Cloud Wandering as a concept originates from the Chinese Daoist traditions, whereby an adept of the Dao ~ someone who is committed to the Way and Virtue, roams about for a period of time, seeking masters and teachers, cultivating discipline and will (somewhat harder to cultivate when you do not have a permanent dwelling/community) and very importantly, helping people along the way in various ways.
The traditions of Cloud Wandering is age old and deeply imbedded in the Daoist literature and stories.
Before "cloud wandering", one should have a solid foundation in the Daoist arts (e.g QiGong, NeiGong, TCM, Geomancy, etc). Without the foundations, a cloud wanderer can easily get lost. For example meeting teachers who are low in skill, insincere or not a suitable match... Or wandering into the wrong neck of the woods... Or not being able to fend or feed oneself when travelling along the way.
2. Knowing what to look for
Wandering can seem like an aimless thing to do, but as Gandalf said "Not all who wander are lost". Cloud Wandering is a stage of progression, where foundations have been solidified and one applies the concept of WuWei 无为, a non-governing approach to progressing further. The aim of Cloud Wandering is to shed layers, roam about freely without social norms and constrictions and ultimately, elevate the spirit to the next level.
3. Being able to help others along the way
Being a Cloud Wanderer may seem like a selfish action and with all honesty, it probably is as one on the way is utterly concerned with personal cultivation and development. However, it is a precept and a required skill that a Cloud Wanderer knows how to help, heal and harmonise places/people.
Traditionally, high level Cloud Wanderers were required to manifest rain or sunshine, manage malevolent ghosts, know how to read signs from wind and weather, know a great deal about medicine/healing and be good in fengshui/geomantic arrangements.
The same applies these days. In order to be a decent Cloud Wanderer, one must be able to bring about harmony and get along with others on the way. Skills in both Traditional Chinese Medicine and conventional medicine are always in demand. Perhaps rainmaking is not the skill in big demand these days, however knowing a great deal about nature, plants, weather patterns, soil, minerals, fungi...these are all helpful skills for a Cloud Wanderer.
Perhaps bottling up ghosts may not be the norm of today, but cleansing and harmonising spaces that are "disturbed" is very a useful skill. All in all, a Cloud Wanderer needs to be able to utilise skills that are helpful to others, complimentary to internal cultivation and sufficient to be rewarded with food and shelter.
4. Know Chinese language and Daoist Classics (to a degree)
The tradition of cloud wandering stems from the Daoist traditions of China. No point Cloud Wandering if you do not have a good grasp of the language and culture where these traditions stem from. Instead, perhaps consider an adventure or road trip. Since this is written in English for English speaking people, assumably not every will be fluent in Mandarin (in fact mine is only semi fluent). However core understanding of a broad range of Chinese and especially Daoist concepts is vital in order to Cloud Wander.
5. The aim is spiritual
Clouds in Daoist art elude to spirit, the deeper, cognitive, conscious, sub-conscious and even etherial aspects of the self.
The Daoist arts traditionally start with body cultivation and familiarising with the Daoist code of conduct, ethics and morals. From there, one seeks to work with internal energy (Qi) and consolidate the essence (Jing). There are a number of practices such as QiGong, herbalism, calligraphy, drawing talismans and others, that are all important in their own right. However, the aim of Daoist arts is spiritual awakening and elevation beyond the that of the norm. The road to such heights is long, the way is hard and full of difficulties. Nevertheless, one should always know the destination...
6. The journey/road is your home
Humans and other animals have a tendency for permanent dwellings. For this very reason, the Cloud Wanderers roam. In order to free oneself from the patterns and comforts of the mundane daily life and to invigorate the spirit. This does not last forever, but it is necessary to awaken certain qualities within that are invaluable later when settling down for longer periods of time. For a Cloud Wander, the road is home, taking refuge in not knowing where one will be tomorrow, making peace with the impermanence of the situations, appreciating good meals and shelters, humbly accepting hard conditions as valuable lessons.
This article is a short summary of some aspects of the "cloud wandering" that may be useful for those interested in this topic.
There is so much more to explore about this tradition, what has been mentioned is barely the tip of the iceberg. Hopefully the high level Daoist sages approve all the content written with a nice smile and a friendly nod. By Henri Lebedev