how to take vacation when there's always work to be done

A reader writes:

Summer's almost here, and I'm meant to be taking a week off for holiday. The trip is booked, it's been approved months ago by my boss, I've scheduled my requested time with an eye to our work cycle and done my best to get everything done and covered before I'm gone. However, two days before departure, my manager says perhaps I can't go, as we are not as far along as she'd hoped (it's impossible to do a month's load of work in three weeks, and while I attempted to get all of it done and create the minimal amount of stress and bother for those left behind, there is still work to be done of mine in that week I'm away that will have to be covered by someone else). She says I can either not go, or be available during my leave at all times for work, or I can pay, out of my own pocket, for a freelancer to come in to backfill me.

There may be no way to save this vacation, however I wonder: how does one responsibly actually take some time off? I haven't had a holiday in nearly two years for this exact reason, that every time I try, there always seems to be more work or responsibilities that only I can attend to that can't be put on hold even for a weekend. How does a responsible employee in a management position get away for a break?

Well, the real way is that one works for an employer who recognizes the importance of time off.

Did you make any agreement with your manager about how much you'd have done before you left, and she just discovered that you didn't meet that agreement? Because that would be the only thing that would justify her now telling you that you can't go.

But I'm betting that that's not the case, because her suggestion that you hire a freelancer at your own expense is a little absurd.

The nature of many jobs is that there's never a time where all the work is done and where you can take a vacation without some accommodations being made, no matter how well you plan for it in advance. But because good managers recognize that it's in the employer's best interest to have well-rested and recharged employees, they find ways to help employees take time off anyway. It's in their best interest not only because employees who get breaks from work generally do a better and more focused job in the long run, but also because good people will eventually leave if they're working in a culture that doesn't support their quality of life. And good management is about getting good results in the long run, not just the short-term.

I recommend addressing this head-on with your boss: "I haven't been able to have a vacation in two years because it's so hard to get away, and obviously that's not sustainable in the long-term. Can we talk about how to arrange things so that I can plan for some time off with confidence?" Sometimes some bosses are so caught up in the day-to-day rush of work that they need prodding to step back and look at long-term needs like this. By helping frame the issue for them, you can sometimes come to a good solution that everyone is happy with. But if you get the sense that you're never going to be able to be confident you can keep vacation plans, or if it's given only begrudgingly, or will be so rare that your mental health will slowly degrade until one day you'll just need to run screaming from the building -- well, this is not a great employer. So make your decisions accordingly.