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@Jeroen said:
Well, the Dogen quote is about how one finds enlightenment through Zen. It’s not quite the same thing as my original statement which was about playfulness. And from the statements of the Buddha, I don’t know if enlightenment actually leads to playfulness, or playfulness to enlightenment.

I have posted some pieces of Osho talking about Hotei in the Buddhist Quotes thread, which aren’t actually the one known story about Hotei in the official Buddhist texts but they are more Osho expanding upon laughter as the flowering of spirituality. I thought they were interesting, although Osho also gave a treatment of the one official story.

What comes to my mind when talking about playfulness, amusement, spontaneity in a spiritual context are the many realized teachers who are joyful and funny, not at all sticks in the mud. Or from another map, that of Maslow and the self realized individual. An AI overview:

According to Maslow, self-actualization is the highest level of human need, characterized by traits like autonomy, authenticity, creativity, self-acceptance, a sense of purpose, and the ability to have meaningful relationships. Self-actualized individuals also experience peak experiences and a continued freshness of appreciation for life.
Key characteristics of self-actualization, according to Maslow:
Acceptance of self, others, and nature:
Self-actualized individuals embrace their own flaws and imperfections, as well as the strengths and weaknesses of others and the natural world.
Spontaneity and naturalness:
They are authentic and genuine in their thoughts, feelings, and actions, rather than trying to conform to social expectations.
Problem-centered:
They are focused on solving problems and making a positive impact on the world, rather than being self-centered.
Autonomy and independence:
They rely on their own experiences and judgments, rather than being overly influenced by external opinions or authority.
Continued freshness of appreciation:
They experience a sense of wonder and awe in everyday life, seeing beauty and value in simple things.
Deep interpersonal relationships:
They form meaningful and lasting connections with others, characterized by trust, respect, and empathy.
Sense of humor:
They appreciate the absurdity and irony of life, and have a good sense of humor.
Creativity:
They are original, inventive, and expressive in their thoughts and actions.
Moral and ethical standards:
They have a strong sense of right and wrong, and are guided by their own values and principles.
Peak experiences:
They experience moments of intense joy, ecstasy, and awe, often associated with a sense of oneness with the world.
Resistance to enculturation:
They are not easily swayed by societal norms and expectations, and are willing to challenge the status quo.
Unconventionality:
They are not afraid to be different and to express their individuality.
Gratefulness:
They appreciate the blessings in their lives and are not easily discouraged by setbacks.
Purpose:
They have a sense of meaning and purpose in their lives, and are driven by a desire to contribute to the world.
Self-actualization is an ongoing process:
It is not a destination but a journey of personal growth and development.

Maybe you're talking about something slightly different? You referred to Osho, I'm not that familiar with his teachings, I think I remember something about laughing practice or something along those lines. I don't understand it, so its hard to give an opinion about their validity according to my understanding.

“Man suffers only because he takes seriously what the gods made for fun.”

― Alan Watts

I like that this implies that the meaning of the universe is for amusement. It seems a better reason than many… when you are young and go skipping through the park and looking at the clouds while you are full of dreams about what you might do later in your life you don’t appreciate that you are perhaps closer to the real meaning of the universe than many an aged philosopher.

I think as you get older the mind and the brain get clogged up with “facts” and “methods” and “seriousness”… and you lose “magic” and “dreams” and “spontaneity”. The mind becomes a burden, casting the same world that seems wondrous in childhood with somber, dreary and grey overtones. It is what happens to many in old age.

Which is why I love Alan Watts, he has a great and playful understanding.

@Jeroen said:

@lobster said:

I thought this was pretty good, certainly in the Western world today there is a great culture of individuality, and it is usually considered healthy for even young children to develop boundaries and a sense of what they do and do not want. In the East the collective is emphasised far more, although there too there are signs of the rise of individualism.

It leads to problems with being accepted, with feeling part of a greater whole.

I think there is an important note about balance here. In the west we've been on the path of individualism for a while and its leading to some unhealthy extremes. Before we jump fully back on the collective train, remember some of the things about collectivism we fought to leave behind. The notion that a child has to follow in the footsteps of the parents or live a life that brings respect to the family or village rather than follow their own interests is collectivism. That there are cultural norms or values, such as heteronormativity that one needs to adhere to because its best for society, or simply because that is what everyone else is doing is collectivism. Tall Poppy syndrome, don't stand out, don't be exceptional, collectivism.

What I generally strive for in my own mind is to be an individual that understands and appreciates my place in society and what others do for me and what I do for others, often invisibly.

@lobster said:

I thought this was pretty good, certainly in the Western world today there is a great culture of individuality, and it is usually considered healthy for even young children to develop boundaries and a sense of what they do and do not want. In the East the collective is emphasised far more, although there too there are signs of the rise of individualism.

It leads to problems with being accepted, with feeling part of a greater whole.