The moment I landed my first retainer client, everything about freelancing changed.
Before that, I was constantly hustling for the next project. One client would finish, and I’d be back on Upwork sending proposals, checking job boards, wondering where the next paycheck was coming from.
It was exhausting.
Then I got a client who paid me the same amount every single month for ongoing work. No proposals. No pitching. No anxiety about where the next dollar was coming from.
I became obsessed with getting more of them.
If you’re still doing one-off projects and wondering why freelancing feels like a feast-or-famine roller coaster, retainer clients are the answer. Here’s everything I’ve learned about landing them and keeping them.
What Is a Retainer Client?
A retainer client pays you a fixed monthly fee for an ongoing scope of work.
Instead of hiring you for one blog post, they pay you $1,500 a month for four blog posts every month. Instead of a one-time social media audit, they pay you $800 a month to manage their accounts consistently.
The work is predictable. The income is predictable. And the relationship goes deep enough that the client stops thinking of you as a vendor and starts thinking of you as part of their team.
That’s when freelancing starts to feel like a real business.
Why Retainer Clients Change Everything
Let me put some numbers on this so it clicks.
Say you charge $300 per blog post. To earn $3,000 a month, you need to find ten different clients, send ten different invoices, and manage ten different relationships. That’s a lot of moving parts.
Or you could have two retainer clients at $1,500 a month each. Same income. Two relationships. Two invoices. Significantly less stress.
Retainers give you the mental space to actually focus on the work instead of constantly chasing the next project. And when you do better work because you’re less stressed, clients stick around longer.
It compounds in the best possible way.
How to Land Retainer Clients
1. Start with existing clients first
The easiest retainer to land is with a client who already knows and trusts you.
After you complete a project successfully, don’t just say thank you and disappear. Have a conversation about what comes next.
Something like: “I’ve really enjoyed working on this project with you. I’d love to keep supporting you on an ongoing basis. Would it make sense to set up a monthly arrangement so you have consistent help without having to brief a new person each time?”
Most clients who liked working with you will at least hear you out. Many will say yes.
I landed my first retainer this way. The client had hired me for a one-time project, liked the work, and when I asked about ongoing support, they said “actually, that would be really helpful.”
That client stayed with me for two years.
2. Position yourself as ongoing support, not a one-time fix
The way you talk about your services matters more than you might think.
If you pitch yourself as someone who “writes blog posts,” clients will hire you for one blog post.
If you pitch yourself as someone who “helps businesses maintain a consistent content presence that builds trust and drives organic traffic over time,” clients start thinking about you in terms of months, not projects.
The service is the same. The framing is completely different.
Update how you describe your work on your website, your Upwork profile, and in your proposals. Lead with the ongoing value, not the one-time deliverable.
3. Create retainer packages instead of hourly rates
This was a game changer for me.
Instead of quoting an hourly rate that makes clients calculate every minute, offer defined monthly packages.
Package A: Two blog posts per month — $800 Package B: Four blog posts per month — $1,500 Package C: Four blog posts plus a monthly newsletter — $2,000
Now the client isn’t thinking about hours. They’re thinking about outcomes and what level of support fits their budget. It’s a completely different buying decision.
Packages also make your income more predictable because clients know exactly what they’re getting and what they’re paying every month.
4. Look for clients who need consistency
Not every client is a good retainer candidate.
The best retainer clients are the ones who need something done repeatedly — blog content, social media posts, email newsletters, bookkeeping, customer service coverage. These are recurring needs that don’t go away.
When you’re applying for jobs or reaching out to potential clients, look for signals that they have ongoing needs. Job postings that mention “ongoing,” “long-term,” or “regular content” are telling you exactly what they’re looking for.
Those clients already want a retainer. They just need someone to propose it properly.
5. Propose it directly — don’t wait for them to ask
Most clients won’t think to suggest a retainer arrangement on their own.
They’re used to hiring people project by project. That’s just the default way they think about it.
Your job is to introduce the idea. After a successful project or even on your first call with a good-fit client, bring it up naturally.
“A lot of my clients find it easier to set up a monthly retainer rather than going back and forth on individual projects. It means you always have support when you need it and you don’t have to brief someone new each time. Is that something that might interest you?”
You’re not being pushy. You’re offering them something convenient. Most clients who are a good fit will at least consider it.
How to Keep Retainer Clients
Landing a retainer is one thing. Keeping it is where the real money is.
6. Deliver consistently every single month
This sounds obvious but it’s where most freelancers drop the ball.
The number one reason retainer clients leave is inconsistency. They hired you for ongoing support because they wanted reliability. The moment you start missing deadlines, going quiet, or delivering work that’s noticeably below your best, they start wondering if the arrangement is worth it.
Treat your retainer clients like your most important clients — because they are.
Set reminders. Build the work into your weekly schedule. Deliver before the deadline whenever possible. Never let a retainer client have to chase you.
7. Communicate proactively, not reactively
Retainer clients don’t want to wonder what you’re working on.
Send a short update at the start of each month confirming what you’ll be delivering and when. Let them know immediately if anything changes on your end. Flag a potential issue before it becomes a missed deadline.
This kind of proactive communication is rarer than it should be. When you do it consistently, clients notice. And clients who feel informed and taken care of don’t go looking for someone else.
8. Add unexpected value occasionally
Every few months, do something that wasn’t in the contract.
Send them a relevant article you came across. Notice an opportunity they haven’t mentioned and flag it. Offer a fresh idea for their content strategy without being asked.
These small extras cost you very little time. But they remind the client why they hired you in the first place and make the relationship feel like more than a transaction.
Clients who feel that their freelancer genuinely cares about their success don’t cancel retainers.
9. Review and renegotiate annually
Your rates should grow over time. Your retainer rates are no exception.
Once a year, review each retainer relationship. Has the scope of work expanded? Have your rates increased for new clients? Has the value you’re delivering grown?
If yes to any of those, have a conversation about adjusting the monthly fee. Frame it as a normal annual review, not a confrontation.
Clients who have been happy with your work for a year are the easiest people to renegotiate with. They already know what life looks like without you — and they don’t want to go back to it.
How Many Retainer Clients Do You Need?
That depends on your income goal and your capacity.
But here’s a simple way to think about it.
If your goal is $5,000 a month, you could get there with three retainer clients at around $1,600 each. Or five clients at $1,000 each. Or two clients at $2,500 each.
Pick a number that feels achievable based on the services you offer and the clients you’re targeting. Then work backwards from that number to figure out how many clients you need at what monthly rate.
Most freelancers are shocked by how few retainer clients it takes to replace a chaotic project-based income.
My Final Thoughts
Retainer clients are the closest thing to job security that freelancing offers.
And the best part? They’re not as hard to get as most people think. They come from doing great work, asking the right question at the right time, and positioning yourself as someone worth keeping around.
Start with one. Do excellent work. Ask about ongoing support. Repeat.
One retainer client can change the entire feel of your freelance business. Build enough of them and you’ll wonder why you ever did it any other way.
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