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3 Steps I used to book $7,000/month in retainer clients

Table of ContentsUpdated May 26, 2020

As a freelancer, it absolutely sucks to start out booking work for each month at $0.00.

Because starting over from nothing means that every single month—while you’re also trying to juggle client work, produce your own content, and respond to the pile of emails that come in every day—you’ve got to hustle yourself silly to market yourself and just hope the prospects you’ve collected are ready to hire you.

Because if you don’t?

You’ll be sitting around twiddling your thumbs into boredom… and eating ramen because you don’t have the income you need to afford the produce section.

But if you’ve got a few contracts where clients agree to pay you on a month-by-month basis, that kind of recurring revenue means you don’t have to start out each month’s income budgeting at $0.00. Instead, you can start out at $2,000.

Or $3,500.

Or even $5,000+.

You might not even have to market for new work at all if you stick with it and manage to land that many retainer agreements. (It’s totally possible.)

This month alone, I started off with $7,730 worth of retainer agreements booked.

Which meant my bills were paid, and I had more than enough cash to have plenty of spending money and savings funds.

Curious how I did it? I’ve adopted these three work principles, and it’s totally shifted my need to market myself to almost nothing:

1. Always, always, always pitch a retainer (always)

Yes, always.

Especially when you get clients coming to you who want to order multiple a la carte services.

Even if they sound 100% sure of what they want from you, it doesn’t hurt to put together a proposal with a few different options—one being what they think they want, another one presenting another a la carte option, and a retainer.

For example, I had a client come to me who wanted me to re-write his website, write some ads, and get his blog going for him.

He had the a la carte items picked out, and seemed rather sure of himself.

In my proposal, I pitched him the cost of his idea, and right next to it, I put in an idea for a retainer, where I’d take care of everything he’d asked for plus make myself available for consulting when needed.

(Pro note: I also pitched how we could grow his business together over the next six months, which was a huge selling point.)

It was fully his choice to choose which option he wanted.

I didn’t push one option over the other in my conversations with him.

But the freelance retainer agreement was such a good deal for him, he couldn’t say no.

I turned what would have been a $4,000, two-month project into $10,000 over the stretch of a few more months.

Plus, his business is way more solid and better off because of it. Win-win.

2. Base your rates on value, not time

In order to keep your retainer agreements as profitable as possible, you’ll want to base them off of your client’s perceived value rather than the number of hours or the amount of effort you’re putting in.

This can be a really hard one to get over, and I felt super guilty about it at first.

But here’s the thing: the reason your clients are coming to you is because you have an expertise, a talent, and a skill that they don’t have.

And because they don’t have it, they value it more than you do.

I’m not saying that you don’t value your own skill set, but we do tend to put a lower value on the things we do day in and day out.

So if you spend five hours a day optimizing landing pages for conversions, you could probably do it in your sleep.

Meaning, it’s something that’s so easy for you it seems like second nature.

But there’s people out there who don’t even know the first thing about conversion rate optimization. All they know is they want more results squeezed out of their website.

So to them, the stuff that you can do in your sleep is incredibly valuable and worth paying well for.

When I set up retainer agreements with my clients, I usually outline what the work outputs will be for the first couple of months, but them let them take the lead on deciding what we should work on and what our outputs should be after that.

This way they have a good grasp on the “amount” of work to expect in terms of value to them, and they feel like they’re getting exactly what they need and ask for in exchange for their money.

And if the work we decide on doesn’t really take me that much time?

All the better.

I still know I’m fully living up to and exceeding their expectations, that they’re getting exactly what they came for, and my time is more profitable.

3. Make your site (and by default, yourself) irresistible

Okay, unless you’re a designer, I’m not talking about how your website looks.

As long as it doesn’t look like it stepped straight out of 1993, you should be fine.

What I mean is you should focus on publishing such irresistible content on your static pages and your blog that your prospects just can’t stop reading it.

I mean pinpointing your target audience’s most frustrating pain points and their biggest dreams and writing your message around those things to create a strong emotional attachment.

Nothing about my website design and branding is professionally done, and I have absolutely zero problem getting booked solid and finding new clients to take on as and when I need them.

And the reason why is because I’ve done a good job with using my on-site copy to speak to my target audience’s emotional connections to the topics of copywriting, selling, and marketing.

Because think about it: when you make an emotional connection with someone you meet in real life, you want more of them.

If it’s a date, you want to kiss him. If it’s a new friend, you make sure you get her contact info so you can find a time to hang out again.

And even though you’re not there to charm your site visitors in person, you can create the same feeling with your website copy.
You just can’t be afraid to break out of the jargon-y, expected language for your niche.

You’ve got to speak up on the emotional issues associated with your niche that really get people hot.

For example, though earning more money is a pain point for most freelancers (most of us always want more), the part that’s the real—the emotional pain point—is the part where you have to hustle yourself silly to get it.

So call out that real, deep pain point and talk about it.

Unsure how all this ties back into booking retainer agreements?

It’s a little more subtle, I’ll admit, but the fact is that if people enjoy “hanging out” with you on your blog posts and other website copy, they’ll relish in the idea of being able to “hang out” with you one-on-one for items that extend beyond your one-and-done a la carte items.

They already know that you’ve got a larger expertise that stretches beyond whatever item it is they want to hire you to do for them, so pitching them a retainer gives them the opportunity to take advantage of it in more ways.

More retainers = happier business, happier life

Once you book your first retainer project, you’ll see how refreshing it is not to start out each month from zero.

And even if you’re already working with one or two retainer agreements, having more will help you realize a greater ease in your life and your business—one where you don’t have to worry so much about money and can just enjoy the work you do.

Do you have any tips for getting retainer projects? Tell us in the matermind group!

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Written by Chelsea Baldwin

Contributor at

Chelsea Baldwin is a freelance writer, turned agency owner, turned business coach. She helps freelancers, solopreneurs, and small business owners grow their businesses quickly and become way more profitable. Each week, she sends out a free weekly dispatch with business advice, easy-to-complete business hacks, and behind-the-scenes looks at what it’s like for her to run two separate businesses.  

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  1. Chelsea, I’m in a little different situation where I have 6K a month in retainers that I have established over 5 years. Now I want to sell this intangible portion of my business to someone else. What should my exit strategy look like? Provide some interim training support to the new company? Should I ask for 1 years retainer as a selling price or more? I’ve lined up a buyer who would be able to provide the same level or better support for my clients. How shoudl I tell my clients that someone new will be taking over?

    1. Hi Brian – I’m not really the right person to ask for advice on selling a business, but for the telling your clients part, I think giving them a notice period before the transition happens & some sort of transition plan would be good.

  2. Tim Kavermann says:

    I’d love to see what your proposal looks like! Great article as always!

  3. Great article, Chelsea! It’s always difficult for freelance designers to create a system that gives us consistent income. This will really help.

  4. Thanks for this post! I am currently in the throws of trying to look for potential retainer clients so this was timely. I spent some time reaching out to people who were posting job postings wanting ongoing social media work, but those never wanted to use our company because they were stuck in the idea they needed one singular person. I’ve switched gears a bit now and am trying to just meet one on one with past business connections to see if they or anyone they know has that need. I like that you said to pitch retainer services to everyone, no matter what they ask for or how set they are on what they want. Because…you never know, right?

    1. Exactly, you never know! And the more you do it, the better you get at predicting what type of client will be on board with what type of retainer.

  5. Ihsaan Muhammad says:

    Great Advice! Thanks for the post.

  6. This is something I have always struggled with as it seems like most local companies I work with just want a website set up and that’s it. Maybe I am not the best salesman, but this article makes me want to try harder because it would be VERY refreshing to not start out from zero each month!

    1. David, I find the EXACT same thing with most of the small businesses and local companies I work with too. Like yourself, I would also agree that I may not be pitching it the right way either, but I seem to find that the majority of the businesses do not see the need for anything further once the site has launched. Kind of a ‘set it and forget it’ type mentality. Whether it’s maintenance plans, backups, etc I find it tricky to show them just how important something like that can be, and they generally just pass on it. But I agree, it would be awesome to not start from zero each month!!

      1. Hey David & Mike – Totally understand. Some smaller clients just won’t want to do a retainer, and that’s fine. But sometimes, the retainers can be really small, but still beneficial. Other times, it’s nice to offer a free “review” a few months later to show things that could be improved, and that sometimes works as well.