If you’ve been driving for a company for a while, you’ve probably thought about it: “I could do this on my own.”

You’re not wrong  thousands of drivers take that leap every year.

But if you’ve ever scrolled through trucking forums or talked to a few owner-operators, you’ve probably heard mixed stories. Some drivers are earning six figures and loving the freedom. Others warn that it’s stressful, complicated, or “not what they expected.”

So which is it?

The truth is, being an owner-operator isn’t easy - but it’s worth it when you go in with the right plan, tools, and mindset.

In this post, we’ll break down what actually makes being an owner-operator hard, what most drivers wish they knew before they started, and how programs like CloudTrucks’ Road to Independence make the transition smoother, so you can enjoy the freedom without the overwhelm.

1. The Honest Answer: It’s Harder, but in the Best Way

When you go from company driver to owner-operator, you’re no longer just running miles. You’re running a business.

That means:

• You make the decisions.
• You manage the money.
• You deal with breakdowns and downtime.
• You pay your own taxes.

But that also means you control your schedule, your income, and your future.

Being an owner-operator is like stepping out of the passenger seat of your career, you finally get behind the wheel.

2. The Hard Parts (and How to Handle Them)

Let’s break down the most common challenges new owner-operators face and how successful ones overcome them.

Managing Money Like a Business Owner

As a company driver, you probably get paid weekly or biweekly and your only biggest work related expense is meals on the road.

As an owner-operator, you have to budget for:

• Fuel (your biggest cost)
• Truck payments or lease costs
• Maintenance and repairs
• Insurance premiums
• Taxes and registration fees

That means discipline matters. The drivers who succeed aren’t necessarily the ones who run the most miles, they’re the ones who track every dollar.

‍CloudTrucks automatically tracks your pay, deductions, and settlements, so you always know what’s left after expenses.

Handling Maintenance and Downtime

When you drive for a company, breakdowns are their problem. As an owner-operator, they’re yours.

A single blown turbo can cost $3,000+. A full rebuild? $20,000+.

That’s why successful owner-operators treat maintenance like insurance - they set aside $0.15–$0.25 per mile for future repairs.

Understanding Freight and Market Changes

Rates go up and down. Fuel spikes. Freight volumes shift by region and season.
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That unpredictability can be tough at first, but it’s also what gives experienced owner-operators an advantage. You learn which lanes pay best, which seasons are strong, and how to plan ahead.
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Through the CloudTrucks Road to Independence Program, you get access to our unified load board, which pulls loads from DAT, C.H. Robinson, UberFreight, and more into one place. You also get access to a dispatcher, helping you make informed decisions instead of grabbing random freight just to keep moving.

Staying Compliant

ELDs, IFTA, permits, and insurance - all critical, all time-consuming.

If you’re running under your own authority, managing this can be a job in itself.

That’s why many new owner-operators choose to lease to a carrier like CloudTrucks at first. You still have full independence, but the compliance, insurance, and authority are handled for you - freeing you up to focus on driving and building your business.

Taxes and Bookkeeping

No more W-2s. You’re a 1099 contractor now.

You’ll handle:

• Quarterly estimated tax payments
• Self-employment tax (15.3%)
• Business deductions (fuel, per diem, etc.)

3. The Easy Parts (That No One Talks About)

Yes, there’s more responsibility, but some things actually get easier when you become your own boss.

No Forced Dispatch

You choose your own loads and schedule. Want to be home for your kid’s birthday? You can plan for it - no begging dispatch.

No Cap on Pay

You’re not stuck at 65 CPM forever. The more efficiently you run, the more you keep.

Pride and Purpose

Every load builds your business, not someone else’s. You’re driving for yourself and that changes everything.

4. The Emotional Side: Discipline and Mindset

Many drivers underestimate the mental shift that comes with ownership.

As an owner-operator, you’re responsible for:

• Saving instead of spending
• Thinking long-term instead of week-to-week
• Understanding your CPM (cost-per-mile) to stay profitable

This mindset takes time to build - but once you have it, you’ll never want to go back to being a company driver.

The most successful owner-operators treat every decision like a CEO:

“What’s the ROI on this load? How does this lane affect my fuel costs? What’s the long-term gain?”

That mindset separates drivers who survive from those who thrive.

5. How CloudTrucks Makes It Easier

CloudTrucks built the Road to Independence program specifically for drivers who want to go independent, without the confusion and risk that normally comes with it.

Here’s how it helps simplify the hard parts:

1. Equipment Access: Unlock favorable underwriting and pricing with our truck leasing partners, who offer carriers like us special pricing.

2. Maximize your revenue: Earn as much as you’re willing to work. CloudTrucks only takes 21% (and that includes dispatch and insurance fees).

3. Tap into big-carrier resources: You'll have the tools and team you need to succeed, including a dedicated business consultant, dispatcher, and 24/7 support.

4. Get paid instantly: Never wait for a weekly payment again. With CloudTrucks, you get paid within 2 hours of each delivery.

6. What Experienced Owner-Operators Say

When you ask veteran owner-operators if it’s hard, most will tell you the same thing:

“It’s hard work, but it’s my work.”

You’re no longer just earning a paycheck - you’re building equity, independence, and generational freedom.

It’s a learning curve, sure. But it’s also one of the most rewarding experiences in the trucking industry.

7. The Bottom Line: It’s Harder, But It’s Yours

Being an owner-operator takes discipline, patience, and planning. You’ll have long nights, tight margins, and tough calls with brokers.

But you’ll also have:

✅ Unlimited earning potential

✅ Control of your schedule

✅ Ownership of your business

And you don’t have to do it alone.

With CloudTrucks’ Road to Independence, you can step into ownership with confidence, knowing your truck, freight, and back-office support are set up for success.

You’ve already proven you can handle the road. Now it’s time to handle your business.

👉 Start your Road to Independence today.