People expect most conversations will remain on the surface and that you won’t stray from the norm; that you’ll keep it safe. When you make a bold comment about someone’s new look, weight loss, attitude or lifestyle, it rattles them a bit. This level of engagement can be remarkably profound.

I used to be embarrassed to make comments that were overtly kind and seemingly out of the blue. I feel it often, but saying it can be scary and intimidating. I would fear that people were going to think I’m nuts, or that I’ve watched Jerry McGwire one too many times.

But I do it. I’ve made a habit of it. Why? Because I’ve seen the power of a boldly kind and caring comment. I’ve seen the impact it can make, and the joy it brings into the world.

Lots of people notice these opportunities but don’t say anything because it’s too uncomfortable or risky. “What if people think I’m weird?” I’ve got news for you. We’re all weird. Why not use that dynamic to bring more love into the world?

I notice the nuances of life around me because I care. I take the risk of being boldly kind because I care enough to forego my own comfort for the possibility of bringing more joy into someone else’s life.

It took a lot of time and conditioning to create this habit. But now it’s not so scary; it’s fulfilling. And lots of people that know me well have come to expect it from me. I’ve never looked back and regretted being boldly kind with my comments. Never.

People are often scared of engaging too deeply with others because too many variables come into play. It could all go wrong. It could result in hours of conversation you weren’t prepared for or willing to engage in. It could make you look stupid.

Or, it could bless someone immensely and enhance your relationship with them. It could result in something more beautiful than you ever imagine. It could give you strength to show more kindness to others.

People are typically pleasantly shocked when I make a comment like this. They think, “Wow, he noticed, AND took the opportunity to mention it to me”. Remember, most people are scared of making these types of comments. So when they experience it from you, they recognize what you’ve chosen to overcome in order to deliver it.

If you have the opportunity to say something boldly kind to someone, go for it. Say something extraordinary. Chances are, it will bless you just as much as it does the person you’re complimenting.

In my family, Tommy Boy is considered a “classic film”. I think most of our family members could recite the bulk of it. In addition to being hilarious, it has a few decent life lessons we can all learn from.

The most notable may be when Tommy Boy stumbles upon his hidden ability to sell. He knows he habitually destroys every sale he tries to make. But ultimately, through his struggle, he connects with another human being, the waitress.

Through this moment, he realizes that if he truly connects to someone, considers their feelings and shows them genuine kindness, he can sell just about any concept he wants.

In this clip, Tommy Boy inadvertently causes the waitress to do a 180. She had previously shut him down. But he took the time to connect with her personally, relate to her, show her kindness and remind her of their humanity. It’s remarkable how disarming that process can be.

Over the years, I’ve referred to this clip many times, calling it “The Ole Tommy Boy Turnaround”. I think it’s powerful, and worth noting.

Circumstances shouldn’t dictate how you treat people. Your actions should always be deliberate, and in my opinion, they should be deliberately kind and humane. If you take the time to connect with someone, you can almost always come to a peaceable resolve.

The next time you’re in a difficult situation, I suggest you try the Ole Tommy Boy Turnaround. Kill ‘em with kindness and see if that gets you sorted out.

The next time you want to change or accomplish something, take a step back, be patient, be kind and connect with the humanity around you. I think you’ll be pleasantly surprised at where that gets you.