I’ve Hired Independent Contractors for 20 Years. Here Are 7 Downsides Every Business Owner Should Know

After more than two decades of working with independent contractors, I still believe they’re one of the best ways to run a flexible small business. But I’ve also learned that they’re not nearly as cheap, simple or risk-free as many business owners assume.

There are plenty of advantages. I can hire contractors for specific projects without making a long-term employment commitment. I don’t have to provide employee benefits, paid vacation or other traditional employment perks. I can negotiate project rates, define deliverables and avoid worrying about keeping someone busy when the work dries up. Contractors generally manage their own schedules, tools and methods.

It can be a flexible and cost-effective model. But it’s not all rosy.

Here are seven things I’ve learned about working with independent contractors — and what every business owner should consider before building a business around them.

1. Weigh the savings against the costs

When you hire a contractor instead of an employee, you may save money on payroll taxes, benefits and other employment-related expenses. But contractors have their own business expenses, and those costs have to be covered somehow. That’s why their hourly rates are often higher than what you’d pay an employee doing comparable work.

Their rates can also change as market conditions shift, making long-term costs less predictable.

This may still be a financially sound decision for your company, but I recommend projecting the total cost of hiring a contractor versus an employee for every position you consider. Don’t assume you’re saving money just because you’re not running payroll.

2. Invest in compliance

Independent contractors are independent business owners, freelancers and professionals who provide services to other businesses. When you work with them, you need to understand and comply with federal, state and local tax and labor laws.

The distinction between an employee and an independent contractor generally comes down to the nature of the working relationship, including how much control the company exercises over the worker. Factors can include how the work is performed, who provides the tools and equipment, how the worker is paid and whether they operate an independent business.

I generally don’t have the same payroll tax, benefit and wage-and-hour obligations associated with employees — assuming the worker is properly classified as an independent contractor.

I have written agreements with all my contractors. These agreements document the scope of work, payment terms, deliverables and expectations. But a contract alone doesn’t determine someone’s legal classification. Government agencies look at the actual working relationship, not just what the agreement says.

Tax reporting requirements also apply. Depending on the circumstances, you may need to issue Form 1099-NEC to report payments to contractors.

Run these relationships by your accountant and attorney to make sure you’re compliant. Misclassifying an employee as an independent contractor can result in penalties, back taxes and liability for unpaid benefits and wages.

3. Prepare for a changing regulatory landscape

The rules governing independent contractors aren’t necessarily permanent. Federal and state governments have different approaches to worker classification, and regulations can change with new administrations, court decisions and legislative priorities.

Some regulatory changes make it harder for businesses to classify workers as independent contractors, while others give employers more flexibility. These debates often center on worker protections, benefits and the degree of independence a worker actually has.

The takeaway for business owners is simple: Don’t assume today’s rules will remain unchanged. Pay attention to developments in the jurisdictions where you operate, and periodically review your contractor relationships with your legal and accounting advisers.

4. Always have backups

Because independent contractors are independent, they’re free to follow the money wherever it takes them. They can take on other clients, accept new projects or move on when a better opportunity comes along.

Many of my contractors serve multiple clients, which I actually encourage. It reinforces the independent nature of the relationship and allows them to maintain their own businesses.

But contractors come and go. Some are more entrepreneurial, restless or focused on short-term opportunities than others. That’s why I’ve built relationships with multiple contractors, including some who compete with one another.

This gives me options when someone becomes unavailable, misses a deadline or doesn’t deliver. It also means I’m not dependent on one person to keep an important part of my business running.

Just remember: Finding good people isn’t easy. Building a reliable network of contractors takes time, and you need to invest in those relationships before you need them.

5. Don’t confuse ‘independent’ with ‘expert’

I’ve also learned that hiring an independent contractor who presents themselves as an expert doesn’t guarantee that they actually have the experience or skills you need.

Anyone can hang out a shingle and call themselves an expert. I’ve worked with so-called professionals who were hired to perform specific jobs but misrepresented their experience and capabilities.

When you hire an employee, there’s often a formal vetting process. You review resumes, conduct interviews, check references and involve other people in the decision.

Hiring a capable contractor requires the same level of due diligence. Ask for work samples, speak with previous clients, check references and clearly define expectations before signing an agreement.

Don’t assume someone knows what they’re doing just because they have a website, a business name or an impressive title. You still need to do your homework.

6. Your customers may not be thrilled

There’s a difference between the relationship a manager has with an employee and the relationship with an outside contractor. Employees generally work within your organization, while contractors maintain their own businesses and client relationships.

My customers understand this, but sometimes I have to explain that the people I’m sending to their projects aren’t my employees. That can raise an eyebrow.

There’s a perception that employees are more dedicated, accountable and easier to manage than outside contractors. Customers may reasonably believe I have less influence over a contractor servicing them than someone on my payroll. They’re not necessarily wrong.

You can’t hide the relationship, and you shouldn’t try to. Customers aren’t necessarily bothered by contractors. They’re bothered by uncertainty over who’s accountable when something goes wrong.

You need to be prepared to explain how you manage quality, communicate expectations and remain responsible for the work being delivered. The customer is hiring your business, and you need to stand behind the results.

7. Your employees may not be thrilled

Using too many independent contractors can also affect internal relationships and company culture.

Employees may resent the flexibility contractors enjoy or question why certain responsibilities are outsourced instead of handled internally. They may also wonder whether their own contributions are valued if the company regularly turns to outside professionals.

Contractors can become part of a team, but they aren’t employees. How you manage those relationships matters. There are also practical considerations involving confidential information, company data and access to internal systems. Make sure contractors have appropriate agreements and access controls in place to protect your business.

Hiring a contractor for a short-term project is one thing. Relying on contractors for essential, ongoing responsibilities is another. Think carefully about how those decisions affect morale, accountability and the culture you’re trying to build.

Independent contractors can be a great business model — with the right expectations

I don’t want to discourage business owners from using independent contractors. After more than two decades, I still rely on them, which should tell you something.

But it’s important to understand the trade-offs. Contractors can offer specialized expertise, flexibility and defined deliverables without the long-term commitment of traditional employment. They can also introduce uncertainty around availability, costs, compliance and continuity.

My advice is to use contractors when you need specialized skills, project-based support and flexibility. Hire employees when you need consistency, direct oversight, institutional knowledge and long-term commitment. The right mix can help you build a more flexible and efficient business. Just don’t assume that outsourcing the work means outsourcing the responsibility.

After more than two decades of working with independent contractors, I still believe they’re one of the best ways to run a flexible small business. But I’ve also learned that they’re not nearly as cheap, simple or risk-free as many business owners assume.

There are plenty of advantages. I can hire contractors for specific projects without making a long-term employment commitment. I don’t have to provide employee benefits, paid vacation or other traditional employment perks. I can negotiate project rates, define deliverables and avoid worrying about keeping someone busy when the work dries up. Contractors generally manage their own schedules, tools and methods.

It can be a flexible and cost-effective model. But it’s not all rosy.