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Independent Contractor

How Does an Independent Contractor Truck Driver Get Benefits?

February 2nd, 2022

Samantha Dwyer

Samantha Dwyer

Samantha joined the Anderson Trucking Family in November of 2012 as a specialized driver manager and managed a fleet of mixed company and contractor drivers. In the spring of 2014, she transitioned to the driver administration department and began working in contractor services. While in contractor services, Samantha familiarized herself with all processes, procedures and information in regards to driver contracts, pay and settlements. She is currently the operations support manager and oversees both the contractor services department as well as the driver settlement department and leads both of her teams to ensure our drivers receive the highest level of service required to help navigate their accounts and settlements on a daily basis.

Truck and equipment insurance. 

Health insurance. Vision. Dental. Life. 

Retirement planning. Stocks. Bonds. Mutual funds. 

Where do you start when there’s so much to do?

Trying to understand insurance and benefits plans is confusing. Overwhelming. Exhausting. Daunting. There’s so much to figure out that it’s difficult to know where to begin. 

If you’re new to the independent contractor lifestyle, you probably know by now that you need to secure benefits for yourself and your family. But you may not know how to do it. There are a lot of resources out there; the information isn’t in one central location. That can make it even more difficult to find what you need to set up insurance policies and retirement accounts. 

As the operations support manager at Anderson Trucking Service (ATS), one of my goals is to help ensure drivers feel supported — especially when they’re navigating their accounts and settlements. 

I’ll discuss how you can set up truck and equipment insurance, health insurance and retirement accounts.

When you finish reading, you won’t feel so overwhelmed about getting insurance and setting up retirement accounts. You’ll know exactly how to get started. 

What Kind of Benefits Do I Need as a Trucker? 

As an independent contractor, you will need to secure truck insurance and health insurance, and you will need to set up retirement accounts.  

You might not have a clue how to get started. My best advice is this: Start small and ask for help from your carrier.

Truck and Equipment Insurance 

Talk to your carrier first to see if they offer truck and equipment insurance. Many carriers do offer equipment or truck insurance for rates that are comparable to other insurance companies. Every carrier does it differently, but if they do offer insurance, you may be able to have the money taken right out of your settlement checks. It’s one less payment you have to worry about sending in.

If your carrier doesn’t offer truck and equipment insurance or you want to shop around and peruse your options, first talk to the company you already have insurance through for things like homeowners insurance, renters insurance or car insurance. See if they also offer truck or trailer insurance and if you can bundle it with your current policy. 

Otherwise, you may want to source the market to try to find the best rate. 

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Health Insurance

When you’re looking for health insurance (including vision, dental and life) start with your home state to see what they have to offer you. You can either go onto the HealthCare.gov website to apply for health coverage or you can search your state’s marketplace.

By searching your state’s name followed by “state health insurance marketplace” on your preferred search engine, you will be able to find the healthcare marketplace in your state. For instance, if you live in Pennsylvania, you would Google “Pennsylvania state health insurance marketplace.

You may qualify for financial assistance. For instance, you may get a discount on your premiums because you work in the transportation industry. 

With the Affordable Care Act in place, you can peruse the open market for health insurance as well. When you’re looking at policies, keep your family in mind. Which option is the most comprehensive and best suits the needs of you and your family? 

Determine how much you will pay each year in premiums and compare that to how much you expect to make in the coming year. Are the premiums affordable?

The Universal Trucking Benefit Association (UTBA) may be a good spot to start looking. UTBA offers assistance to independent contractors and owner-operators that are looking for affordable health and life insurance plans. They partner with countless trucking companies 

You also need to consider your age when you’re thinking about health insurance. Are you old enough to start looking into Medicare? You’ve worked hard; you should take advantage of those benefits. Do a little research and see what you can apply for — it might surprise you. 

You might be skeptical about getting health insurance, but consider this: What will happen if you get into an accident out on the road and you need to go to the hospital? Health insurance could make that hospital bill go from $20,000 to $2,000 — a significant difference that could make or break you. 

Are you the sole provider for your family? Or do you pull in the highest income? Consider how that hospital bill could prevent your ability to provide for them. If you’re paying off your hospital bills, will you still be able to provide for them? 

Taking care of your health is one of the best ways you can also take care of your family. 

Prioritize your health — after all, you do need to be in good health to pass your Department of Transportation (DOT) physical to be able to drive.

Retirement Planning Accounts

How do you retire as a truck driver? 

Retirement planning might not even be on your radar. Maybe you’ve just thought it’s something you’ll never do and you’ll just work forever.

But retirement is something you should most definitely plan for. And while it’s certainly never too late to start setting money aside, the sooner the better. 

To get started, head to your bank, credit union or other financial institution that you use. Utilize their resources and set up retirement accounts with them. You can also talk to the insurance companies you work with for renters or homeowners insurance. They normally have links to financial planning companies that can help you with retirement planning.

You can have money taken directly from your settlement checks and funneled directly into your retirement accounts, like a Roth IRA. Out of sight, out of mind. 

You’ve worked hard for your money; now make it work for you.

You may hesitate when it comes to retirement. You might be thinking, “I’m going to die in this truck. I don’t need life insurance or retirement accounts.” 

It’s sad to say, but I’ve had drivers say this to me

You deserve to retire. You just have to do a little planning to prepare for it. You’ve worked so hard. You’ve single-handedly helped keep the country running by delivering important goods.

Consider what you want to do where you want to go and what you want to see in your retirement. Then start setting that money aside so you can make it happen. 

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Get the Benefits You Deserve and Get the Tax Help You Need

Maybe you don’t know where to start and you’re still feeling overwhelmed. Start small. Ask for help and reach out to the driver administration department at your carrier. Someone on the team should be able to guide you on the right path. It’s important to find a carrier that cares and has the resources to help drivers like you. 

It’s never too late to get your first insurance policy or open up your first retirement account. It never hurts to ask your carrier about it. Reach out to your recruiter or dispatcher. They should have recommendations for services and businesses that can help you. 

As you’re navigating the world of insurance and retirement planning, you will likely have some questions about financial planning and tax prep. If you’re new to being an independent contractor, you may not have a clue about how to keep track of your tax-deductible expenses or file your taxes. 

That’s why we’ve put together an article that explains exactly how to manage your finances and get the help you need with taxes.