When Your Boss Never Stops Working... What Are We Teaching the Next Generation of Leaders?

My Gen X boss works every weekend. She answers emails on vacation. She’s dialed into meetings while in the airport, while sick, while grieving, while allegedly “off the clock.” She is, without a doubt, dedicated. But as a millennial manager tasked with growing the next layer of leadership beneath me, I’m left asking: what are we modeling — and what are we passing down?

Because here's the thing: the people we lead are watching us. And if the example at the top is constant availability, blurred boundaries, and productivity as a measure of worth, we’re not just inheriting that system. We’re silently reinforcing it.

The Generational Divide Isn’t Just About Age

For many Gen X leaders, hustle was survival. They came of age in an era shaped by layoffs, corporate mergers, and the normalization of being "always on." Technology wasn’t native, but it quickly became a tether. Many Gen X executives still carry the unspoken belief that leadership means self-sacrifice — that visibility, endurance, and overcommitment prove you're serious.

Millennials, and now Gen Z, are bringing a different philosophy. We value rest, flexible schedules, mental health, and the ability to care for life outside of work. We’ve seen burnout up close, and many of us have no interest in trading our health or relationships for a title. But that cultural shift doesn’t stick unless it's modeled by leadership — and many executive teams aren’t quite there.

When the Model Conflicts with the Message

It’s not enough for your boss to say they support work-life balance if they respond to emails at midnight or praise the colleague who “stepped up” by canceling their vacation. And it’s hard to set boundaries for your team when you know your own supervisor may see that as disengagement.

This disconnect creates a tricky reality for middle managers: you’re expected to coach your staff into healthy work habits while performing loyalty to a leadership culture that implicitly rewards burnout. You're trying to build a new culture from the middle out, while being held accountable to old expectations from the top down.

So What Can You Do?

You probably can’t change your boss — but you can choose what kind of leader you want to be. Here are a few ways to create space for healthier leadership habits, even in a work culture that still idolizes overwork:

• Narrate your choices. When you take time off and actually unplug, say that you’re doing so. When you decline a weekend meeting or hold a boundary around your evenings, name it as intentional — not optional or apologetic.

• Praise rest as a leadership move. When your team members take time off, celebrate it. When they model balance, recognize it as an asset, not a luxury.

• Teach output over hours. Encourage your team to focus on outcomes, not availability. Make it clear that showing up burned out isn’t a badge of honor.

• Offer coaching that includes boundary-setting. Include conversations about energy, time, and sustainability in your regular check-ins. Make it normal to ask, “What would support your capacity this month?”

• Name the generational gap without shaming it. You don’t have to throw your boss under the bus. But you can say, “We’re trying to build a culture where leadership doesn’t require self-erasure. That may look different from how previous generations did it.”

Leading in the In-Between

If you’re in middle management, you’re likely stuck in the squeeze — translating outdated norms upward while trying to model something better downward. It’s exhausting, but also powerful. Culture changes slowly, but it does change. The next generation is already forming their view of what leadership looks like — and a lot of that is coming from you.

So while your Gen X boss may never stop working weekends, that doesn’t have to be your legacy. Show your team that leadership can look like balance, care, and clarity. Show them that it’s possible to lead with boundaries. And remind yourself that just because someone else is burning the candle at both ends doesn’t mean you have to light the match.