Last week we were talking about ways to prime a client for follow up work throughout your project process. 

This week we’re talking about taking advantage of the easiest money freelancers can make, but most ignore: 

Past clients.

The problem: 

Your previous clients loved your work. They promised to reach out again soon. But that was months ago, and you’ve heard nothing since. 

The benefit of solving it: 

There’s a warm pipeline of clients who trust you and are ready to work with you again, without you having to hustle and get burnt out constantly pitching. 

Why what you’ve tried has failed: 

You’re not re-engaging clients who already liked working with you, and instead defaulting to cold pitching to land new clients (while pretending you’re not low-key panicking about rent).

Here’s how to solve it: 

Follow my 5-step system to re-engage your previous clients, and you’ll book your calendar months in advance → 

Step 1: Gather Your Contacts

Make a simple spreadsheet with every client you’ve worked with as a freelancer (or hey, from corporate too if you’ve got ‘em!)

For each contact, note:

• What you did

• How it went

• What you wish they’d hired you for next

• Ideas of potential projects you could help them with 

Step 2: Do Your Research

Go to Google, check their LinkedIn, revisit their company website. 

You’re looking for any recent shift: new offer, team change, product update, press mention.

That’s your opening.

Step 3: Identify a Relevant Hook

Think about what small thing you could help them with right now that connects to the previous work you did for them. 

This might be: 

• A follow-up to your last project

• A fix for something new you spotted

• An opportunity they’re not capitalizing on

Step 4: Send a Sharp, Specific Message

No “just circling back” or “checking in.” 

Be short and useful: 

Hey Sam, Saw your new product launch. Congrats, it looks sharp. Made me think: we could build a quick landing page variation to test conversions on paid traffic. Something light, maybe 2-3 sections. Could be a fast win. Want to discuss it more next week?

They can say yes, no, or later. 

Either way, you’re back on their radar with purpose.

Step 5: Track It

Update your spreadsheet to log:

• When you last reached out

• What you pitched

• If/when to follow up

This is how you stay organized and actually see the compounding effect over time.

^^^ Make this a habit every week, and you’ve got a system for rebooking great clients without relying on cold outreach to generate income.

Even reaching out to just 1 client per week will help you build income you can actually count on! 

Best,
Jamie

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