Although it is a difficult question to put emphasis on IMO because it also makes you in a way "reveal" your bad morals... which I am sure many people don't feel comfortable doing.
Why would you ever want to openly admit you beat ie. cheated a system be it government, academic, or private? Not to imply that I ever have... err... gotta run!
Sometimes your audience is sympathetic because they perceive that the system you're beating is broken.
I read Victor Kiam's "autohagiography," and in it he recounts a story about how parking at a baseball game was impossible to get, but there was a special lot just for limos. So he grabs a peaked cap, puts on a dark suit, and drives his buddies to the game, right into the limo lot.
That (possibly apocryphal) anecdote is a perfect little story of ingenuity and hacking the system without confessing to moral corruption, more of a right the imbalance and tweak the nose of a big, unlikeable organization kind of thing.
Any system that loves its rules is ripe for this sort of thing. My wife's mother was born in Canada but came over as a child and had to renounce her citizenship at one point. They changed their rules so we were able to get her citizenship re-instated and my wife can be a Canadian citizen too. She's never even been to Canada.
I always get a little thrill out of beating rules people with their rules. These things aren't harmful (generally) to members of the system, though these kinds of loopholes only tend to exist as long as they aren't too greatly used.
Now being a welfare cheat or talking about how much you like shoplifting is probably not a good idea, but doesn't everyone commit a little harmless loophole exploitation from time to time?
EDIT: The general weakness of institutions are rules. Anyone wanted to disrupt such things needs to know how to exploit those weaknesses.
It just requires a certain amount of "ballsiness" in putting yourself out there to try to change something that already exists, and a certain amount of opportunism in recognizing when things can be done differently without violating rules/personal ethics/the law.
Anyway, it worked well for me. I didn't get any drama, and I ended up graduating and landing a job with a top 25 software company.
It's not by definition an immoral thing to do. e.g. a real-estate broker wants to sell a house as quickly as possible, so they tend to sell houses slightly below market-value and then convince you it's the best you'll get. you can rig this incentive in your favor by telling the broker you've contacted two brokers and will accept the highest bid.
I actually applied this one recently as my sister was looking for a renter and had contacted only 1 broker. I convinced her to get a second opinion and she got a way better offer.