The surest way to know what your future in trucking will be is to move to a trucking company where people you know are already working and doing the work you will be doing. That’s to say, knowing a driver at Schneider, for example, doing one specialized sort of work for them making $65k per year does NOT mean you can work as a general OTR driver for the same company and make as much or more than the $65k per year driver you know.
There are many trucking companies that have resigned themselves to a constant churn of new drivers becoming dissatisfied becoming former drivers making about $30-40k. Those same companies will advertise using numbers from their long-term drivers working with special circumstances. They may advertise “our average driver makes X per year” without disclosing they are averaging a $30k driver with a few $90k drivers.
It’s important to connect with current working drivers at the companies you are considering. It’s important to ask open-ended questions and LISTEN to what they say. Ask again if they don’t answer your question, which many of us don’t. Questions like “is this a good company, do you get enough miles” are not as informative as “how many miles are you getting?” How long have you been with X?” What type of driving do you do for X?” etc.
I find TheTruckersReport.com to be pretty valuable for direct information from working drivers at the companies you want to know about. Ignore the drivers that are only re-telling what they have heard about X. Working drivers that have been at that company for a few years are your best source of info on working conditions.