A realistic guide for professionals who want campaigns that work—not campaigns that just fill the calendar.
TL;DR: Not every holiday deserves a campaign. Some dates convert, some simply sustain presence, and others should be acknowledged lightly—if at all. The 2026 Holiday Playbook helps financial advisors, tax professionals, and service-based business owners decide where to invest, where to step back, and how to make holiday marketing clearer, calmer, and more effective.
1. The real issue: the pressure to “do something” for every holiday
If you’re an advisor, tax pro, or service business owner, you’ve lived this:
- “This holiday is coming up—shouldn’t we post something?”
- Endless pressure to “tap into the season.”
- A feed full of decorative posts that don’t produce a single conversation.
Here’s the truth:
Not every holiday is meant for sales. Not every season needs a campaign. And forcing relevance is what exhausts your audience—and you.
Most businesses fall into two traps:
- Over-creating empty holiday content that blends into the noise.
- Feeling guilty for not posting, even when silence would have been the strategic choice.
This playbook exists for one reason:
To help you decide better, not do more.
2. Three types of holidays (and what each one is actually for)
Stop treating every date like a sales opportunity.
Start treating holidays as strategic touchpoints.
Holidays that convert
These are tied directly to planning, urgency, or decision-making:
- New Year / Q1 kickoff (clarity + planning)
- Tax Season
- Medicare AEP / OEP
- Back-to-School
- 5/29 Day (college savings)
These are your high-value, high-intent marketing moments—ideal for direct mail, funnels, and friction-based content.
Holidays that sustain presence
They keep relationships warm without pushing a sale:
- Mother’s Day
- Father’s Day
- Labor Day
- Thanksgiving
A simple message is enough. No pressure. No overproduction.
Holidays to acknowledge, not activate
These do not convert and shouldn’t take weeks of content planning:
- Valentine’s Day
- Halloween
- “National [Everything] Day”
- Decorative micro-holidays
A quick, human post, optional.
A full campaign, wasteful.
The goal isn’t to show up everywhere; it’s to show up meaningfully.
3. The only question that actually matters:
“What is happening in my client’s life during this holiday?”
This is where real marketing decisions get made.
December
Clients are overwhelmed, closing financial loops, tired.
Pushy December campaigns backfire.
Clear, human, steady communication wins.
April (Tax Season)
Clients want clarity, not creativity.
Your job is to remove friction, not add decoration.
Summer
People are inconsistent and distracted.
Perfect moment for light presence, not heavy selling.
When you shift from “What should we post for this holiday?”
to
“What does my client actually need right now?”
—your marketing becomes relevant again.
4. The most common mistake: trying to convert on every holiday
This is where campaigns lose trust.
Examples you’ve seen (or maybe posted):
- “Happy Valentine’s Day! Book your consultation.”
- “Happy Halloween, also, let’s talk retirement planning.”
- “Merry Christmas! Reminder that you still haven’t updated your insurance.”
These messages feel forced because they are forced.
Clients don’t want holiday-themed selling.
They want clarity, direction, and a professional who understands timing.
5. What does work: Plum’s 2026 holiday strategy
A three-layer approach
- Performance campaigns (high-intent dates)
- Human presence messages (relationship-driven)
- Simple holiday acknowledgments (optional and light)
Direct mail as your competitive advantage
When digital feeds turn into red-green clutter, promotional graphics, and templated posts, direct mail remains:
- tangible
- calm
- intentional
- impossible to ignore
Direct mail stands out precisely because everyone else is shouting online.
Clear messaging over seasonal clichés
Instead of:
- “Happy Holidays!”
- “Wishing you a prosperous year!”
Try clarity:
- “You don’t need more decisions this month—just clarity. Let’s start fresh in January.”
- “If something didn’t get resolved in 2025, we’ll tackle it together in Q1.”
Useful. Human. Professional.
6. A simplified 2026 holiday roadmap
Q1 — Activate
New Year, Tax Season
Goal: conversion, clarity, planning
Q2 — Deepen
5/29 Day, early summer
Goal: nurture, answer friction, educate
Q3 — Maintain
Back-to-School
Goal: meaningful presence without pressure
Q4 — Humanize
Thanksgiving, year-end
Goal: steady presence, strategic positioning
7. The filter that keeps your marketing clean
Before creating a single holiday asset, ask:
- Does this help my client make a decision?
- Does this reduce pressure or add it?
- Is this useful, or is it decorative content?
- Would I appreciate this message if I were in their position?
If the answer is unclear, the campaign probably is too.
8. The bottom line: This isn’t about creativity—it’s about intention
Clients aren’t waiting for “cute holiday posts.”
They’re waiting for professionals who communicate with purpose, clarity, and respect for their time.
The 2026 Holiday Playbook helps you:
- Stop forcing relevance
- Reduce marketing fatigue
- Strengthen timing and positioning
- Show up in ways that actually matter
Not every holiday deserves a sales message.
But every holiday deserves a smart decision.
FAQs
Should financial advisors run campaigns for every holiday?
No. Most holidays don’t convert. Focus on high-intent dates like New Year, Tax Season, Medicare periods, and Back-to-School.
Which holidays actually drive financial planning conversations?
New Year, Q1 financial reset, Tax Season, Back-to-School, and 5/29 Day.
What holidays should advisors avoid marketing around?
Valentine’s Day, Halloween, and micro-holidays. These rarely generate meaningful engagement.
How can I keep holiday marketing from feeling forced?
Use clarity, relevance, and timing. Ask what your client is experiencing—not what the calendar expects from you.
Is direct mail better than digital during the holidays?
Yes. Digital channels become crowded and repetitive. Direct mail remains calm, tangible, and impossible to ignore.
Clear Next Step
If you want support building a 2026 holiday content calendar and direct mail plan, Plum can help you design a strategy rooted in clarity—not volume. Start here.
