There’s a saying that it’s better to ask forgiveness than ask permission. This may be true in some situations and is surely a bad idea in others. Consider the downside risk; if it’s relatively small, go for it and ask forgiveness if needed. Big risks warrant a different approach. (Discretion is the better part of valor.)

Trish and I have joint accounts for all of our finances. I regularly spend moderate amounts of money on training, equipment or things to support my hobbies and I expect she will do the same for herself. I am comfortable that it’s fine and either of us could ask forgiveness if we push the limits.

On the other hand, I wouldn’t go out and buy a new car without discussing it. Surprising Trish with a huge purchase or a new monthly payment seems unreasonable. I wouldn’t “ask permission” so much as make sure she’s comfortable with the risk.

When do you go for it and when do you discuss before you act?