How to Start Working with Freelancers and Independent Contractors Today

There’s an economic freight train gaining speed in our economy and it’s being driven by freelancers and independent contractors.

A recent survey conducted by Upwork and Freelancer’s Union estimates that this group is earning some $1 trillion a year and that freelancers make up 35 percent of the workforce. That represents a lot of money flowing through the economy and some of today’s convenient new payment services, such as Mastercard Send, facilitate the delivery of funds quickly and securely to support this commerce. I’ll touch on that again in a moment.

The questions you need to ask yourself right now are: should you jump on this train, and if so, how?

Several currents running through modern life have come together to create an ideal climate in which freelancing is poised to gain momentum:

  • The Internet makes the location of workers irrelevant in many cases.
  • Specialized skills are increasingly required for business success.
  • The Great Recession forced many workers to become freelancers or independent contractors.
  • Millennials tend to value the freedom to control their own schedules and working conditions.

Before I make some suggestions on aspects of your small business that you should consider outsourcing to freelancers and contractors, I encourage you to review the IRS criteria that you must meet in order to stay on the right side of the law. If you fail to meet these guidelines, the IRS may consider your contractor an employee and you would be required to pay all the additional payroll taxes. The Department of Labor could also get involved.

Let’s now take a look at the positive side of using freelancers and independent contractors in your business. With today’s fast Internet connections and powerful personal computers, fewer and fewer workers need to actually be at your location, or even in the same state.

Today there are entire companies made up of individuals working around the world who only know each other through online meetings, chat apps, email, and maybe a once-a-year “company” meeting at some resort location. And there are many more businesses who outsource chunks of their operations and/or bring on talented individuals to handle a wide range of projects. Here are some of the tasks most commonly (and successfully) outsourced to freelancers and independent contractors.

IT, networking, web and software development

Most small businesses don’t want to carry a full-time IT staff, so outsourcing website design, app development, and all kinds of internal software creation makes a lot of sense. But, anyone who has worked with a bad or “difficult” developer knows how painful these relationships can be, so make sure you carefully vet all candidates.

Graphics and visual design

To “put your best foot forward” you need to have an engaging, communicative, and consistent visual presence wherever you are –online or on printed materials. Few small businesses can fund a full-time graphic arts department, so find someone who meets your artistic needs and stick with that artist so you can maintain continuity.

Content creation

Creating content can eat up a lot of time. Unless it’s your strong point and you have the time to devote to it, consider hiring a freelancer or independent contractor to take over this responsibility.

Administrative assistant

“Virtual assistants” have become one of the most popular categories for engaging an independent contractor. Depending on your needs, you can find very inexpensive VAs located in countries like the Philippines and India. If your work requires someone who is based in the U.S., they are also widely available.

Legal services

Small businesses have been engaging attorneys as individual contractors forever, but now you can connect with lawyers through freelancing websites such as Upwork. This can be especially useful if you need an attorney that practices in a specialty area, or if you just have a quick question or two you need answered.

Customer service

You probably already know about large call centers that handle outsourced customer services, but did you know that small businesses can now contract with individuals to do customer service jobs? With online – and affordable – customer service apps like Freshdesk and Zendesk, freelancers are being brought onboard to handle a wide range of customer service tasks.


Independent contractors have always been an integral part of sales teams, but the Internet has extended their reach. Small businesses can even have an overseas presence through a remote and independent contractor who is connected via the Internet.

Marketing and public relations

Social media marketing is another area that can eat up a lot of your time, but fortunately it’s also one that is ripe for handing off to a freelancer. Other aspects of online marketing can also be handled this way, such as lead generation, search engine optimization, and email marketing. You can also find contractors who can handle all of your public relations needs.


Virtually every popular small business accounting system today is cloud-based and because of that, your bookkeeper or accountant no longer has to be located in your area. Further, you can find good financial planners and other consultants you can engage over the Internet.

This list highlights the areas where freelancers and independent contractors are the easiest to find, but I think that with some smart searches, you could probably discover someone in cyberspace to provide your small business with any service it requires.

There is, however, one requirement all of these contractors will have: getting paid.

Having worked with many online freelancers, I can tell you that they appreciate prompt payment. In fact, when one major freelance site recently put a five-day hold on payments between contractors and clients, many freelancers decided it was time to end the relationship.  Mastercard Send has solved these problems. If you pay your contractors via the Mastercard Send platform, they will get paid typically within seconds with the use of virtually any U.S. debit card.   Mastercard Send is a first-of-its kind service that provides greater convenience, choice and security to both payment senders and receivers.

If you haven’t yet taken advantage of independent contractors, I suggest you study my list above and get onboard. You will be able to achieve greater productivity and be able to pull off projects that would otherwise be impossible.

Ajeet Khurana
Ajeet Khurana
Ajeet Khurana wears many hats: author, angel investor, mentor, TEDx speaker, steering committee of the NASSCOM Start-Up Warehouse, Director of Founder Institute, Venture Partner with the seed initiative of a top Venture Capital firm, and former CEO of IIT Bombay’s business incubator, among others. Before all this, he was entrepreneurial twice in the field of education and web publishing. As a lecturer at the University of Texas at Austin, he taught e-commerce back in 1993, when the term "e-commerce" had not yet been coined. An undergrad in computer engineering from the University of Mumbai, and an MBA from the University of Texas, Ajeet is presently an active name in the startup ecosystem. From starting two ventures as a solopreneur, to helping a large number of startups with their go-to-market, he has never shied from getting his hands dirty. At the same time he has helped dozens of startups raise investment. He truly believes that small business owners are driving change in the world, and need to be facilitated as much as possible. Innumerable small businesses have gained from his attitude, vast professional networks, financial acumen and digital mindset.

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