Your First 60 Days as a Truck Driver: What to Expect & How to Start Strong

Your First 60 Days as a Truck Driver: What to Expect & How to Start Strong

Post Date - Jan 28, 2026

Starting your first trucking job is a big milestone — and it’s completely normal to feel a mix of excitement and nerves.

You’ve earned your Class A CDL, finished school, and now you’re stepping into real-world trucking: live loads, real deadlines, unfamiliar customers, and situations CDL school can’t fully simulate. For many new drivers, the first 60 days are where confidence is built — or where frustration sets in.

The good news? Those first two months don’t have to feel overwhelming.

With the right expectations, the right mindset, and the right company behind you, your first 60 days as a truck driver can be productive, confidence-building, and even enjoyable. Here’s what most new CDL drivers experience during their first two months on the job — plus what separates a strong start from a stressful one.

Days 1–7: Orientation & Real-World Preparation

For most new drivers, the first week on the job begins with orientation. This isn’t just paperwork — it’s where you start learning how trucking actually works day to day.

During your first week, most new CDL drivers can expect to cover:

  • Safety policies and expectations
  • Hours of Service basics and trip planning
  • Communication with dispatch and operations
  • Pre-trip and post-trip inspections
  • Backing refreshers and skill reviews
  • Company processes, technology, and paperwork

Even confident CDL graduates often realize quickly that the road feels different once it’s “real.” A strong orientation helps bridge the gap between school and the job.

Why orientation matters more than new drivers expect

Many new drivers struggle early not because they lack skill — but because they’re rushed or underprepared. Companies that prioritize orientation focus on building confidence, not testing limits.

At Paper Transport (PTI), orientation is paid and designed specifically for new drivers. It takes place over four days in Green Bay, Wisc., and combines classroom learning with hands-on preparation to make sure drivers feel ready — not overwhelmed.

PTI’s orientation includes:

  • Paid training ($750/week)
  • Travel to Green Bay
  • Hotel accommodations
  • Lunches during training
  • No training contract — ever

The goal is simple: prepare drivers for success before they ever go out on the road.

Days 8–30: Mentorship & On-the-Road Learning

After orientation, most new drivers enter a mentorship or trainer phase — one of the most important parts of the first 60 days. This is where CDL knowledge turns into real-world experience.

During this phase, new drivers typically focus on:

  • Trip planning and time management
  • Backing at customer locations and tighter docks
  • City driving vs. highway adjustments
  • Fuel-efficient driving habits
  • Communicating with shippers and receivers
  • Driving safely in bad weather
  • Making confident decisions under pressure

This stage isn’t about speed — it’s about readiness.

The best training programs allow drivers to progress at a pace that builds confidence. Some drivers are ready quickly. Others need extra time. Rushing this phase often leads to stress and mistakes later.

PTI’s Accelerate Program pairs new drivers with experienced, certified trainers who focus on coaching — not criticism. Most drivers complete Orientation + On-the-Job Training in about three weeks total. On-the-job training with a trainer is two weeks, with the option to extend OTJ training into a third week if additional time is needed. Safety and confidence always come first.

Days 31–60: Going Solo (and Finding Your Rhythm)

The transition to solo driving is a major milestone — and often the most intimidating part of a new driver’s journey.

This is when everything becomes yours:

  • Your decisions
  • Your timing
  • Your backing
  • Your communication

Common challenges during this phase include:

  • Backing alone for the first time
  • Managing unexpected delays or traffic
  • Handling weather without a trainer present
  • Staying calm when plans change
  • Building consistent daily routines

It’s normal to feel nervous at first. Confidence doesn’t come overnight — it comes from repetition, support, and knowing help is available when you need it.

At PTI, new solo drivers aren’t left to figure things out alone. Support continues from operations, safety, trainers, and experienced drivers as you build independence and consistency during your first months on the road.

What New Truck Drivers Should Focus on in Their First 60 Days

No matter which company you choose, these principles can make your first two months smoother and more successful:

1. Prioritize safety over speed

Backing slowly and asking for help will always beat rushing and risking a mistake. Confidence comes from doing things right — not fast.

2. Ask questions early

Strong drivers communicate. Asking questions prevents small issues from becoming big ones.

3. Build solid trip planning habits

Good trip planning reduces stress, improves on-time performance, and helps your days run smoother.

4. Manage your mindset

Some days will go perfectly. Others won’t. Learning to stay steady through both is part of becoming a professional driver.

5. Choose the right first company

Your first trucking company sets the tone for your career. Training, mentorship, and culture matter more than many new drivers realize.

Why Many New Drivers Choose Paper Transport (PTI)

Not all trucking companies are built the same — especially when it comes to supporting new drivers.

Some companies expect you to “figure it out.” PTI is built to guide you through it.

With PTI’s Accelerate Program, new CDL drivers receive:

  • Paid training from day one
  • No training contracts
  • One-on-one mentorship
  • Consistent, reliable freight
  • A culture built on communication, safety, and respect

The focus isn’t just getting you on the road — it’s helping you build a confident, long-term trucking career.

Ready to Start Your Truck Driving Career Strong?

Your first 60 days as a truck driver shape your confidence, habits, and future success. Starting with the right training and the right team makes all the difference.

If you’re looking for paid training, real mentorship, and a company that supports new drivers from day one, apply to Paper Transport (PTI) today