One of the biggest mistakes folks make when it comes to thinking about using humor at work, or actually using humor, is that they assume that the end goal is actually to produce real lol's. Nothing could be further from the truth. What you want to accomplish with humor at work or in your day to day activities is to produce what actually happens when we type 'lol' into our devices. We seldom actually laugh out loud. We are more often to be found cracking a lopsided smile, giving a quick exhalation through the nose, or perhaps even a hint of a chuckle. But rarely am I really laughing out loud.
Why aren't we typically really laughing out loud? Well, for one thing we're often alone when we're on our device, or at least we're not interacting with those around us. Laughter is primarily a social act. Laughter is much more likely to occur when your with folks than when you're by yourself. Further, deep laughs, laughter that lasts for a long time is pretty rare. Laughter is usually just a sort of conversational marker helping us to navigate what's going on.
So when you're trying to use humor don't write your jokes as if you were going to a comedy club, or as if you were performing for an audience. Find what you think is funny and share it. Find clever ways to say or write the same things. Use a meme here and there. Keep things light in your communications or poke a little fun at yourself. When you remove the goal of getting comedy club style laughs, you'll find that humor will come more easily.
And just FYI, Laugh at work week is just about a month away, April 1st through the 7th of 2020. Get ready to bring a little levity to your life.