"Feeling judged" is a phrase people use when someone (or, in the case of Mint, some software) calls them on their bullshit when they would rather pretend it doesn't exist. By "judged", they mean "punished unreasonably, arbitrarily, and unfairly by someone who has no authority to do so".
Often, you see people use fitness trackers, hire personal coaches or tutors, and do all kinds of things to make sure they stay on track, but in reality they are sabotaging themselves because they want that next cookie more than they want visible abs or a smaller pants size. A person who is serious about a goal welcomes feedback and correction (even if it feels negative) from a qualified person because it improves their progress toward the goal. A person who is NOT serious about the process, but who wants to appear as though he or she is, will blame the person or electronic device for providing the feedback. It's like getting angry at a bathroom scale because you don't like the number you see on it... a mature person will recognize that if anger is warranted at all (and it may not be), it should probably be directed at the person responsible for the bad decision making that led to the bad result. An immature person will blame the tool.
The thing is, when a person programs Mint software or hires a personal trainer, he or she does give that person or software the authority to make corrections. The feedback that occurs is therefore NOT unreasonable, arbitrary, or unfair because the person receiving the feedback consented to be "judged", sought out a person or software package that is qualified to provide the necessary feedback to identify actions that are out of step with their own stated goals, and generally paid for the privilege!