I Found My Longest-Running, Highest-Paying Client on Craigslist (Yes, Really)

When I first dipped into freelance writing, I thought I had to “do it right.” You know… stick to the freelance platforms, polish the perfect portfolio, stalk the “legit” job boards everyone in Facebook writing groups swore by.

And yet, one of my longest-running, highest-paying clients?

Craigslist.

Yes, you read that right. The site better known for sketchy roommates and questionable used couches turned out to be the place where I landed a dream gig. That was four years ago, and the relationship is still going strong today.

That one Craigslist ad? It blossomed into consistent work, a steady paycheck, and even referrals. It became one of the cornerstones of my writing business.

The takeaway: you can find great clients anywhere and not just the “expected” places.

If you’re a freelance writer or aspiring one, this story is your reminder to widen your scope. Because the internet is full of opportunities disguised as random posts, overlooked ads, or casual connections.

Let’s unpack all the places your dream client could be hiding.

The Myth of “Real” Clients

I used to think a “real” client only came from certain pipelines. Platforms like Upwork or FlexJobs. Big-name agencies. Fancy LinkedIn connections.

But here’s the truth: great clients don’t care where you find them. They care that you can solve their problem, make their life easier, and deliver good work consistently.

When you zoom out and think of it that way, suddenly Craigslist doesn’t sound so crazy, does it?

So, let’s break this down. Where else can you discover writing work that might just turn into the gig that changes your business?

1. The Obvious Spots (Yes, They Still Work)

There’s a reason writers flock to these first. They do work. But they’re also crowded. The trick is knowing how to stand out.

• Job Boards: Sites like ProBlogger, Freelance Writing Gigs, and Contena list fresh opportunities almost daily. The challenge? You’re competing with hundreds of other hopefuls. My pro tip: apply fast and personalize every pitch. Generic copy-and-paste pitches land in the trash.

• LinkedIn: Forget the “resume site” stigma. LinkedIn is where business happens. I’ve seen writers land clients just by posting, “Hey, I’ve got two openings for new clients this month. DM me if you need content help.” Simple, effective, and free.

• Content Platforms: Yes, the pay can feel low to start. But it’s also a chance to get bylines, practice process, and sometimes land a hidden gem of a client who sticks.

Pro Tip: Don’t treat the “obvious” spots as your only play. They’re just one piece of your writing client pipeline.

2. The Hidden-in-Plain-Sight Sources

Now, here’s where things get juicy. These are the spaces most writers overlook. And yet? They can deliver the exact kind of clients you’re dreaming about.

• Craigslist (My Big Win): I almost skipped over the ad that led to my long-term client. Why? Because like most people, I thought Craigslist = scams. But the ad was short, sweet, and professional. I decided to try. I sent a thoughtful pitch explaining how I could help. That was four years ago, and I still send them invoices every single month.

• Local Facebook Groups: Community groups are underrated goldmines. Business owners pop in all the time asking, “Anyone know someone who writes content?” If you’re in the group, you’re in the conversation. I’ve seen everything from fitness coaches to realtors find writers this way.

• Your Own Inbox: Don’t underestimate old connections. College classmates, coworkers from your 9-to-5, or even that friend running a bakery, they all need words. A casual “Hey, I’m freelancing now if you ever need writing help” email can unlock doors.

Pro Tip: Don’t roll your eyes at “small” gigs. Some of my highest-value relationships started tiny and grew as the client’s business grew.

3. Create-Your-Own-Luck Opportunities

If waiting for clients to post gigs feels like a hamster wheel, you’re right. The best freelancers don’t just apply to listings, they create opportunities.

• Cold Pitching: Think of businesses you’d love to write for. Visit their site. Do they have a sad blog last updated in 2021? No blog at all? Send them a short email: “I noticed your blog hasn’t been updated in a while. Here’s why fresh content matters and how I can help.” You’d be surprised how many respond.

• Guest Posting: Writing for industry blogs builds credibility. Even if it’s unpaid, you now have a live sample to show in pitches. One guest post can snowball into invitations, partnerships, and yes, paid gigs.

• Networking Events: Virtual or in-person, networking works. That marketing manager you met at a Chamber of Commerce happy hour? They might hire you three months later when they realize they need a content writer.

Pro Tip: Think of pitching as planting seeds. Not everyone will grow, but some will sprout into long-term, profitable relationships.

4. The Weird + Wonderful Places

Some opportunities are so unexpected they almost feel random. But randomness is sometimes where the magic happens.

• Podcasts: Hosts need show notes, transcripts, and blog spin-offs. If you listen to a niche podcast, pitch them. You already know their voice and audience.

• TikTok + Instagram Creators: Influencers are busy creating video content. Many desperately need help turning that into captions, newsletters, or website copy. Offer to repurpose their content. It’s a win-win.

• Niche Forums + Discord Groups: From Reddit communities to Slack channels, business owners hang out everywhere. Join the conversation, drop value, and when someone says, “Ugh, I need content help,” you’re right there.

Pro Tip: Keep your ears open. Sometimes a random comment thread is all it takes.

5. Why “Random” Clients Turn into the Best Ones

Here’s what I’ve learned after years in this business. Those “random” opportunities often stick. Why?

Because they’re less saturated. You’re not one of 500 people applying. You’re one of 5. That client already feels lucky to have found you.

And when you deliver? They hold on tight. That Craigslist client? They don’t just pay me well. They refer me to others, they expand the work, and they trust me with projects I never thought I’d get.

All because I answered an ad most people ignored.

The Big Takeaway

The path to your dream freelance life isn’t linear. It’s not just one big break. It’s saying yes to the weird, the random, and the overlooked.

You can find writing work:

• In job boards everyone knows about.

• In inboxes and Facebook groups nobody’s paying attention to.

• In connections you create yourself through pitching and networking.

• Even in places like Craigslist.

The key? Keep your radar on.

Your dream client may not look shiny at first. But with the right pitch, consistent delivery, and a little patience, they could turn into the gig that pays your bills for years.

Ready to Build Your Freelance Writing Business?

If you’re serious about finding clients in all the places they’re hiding, you don’t need luck. You need a system.

That’s where my tools and downloads come in. I’ve put together guides that help you:

• Pitch like a pro (without sounding robotic)

• Spot the gigs worth chasing (and avoid the scams)

• Build repeat income so you’re not starting from scratch every month

• Grow your writing business into something sustainable, consistent, and profitable

👉 Grab the downloads and tools here. They’ll shortcut your learning curve and help you turn “random” opportunities into bankable, long-term success.

Because if a Craigslist ad can turn into four years of high-paying work, imagine what’s waiting for you out there.