I'm trying to get my youngest child through his college applications. I don't remember it being so challenging for the other two to complete theirs, but maybe I'm misremembering. I do recall a couple of panic attacks my daughter had that perhaps her essays weren't that good, or that she'd forgotten some extracurricular activities, but otherwise it required no effort on my part to make sure she'd gotten them done.
Likewise, my older son didn't need any nagging (or what I like to call 'persistent reminding'.) He had an advisor to help him out, since he was applying for a specialized music program, and he knew the importance of deadlines for auditions and whatnot.
But my youngest. Oh, the youngest. I don't know what's up with him. I even hired a college application assistant to be his program manager on the subject, but he is still unable to get through the most simple of tasks, such as inputting a class name, or adding a suggested comma to his essay. Some of his apps are due November 1st, and it feels like he's years behind.
His college application assistant actually called me on the phone and said that of all of his clients who are behind, my son is the most behind.
I like to call that winning the losing game. It all counts.
Such is the nature of the six of cups reversed, though. While it's often about a child leaving the nest, it can also represent one being unable to leave the nest, like one thing is missing before a child can launch himself into adulthood. For my son, that one thing is getting a college application in so that hopefully he has a place to move to next year. For others, it just might be a missing spark of ambition or something. What's your six of cups reversed?

Upright, the Six of Cups is about childhood, nostalgia, homesickness, and those old dreams that may no longer be realistic.

Reversed, the card indicates a maturity or growing up. It could represent someone moving out of the family home or letting go of a difficult past. In a negative sense, it might also represent being bored or lacking that youthful spark of creativity.
 
Questions answered by the reversed Six of Cups:
Who? A new adult; a child moving out of the house 
What? Broken toys; memories
Where? In a new location; away from home
When? The first week of November; In the recent past; When a child moves out
Why? “A ship does not sail with yesterday’s wind.” ~Louis L’Amour
Yes or No? Yes
 
The reversed Six of Cups as:
…an action?

• Do the mature thing
• Get married

• Buy a house
• Cooperate

 
…a place in your house?

• A stack of bills to pay
• The kitchen prep space

 
…a place in your city?

• The courthouse
• A continuing education center
• A real estate office

 
…a place in the world?

• The next biggest city
• A concert hall
• The DMV

 
…something to eat?

• Wine and cheese at a fancy restaurant
• Waffles
• Sliders

 
…something to clean?

• The office
• Scrub the pet litter box or kids’ dirtiest toy

 
…where to find your missing item?

• Under a stack of paperwork

 
…a color? blue, green
 
…a movie theme? Maturing, empty nesting

• Lady Bird
• Pleasantville
• Bao

 
…a new career?

• Working with new adults or college graduates
• Archaeologist
• Social worker

 
The reversed Six of Cups
Before any card: Letting go of (card)
After any card: maturity, leaving the nest

For more on the reversed Six of Cups, read Applied Tarot Reversed

In its simplest form, the Six of Cups is about childhood. It could mean literal children, or it might represent a nostalgia for those moments where we were at our most innocent.
Take a deeper look at the meaning, and you may find you are stuck in the past or clinging to memories that are no longer realistic. The playfulness depicted in the Six represents a type of joy that adults find hard to obtain - that of innocence and purity. 

Questions answered by Six of Cups:
Who? A child 
What? A toy
Where? In a child's space
When? The first week of November; In the distant past; When a child is a little older
Why? The past is the past
Yes or No? Yes
 
Six of Cups
​Before any card: Nostalgia or memories about (card)
After any card: childhood, memories
 
The Six of Cups as:
...an action?

• Play
• Don't linger on what was, focus on what is
• Hang out with the kids

 
...a place in your house?

• A child's bedroom
• The playroom

 
...a place in your city?

• A play park
• An amusement park
• A primary school

 
...a place in the world?

• Disney
• An amusement park

• Toronto
• San Diego

 
...something to eat?

• Dino nuggets
• Grab and go snacks
  
• A happy meal

• A banana

 
...something to clean?

• The child's bedroom
• The playroom

 
...where to find the missing item?

• Your kid or dog probably took them

 
...a color? yellow, red
 
...a movie theme? childhood, nostalgia

• Hot Tub Time Machine
• Pleasantville
• The LEGO movie

 
...a new career?

• Working with children
• Forensic investigator or historian

Six of Cups combinations
With High Priestess: Trust your inner child - what would you have done way back then?
With Seven of Wands: Something related to children has you on the defensive. Find a way to persevere without compromising your values.
With Four of Cups: You are wallowing about something in the past.
With Five of Swords: You may be fighting a losing battle - Are you repeating past mistakes?
With King of Pentacles: A successful matriarch or patriarch leaves a legacy to many children.