Vacations Sound Relaxing Until You Remember You Have a Job
Finding the courage to step away when work never truly feels finished.
Vacation and Work: Why Is It So Easy for Everyone Else... and So Complicated for Me?
Am I the only one?!
Let's talk about it.
I have coworkers who vacation almost every month, some every other month, and a few who take one or two trips per year.
Every time they come back, they share stories, pictures, and tips for your next trip to that same destination. Without fail, I get asked the same question:
"When is your next vacation?!"
Let's put that into perspective, shall we?
I got married almost two years ago, and our honeymoon was a last-minute trip to my hometown simply because we already had time off and decided at the last minute to treat it like a temporary honeymoon until we planned the real one.
Welp... we still haven't planned it.
After Everything Is Under Control
I used to think a vacation was something you took after everything was under control.
After the inbox was clean, after the last email was sent, and after every loose end was tied up in a neat little bow.
However, somewhere between back-to-back meetings and a calendar that never quite slowed down, I began to wonder: Do we ever actually get to that point, or do we just keep moving the finish line?
If you're anything like me, the hardest part about taking time off isn't asking for it or even planning it. It's that quiet thought that shows up right as you're trying to relax:
"What exactly is waiting for me when I get back?"
And then come the not-so-quiet answers:
"Emails. Follow-ups. The things that paused the moment you stepped away..."
Now, suddenly, you're on vacation, but your mind is still very much at work, wondering if you should log in for a "few minutes" just to answer a couple of messages. Your family gets annoyed and tells you not to, but you convince them—and yourself—that if you don't take five minutes now, it could mean leaving work a couple of hours later next week.
Then, at some point during those five minutes that turned into two hours, you think:
"Wait, what am I doing?!"
When did taking a break start feeling like something we have to recover from?
We Care—And Perhaps a Little Too Much
Contrary to popular belief, we didn't get here because we don't know how to rest.
I believe we care—and perhaps a little too much.
We care about being the person people can count on. We care about staying ahead. We care about not dropping the ball.
And to add to that list, for many of us—especially in roles where expectations are high and visibility matters—stepping away can actually feel less like freedom and more like risk.
But have no fear! I've been learning—and slowly putting into practice—that the goal isn't to leave with everything perfectly done.
Oh, nay nay!
The goal is to leave while making sure everything is understood.
Understood in terms of what's in motion, what's waiting, and what actually needs you versus what just feels like it does. Because there is a difference.
I've also realized that handing things off isn't about asking someone to "keep an eye on it." It's about letting go and trusting that things can—and will—move forward without you directing every detail.
It may not be handled exactly the way you would do it, but it will move forward successfully while you enjoy every second of your vacation.
The Return Is Never as Dramatic as We Imagine
The other thing no one ever really tells you is that the return is never as dramatic as we imagine.
Sure, the inbox will be full, and there will be things to sort through. But there's something powerful about coming back with a clearer head and a fresh perspective.
Things that felt urgent before suddenly look, well, not so urgent—just different.
They look more manageable, more defined, and sometimes even easier to navigate and resolve than they did before your much-deserved break.
Perhaps that's the real value of stepping away.
Not necessarily escaping the work, but seeing it differently after you've had time to rest and recharge, leaving you with more energy to successfully tackle the next project.
So before summer ends, book the trip. Put in the PTO request. Trust that you have done enough to step away.
Trust that your team will step in, hold things down, and get you back up to speed when you return.
But more importantly, trust yourself to actually be off while you're gone.
Because the truth is, the work will always be there.
But flight prices will keep going up. 😉
