We know how December feels—like a final sprint in a marathon year, complete with looming deadlines and endless notifications. In all the hustle, it’s easy for those holiday greetings to slip off the radar. But even at this late stage, a small, personal effort can turn your outreach into something memorable. Let’s talk about why this matters, what to say, and how to make it happen.
Simply put - we live in a world overflowing with generic greetings and automated emails. So adding a personal dimension makes your outreach instantly more meaningful. When someone sees their name, recalls a shared memory, or notices a thoughtful detail, they feel acknowledged and genuinely valued. Personalizing your outreach shows you remember who someone is and what matters to them, helping you create connections that go beyond a single transaction - leaving a lasting, positive impression long after the holidays have passed.
Use real names, of course, but consider weaving in a reference to a recent conversation or memorable moment. This can range from a product or campaign you launched together, to a coffee or lunch you shared. These specific details help your greeting feel like it’s meant for them, rather than plucked from a stack of templated messages.
“[Name], I keep thinking about the lunch we had back in October. Hard to believe the nuggets that came out of that meal formed the foundation for our marketing strategy next year. Thank you for sharing your insights—it truly shaped our approach. Warmest wishes this holiday season!”
“[Name]: remember when we chatted about the eco-friendly [product] at your office last month? Your enthusiasm was just what I needed to turn that into reality. I hope this season brings you some equally inspiring moments.”
“[Name], I’m still thinking about that matcha we grabbed at your favorite cafe last month. Your recommendation was spot-on, and I hope the holidays bring you just as much warmth and comfort.”
Think beyond the ecard. Have a client who loves fine stationery? Pick a card style that echoes their taste. For someone who values sustainability, choose recycled paper. Matching the medium to their personality shows that you put real thought into your outreach.
“[Name], I chose this card because it reminded me of the sleek branding we worked on together earlier this year. Here’s hoping your holidays feel just as polished and full of creative sparks.”
“Dear [Name], since we’ve both been talking about sustainable business practices, it felt right to send this eco-friendly card. May your holiday be as thoughtful and grounded as the choices we’ve been making together all year.”
“Your travels to [Country] reminded me of this artist I love – her work is on the front of this card. I hope it brings you a smile and fond memories of your journeys. And of course, plenty of inspiration for the year ahead.”
A short reading recommendation, a quick travel tip, or a relevant industry insight can remind them why they value your relationship. It adds substance to your message, making it more than just a holiday greeting—it becomes a small gift of knowledge or inspiration.
“[Name], I know you’re interested in global markets, so I thought you’d enjoy this short article on emerging consumer trends. Consider it a little holiday reading. Thanks for always keeping our conversations so forward-thinking!”
“[Name], since we bonded over travel stories, I wanted to pass along a quick tip: here’s a new boutique hotel I think you’d love in Kyoto. May your holidays bring the same excitement as planning your next adventure.”
“[Name], you’re always on the lookout for productivity hacks. I just discovered a short podcast series that might be right up your alley—consider it a small gift of inspiration for the new year.”
A hand-signed note or a brief personal sentence in your own handwriting goes a long way in setting your outreach apart. If time is tight or your handwriting isn’t exactly elegant, consider a partner like PenPals to help you achieve that individual touch at scale.
PenPals makes it easy to send personalized handwritten holiday cards at scale. We make it effortless to pick out & write messages to each of your contacts right from your screen.
From there, our robots get to work in putting real pen to paper writing your message, addressing your envelopes, and then mailing them directly to your recipients.
Browse our cards below or click Start Writing above to get started.
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