My Goal, is is doable?

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Do self dispatch. Hit them all in four months. Heck, why limit yourself - do Alaska too. I'm working on the Canadian provinces now. You haven't trucked a day until you've spent a night at the Pilot in Moose Jaw, Saskatchewan.

 

Why not just drop a load in the first 48 truck stop parking lots you get to? It seems to be what most big company drivers do for kicks so seems to me like about any of the big trucking companies would hire you.

 

Probably your best bet is any of the very large carriers like Schneider,JB Hunt,Werner etc. Tell the recruiter what your plans are and eventually you will accomplish your goal. If you think that this will happen immediately you are dreaming... these are big huge multi billion dollar trucking conglomerates not travel agents. Because of their size they have the abilities to hire and insure new drivers. I’m guessing that it is going to take 2-5 years to reach your goal. Be safe and good luck.

 

I’m a retired Accountant turned truck driver (wanted to do something interesting for about 10 years until I fully retire).

That’s pretty much what I did. Been in all lower 48 (OTR for about 5 years) & now a local driver. I work M-F, always home by 5:00-5:30, earlier most of the time.

Oh, and if my sources inform me of an inbound Kentuckian, I take the day off and lie in wait.

 

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USA Truck has self dispatch for company drivers and hires new cdl school grads.
Do your planned 48 state runs, then look for a company that has flex work schedule in your area; several of those around.
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USA Truck - Capacity Solutions
USA Truck - Capacity Solutions
USA Truck provides comprehensive capacity solutions to a broad and diverse customer base throughout North America.

 

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It's against the rules on here to offer or accept referral money.
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Where is your location; maybe we can find that flex work schedule for you and you can plan accordingly after running 48 states.

 

Like this guy? (zoom in)