Featured image for a blog about holiday marketing strategy showing an hourglass on a phone screen, symbolizing reflection, timing, and thoughtful communication on sensitive dates.

Holiday Marketing Strategy: How to Communicate Thoughtfully on Sensitive Dates

Featured image for a blog about holiday marketing strategy showing an hourglass on a phone screen, symbolizing reflection, timing, and thoughtful communication on sensitive dates.

TL;DR

A strong holiday marketing strategy isn’t about posting more; it’s about posting smarter. Columbus Day and Indigenous Peoples’ Day (October 12) remind us that not every holiday is a marketing opportunity. The best advisors and service professionals know when to promote, when to pause, and when to reflect. This guide shows how to plan your holiday marketing calendar with intention, balancing relevance, respect, and results.

Why October 12 Is More Than Just a Day Off

For many professionals, October 12 looks simple on the calendar, but it’s not.
Some communities celebrate Columbus Day, others Indigenous Peoples’ Day, and others quietly skip it altogether.

That mix of meanings is exactly why holiday marketing strategy matters. It’s not just about timing; it’s about context.

If you post something generic (“Happy Columbus Day!”), you risk sounding disconnected.
If you stay silent out of fear, you miss a chance to show awareness.
The middle ground? Thoughtful, relevant communication that connects with your audience’s real values: Legacy, resilience, and stewardship.

Because for your clients, especially those planning for their families’ futures, those themes matter.

What a Real Holiday Marketing Strategy Looks Like

Let’s be honest: in 2025, a lot of what passes for “holiday marketing” still feels surface-level.
You’ll see plenty of posts built around hashtags and seasonal graphics that don’t say much.
That doesn’t mean every brand is doing it wrong; it just shows how easy it is to post without a clear plan.

A stronger approach starts with clarity: understanding which holidays genuinely connect to your audience, and how to communicate around them with purpose instead of routine.

Step 1: Map the Calendar With Intention

Group holidays into three categories:

  • Promotional: Obvious business ties (e.g., Small Business Saturday, Financial Literacy Month, Tax Day).
  • Reflective: Emotionally charged or cultural dates (e.g., Columbus/Indigenous Peoples’ Day, Memorial Day).
  • Neutral / Skip: Dates unrelated to your goals, clients or services.

If it doesn’t fit your message or your clients’ mindset, it’s better to skip it. Silence builds more trust than a misplaced and unrelated promo.

Step 2: Match the Tone to the Context

When a holiday carries weight, you don’t need a design-heavy post or fancy caption. You need humanity.

Example:

“Today, many communities observe Indigenous Peoples’ Day, a reminder that legacy is about what we preserve, protect, and pass down.”

That single line shows emotional intelligence. No sale. No over-explaining. Just awareness.

Step 3: Tie It Back to What You Actually Do

Reflection only matters if it connects to your work.
For financial advisors, it might mean legacy planning.
CPAs can highlight charitable giving or end-of-year tax moves.
Service-based businesses, on the other hand, can focus on resilience and community support.

Relevance is what separates marketing from noise.

Step 4: Review Your Language and Visuals

Ask:

  • Would this sound right to every segment of my audience?
  • Is my imagery inclusive, simple, and inoffensive?
  • Am I using words that match the tone of my market?

Step 5: Measure and Adjust

Track engagement, not to chase numbers, but to understand tone. Which posts resonated? Which were ignored? That’s how you refine your future calendar.

Real Examples From the Field

Financial Advisor in Arizona

Posts a 60-second video reflecting on Indigenous Peoples’ Day, linking legacy and stewardship. It performs 3x better than his generic “Happy New Year” post because it feels real.

Attorney in Massachusetts

Writes a short blog explaining how communities observe the day, transitioning naturally into estate planning. No sales pitch, just clarity and empathy.

CPA in Illinois

Emails clients:

“Today’s holiday means different things to different people. For us, it’s a reminder that stewardship—of finances, culture, and family—defines legacy.”

Each of these examples proves the same point: awareness beats automation.

The Strategic Benefit of Reflection

Handled right, reflective holidays like October 12 do something marketing rarely achieves anymore; they humanize your brand.

They remind clients that behind every logo and tagline, there’s a person who thinks about context, not just content.

That’s what builds trust, and trust is what converts.

Your holiday marketing strategy isn’t just a schedule, it’s a signal of how self-aware your brand is.

The Blunt Truth

If you post every holiday just to stay visible, you’ll eventually sound invisible.

Smart advisors and business owners know when not to post. That restraint reads as maturity, not absence.

Holiday strategy is about respect, rhythm, and restraint, not about how many dates you fill on your calendar.

Key Takeaway

A thoughtful holiday marketing strategy does three things:

  1. Brings clarity to your message.
  2. Builds relevance around shared values.
  3. Earns trust through awareness.

October 12 is your reminder: the best marketing isn’t louder—it’s wiser.

FAQs About Holiday Marketing Strategy

What is a holiday marketing strategy?

It’s a structured plan for how your business communicates around holidays, knowing which dates to highlight, which to approach with sensitivity, and which to skip entirely. A strong strategy aligns your tone with your audience’s emotions and expectations.

Should I post on every holiday?

No. Most professionals benefit from focusing on relevance, not frequency. For example, Memorial Day might call for reflection, while Tax Day calls for action.

How can financial advisors and CPAs apply this strategy?

Use holidays to spark meaningful conversations, like legacy planning, charitable giving, or financial resilience. These topics connect naturally to your services and client goals.

What happens if I stay silent on a holiday?

Nothing bad. Silence can be part of your strategy. It shows discernment. Posting without purpose can do more harm than good.

What’s the best way to plan ahead?

Build a 12-month content calendar that labels holidays by category (promo, reflective, skip). That way, you’re never reacting, you’re planning with intention.

Want your holiday calendar to build trust instead of tension?

Work with Us to design your marketing strategy that aligns with your values, speaks to your clients, and delivers measurable impact, every month of the year.