What will I need to hit the road?

A shingle hammer works well for most chores you'll do.
Weapon
Notch for pulling nails. (wood floor trailers)
Tire thumper
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In recent years, I've come to love my tread depth gauge, granted with intermodal flat-spotted tires are the norm, but we've pulled some trailers owned by other people (including some mega's) recently with some really bad tires. I had one last fall from a large carrier that I refused to pull because two of the tires were very low on tread. Carrier told my boss not to worry, I slipped my tread gauge in there and snapped pics, sent them to my boss, he told the trailer owner "sorry, based on pics, driver is within his right to not pull that trailer". Trailer owner begrudgingly sent us to their contractor for two new trailer tires.

 

Credit Card with zero balance.
Coffee mug
Coffee pot

 

In this business don't leave home without it!

 

No worries, a lot of this is common sense when you think about it. Getting stuff otr can be hard so having the basics on hand is nice, trucks are machines break so tools can help avoid down time and help you limp to safety at a minimum. Truckers wont always have good shelter so being ready for bad weather is good planning especially as you can end up trapped for days.

Really just think of anything you MUST have like clothing or meds and the like and carry it. For local stuff you can get away with very little. For OTR there are a lot of things you want which make your life easier.

 

Apply post 2 to post 1. You'll be spending all your money paying down to post 1.

 

Get the thickest heaviest blanket you can find, the bigger the better, fold it once or twice, and put it under your mattress so it covers the entire underneath.

Also:
Simple green (1 gal concentrate)
White vinegar
2 spray bottles (1 for each)
Rain X (sold in sprayer)
Hammer (3lb sledge)
Hammer (claw)
Crowbar
Dustpan (plastic so it doesn't rattle when driving)
Hand broom
Full size broom (can often be stored outside truck on back of cab)
Assorted bungee cords (half a dozen at least, different lengths, heavy duty solid black, in case you lose an air line spring or mudflap bracket weld, etc, so you can make it to repair shop safely)
Lock jaw plier
Channel lock plier
Ratchet set
Tin snip
Lock cutter
Portable/clamp-on electric fan
Fitted window screens (sold at truck stops, worth their weight in gold)
1 gal oil
1 gal 50/50 antifreeze
1 gal windshield washer fluid
1 quart medical grade alcohol
Bandaids
Heavy disposable paper shop towels
Spare wiper blades
Spare fuses
Notepad/pen
Reusable watter bottles (from any half-gallon size beverage, fill with water at truck stop sink next to coffee makers)
Repurposed large mouth jar (such as 1lb peanut jar, serves as mini sink for morning washup/toothbrushing, also for liquid cooking waste/rinsewater)
Large multi-wick candle
Lighter
Books
Dvd's
Dash cam
2 folding tables / laptop / 24 inch monitor, for turning bunk area into fold up office/gaming studio

 

If they assign you a white Volvo. You're going to need an Adidas tracksuit and flip flops. The gold chains are optional.

 

If you're a company driver, you don't need to carry a heavy truck mechanics entire shop with you.