Do you want to make money (Or more money)? Would it be empowering to know that the ability to increase your monthly income was within your control, and not at the mercy of your boss’ temperament, your company budget, or the now-tumultuous economy?

If the answer is yes, you can use a form of writing to better sell your services. And there’s good news: If you have a computer or smartphone and a hunger to grow your business, side hustle, or bank account, you have everything you need to succeed.

We often see writers with a clear career path and metrics of success: Thousands of followers, book deals, giant launches, national press coverage. This ‘publisher author’ path is achievable, but also a long game. If you’re serious about making money via the written word, there’s one skill that will pull money into your pocket way faster.

It isn’t a branded website. It isn’t a giant email list. It isn’t an automated online course, advertisements, or a funnel, and it isn’t a sexy contract with a major publisher. What is it?

Putting Yourself Out There

2016 was the year I embraced online dating fully. I put the “I’ll magically bump into prince charming on the street one day” fantasy aside, joined OKCupid, declared 2016 the year of relationship revolution, and went on offense. And before I settled into a long-term relationship which was wonderful and lasted about four years, I racked up about 50 first dates in a nine-month period. (I actually can’t drink whiskey anymore because my go-to cocktail for these dates was an Old Fashioned and I burned out on them; you can only tolerate getting punched in the face so many times. 🥃)

When I started out, I was passive, waiting to see who would come to me. Wrong approach! After a few months of lackluster dates and progress, I reset my expectations, my ego, and my intention. “I am here to go on dates and flirt. What happens in response to that is not in my control.” I shifted. I started reaching out cold, initiating conversation, and making it all about them and not me. (Pro tip: Why does everyone put a travel pic in their dating profile? It’s because they want you to ask them about it.)

The funny thing is that I ended up getting dates (and even some friendships!) I never would have drummed up had I not put myself out there. So while I got more than a few no’s and a dump truck’s worth of non-responses, I was far more in control of my experience and felt a boost in my confidence and self-esteem.

So what’s the #1 skill you need to make more money writing right now? My sordid OKCupid anecdote just gave it away, actually. The #1 skill, and the bane of every introvert’s existence, is manual prospecting.

What Is Manual Prospecting?

Manual prospecting is non-automated outreach to people in your network you either know or don’t know to pitch your services. When it comes to sales and marketing, prospecting is really the skill that separates successful freelancers and side hustlers from the world of “wantrepreneurs” who never start. The ability to reach out cold, strike up a relationship, make an offer, and put money in your pocket is one of the most empowering skills you will ever develop. And really, manual prospecting is ultimately just another category of writing.

Unfortunately, many automated services and bot culture have ruined the direct-message pitch. You also occasionally see aspiring freelancers spray-and-pray dozens if not hundreds of prospects at once with a bland, overly general pitch. Customization was again named the #1 most important trend in marketing, and more than ever consumers expect some sort of customized experience before they buy. Here’s an example of an impersonal stock pitch I once received that referred to my past articles on real estate. I’ve never written about real estate.

Screenshot from the author. An example of poor, automated prospecting.

Let me now state what everyone new to manual prospecting is thinking to themselves anyway: “This blows.” And you’re right! Manual prospecting can feel demoralizing at first because we’re not resilient and not used to having the majority of our efforts be rejected or ignored. Know that it’s ultimately a numbers game, and in fact, when you can identify someone’s unique problems, they listen. Win the ear of a decision-maker and you’ve positioned yourself to send over a proposal, which puts you ahead of tons of competition.

Proposals are key to winning over new clients and growing your side hustle or freelance efforts. But a proposal doesn’t make a sound when it falls in the woods unless there are ears to hear it. You need those ears. This is why you should prioritize manual prospecting each week -- especially if you don’t feel like it.

My 4-Step Manual Prospecting Template

Template time! Here’s my go-to template to give you a running start. Tweak the language as desired to make it your own. We’ll go through each component in detail, but it helps to see the complete pitch in its entirety at first.


Hey <NAME>,⁣

My name is <YOUR NAME> and I’m <A FREELANCE WRITER/THE FOUNDER OF <YOUR COMPANY>>. I’ve been following <THEM/THEIR COMPANY> for some time now — I particularly enjoy <SOMETHING SPECIFIC>.⁣

My guess is that right now, 3 of <THEM/THEIR COMPANY>’s biggest concerns are⁣

<PROBLEM #1: Put in their biggest issues based on research or what you know about them. You’ll need to do some work to get this. Don’t skip it; this is the most important part of the pitch.>⁣



Recently, I <Something impressive about results for one of your clients with a similar problem>.⁣

I’d love to chat with you about the possibility of doing the same for <THEIR COMPANY>, and want to give you something hyper-relevant to <THEM/THEIR COMPANY>’s needs.

Want to connect for five minutes to discuss? My appointment calendar is here, feel free to book any time that works. Looking forward to it.




Step 1: Lead With Specificity And Clarity

It is critical that in the first 50 words of your message, you get straight to the point of who you are and why you’ve invited yourself into someone’s inbox. Flattery can give you some extra oomph; not only do people love being complimented, but they also look for clues that your pitch is not a stock pitch, and a flattering detail will check that box.

What types of compliments work well? You can refer to a post or piece of content of theirs they recently shared, or compliment a recent campaign done by the business itself. Get creative. The number one intention of this section is to clarify that your cold pitch is different from others.

Step 2: Give An “Educated Guess”

This next section is the most important element of your pitch. Show off your X-Men superpowers and demonstrate to your decision-maker that you really get them and understand what they might be going through. Almost no one bothers to provide this level of detail, so by doing your due diligence there’s a much better chance your pitch will capture your prospect’s attention.

My guess is that right now, 3 of <THEM/THEIR COMPANY>’s biggest concerns are⁣

  1. <PROBLEM #1>: Put in their biggest issues based on research or what you know about them. You’ll need to do some work to get this. Don’t skip it; this is the most important part of the pitch.>⁣
  2. <PROBLEM #2>⁣
  3. <PROBLEM #3>⁣

What I like about this particular script is that it takes a risk. Obviously you don’t know the actual inner workings of someone’s business, so you’re making an educated guess on the top two or three things that might be on their mind. What has this person or company already tried, and how can you help them make the results of those efforts even better? Generally, pain points that you can always point back to are

  • How to make more money and/or reduce costs;
  • How to save time; and
  • How to get ahead of potential upcoming challenges (For example, an increase in competition down the line).

When you do this work, your pitch becomes way more interesting. That’s because the law of reciprocity will be in motion; when you reach out and proactively try to help someone, and really spend time showing that you’ve done the work, they’ll be more likely to want to help you in return.

Step 3: Prove You’re Already Getting Results

Are you already doing this kind of work for another client? Do you have examples of results you can speak to? Now that you have your reader’s attention, show off that you already know the drill and that other people are already paying you for it. In ideal circumstances, you can use this section to briefly share benefits and outcomes you’ve helped another client achieve.

If you’re just getting started, you won’t have any past results yet, which is okay; in lieu of client examples, share some past writing samples or a portfolio. You don’t need to go overboard on selling the results here; one sentence gets the job done. Remember, our eventual ask will be for five or ten minutes of your reader’s time, so this pitch shouldn’t overly veer into sales page territory with regard to length.

Step 4: Ask For A Tiny Sliver Of Their Time

Leave them wanting more. Ask if this is of interest, and if so, if they’d like to connect for 5 minutes about it. You may or may not end up doing an actual call, but getting a dialogue going here is important. You’re looking for a yes or no response on whether your educated guesses hit the mark in terms of what people are actually grappling with and dealing with. Once you confirm the pain points, you can maneuver toward pitching a solution that makes these pain points go away.


I’d love to chat with you about the possibility of doing the same for <THEIR COMPANY>, and want to give you something hyper-relevant to <THEM/THEIR COMPANY>’s needs.

Want to connect for five minutes to discuss? My appointment calendar is here, feel free to book any time that works. Looking forward to it.


If someone won’t get on the phone with me for five minutes, but is interested in my pitch, they’ll make arrangements to connect with me such as bringing in another decision-maker to handle the conversation. I proceed on those proposals. If someone won’t get on the phone with me for five minutes, though, it’ll be an uphill battle to convince them to pay you (Especially for my proposals. Which start at $1,000 and up). Since crafting a proposal takes time, only proceed if the receiving party has genuinely shown curiosity and interest.

The most important thing to remember throughout all of this is that prospecting is a different type of writing and a different muscle to build over time. The pipe dream that you’ll write a few blogs and develop a massive audience, while doable, isn’t how most well-paid writers make bank. To get money flowing now, your best next step is to strengthen and develop your sales writing muscles. And the most custom and scrappy form of sales communication is manual prospecting. To bring more money in the door, let yourself be scared, take action anyway, and start pitching yourself today.

Thanks for reading. 🙏🏼

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