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Welcome to the 42nd 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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Last month, a client I've worked with for about five years sent me an email that made me do a double-take.

All these years, I’ve only written travel-focused content marketing articles for her. But in this email, she asked, “We need you to rewrite our corporate website. Can you turn it around in two weeks?”

For YEARS, I'd casually reminded this client that I do more than just write travel articles.

“Please keep in mind that I also take on copywriting projects if you ever need it! I can tackle web content, email campaigns, newsletters, etc.”

But nothing ever came of it. Until it did. That one project? Over $6,500 (plus a 20% rush fee because tight deadlines deserve compensation).

The lesson? Keep planting seeds. Keep reminding clients what you can do. You never know when they'll finally have the budget, the need, or both. Today's newsletter is all about that exact strategy—using the holidays to plant seeds that bloom into Q1 work.

Today’s newsletter highlights a strategic guide to holiday outreach.

🔍 Key Takeaways: 

✅ Strategic, timely emails matter.
✅ Always follow-up.
✅ Proactive outreach fills calendars.

Today’s issue is brought to you by PodPitch. Sponsors help keep the newsletter free, so please click on their link to check out their offer! ⬇️ 

Looking for the last newsletter? Find it here: EF #41: 😮‍💨 Exhausted, Ghosted, and Burned Out: The Brutal Truth About Freelancing Right Now

Survey Says…

In the last newsletter, I asked, “What do you need permission to do right now?” I was curious to see if we're all feeling the same things. Here’s how you weighed in:

42% Slow down without guilt
42% Pivot my business direction
16% Say no to low-paying work
0% Keep going as-is

Nobody—literally zero percent—wants to keep going as they are. We're all craving either a slower pace or a complete pivot, and that tells me everything about where freelancers are right now.

Know of a good resource? Tell me!

Why Smart Freelancers Are Emailing Clients Right Now (And You Should Too)

It's mid-November, and while everyone else's Pinterest boards are filling up with turkey recipes and gift guides, freelancers are eyeing their calendars with a familiar dread—the dreaded January slump.

You know the one: that vast expanse of empty calendar squares staring back at you like a passive-aggressive reminder that maybe you should've sent that client email weeks ago.

So here's the question you’re probably mulling over right now: Should you really bother clients during the holidays?

The answer is yes—but with strategy and timing that doesn't make you seem like the freelance equivalent of a desperate Black Friday shopper.

Know that this approach has consistently generated Q1 work for me, turning what could be a panic-inducing slow season into a calendar that actually has some deadlines on it.

The Two-Touch Strategy That Actually Works

Think of this like a good rom-com: timing is everything, and you need at least two meaningful interactions to make something happen.

Touch #1: Pre-Holiday Outreach (Do This Next Week)

Your first move is to reach out before everyone disappears into a turkey-and-tinsel-induced coma. Here's what you include:

• Warm holiday wishes (keep it brief and genuine—nobody needs a Hallmark movie script)

• Your availability for year-end projects (because yes, some clients suddenly remember that Q4 content initiative is due December 30th)

• A gentle reminder about Q1 planning (you're planting seeds here, not demanding commitments)

Why does this timing work? Because you're catching clients in that sweet spot where they're simultaneously thinking about year-end budget spend (use it or lose it!) and planning Q1.

Plus, when January rolls around and they're frantically looking for help, you're already on their radar. You're not scrambling to introduce yourself when everyone else is flooding their inbox with “New Year, New Me” pitches.

Touch #2: Early January Follow-Up

Come the first full week of January, it's time for round two. Your follow-up should include:

• A hope-you-had-great-holidays opening (because you're a human, not a robot)

• Your January/February availability (specific months = easier for them to visualize)

• A direct question about when they're ready to ramp up projects

• A quick refresher on your services (memories fade over eggnog season)

This lands when they're back in work mode with fresh budgets and a to-do list that's probably already overwhelming. You're not interrupting their holiday—you're offering a solution right when they need one.

What This Actually Looks Like in Real Life

Let me break down the timeline I typically use:

Mid-November: I send a pre-Thanksgiving email to current and past clients. It's friendly, brief, and mentions my availability through year-end plus a “keep me in mind for Q1” line.

Late December: I'm enjoying the holidays and not obsessively checking my email every five minutes because I've already done the work. The seeds are planted. Now I’m enjoying time with my family. (I purposely take on fewer projects in December to go into the holidays with intention.)

Early January: I follow up with anyone who didn't respond and those who specifically mentioned having January projects. This is when the magic 🪄 happens.

The result? Right now, I've already got several Q1 projects on my calendar, and we haven't even hit Thanksgiving yet. That means I'm going into the holidays knowing I don't have a completely empty calendar come January 1st. And honestly? That peace of mind is worth its weight in pumpkin pie.

Why This Approach Actually Generates Work

This isn't just busy work that makes you feel productive while accomplishing nothing. (I’m looking at you, color-coded spreadsheet gathering digital dust.) Here's why it works:

• You're solving their problem: Many clients ARE planning Q1—they just haven't gotten around to reaching out yet. You're making their life easier by being proactive.

• Timing advantage: You're in their inbox at decision-making time, not three weeks after they've already hired someone else.

• Relationship maintenance: This shows you're thinking about their needs and planning ahead, which is exactly the kind of freelancer they want to work with.

• Reality check: January is historically slow for most freelancers anyway (myself included). This outreach transforms potential downtime into booked work. You're being strategic about a problem that exists whether you address it or not.

• The compound effect: Even if they don't have immediate work, you're top-of-mind when something does come up in February or March.

But What If I Seem Desperate?

Let's address the 🐘 in the room: You're worried this makes you look desperate, right?

It doesn't. You're being strategic and professional. There's a massive difference between “Hey, I exist and I'm available if you need me” and “PLEASE HIRE ME I'LL DO ANYTHING!” Your message is the former.

And if they don't respond? That's completely fine. You've still positioned yourself well, and they now know you're available. Not every seed you plant 🪴 will sprout, but you can't harvest what you don't plant.

Should you reach out to ALL past clients? Use your judgment, but cast a wider net than you think. That client you worked with six months (or two years) ago might have a new project budget in January.

The Bottom Line

If you haven't done this yet, there's still time. Two strategic emails—one now, one in January—can literally be the difference between feast and famine in Q1.

So, draft that email. Send it this week. Then go enjoy your holidays without that low-grade anxiety about what January's going to look like. You've done the work. Now let it work for you.

👉 What's your biggest hesitation about reaching out to past clients right now? Hit reply and let me know—I read every response, and your answer might become next week's newsletter topic!

• 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.

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

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. 😊