About a month ago, I was having breakfast with a friend and ranting about the clique-ishness of the tech community, when he said, “You have to admit. They’re a really loyal group.” I replied, “I’m not sure all the blind loyalty is a good thing. Since they cheer about everything, it’s basically become a giant echo chamber where everything is celebrated regardless of how ridiculous it is.”

The conversation got me thinking, is it possible that there’s such a thing as too much loyalty?

In general, I think loyalty is undervalued in our increasingly transactional society so it feels strange for me to question it. But online it often seems as if we’ve progressed into a bizarre world devoid of judgment, consisting only of empty support. Or perhaps, in our quest to provide encouragement, we’ve simply lost sight of what true loyalty entails.

One of the side effects of the social Web is that we now have a constant audience for everything we choose to share. Feeling sad? Send an emotional Tweet about having a bad day, and 10 people will tell you to feel better. Want to brag? Post on Facebook that you’re hustling 24/7 and you’ll get a dozen “Likes.” But are these people really doing us a favor? Is supporting us unconditionally really the loyal thing to do. Or is it just a way to score points for people who are afraid of what consequences a more considered response might carry?

As bad as this incessant cheerleading is in general, nowhere is it more prevalent than with entrepreneurs. Most of us recognize that entrepreneurship is a hard road, but I highly doubt we’re really helping with the endless supply of unwarranted words of encouragement. I think it’s safe to say that an entrepreneur needs constructive feedback far more than blind support telling him that his quixotic dream can really be the next Facebook. But it seems many of us have become so afraid of offering critical judgment that our feedback has crossed the line into irrelevance.

Since I don’t believe this helps anyone, I’d like to propose some new rules for what constitutes loyalty in the online world. Loyalty should no longer be about blind support but about honest feedback. If you don’t have a strong enough relationship with someone to tell them the truth, then don’t say anything.

I know many of you worry about appearing unsupportive or judgmental, but consider it this way. Imagine you were out shopping with a buddy and he asked you, “How do these skinny jeans look?” Only a terrible friend would say “Dude, rock those jeans. You’re crushing it!” Anyone who convinces you to buy skinny jeans is clearly not a friend, and yet in the online world, every idea, no matter how ludicrous, is met with this same kind of unconditional cheerleading.

When one of our entrepreneur friends asks for advice, don’t they at least deserve the same level of honesty that we would give a friend who was on the verge of committing a horrific fashion faux pas? If a buddy was about to embark on a business endeavor that was as ill-conceived as wearing Crocs and an Affliction t-shirt on a date, wouldn’t telling him he’s about to make a huge mistake be the right thing to do? Blindly supporting such absurdity doesn’t make you loyal, it makes you a sycophant.

I realize it sounds strange to encourage people to tell their friends when they’re being stupid, but I think it’s time we end this charade of incessant cheerleading and false loyalty. We’ve gone so far in the direction of only saying nice things that we’ve forgotten how to provide constructive and critical feedback. Maybe the social Web isn’t the right place for honesty. Or perhaps the rules of modern friendship have changed, and we are no longer expected to tell our friends the truth.

Regardless of the reasons, I think we’d all be better off if we were a little more willing to call each other out on our bullshit.

[Illustration be Hallie Bateman]