'Be a tail of a lion rather than a head of a fox'
In his magnum opus, 'Tania', Rabbi Schneur Zalman of Liadi prescribes a meditation for cultivating affection and respect for people both 'great and small'. Granted that 'small' people are often mistreated or neglected, aren't 'great' people usually appreciated anyhow?
Some people enjoy the company of distinguished individuals because they respect their accomplishments or feel themselves important in their company. In contrast, they disregard those they deem mediocre or inferior.
However, some people abhor the company of distinguished people because it makes them feel inferior and inadequate. Typically, they prefer to associate with people they deem inferior to themselves, whose presence makes them feel important and appreciated.
Rabbi Schneur Zalman thus stresses that we should learn to respect and care for everyone.
However, when it comes to progressing in a given skill, such as skateboarding, it is preferable to associate with a group more advanced than oneself.
The obvious advantage is that one has regular opportunities to observe better skateboarders and to ask them for tips. However, another, subtler, yet vital, benefit exists.
People are creatures of contrast and comparison. When one sees a shirt on sale for $10 less than usual, one feels he has stumbled on a bargain. In truth, it's possible that the shirt is heavily overpriced, albeit slightly less when on sale.
The power of relativity/contrast is easily observed when one alternatingly surrounds a single circle with larger and smaller circles. Surrounded by larger circles, it appears small; surrounded by smaller circles, it appears large.
In skateboarding, if one regularly skates with skaters who are better than him, then, when he considers attempting new tricks, since others in the group perform thm easily and casually, one approaches them with a casual attitude as well and is more likely to have the confidence to try them and succeed. However, when one regularly skates with a group of skaters who are less proficient, the same new tricks - which no one else in the group can perform - may seem formidable and intimidating.
One is thus likely to progress much faster when regularly skating with more proficient skaters.