EF #35: 🔥 How My Cold Marketing Outreach Led to New Freelance Work

What worked (and how you can do it), with key takeaways and a timeline

6Me and my 87yo mom this past weekend on a press trip to Ponte Vedra, FL. (Sometimes, on individual media stays, I get to bring a guest.) 💖

Welcome to the 35th edition of Expert•ish Freelancer, a newsletter that helps you grow your freelance business with confidence. Get tips, tools, and insights every other Friday to help you save time, make money, and work smarter based on my 35+ years as a freelance writer.

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Today’s newsletter highlights how my cold marketing outreach led to new freelance work.

🔍 Key Takeaways: 

✅ Personalize your outreach.
✅ Follow up with patience.
✅ Negotiate and build relationships.

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Looking for the last newsletter? Find it here: EF #34: 👀 Want An Exclusive Behind-the-Scenes Peek Into My Freelance Day?

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✅ Read: What am I working on these days? Here are a handful of writing clips from Success, AARP, K&H Pet, IAAPA, Blue Haven Resort, and AAA.

✅ Watch: Master research and uncover hard-to-find facts with The 5 Ws of Research, an on-demand course from Poynter available for free until August 31, 2025.

How My Cold Marketing Outreach Led to New Freelance Work

Does this sound familiar? You’re scrolling through LinkedIn, plotting your next big client move. You read about other freelancers sharing their latest successes🌟, winning new clients, and tackling new projects.

But you’re wondering, “Does cold outreach actually pay off?”

Unequivocally, a resounding YES!

Let me walk you through my recent journey approaching a major brand, step-by-step, and share what really worked (and what might help you, too).

After weighing the options (timeline? step-by-step? key lessons?), I realized: nothing speaks to time-starved freelancers like a combo punch—a real-life timeline for transparency, with clear, actionable takeaways. 

Let’s dive in.

The Real Timeline: From Research to Rate Negotiation

June 16 – The Research Mission

I started the day with a positive mindset: You’re good enough, right now. Despite the challenging market, there’s plenty of work out there. Go get it, girl!

I decided to stop overthinking and just start. I found the Director of Content (let’s call him Mark) at a national brand (let’s say, Travel Your Way) on LinkedIn.

Lesson: Don’t let the “comparison game” or overplanning hold you back. Sometimes, researching the right contact is 90% of the battle!

June 16 – The Connection Request

I sent this message:

"Hi Mark, I write for [similar brands] and wondered if you work with freelance writers. With 35+ years as a journalist, copywriter, & content marketing writer covering travel/wellness/food/lifestyle, I think we’d be a great fit. May I send clips?"

With a dash of confidence 🌟, I kept it simple. I led with my experience, kept it relevant, and asked permission to send work.

Result: Mark replied the same day! (I know, I almost spilled my ☕.) He directed me straight to the content team.

June 17 – The Warm Email Pitch

Subject: Mark sent me your way + writing samples

Here’s the super-short version of my LOI email: I referenced Mark’s intro, shared my background and client list, attached killer clips, and included testimonials/portfolio links. I kept it upbeat and easy to scan.

“As promised, I’m sending along some clips to give you a feel for my writing style and reporting chops. Would love to learn more about your freelance needs!”

June 18 – The “We Want You!” Email

The content lead replied immediately—complementing my style and inviting me to join their freelance roster. (She even mentioned she’d send sponsored content projects my way, and welcomed my pitches.)

But... cue the “patience, grasshopper 🦗” moment: Her vacation started the next day. Clock pause. ⏸️

Happens all the time. So, I waited and continued my marketing outreach with other prospects while still working on existing client work.

But I did my pro freelancer move and marked the follow-up date on my calendar. (When I don’t do this, leads fall through the cracks. Then I find them months later and kick 🦶 myself for not being more organized.)

July 1 – The Gentle Follow-Up

“Welcome back! Hope you traveled somewhere fun.” (Never underestimate the power of a friendly, personal touch.)

I reminded her of my availability and asked for editorial calendars and brand guidelines. (Pro tip: This shows you’re serious, you’re experienced—and it might speed things up.)

July 11-17 – The Waiting Game & Rate Talk

She apologized for the delay (vacation inbox backlog is real), but soon sent me onboarding forms and those elusive project details, including their rates. Now, here’s where many freelancers freeze: the money talk. 💸

“Thanks for sharing your rates. I typically earn $1/word for editorial and $1.25–$1.50/word for sponsored content. Do you have any flexibility?”

She bumped the rate up to $0.65/word (from their standard $0.50)—not ideal, but a win for a first gig and a possible long-term flow of projects. In fact, she gave me not one, but two projects right out of the gate.

July 17 – The Decision

I weighed the pros and cons of working for a lower rate than I’d hoped for. But honestly, my rates range from $0.50/word to $1.50/word for similar work. I wish I could say all my clients pay top dollar, but they don’t.

And in this weird time of freelancing—where AI might replace some freelancers, where the economy is shaky, where the media landscape changes weekly, where political turmoil evokes daily anxiety—I decided to play the long game. I determined that building relationships, working with top-tier brands, and getting ongoing work is worth an initial compromise of a lower rate.

👉Tip: You’ve got to decide what your bottom line is when it comes to rates. For me, I don’t go below $0.50/word on projects that pay per word. You might be the sole breadwinner who pays all the bills, so your bottom line might be different.

Anyway, I accepted the two assignments, showed gratitude, and set the stage for continued collaboration.

💡 Key Lessons and Takeaways for YOU:

  • Research + Personalization = Gold: Find the right person AND make your outreach personal. If you use templates for efficiency (like a LinkedIn connection request), tweak it a bit to customize. Let your personality and creds shine.

  • Move the Conversation Off Social: Transition from LinkedIn messages to email ASAP. It’s faster, more professional, and shows you’re serious.

  • Master the Follow-Up: If you don’t get a reply, wait a couple of weeks, then send a warm, friendly nudge. People appreciate polite persistence.

  • Be Patient, but Professional: Editors and marketing folks get busy. Mark your calendar for follow-ups and never take radio silence personally.

  • Negotiate Like a Pro: Ask for higher rates every time. Even if they say no, you’ve planted the seed. Sometimes, “budget” really is fixed—but asking is the only way to find out.

  • Decide What’s Worth It: Sometimes it’s okay to take a slightly lower rate if it opens the door to steady, high-profile work. Sometimes, it’s better to walk away. Trust your gut.

  • Confidence is Key: Let your self-confidence shine through, knowing you are good enough. Show potential clients how you’ll make their life easier.

Final Pep Talk

Cold outreach feels scary 😱—until it works. Or at least leads to a foot in the door, new contacts, and fresh confidence.

Remember Joey Tribbiani’s classic line in Friends

It’s friendly, (over-)confident, and opens the door to connection—a similar vibe you want to bring to your cold outreach, but with a professional tone. Sometimes all it takes is a simple, genuine approach to get a foot in the door, spark interest, and turn a cold message into warm opportunities.

So channel your inner Joey (the professional version): be confident, be personable, breathe deep, and reach out. The next “yes” might be one well-worded DM away.

👉 What's your best tip for successful cold outreach that works? Hit reply and let me know—I read every response, and your question might inspire the next newsletter!

🥳 Fun Fact About Me: When I worked in public relations at a Six Flags theme park, I coordinated a wedding where Bugs Bunny walked the bride down the aisle. Fun, right? I alerted the media to cover this out-of-the-ordinary event, generating unique coverage for this family-friendly theme park. The scandal? I found out right before the wedding that the bride was several months pregnant. Ooops! 🤭 Not exactly the media angle you want for a family-focused attraction.

  • Share Your Success Story. I would LOVE to hear how you’ve implemented any of the ideas in Expert•ish Freelancer and found success. I might even include your win in a future newsletter. You can always reach me at [email protected]. 

  • Follow me on LinkedIn. I share more freelance tips/insights most weekdays.

  • Turn to Expert•ish Freelancer’s Tools & Resources page, highlighting valuable resources to help you successfully run your freelance business. You’ll find recommendations for apps, tools, training, services, websites, blogs, podcasts, books, videos, and more! If you’ve got a resource you love, let me know about it.

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Thanks for allowing me into your inbox!

I look forward to sharing my freelance journey with you, and I look forward to hearing about yours. I’m just here as your guide. Take what works for you, and tweak it to your needs. Rinse. Repeat.

I’ll be back in two Fridays with another edition of Expert•ish Freelancer.

In the meantime….

Be kind. Do good. Give thanks. 😊

With gratitude,
Lisa Beach

Namaste, freelancers!

FYI: In yoga, the instructor often closes the session by saying “namaste” as a way of acknowledging and honoring the light, spirit, or goodness within each person in the class. 🧘‍♀️ It’s often used as a closing to convey unity (we’re all interconnected), gratitude (thank you for this shared experience), respect (I respect you and your journey), and peace (may you find peace within yourself). Essentially, it's a way to acknowledge the shared experience and to leave with a sense of peace and connection. đŸ˜Š