February 24th, 2026

A friend of mine recently gave me one of the best gifts I’ve ever received. When I opened it, I didn’t find a generic gift card or a bottle of wine. Instead, I found a custom shirt with my dog’s face printed all over it.

It was, objectively, a terrible shirt. I will never wear it outside my apartment. And yet, it instantly became one of my favorite gifts I’ve ever gotten.

In business, we miss this feel good personalization more often than we realize. We are currently living through what feels like the “Era of the Template.” We have automated sequences for everything, AI-generated LinkedIn messages filling inboxes, and “personalized” tags that often glitch in ways that remind us how impersonal they really are. Most of us have received the infamous “Hi {First_Name}” email at least once.

We try to scale by becoming more efficient, but in the process, we unintentionally make our interactions feel interchangeable. The warmth of a real connection gets traded for the volume of a cold sequence. The irony is that while technology has made it easier than ever to reach people, it has also made it harder to make anyone feel genuinely remembered.

The best gifts, and the best business relationships, are built on thoughtfulness. The real competitive advantage today isn’t better technology or faster automation. It’s the “I see you” factor. It’s the ability to make someone feel like more than a contact in a CRM.

The mistake many people make is believing they have to choose between staying small and personal or becoming automated and impersonal. In reality, the sweet spot is somewhere in the middle. The goal isn’t to automate the relationship; it’s to automate the remembering.

Your systems should remind you that a client mentioned their wife was having surgery or that a partner was nervous about a big milestone.

The system does the remembering so that you can do the reaching out.

When technology prompts a genuinely human moment, the entire relationship shifts. It stops feeling transactional and starts feeling like a partnership. A simple message saying, “I saw this and thought of you,” carries more weight than any perfectly optimized campaign ever could.

Trust is built in small moments. The nuances that a robot cannot feel, but a well-designed system can help you acknowledge.

You don’t need to choose between efficiency and empathy. You just need to use your systems in a way that helps you stay human as you grow.

Stay personal,

Sydney