Why is it so difficult to take two weeks off at so many jobs?

TLDR: It’s hard to coordinate a two week vacation with many careers.

More of an observation than a question: I’ve noticed over my two decades of living in the US, that – regardless of the job – two weeks of time off is difficult to arrange. My family is all in my country of origin, but I’ve made the US my home for a variety of reasons and love it here. I have had dual citizenship for 15 years. Because of the travel time and expense, it doesn’t make sense to visit for less than ten days. I have not visited my family as often as I wanted to throughout the years due to the near impossible tasks of getting a two-week block of time off work.

I spent my 20s in a shift-work job, where my position would be covered if I was off work, but I had to “bid” by seniority for vacation time at least 6 months in advance. I spent my 30s in office work (accounting/HR), where you could reasonably request vacation whenever, but anything greater than a week seemed nearly impossible with getting the work covered. Many tasks were specific to the position, or month-end / year-end related tasks, that would be covered at a bare minimum if need be, but you’d come back to an absolute crap show of unfinished work that would then take six months to recover from, let alone your coworkers all resenting you for being gone.

It has also taken at least a year at each job to build up two weeks of vacation time, and most jobs did not allow unpaid time off. I’ve also changed jobs after 1-2 years in my 30s, which meant starting from scratch with building up vacation time all over again.

I’m now moving towards working remotely for myself, which I hope to be doing by 2024, so that I can travel internationally and continue to work via laptop and not have anyone controlling my location. This is the only resolution I can think of aside from quitting jobs each time I need to take an international trip. I’d be interested in hearing how others have dealt with this, or any suggestions for juggling lengthier international trips with office jobs.

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