6 of Wands

Gift: Being successful and popular
Challenge: Other people getting jealous and wanting to knock you off your perch

HA it's 55Degree's favourite

Hierophant (upright)

GIFT: "Hello, let me show you how to approach this particular situation"

CHALLENGE: "Why aren't you doing it the way I told you to?!?!"

Haha, I hate that card.

Ace of Coins.

GIFT: Planning for the future.

CHALLENGE: Living beyond your means.

This just keeps getting better and better, I must be getting more flippant/whimsical as I go

Wheel of Fortune

GIFT: "Whee!"

CHALLENGE: "S---"

9 of Wands

GIFT: Determination and grit.

CHALLENGE: Demoralised and powerless.

4 of Pentacles

GIFT: "Yay I'm stable and secure!"

CHALLENGE: "...I'm kind of stuck and too afraid to let go of what I have in search of something better..."

2 of Swords

GIFT: Discernment.

CHALLENGE: Bad decisions.

The Hierophant

GIFT: Acquiring useful knowledge

CHALLENGE: Being bored out of one's brain and trying hard not to buck the system.