Having fun should never be hard. If creating a fun at work program is proving to be difficult, you are doing it all wrong.
Think about the last time you had a great time, at the end of it all, did you look back and say, wow that was really hard?
No, more likely the time just flew right by. For this reason, I'm not a real fan of a fun at work program. Programs require a lot of work, energy and usually money. They evolve around goals and objectives and suck the natural fun out of it.
After all, play, humor and fun are spontaneous. Just like the minute you try to analyze a joke, it ceases to be funny- the more you try to artificially force fun at work, the less likely it will actually be fun.
The best way to grow a fun workplace is to support it and get out of the way. Fun and funny are organic and most people instinctively know how to have fun. Just notice how children play naturally, they don't have to be forced or taught how.
To encourage fun at work, just get out of the way and don't try to control it.
When funny things happen, laugh and spread the word. Retelling funny stories brings about the same endorphin rush as when it originally occurred. Overtime, these memories create your culture.
You've probably heard the saying, people who play together stay together. Not much bonds a group like laughter does. If people are playful and spontaneous at work, enjoy it.
Give teams opportunities to play. Playful routines, celebrations, group songs and cheers, can be fun. When you make group celebration fun, you will make it memorable.
Laugh at yourself, if you don't you are leaving the job to others. Seriously, people at work love poking fun at each other, their rituals, routines and nuances. Celebrate what makes your work ( or workplace) unique and weird.
Laugh at the Tough Stuff.
Humor relies on tension and conflict to make it funny. Thus, anything that goes wrong, can be funny. Routines that allow people to laugh at group challenges serve to decrease stress and bring the group together. I was a funny motivational speaker for a hospital where they developed a fun routine where colleagues asked each other, what's stressing you out? ... and whatever the answer was, they group found a way to laugh about it.
Looking at conflict through the lens of comedy develop perspective and a more detached, light attitude towards stress.