Typically, the highest paying trucking jobs are the ones with the most challenging cargo types. For example, hazardous liquids, oversized loads and specialty car hauling truck drivers all tend to be better compensated than average. Drivers working on ice roads or in hazardous environments such as mines are all among the highest paid. Typically, the most lucrative (but also financially risky) way to make money as a truck driver is to be an owner-operator. Highly successful independent truckers can make more than $200,000 per year.