Self humor is a very serious matter. It acts as a self-reminder, not to take yourself too seriously. It propagates this attitude to others and helps you be humorous with others.
I think that the coined term for it is self-deprecating humor, however, I don't like the "deprecating" part. Being able to laugh about yourself doesn't have to come with a demeaning attitude. In the same way that humor, in general, is better served if the audience doesn't feel disrespected.
The key here is the difference between "laughing at" and "laughing with". "Laughing at" is exclusive, while "laughing with" is inclusive. The subject of the laugh is included in it.
This inclusion brings the laugh into a safe and fun place. When the other person knows you're laughing with them, it's much easier for them to swallow embarrassing situations.
You should treat yourself the same. Self humor is about laughing with yourself about yourself. You might be the subject of the laugh, but you're included in it.
Self humor is humbling. It reminds you that you're not above humor. No one is and good comedians illustrate it well. We're all prone to looking stupid, acting weird, being awkward, and being able to laugh about it is an act of humility.
You should treat yourself as one of your friends. Our relationships with our friends are, at times, healthier than our relationship with ourselves. We care for our friends, treat them with respect, and make an effort to accept them as they are. We usually don't treat ourselves the same.
We tend to over-judge ourselves and not accept our vulnerabilities, our awkwardnesses, and our quirks with the same affection as we do with our friends. We force ourselves to maintain a certain appearance as if we're constantly being evaluated by the people around us for it. We're less kind to ourselves.
You might think "It's ok for Danny/Charlotte to mess up like that, but I'm different and I have to be more cautious and serious". No, you're not, and no, you don't. You're just like everyone, overwhelmingly human. And if you do something humanly like being clumsy, goofy, awkward, or otherwise funny, then you should laugh about it like you probably would if it was one of your friends.
Self humor is also an act of control. When you can accept being the subject of the laugh, no one possesses the power to laugh at you anymore. You graciously admit you're being goofy or acting foolishly sometimes.
Self humor doesn't make you less important, it makes you less self-important. You can be a serious business-person and still laugh about yourself. Your seriousness as a business-person comes from your ability to execute. Your ability to laugh about yourself will probably make you a better one, for it will help you connect with others.
How do we get better at self humor then? I'll discuss several ways and we'll keep developing this topic in further posts.
One way is to program yourself to look at yourself more humorously. Think about a past situation where you felt awkward and reacted with embarrassment. Now take a pen and list some ways in which this moment was funny. Imagine this happening to a friend instead.
Now, place yourself again within that situation, try to feel the same things you felt before, only this time, picture yourself laughing about it. Release the embarrassment. Think of the list you've just written.
Imagination can fool the brain. Practicing the above, you can program yourself to behave differently in various situations. Instead of anger, calmness, instead of submissiveness, assertiveness. You can practice any new behavior in the safety of your imagination. Just make sure you change your behavior when imagining it otherwise you just practice the very thing you wish to change.
The magic here is that practicing it in your imagination will help you apply it in real situations later on.
Another way to practice self humor is by sharing embarrassing stories about yourself with a group of friends, focusing on laughing with them about it once it's out there. The situation won't surprise you and you'll be able to handle it better.
When talking to a friend, you can also reveal your vulnerabilities, talk about the things that make you feel weak and inadequate, and how stupidly you act sometimes, but tell it with a smile, own your humanity. Fake the smile if needed, one day it'll be natural.
I can assure you that we all feel that way so many times throughout our lives, including me of course. It might even be several times a day. A close friend will engage in the conversation and might open up too.
A trick that I use to loosen the self-importance muscle and get some laughs going: Stand in front of the mirror and try to laugh without smiling, with the straightest face that you can muster. See where it takes you. It's a fun challenge to try with friends as well.
To conclude for now: think of the most impressive person you know or can think of. He is probably being a doofus several times a day. It all depends on how you take it. Permit yourself too.
I'll write more on the topic in further posts. You're invited to share your thoughts.