Can Drivers Leverage the Shortage, Earn More & Outsmart AI?

August 4, 2025

How Drivers Can Make More Money in the Age of the Shortage (and Outsmart AI)

📌 TL;DR: Action List

✅ Get your endorsements.
💼 Look for better-paying gigs (especially in Boston).
📱 Learn basic fleet tech.
📈 Start a simple financial plan.
🤖 Don’t fear AI—learn how to use it.

Howdy!
If you’ve got a CDL, a clean record, and know how to handle the road, this might be your golden era. Seriously. While the rest of the job market zigzags, you’re in high demand—especially in cities like Boston, where transportation chaos meets opportunity.

Let’s break down why this is happening, how you can capitalize on it, and what’s next (hint: AI isn’t stealing your job just yet—but it might give you a raise if you play it right).

🛑 What’s Going On with Drivers in the U.S. (and Boston)?

We’re living through a nationwide driver shortage. According to the American Trucking Associations, the industry was short over 60,000 drivers last year, and that number’s expected to grow.

In Boston? The demand is even hotter. Between university shuttles, airport transfers, biotech deliveries, and people just trying to get to Fenway without losing their minds—transportation companies are scrambling for licensed, reliable drivers.

And it’s not just trucks. Charter buses, black car services, school buses, and even last-mile routes all need professional drivers who show up, show out, and don’t miss turns.

So… How Can Drivers Make More Money Right Now?

Here’s your short answer: leverage the shortage.

✅ Action Checklist: How to Max Out Your Earnings

1. Get Endorsements (Yes, They Pay More)

Add Passenger (P), School Bus (S), or Hazmat (H) to your CDL.
In Boston, Class B drivers with Passenger endorsements can pull in $30–$45/hour on shuttle contracts.

Pro tip: A CDL school can help you get those endorsements easily.

2. Sign Up for Flexible Platforms

Think Uber Freight, Amazon Relay, or apps like Moovs (for chauffeurs).
You set the schedule, and surge pricing = more money during events, bad weather, or last-minute bookings.

3. Get On with a Transportation Company That Offers Bonuses

Boston-based services like DPV Transportation offer referral bonuses, retention bonuses, and overtime.
Some companies may even pay for your endorsements or training.

4. Learn Basic Tech & Dispatch Systems

If you can manage a tablet and GPS app, you’re golden.
Dispatch software knowledge is now a plus for higher-paying gigs.

5. Offer Yourself as a Team Driver

For longer hauls, team drivers split the drive time and double the distance = more pay per week.

But… Is AI Coming for Our Jobs?

Not so fast.

Self-driving trucks, buses, cars? They’re still in beta. The tech’s impressive, but it’s nowhere near replacing humans for city navigation, customer interaction, loading/unloading, or adjusting to Boston’s pothole obstacle course.

What’s happening instead is this:

AI is being used to optimize routes, reduce idle time, and help dispatchers.
This means your job could get easier (if your company’s smart enough to use it well).

So the real opportunity?

🧠 Learn the Tech—So You Stay Ahead

✅ 3 Tech Skills Drivers Can Learn Today (Without a Degree)

1. Dispatch Platforms

Get familiar with Samsara, Moovs, Routific, or Onfleet. Learn how to accept jobs, track routes, and communicate with dispatch.

2. Digital Vehicle Inspection Tools

Apps like Whip Around are replacing paper checklists.
Knowing how to run a digital pre-trip inspection = brownie points with employers.

3. Basic Data Entry or Fleet Reporting

Some high-paying jobs need you to log mileage, fuel, or incidents.
You don’t need Excel wizardry—just a smartphone and 10 minutes a day.

Smartest Financial Moves Right Now

Let’s be real: driving is physical work, and you won’t want to do 14-hour shifts forever. So stack your money now, while the demand is high.

✅ Financial Moves to Start Today:

Open a SEP IRA or Roth IRA if you’re 1099/self-employed.
Save for a down payment on a van or bus if you want to eventually be your own boss.
Track expenses like fuel, maintenance, and meals for tax deductions (apps like Stride help).
Ask your company if they offer training subsidies or tuition for upgrading your license.

This is Your Market—Own It

You’re not just a driver—you’re the backbone of America’s economy. From supply chains to weddings to biotech lab samples, nothing moves without you.

Whether you want to stack cash, build your own fleet, or ride this shortage to a six-figure career, the road is wide open.

Need a starting point? Schools like Boston CDL Driving School offer fast, flexible training for new and current drivers looking to upgrade. And companies like DPV Transportation are hiring with real bonuses and flexible schedules.

So put it in drive—your future’s out there.