Money is a tough conversation, no matter who with, how much, or what it is being spent on. I always feel like the moment a dollar figure comes into play, things turn serious. Money puts a value on things and whether that is your time, your effort, or someone else's effort and sometimes you may be surprised by the answer. This is beyond the usual make vs. buy (to DIY or not DIY) conversation into a whole other realm of is it worth it. Here are some trick questions that might help you get to the bottom of a money question.

1. Would you pay 10% more for the same thing?
• Sometimes simply putting the ball in the court of "more" is enough to tip the scale from a "need" to just a "nice to have". This is a great technique if going from a $0 to a not-$0 amount say in an all-encompassing contract. If the extra cost of quality on something specific is worth an added fee though, go for it.
2. If all of a sudden it was free (or highly discounted), would the value stay the same?
• Sometimes the price tag alone can be a status symbol. Take a new 2015 BMW 7 series for example. Would it means the same if everyone could pick one up tomorrow at the cost of a 3 series? Probably not. Even if you still enjoyed the car, the uniqueness would be lost along with the desire for the competitive speed.
3. Would you still need/want this in 6 months?
• Does the age of something increase or decrease its importance? A bottle of wine might be worth a few percentage points more but a computer game would be on the discount shelves as old news. Maybe you bought an alternative or the development time has doubled unexpectedly and now the sunk costs make you rethink your original decision. Technology moves quickly so assess the long term implication of the cost... or cost savings.