Why Labor Day Beats New Year's for a Life or Team Check-In

I've always been a bit puzzled by New Year's Resolutions. They seem high on goals but thin on the methods to achieve them. I once resolved to lose a few pounds and then went about eating a bit less without any real system in place. It lasted a few weeks and then I quietly abandoned the pursuit.

One way to improve on the usual resolution is to ground it in actual systems and methods—and, most importantly, in our values. A resolution then becomes an intention we can live out daily as best we're able, trusting that we can begin again when we make an unskillful choice. Repeating this with a mix of self-compassion and gentle discipline builds an inner capacity to live in the new way. No beating ourselves up is required (or desired).

But even a well-structured resolution is still being made at an odd moment of the year. I was walking our boxer, Hazel, along the ocean today when a small insight arrived: what if the time of year is wrong too?

The calendar turning over is a natural prompt to look back on the preceding year. But it seems obvious after a moment's inspection that trying to reflect on and refine your life in the immediate aftermath of the stress of the holidays is not a good idea. I'd like to propose that Labor Day is the better time to reflect, renew, and adjust. Here's why.

First, at the end of summer you're often at your most relaxed and reflective. I've had more insights about my own life and the organizations I've led while on vacation than at any other time, and I know I'm not alone. Maybe it's a change to how I want to spend my time, a relationship I want to invest more in, a challenge I want to take on at work, an update to how our team makes decisions, or something more fundamental.

Those insights are fragile. If you wait until December to act on them, most will have withered on the vine, and the clarity a vacation gave you gives way to the inertia of the status quo. Labor Day lets you catch the idea while it's still alive—and if you can carry it back into your usual routine, you get to see that routine with new eyes.

Second, for those of you in the business world, Q4 is a critical quarter for whatever business you're in, and Labor Day sits right before it. What better time to get you and your team aligned than before the most important few months begin? Contrast that with January and February, when many companies are in the thick of annual budgeting—adjusting plans, headcount, financial targets, and the like. I've tried to run team offsites in that window and they haven't always been great.

Folks are distracted thinking about their headcount allocation, their targets, or whether there's enough budget for a big engineering refactor that's overdue. That is not the head-space for bringing a team together to align around a core set of values and ways of collaborating. Around Labor Day you get a rested, more open-minded team, and you get to leverage all the ideas they came up with during their time off.

Third, for anyone whose life runs on a school calendar—students and parents alike—Labor Day arrives a week or two after classes have started but comes with a three-day weekend. Students get a wonderful moment to decide how they want to show up for their education, ideally with a bit of insight into what really matters to them. Parents have gotten a taste of the old routines with the kids back in class (whew!) and now have a "do over" option to reimagine the year before momentum makes change harder.

What time of year do you reflect on your life and what matters most to you? I'd love to hear from you.

And if you'd like support with an intentional check-in about your life, your values, and your priorities (or if you lead a team and would like help facilitating that kind of introspection across your organization), I would welcome having an exploratory conversation with you.

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