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January Reflections Leading with Joy on the Calendar

Work, work, work. 

The start of a new year often feels like an unrelenting sprint. Your back from vacation, heads down, task lists full, inboxes overflowing, January rarely tiptoes in, it barrels through. And in all that early-year hustle, it’s easy to forget something essential: to carve out intentional time away from it all. I know, LOL, you just got back from vacation and already thinking of another – but Yes. 

Our friends at Strategic Coach call these free days – time to completely disconnect from the day-to-day demands of work. No email. No meetings. No “just one quick call.” These are days when your mind can breathe, and you can zoom out and see the bigger picture of your life, your leadership, and your priorities. 

Every January, I sit down with my calendar and do something that brings me real joy: I plan. But not work planning but life planning. I schedule trips with my kids, time with friends, and a girls’ trip or two 😊. I make sure there’s always something to look forward to, some respite carved into the chaos. And I’ve learned that it’s not just about me, it’s about what we model for our families and teams. 

One of our family traditions is what we call the Kaila Family Adventures. Every year, we choose a new country to visit together. The kids debate and pitch ideas, sometimes with a little sibling intensity. Sunny and I chime in when needed (with a parental veto in our back pocket). But ultimately, it’s their adventure to shape. 

Over the last 27 years, since I married my Sunster, we’ve visited 33 countries. And those annual trips, completely disconnected from work, have become sacred. No conference calls. No email check-ins. Just time fully dedicated to the people who matter most. 

This past week was one of those “when it rains, it pours” weeks at work. But even in the thick of it, I paused to feel grateful. For the seat I sit in. For the choices I get to make. For the ability to take a quick spa day, or a weekend away with girlfriends – not just because of financial freedom, but because of time freedom. That’s the piece we overlook: time freedom is earned through intentional leadership. 

So, as we plow through this first stretch of the year, here’s the reminder I needed and maybe you do too: 

Leadership Learnings:

  • Time Off Isn’t Indulgent It’s Strategic
    Planned rest fuels better decision-making, stronger relationships, and sustainable leadership.
  • Model Joy-Planning for Your Team and Your Family
    When you prioritize your own well-being, you give others permission to do the same.
  • Create Anchors, Not Just Goals
    Having something to look forward to brings balance in the busyness. It’s not just about productivity, it’s about presence.

So yes, we’ve had our heads down this January. Now look up. Be intentional. Lock in your free days. Build space for joy on your calendar. It matters. 

Your brain (and your people) will thank you for it. 

For more content like this, be sure to follow IT By Design on LinkedIn and YouTube, check out our on-demand learning platform, Build IT University, and be sure to register for Build IT LIVE, our 3-day education focused conference, August 3-5, 2026 in Jersey City, NJ!