Overthinker? Over-Critical?

02 Nov 2022

aka, Can’t Take Off the Developer or Designer Hat? Do you find it easy to find “creative problems”?

No worries. I found a way that you don’t need to fight it. Keep on the hat or hats. They look nice, 🚫🧢! How?

Before I get there, let me provide context on where over-thinking and over-criticism is more harmful.

During lecture, we discussed one of the discount usability methods. When diving specifically into heuristic evaluation – in which you gather typically 3-5 experts, usually internal to the organization, to independently work through different heuristics and apply them to the design; they don’t reconvene to share ideas until after evaluation! They don’t reconvene until after, as different people are able to find different problems. Arvind mentioned the various pro’s of cost-effectivity, while being able to find easy issues from the jump.

But the downside is that working with exeprts on the team internally can create room for over-analysis and getting ahead of themselves – we can start digging in too deeply, when there aren’t really problems there. We can even hypothesize and create problems that don’t exist.

As an over-thinker, I’ve found many ways to “creatively mess up” in life. For example, my friend and I drank a whole gallon of milk in the Brothers grocery store, and we had planned to pay for it at the end. When we brought the empty glass of milk along with other grocery items to the cashier, the cashier ended up totaling up the costs while giving us a $3.00 return – as the cashier thought that we were returning the glass gallon to retrieve our deposit. In the confusion, my friend and I left, and when we realized what had happened, we started laughing hysterically. As the good citizens and milk-drinkers we are, we returned to the store, and explained to them that we should’ve been paying, rather than getting paid for drinking their milk (also, that milk was from a local farm in Sharon, MA, and it was the best. milk. I. ever. had.)

The cashier was super confused, and brought the manager along. After a step-by-step cognitive walkthrough to the loophole we created in the system (the “creative error”), the manager and cashier burst out laughing as well. The manager said something along the lines of, “Of course, only MIT students would’ve figured out how to get paid for taking our milk.” We ended up paying the full cost of the milk, but they let us keep the deposit because, once again, as good citizens… of the earth (? lol)… we brought back our glass gallon – probably breaking record times on when a customer returned a gallon-sized glass for the deposit to a grocery store :)

In our tomfoolery, we found a design flaw in grocery stores – the largely accepted assumption that all glass containers being brought to the grocery store is to be rewarded with the deposit. A way to fix this would be to require receipts, or to ensure that the ID of the glass gallon has been purchased. But is this a problem that really exists? Do people drink whole gallons of milk while shopping?

So not only do we tend to over-think, we tend to find creative errors as the interesting thinkers we are – to anyone who thinks outside of the box, willingly or unknowingly, and to anyone who over-analyzes, and over-criticizes to find loopholes – the way you don’t have to fight to keep on the hats is by becoming a Bug Bounty Hunter. That’s right! You can get paid for discovering bugs :)

Years ago, I had heard of one of these bug bounty hunters who found a bug that allowed for unlimited free orders on UberEats. Not only did he order a couple of free UberEats orders in testing out the bug’s persistence, but he also reported the bug to Uber and got paid for finding it!

I enjoy that when finding creative loopholes and errors, software companies like Uber and Google (can explore more on hackerone) reward over-thinkers, problem-creators, and unassuming tomfoolerers.

Here are some other posts of bugs found specifically in Uber:

• Quote: What was the glitch on the Uber Eats app that enabled users to get free food while paying for the order through empty Paytm wallet?
• “Researcher Finds Bug That Allowed Free Uber Rides”

On the flipside, when creating an app, it may be good to start diving into exploring such creative problems once you establish basic functionality. To have users unlock unlimited free rides and food deliveries for Uber/UberEats is a terrible nightmare – and that bug couldn’t have been found if it weren’t for hackers willing to criticize and think about possibilities of loopholes within the payment method system. Happy hacking!