How to Land Retainer Gigs as a Freelancer

As a freelancer, your dream scenario goes something like this:

You have a client who loves your work so much that they beg you to keep working with them “on retainer.”

Every month they pay you a nice fat fee.

The work they want is so simple you can pretty much do it in your sleep.

And the checks keep rolling in month after month, so you have a nice stable baseline of income.

Sound about right?

Freelancer Christiana is hoping to get there. She asks:

I totally believe in long-term client relationships. However, I struggle with how to “frame the ask.”

What’s your approach to creating a retainer agreement out of a small or one-off project?

Also how and when do you introduce the idea to your client?

I’m not sure whether to put it on the table during the proposal stage (when I know it would be the most valuable investment for them) or after we’ve worked together and built up some trust.

Now I understand why Christiana’s feeling some awkwardness here.

“Um, excuse me, but would you be willing to pay me $5,000 a month indefinitely?”

This is one area where your desires and those of your client are potentially in conflict.

What does the client want here?

First and foremost, they want to control their risk.

Ideally they’re like to hire the best freelancer in the world for a (low) fixed fee, then get as much work as possible for that initial investment.

They do NOT want to get sucked into a never-ending engagement that bleeds them and their business dry.

Your dream is their nightmare.

Your nightmare is their dream.

Hence the awkwardness.

So an important key to landing a retainer deal is eliminating the risk by proving that you’re earning them more than you’re costing them.

Here’s how I’ve approached this:

First of all, don’t go for the retainer right away.

Instead make that first engagement something small and finite.

Once you’re “in” with the client you have a huge advantage, because you’re privy to the inside of their business, their goals and frustrations, etc.

As you’re working with the client on the initial project, start taking note of all the other things you can do to serve them that will have an immediate benefit. Preferably things that will make them more money right away.

Include on your list things you notice yourself, but *especially* things that the client calls out to you: “Ugh, yeah our homepage is a disaster, we’ve been wanting to get that redone for months.”

Also look for ongoing needs that they’re treating as one-off expenses.

If you’re a designer, they might need a blog post graphic created every week, for example, and they’re paying someone else $50 a pop.

You can probably put together a list of 20–30 items easily if you pay attention.

(I know I’ve got hundreds of things I want to fix in my biz but don’t have time to get to.)

Then I’d start talking to them about a few of those items, the ones with the highest payoff, and see if you can get them thinking about how it would help their business to get those things fixed.

Once you get this buy-in, really all you have to do is agree on terms.

I’d give them a choice of paying a much higher per-project fee, or you can bundle several projects together and handle them under a retainer.

For clients, the idea of paying a monthly retainer is daunting.

Use your insider knowledge to make the retainer option look like a bargain, and they’re more likely to jump on it.

Starting out is tough — here are a few tips to catch your first few clients.

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