Sometimes It's the Least Bad Choice
Just like in life, sometimes when we're making technology or management decisions, we're faced with few good choices. And very often I'll tell my clients, what we're looking to do is make the "least bad" choice.
For example, during a new system implementation, the vendor will ask for "blackout" dates, dates where we know staff won't be able to focus on the implementation because their "real jobs" will be too busy. Common blackout dates are around annual meeting time, annual renewal time, and other programs that require many or all staff to be involved.
When discussing blackout dates with my clients, I'll often hear "We're busy all year round." It is those times when I suggest "Then let's find the least bad time to do this."
No situation, no solution, no time is ever going to be perfect. Sometimes it's easy to see the best choice, but often it comes down to making the "least bad" choice. Get comfortable with that.