Actually Off: Why Full Disengagement Matters for Leaders
If you caught this week's newsletter, you already know how the vacation went. This is the fuller argument, including what it means for the people you lead, not just for you.
I took the last two weeks off.
Like, actually off.
My family and I enjoyed a long-anticipated vacation in Maui.
I brought my laptop.
Of course I did.
Not because I had to. It was reflex.
After years of traveling for both work and pleasure — 40 countries, six continents — I apparently no longer feel fully packed without my rectangular metal security blanket.
And then there was the negotiated joy.
Maybe I'd review the website changes from my brand designer.
Maybe I'd make a few tweaks to the client proposal they had asked for — even though they had explicitly said we could finalize it when I returned.
Maybe if I woke up before the kids, I could get a little work done.
The "kids," by the way, are no longer 4, 8 and 11.
I know better.
And yet there was still that little voice saying, just in case…
So the laptop came to Maui.
And then it never left the bag.
Not once.
Thankfully, I never pulled it out of the bag much less opened it.
No calls. No writing. No email. No checking in on anything related to work.
And somewhere along the way, I remembered how different taking time off is from actually disengaging from work, because we can be technically "off" and still very much at work.
We check one email.
We glance at Slack.
We replay the conversation we had before we left.
We think through how we're going to handle the issue waiting for us when we get back.
We mentally rewrite the proposal while sitting by the pool.
Someone asks us a question over dinner, and we realize we heard about 40 percent of it because the other 60 percent of our brain was still sitting in Tuesday's staff meeting.
Our bodies may be on vacation. Our minds are still on call.
The boy with the snorkel gear
On the same trip, I watched something else.
A boy — maybe seven, maybe eight — stood at the edge of the patio leading to the beach in his snorkeling gear. He kept looking back toward a shaded spot where his dad had set up with a laptop.
"Dad, come on…"
"Just one second, bud. Just one second."
So the boy would head toward the patio edge. Then come back to the chair. Then head toward the patio edge leading to the beach. Then come back to the chair again.
His dad, by every visible marker, was a successful, accomplished guy. He also did not close the laptop to go help his son snorkel…not for the 20 or so minutes we were in the area.
I don't know what was on that screen. I'd bet it mattered less than it felt like it did in that moment. What I do know is that the moment itself couldn't be renegotiated. That boy is not going to stay seven. The laptop was always going to be there when they got home. The trips back and forth to that chair, hoping this time was the time, that part is what will stick with this boy about 'dad on vacation.’
Here's the truth beneath the presenting problem: most leaders who can't disconnect will tell you it's about workload.
Sometimes it is.
But I've watched this enough times to know that for some of us, it isn't that we can't put the laptop down. It's that work is where we feel competent, useful, and in control — and family, in its unscripted, un-optimizable way, can be a harder place to sit than a spreadsheet.
If that's true for you even a little, it's worth naming. Not as a confession or an indictment. As information.
Time off is not the same as disengagement
There is a difference between being away from work and being unavailable to work. That difference matters.
We have normalized a strange version of rest in which we technically leave but keep one hand on the wheel. Just in case. Just one quick email. Just checking to make sure nothing is on fire. Just making one tiny adjustment because it will only take five minutes.
Except the five minutes are rarely the point. The point is that work never fully releases its grip on our attention.
And attention matters. Presence matters. There is something profoundly different about being with the people you love and actually being with them — not half-listening, not anticipating the next issue, not mentally solving a problem no one has asked you to solve while someone you love is trying to tell you a story.
That kind of presence is not a productivity hack.
I think we get ourselves into trouble when we try to justify everything that matters by proving it makes us better at work. Yes, there are plenty of arguments to be made about rest improving performance, creativity, decision-making, and resilience. Fine. But I don't want to make that argument.
Your vacation should not need an ROI. You are allowed to step away because your life deserves your attention. Full stop.
We may have the "big rocks" wrong
Nearly three decades ago, when I was a college intern at Pepsi, I had a boss named Fred.
Fred was a serious planner. He had one of those enormous leather Franklin planners — the kind that looked like it should have its own seat on the airplane — filled with color-coded pens, highlighters, and a level of organization that fascinated me.
I watched how he planned his work. But more importantly, I watched how he planned his life.
Around that same time, I went to a Franklin Covey class, where I learned the familiar idea of putting the "big rocks" in first. That lesson stuck.
But over the years, I've come to believe many leaders have misidentified the rocks.
We call the board meeting a big rock. The executive offsite. The annual planning session. The industry conference. The major client commitment. The big project.
Those things matter. Of course they do.
But they are not the biggest rocks.
You are. Your health. Your relationships. Your family. Your friendships. The life you are actually living while you are busy building everything else.
I love work. Truly. Give me a documentary about the companies, foods, cars, banks, or industries that built America and I am all in. I'm fascinated by business, leadership, strategy, and the systems that make organizations work.
But work is not first in my life. It isn't second, either.
That belief has shaped not only how I manage my own calendar, but also how I have led others.
Full disengagement is a leadership practice
Years ago, I was responsible for global strategy and leadership work in an organization operating across 25 countries in Asia, Africa, Latin America, and the Caribbean.
The executive calendar was chaotic. People were constantly traveling. Meetings collided. There was little rhythm. Everyone was everywhere.
So we redesigned it. We built an executive cadence years in advance: which weeks we would be together, which weeks were protected, when travel would happen, and how major organizational commitments fit together.
Personal lives were part of that design.
Kids' birthdays mattered. Weddings mattered. Family vacations mattered. Halloween mattered.
There were times when we were coordinating travel between countries in Asia and asking a very practical question: how do we do the work that needs to be done and still get the parents of young children home in time for Halloween?
That may sound like a small thing. It wasn't. It communicated something: you matter here as a whole person. Your family matters. Your life is not an inconvenience to be worked around after we finish arranging the organization.
That is not softness. That is leadership.
Because one of the responsibilities of leadership is not simply to take care of your own life. It is to build environments in which other people are allowed to have lives, too.
Systems communicate values
Organizations can say all the right things about well-being, family, flexibility, and balance. But people watch the system, not the poster.
They watch whether leaders send emails at midnight and expect responses. They watch whether vacation actually means vacation. They watch whether someone is praised for checking in from the beach. They watch whether the person who protects family commitments is seen as less committed than the person who is perpetually available.
And they adjust accordingly.
Culture is shaped much more by what gets rewarded and normalized than by what appears on a values poster.
If leaders say "take your time off," but the operating rhythm makes true disengagement impossible, the rhythm wins. If leaders say "family matters," but calendars are built as if people have no lives outside of work, the calendar wins. If leaders say "you don't need to respond while you're away," but everyone knows the fastest responder is admired and promoted, the behavior wins.
Systems communicate values. So if we want people to disengage, we have to make disengagement possible. Not theoretically possible. Operationally possible.
A few questions worth asking
For yourself:
When you take time off, are you actually unavailable? Do you carry work with you "just in case," even when no one has asked you to? What personal commitments do you put on the calendar first, before work fills the space? When you are with people you love, how often is part of your attention still somewhere else?
And for the people you lead:
Do they know they can fully disconnect without consequences? Have you built enough clarity, coverage, and trust that the organization can function without constant access to them? Are important personal commitments treated as legitimate calendar constraints? Do your own behaviors reinforce the culture you say you want?
Those questions are not separate from strategy or leadership. They are part of both.
Be where you are
My laptop traveled all the way to Maui and never got its moment.
It sat there while we laughed, explored, ate ridiculous amounts of good food, made memories, and repeatedly defended our breakfast from extremely confident birds.
And I'm glad. Because the work was still there when I came back. It always is.
The people you love deserve more than whatever attention is left over after work has taken its share. And frankly, so do you.
Take the vacation. Protect the time. Close the laptop.
Be where you are.
Lead boldly. Live fully.
I think about this with leaders further down the road, too, the ones who are, on paper, ready to retire, and don’t.
Not because the finances aren’t there.
Because vocation was the whole vision, and nothing else was ever built out with the same intention.
Here’s what I know to be true: if your vision for your whole life isn’t as clear and as strong as your vision for your career, eventually that imbalance has a cost.
Maybe not now.
Later.
When what you’re actually remembering isn’t the industry conference or the deal that closed, but whether the people who used to reach for you still do, or still want to.
It’s never too late to build the other vision. It’s just easier to start before you need it.
If work is where you feel most like yourself, what happens the day it isn’t there?
LifePlan® helps leaders bring the same intention to the rest of their lives that they’ve brought to their careers — building clarity around identity, relationships, purpose, and what matters most.
Cassandra Shepard is the founder of Shepherd + CO, a boutique strategic advisory firm. She works with senior leaders navigating the intersection of enterprise strategy and advanced leadership. www.cassandrashepard.com