Grab your coffee, because we’re not coasting into the end of the year — we’re closing it out strong.
Every holiday season, the same thing happens. The lights go up, the calendars fill up, and a whole lot of real estate agents mentally clock out because “no one is working.” Meanwhile, the ones who stay focused quietly load their pipeline and get paid in January, February, and March. You get to decide which group you’re in.
I love the holidays. I’m happier during this season. I love the decorations, the music, the energy, the Mag Mile lights, Santa’s Rockin’ Lights in Geneva, Holiday Magic at Brookfield Zoo, all of it. But here’s the truth: loving the holidays doesn’t give you permission to abandon your business. You can do both — enjoy the season and get the work done — if you plan it.
Step 1: Put Your Life on the Calendar First
Before we even talk lead generation, sit down with a calendar — digital or old-school paper — and map out your life.
- Block time now to holiday shop.
No more “Christmas Eve at 3am still wrapping gifts” chaos. Put shopping time in your calendar like an appointment. Aim to be done by around mid-December so you’re not stressed and broke. - Add family, friends, and fun to your calendar.
Schedule family time, Friendsgiving, gift-wrapping time, date nights, whatever matters to you. If you don’t block it, real estate will eat it. - Plan one fun holiday outing.
If you’re in the Chicago area, go see the Mag Mile lights, State Street windows, Holiday Magic at Brookfield Zoo, or a drive-through light show like Santa’s Rockin’ Lights in Geneva. Pick something and put it in writing. - Schedule “sit-and-soak-it-in” time at a coffee or tea shop.
Find a cozy, local spot (not just the big chains), sit down with your planner or laptop, and just breathe for a minute. That’s also instant content, by the way — more on that in a second.
Once your life is on the calendar, now we build around it. If it’s not written down, it won’t get done. Period.
Step 2: Work the Money Moves – Holiday Lead Gen Strategy
Now let’s talk about how you actually win the last 30 days of the year as a real estate agent.
1. Schedule your expired marketing for January 1
January 1st is prime time for expired listings. Why? Because a lot of agents are hungover, checked out, or “starting Monday.” MLS doesn’t care about your feelings — listings still expire.
- Block December 31st / January 1st in your calendar for expired marketing.
- Get your postcards / notes / scripts ready now.
- You can’t pull the labels until those listings actually expire, but you can have your marketing pieces done and waiting.
2. Go after old expireds that were never re-listed
This is where the real money is.
Use tools like Realist, Remine, RPR, or IMAPP to look up expired listings from older years that never came back to market. I’m talking:
- 2008, 2009, 2010, 2011, 2012, 2013…
- Properties that were listed, went expired, and then disappeared.
I didn’t say they didn’t sell — I said they weren’t relisted. That’s a conversation starter.
3. Soft-touch marketing to pre-foreclosures
If you’re going to market to pre-foreclosures, do it with empathy and skill, not shame.
A postcard script I like for this season:
“Whether times are hard or easy, we all have to make hard decisions. Enjoy the holidays, and plan to sell at the beginning of the year.”
Soft. Respectful. Clear.
You can use Realist, Remine, RPR, or other tools to identify pre-foreclosures, but remember — these are people, not leads. Your tone matters.
4. Holiday cards or New Year cards
Get your holiday cards in the mail ideally by early–mid December. If you don’t celebrate the holidays or just don’t want to deal with that:
- Send a “Happy New Year” card that hits the first week of January.
- Or do a fun Valentine’s Day mailer like, “We ❤️ Homeowners, Let’s Talk About Your Equity.”
Point is: something should show up in their mailbox that reminds them you exist.
5. Schedule all December email campaigns this week
Whatever you use — Mailchimp, your CRM, your brokerage platform, schedule:
- Your December emails (market update, holiday message, homeowner tips).
- At least one email for the first week of January.
Because you already know how this goes: you think you’ll do it later, then it’s December 27th, you’re eating leftovers in fuzzy socks, and email is the last thing on your mind.
6. Use Canva to post holiday “things to do” content
This is free, easy content that positions you as the local expert.
- Make simple graphics in Canva with “Things To Do This Holiday Season in [Your City].”
- Examples:
- Magnificent Mile Lights Festival
- State Street holiday windows
- Santa’s Rockin’ Lights in Geneva
- Holiday Magic at Brookfield Zoo
- Post this content daily or at least twice a week on Instagram, TikTok, Facebook, and Stories.
Don’t overthink it. If you really don’t want to be on camera, film short clips of the lights, streets, or windows and then record a voiceover later. Everything is content. Everything.
7. Plan your renter-to-buyer mailers now
If you’ve never done this, you need my buyer boot camp, but here’s the quick version:
- Pull a list of renters or likely renters.
- First mailer (December): “Give yourself the gift of homeownership. Ask me about down payment resources.”
- Second mailer (January): “It’s tax season. Leverage your tax refund for your down payment.”
Add a QR code that goes to:
- A Google Form
- Your landing page
- A YouTube video that explains the buying process
You need a way to capture their information. Marketing without a capture point is just charity.
Step 3: Use Social Media Like You Actually Want to Get Paid
Some of you are still stuck because you’re waiting to be perfect on camera.
Newsflash: you’re Never. Going. To. Be. Perfect.
Put on a baseball cap. Tie your hair up. Fix the one thing that’s really bothering you and press record anyway.
You don’t have to show your whole life, but you do need to show up:
- Do a “day in the life” vlog as an agent during the holidays.
- Wrap a gift on camera while talking about the “gift of homeownership.”
- Do a voiceover over clips of your city, your favorite coffee shop, or your family’s traditions.
- Talk about your hourly rate and why you’re not wasting time this month.
If you’re new, you simply have to work harder than the seasoned agents — you’re still learning the business and building your name. But all of us have the same free tools: Instagram, TikTok, YouTube, Facebook. Use them on purpose. In all of this — calendars, cards, content, mailers — you still have to ask.
Ask for the appointment.
Ask for the referral.
Ask, “Who do you know that needs to buy or sell next year?”
The worst thing that can happen is they say no. The best thing that can happen is you start your new year with a full pipeline and the confidence that you didn’t coast through the last 30 days — you owned them.
