For me it has a sense of retaining control over the situation rather than allowing the situation to control you. This implies that you have some understanding of circumstances around you.
A classic example would be Preventative, scheduled or proactive Maintenance (say in a factory) where things are checked regularly, worn items replaced before they break and so on.
In your personal life or career, regular exercise might be considered proactive health maintenance ; while reading recent publications relating to your career, or attending conferences keep your career skills and knowledge up to date.
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