A whimsical, carefree attitude is not typical for this careful, structured, risk averse man. I met Tyler years ago when I was a funny motivational speaker for a group of construction contractors and over the years we have maintained a good friendship; but I have always felt he needs to let go of some of his pretenses and have fun.
Encouraging ( forcing) my friend to lighten up was actually fun and rewarding and was accomplished in just one night. Through this experiment, for the first time Tyler wasn't obsessed with every detail of his life, constantly preparing for the worst. Instead he seemed more alive and willing to participate in the evening, even without an agenda.
Below are some of the things that helped him decrease his resistance and lighten up:
Make Em Laugh
Actually alcohol wasn't involved, instead I used comedy. Before painting the town, I popped in a DVD and we watched some classic re-runs of his favorite sitcom Will & Grace. After a healthy dose of laughter, he was much more receptive to the night. The good mood forming endorphin rush produced from laughter is a sure fire way to prime a person to have fun.
Remove Them from Their EnvironmentStability, routines and mental attitudes tend to be caught up in a space you regularly inhabit. Simply by entering a new space, people are more receptive to changing their demeanor. As a humorous motivational speaker, I try to imagine how an audience's work environment affects their ability to let go in real life. Usually stress gets wrapped around where people work, so the easiest way to elevate this stress is to remove people from their environment.
Encourage Them to Laugh at ThemselvesLightening up requires taking yourself lightly. The best way to do this is to laugh at yourself (or leave the job to others). Some lighthearted banter progressed through the night ( I would poke fun at myself and slowly point the finger at Tyler) until my somber mate started laughing at his own serious demeanor.
Do Silly StuffThe quickest way to drop your pretenses is to just be silly and let go of the facade. Just consider that children don't have the need to look good and play up a serious side; being playful and silly comes naturally to them.
Once Tyler wasn't obsessed with looking good and being rational and responsible he was able to let go and..... finally lighten up. Like a lizard shedding it's skin, it revealed a new more vibrant side of him.