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My secrets to generating recurring income every month

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A typical work process for a freelancer is quite simple.

The client finds you, a rate is mutually agreed, you complete the service and hand over the bill.

But what if you take a break, and decide to go on a vacation?

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Or when you’ve got nothing lined up for the next few months? Or when you’re overworked and you aren’t able to deliver on time?

If you’ve ever done freelance work, you know it very well that if you stop working right now, your “OMG, I’m making a ton of money” routine could soon come to a halt.

Let’s be honest.

Your freelancing hamster-wheel should never pause. Otherwise, your competition could easily outclass (and out-work) you.

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This is the exact reason why you must stop expecting a magical work opportunity to come from nowhere and why you seriously need to consider generating recurring income from your freelancing business.

Is Recurring Income a ‘make money on autopilot’ system?

Just think of relaxing on some white sand beach drinking coconut water and getting “Money Received” emails to your phone every hour.

Feels so amazing right?

But that’s not what recurring income for freelancers look like. SORRY.

Recurring income is something more than that. And it wouldn’t be wrong at all to say that recurring income is predictable and scalable income. After all, you could predict how much (more or less) you’d be making this month, by the next six months, and by the end of this year.

For example: If you have six consulting clients in January and you predict three of them would bail by the end of February, your income might be cut in half by 50% in March.

Here’s another example: From January to July, you made $5000 a month with only two consulting clients. That’s exactly $35k gross total in 7 months. In order to hit a $100k income goal by the end of the year, you need to double your efforts and work with two additional clients every month till December.

That’s how you predict and scale your income as per your goals and needs.

Now I’m going to show how you, a random freelance consultant, can use one of my solid strategies and develop a powerful freelancing business that not only generates recurring income every month, but quickly builds up a high-quality client base.

The Pentagon Strategy

Alright, it could be any other name, but I like to call my very own sales formula – Pentagon Strategy because of its 5-step framework.

I’ll explain everything about in a minute, but first, here’s a quick overview of what it’s like:

  1. Pick out a specific group of people who would love to work with you
  2. Pitch them with your idea
  3. Propose your qualified leads impressively
  4. Perform a small ‘demo’ task
  5. Partner with the client for longer term engagements

If you’ve been into freelancing for a few years now and have used cold-emailing once in your career, you would find this action-plan quite common.

But let me tell you that I’ve built this sales strategy only for service-based businesses like freelancers and consultants, and this entire framework is based on the core principles of the modern day sales method.

The best thing about the Pentagon Strategy is that it doesn’t require you offering any type of free services to get clients on the hook. You’ll instantly filter out all those prospects that couldn’t afford you and are a waste of time.

In short, you’ll only be working with clients who are worth going after.

Let’s begin.

1. Pick out

You’ve to be very precise and choosy about whom you’re going to sell and whether you could continue to sell them repeatedly or not.

The very first time I used this strategy to sell my growth-driven design services, I was targeting bloggers in self-improvement and online business niche, who were getting at least 1,000 unique visitors per month on their blogs.

That was my target audience.

Similarly, a student of mine who’s a graphic designer by profession, used the Pentagon Strategy to sell his infographic design service to high-traffic blogs on fitness and nutrition niche that use a lot of visuals to deliver a message to their audience.

So it’s totally up to you whom you plan to sell your services to.

You might not get your ideal client in the first attempt but you could continue to improvise your target audience by applying a few smart techniques that I’m going to show you in this post.

2. Pitch

Once you’ve defined your ideal customer profile (ICP), you need to pitch them with strong personalized messages. Obviously, email’s the best option to reach out to them.

Just to keep things to the point and precise, here’s a sample email script that you could use to pitch target prospects with your creative services:

“Hi Name,

I found your website through FACEBOOK and I noticed that you aren’t using enough animated explainer videos to reach out to your audience while your competitors such as ENTER COMPETITORS are heavily using this feature to get their message delivered to the right people.

I’m an animator with 3+ years of experience in animation and video design for SaaS businesses and I would like to assist CLIENT’s COMPANY NAME increase user engagement on your landing pages and ultimately drive more sales using informative explainer videos.

I’m willing to share a few more ideas on how you can use animated explainer videos to educate your audience and boost your sales. Would you like to hear them?



Although this sample email I’ve just written is for animators who want to sell explainer video design services to SaaS businesses, you could use this email template to pitch your target customers with any freelance creative services you’re offering.

Note that, the email doesn’t directly ask for any work and completely emphasize on helping the prospect.

Your pitch email should be precise and clear. Make sure it’s error-free and talks more about the prospect’s business rather than what you have to offer.

What your company does and what it’s all about can be later discussed with the prospect when they become qualified.

But, this is a very time consuming process. Emailing two or three hundred well-researched leads by yourself is not a good idea. Therefore, I’d recommend you to outsource this task to any affordable virtual assistant.

The best place to hire one at a very dirt cheap rate is Fiverr or Upwork.

Just provide them your best email template and a list of leads that needs to be reached out. If you use a CRM, make sure you’re logging every email sent so that you could keep a track of each conversation.

Moving on…

3. Propose

The step #3 of the Pentagon Strategy is to propose your qualified leads with a highly-specific solution they cannot resist.

The reason I’ve made the term highly-specific italic is to emphasize that your solution must be relevant to your potential client’s business otherwise there’s a definite chance your offer could be turned down.

What most freelancers or salesmen do at this stage is that they send out each customer with a same generic PDF document that describes company profile, services, common problems and their solutions.

Your clients aren’t looking for all this fluff that’s already available on the internet.

They want to know clear, actionable solution to their problem(s), and that’s exactly what you’re going to do that at this stage.

All you’re going to do is to either create a very appealing PDF presentation or a short explainer video.

It’s up to you. My team and I at our digital agency usually prefer to go with a well-designed, customized PDF presentation that highlights all the major loopholes in our client’s business and two or three of our best solutions that could fix those problems.

That’s all.

You don’t need to make a lengthy, all-text 20-25 pages of technical report.

A visual document with maximum 10-15 pages should be enough to deliver your ideas. Keep in mind that you don’t need to mention all your ideas in one document.

Just let your prospects know the main ones and add a catchy call-to-action in the last page of the document such as “Let’s work together!” or “Call now to get more details”.

(Note: I’ve shared my original PDF presentation at the end of this blog post that will give you the exact ideas on how to come up with a creative report like that)

4. Perform

The fourth step of the Pentagon Strategy is quite interesting.

Most freelancers who use cold emailing to find customers usually offer a free ‘demo’ of their service to engage the client first and after that if the client thinks the work is worthy, they’d then invest.

That’s not at all a good idea!

In fact, free customers are usually the cheap ones, always wanting more and more from you. They’re a real time-wasters and won’t stick with you in the longer run.

At this step, I always ask my potential clients if they want to make an initial investment in a micro-test and see if my offering works for their business.

This is a real game changer and the only way to help me distinguish high-value clients from the cheap ones.

I usually charge somewhere between $100 to $700 for the micro-test I offer depending on the service I’m rendering.

Clients who’re serious and really are concerned with improving their business, wouldn’t hesitate to make an initial investment.

If a client cannot make an initial investment to try your service, they’re not ready to afford your premium rates too. If a potential client can’t spend hundred bucks to try out a service, then you shouldn’t expect them to pay up a thousand dollar in monthly retainers.

That’s why asking for a minimum investment is a perfect decision maker for a freelancer whom they should go after.

5. Partner

The last step of this strategy is to partner up with your client for a longer term engagement once they’re impressed by the results of the demo task and are happy to proceed.

Many of my students ask me why should they work with an existing client on a regular basis rather than acquiring new customers every time. After all, the client base must continue to grow.

You might be thinking the same.

But let me tell you that ideally it’s way much easier to sell to an existing client rather than running after new clients, every time you’re done with a project.

Don’t get me wrong.

I’m not saying you shouldn’t find and close new clients. But don’t leave the existing ones behind as well. You’d be leaving money and a lot of opportunities on the table if you do this.

For example: If you’re a web designer, you could provide monthly web maintenance service for a fixed price.

Similarly, if you’re a freelance writer, you could offer monthly blog writing service to your clients so that their blog is always full of fresh content.

The reason I recommend my students to go for recurring job types such as content marketing or social media management is that they aren’t a one-time task like web development.

Although there’s a huge demand for developers out there, I’ve experienced that clients don’t usually require development services on monthly basis unless it’s a longer-term contract.

You have to pay the bills. That’s why it’s good to be on the safe side.

And there you have it, the foolproof strategy to help you start generating recurring income from your freelancing business every month.

Good luck!

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About Shaiq Uddin

Shaiq Uddin is the Chieflancer at Freelance Supremacy where he teaches freelancers how to attract better clients, earn more money, and live a stable freelance lifestyle. To learn how to ‘productize’ your services and generate recurring income from your freelancing business every month, join his free 9-lesson email course. You can also use his PDF presentation to help you create your own client proposals.

Leave a Comment



  1. Thank you for this, loved it!

  2. Awesome post.. Shaiq sir.. Thanks for the info.. I’m implementing this strategy now!

  3. This feels like ‘real advice’. And worth pursuing. I will keep it handy and refer to it a lot more. Thanks.

  4. Patricia LaCroix says:

    Hi, Shaiq! I LOVED this article! Your “Pentagon” system sounds like a great way to create and nurture clients. I’m definitely going to implement it in my own business.

    • Yes, indeed it’s a great way to attract and nurture more clients. Give it a shot and let me know how good my strategy works for you.

      I’ll be publishing more detailed guides on my Freelance Supremacy blog and here as well 🙂

  5. Thank you!

    I am a designer that is struggling to find new clients and your method could really help me out.

    Really appreciate it!

    • You’re welcome, Matthew.

      I initially implemented my Pentagon Strategy to sell my design services and trust me, I’ve closed dozens of high-ticket clients with this framework.

      Don’t forget to share your results with me. I’ll be publishing more strategies like these on my Freelance Supremacy blog and here as well 🙂


  6. Just what I needed. Great advice with the Pentagon Strategy. I’ll have to try it out for myself.

    • Fabio, thank you so much for appreciation.

      Give it a try and do let me know how well it works for you 🙂

      Keep supporting my work on Freelance Supremacy and Millo.

  7. Thanks a lot Shaiq, I am a full-time freelance graphics designer. I am going to try these awesome tips, Surely they will help me.



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