said to myself, slipping into that same old mantra, “I’ll be set!”

Radio silence.

As usual, I moved on and forgot about my email, but in an insecure moment, when I couldn’t seem to find anything online worth bidding on, I opened up my sent-box to see how many pitches I’d sent out over the past week.

When I saw the email to the job for $0.30 a word, I opened it, out of curiosity, and looked over my proposal again.

That’s when I saw my mistake.

The client specifically mentioned he wanted articles about online marketing strategy for attorneys. Yet, my entire email introduction focused on my freelance experience and all the huge corporates I had worked for – most of which were big insurance companies or investment firms.

Not once did I mention any of the companies I had worked for in his niche. And, in fact, not once did I mention any online marketing experience whatsoever!

This was a serious client willing to pay serious rates and I essentially sent him a cookie-cutter email in haste that focused on myself, ignoring his needs completely.

It might as well have been one of those spam messages from Nigeria, “Hello, Sir, and a good day to you…”

For a moment, I thought to write it off as a lesson learned…

Then I thought better and took action.

A Split-Second Decision That Yielded a Big Payday

Payday Cash


My sudden epiphany about my mistake got me thinking, and decided to try something new. I scratched out a quick email…


I thought I’d take a moment to check back in on this project. Are you still looking for writers?

To expand on my initial email, in case it wasn’t clear, I have plenty of experience writing about online marketing as well. In my time, I’ve written extensively on a wide range of different ecommerce subjects, including social marketing, web conversions, copywriting, email marketing, mobile tech, and a lot more. You can find posts published under my name at [WEBSITE], where I’m a regular blogger.

If you’d like some direct links, please just let me know.

Attorney marketing is not exactly a specialty, but I have worked for clients in this niche in the past as well.

All the Best,
James Druman”

That was it. I sent this message off and committed to my usual set-and-forget philosophy.

And believe it or not it worked!

The very next day, I received an email back from the client asking for specific examples.

This is one thing I love about pitching freelance services. You almost always know if you’re doing it right because the clients who need you really, really need you and get back to you right away as long you’re a good fit.

My samples weren’t quite as meaty as the client wanted (as tends to happen when you start out too cheap), but he could see I understood the niche and gave me a shot.

My first article cleared a good $450, and the second was well over $500.

And the next cleared me about $600…

These are the most profitable articles I’ve ever written, and I must say, it’s interesting how exciting writing becomes when you start making real cash…

What are the Takeaways?
Lest you misunderstand, I’m not making it my new policy to chase after every email that doesn’t get a reply.

“Hey, it’s me again.”
“Hey, it’s me again.”
“Hey, it’s…”

No, no, no – that won’t do at all. But there are some takeaways to learn from this successful little experiment.

1. Evaluating When A Follow-Up Does Make Sense
Does a follow-up always make sense?

Of course not.

But a second email can make sense if:
a) you’re extremely qualified for the job
b) you can improve upon your original pitch with additional value

2. The Easiest Way to Save Time and Energy on Bidding
Get the bid right the first time!


Even though this story has a happy ending, it just as easily could have gone the other way. And no pitches are more wasteful of your time than the ones that get completely ignored.

If you don’t have the energy to bid right, you shouldn’t bid at all.

3. The Missing Step That Gets You in the Door
Make your pitches relevant! Even if you use a prewritten template, edit it first. Because no matter how good you sell yourself, a pitch sent to a high-value client that doesn’t take their needs into account is about as useful as trying to sell teenagers cassette tapes.

Pitch more qualified clients and tailor each to the job at hand as much as possible.

That’s how you close deals with real people.

4. A Weak Link That Can Make Any Bid a Wasted Effort
So, there I was…

Foot in the door thanks to my follow-up. Got the client’s attention, and he’s reading my email this time.

Nice work! Right?

Well, kind of…

Because I almost lost this job again. Why? For the stupid reason that my samples weren’t quite up to par. In my case, probably time for a portfolio update. If you’re new, get your online “face” looking nice and tidy so you can pursue high-dollar clients from the get-go.

5. Hot Freelance Writing Niches That Pay
An unrelated thing I learned from this incident is a niche to target that’s just as lucrative as writing for offline companies.

And that’s other online companies that ALREADY serve these businesses.

In this case, it’s marketing companies who sell to attorneys, but marketing companies who target any other specific, lucrative industry are no doubt doing very well for themselves right now too.

I’ll be pitching more of them in the future. And so should you.

It just so happens I’m negotiating with another as we speak.

The Bottom Line
One thing I am reminded of over and over again as I stumble and fall and get back up is this…

If you want to make real money with freelance writing, you’ve got to approach REAL businesses. They might be online businesses or they might be offline businesses, but they’ve got to be making serious enough cash to pay you what you’re worth.

And the bottom line is that if you want to work for real businesses, you’ve got to be a real business too.

That means not just haphazardly casting a net full of holes out there and wondering why the big tasty fish swim right through it.
It means putting time and effort into your marketing. Using your email not like a scatter gun but like an actual attempt at human-to-human communication.

Consider exactly what the client is looking for, figure out if you can be that somebody, and then tell them why you make the perfect fit.

One careful word at a time.

Get it right and you really can land those big fish clients. Treat it like a business, and you really can be proud to tell people what you do for a living.

Now go pitch like you mean it…

James Druman currently lives in Southeast Asia, where he uses his writing skills for complete location independence. Click here to access his free report, “World Wide Words: An Introduction to Real Opportunities in the Online Content Markets.” Or, for client queries, contact him here. (Google+)





One response
  1. Stephanie Faris Avatar

    Interesting! As someone who worked for 20 years to get a book deal (and finally succeeded!), this blog reminded me more of that than my quest to land freelancing jobs. I have been fortune enough to get a couple of high-paying gigs, but interestingly, those jobs were not labeled as high paying, so I didn’t have the chance to worry about it. They slipped the pay rate in after they hired me! I guess the lesson in that is that we should always customize each query? Maybe just the first paragraph!

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