The context of the following conversation is Casey's pool was not kept up properly every year, so now it leaks water.:
Casey says I've learned that I haven't been on top of things recently..
The friend responds I know the feeling. That's when you keep putting things off and avoid starting on tasks..
Casey responds Exactly right, and I finally learned that the hard way. I had a swimming pool for years that I just took for granted..
The friend responds That's a nice luxury to have. It can be a great way to relax..
Casey responds Unfortunately, I haven't been maintaining it properly and it's started to leak water. I should have been more careful..
The friend responds That's a tough pill to swallow. I wonder if you could hire a contractor to check it out..