The Ultimate Guide to Outsourcing as a Freelancer

Freelancing is fantastic. We’ve hammered this point home a bazillion times. Freelancing, while not free, offers freedom. Freelancing puts you in charge of your schedule and grants you creative control.

Freelancing, my friends, is the bee’s knees and we will never stop being freelance cheerleaders.

That doesn’t mean, though, that freelancing comes without drawbacks like creative ruts, financial anxiety, and general burnout. These obstacles are a freelance reality, and via tips and helpful fixes, we’re here to help you through them. Today’s magic fix? Outsourcing.

I should rephrase that, actually. Outsourcing is by no means a “magic fix.” It takes preparation, patience, and a hefty amount of business-related soul-searching. I mean, we’re talking about your business here… your livelihood, your entrepreneurial baby, right?

Now, sure, we could run through a list of outsourcing pros and cons. Why should you outsource? Why shouldn’t you outsource? The fact is that outsourcing is a perfectly viable option for some entrepreneurs… but not all. So we’re going to treat it like the viable option it is and break it down for you on a level that’s a bit deeper than “outsourcing pros and cons.”

When is a good time to outsource?

If you’re freelancing, feeling uninspired, and freaking out over your workload all at the same time, there’s a good chance that the solution to your problem might be outsourcing.

Remember, doing what you love comes with administrative duties. These duties, like tracking expenses, posting on social media, and scheduling meetings, all take time and brainpower that could be used for designing book covers or building websites that make your clients tear up with joy.

The first question to ask is: Can you afford to outsource?

If you’re at the point in your freelance career where non-billable tasks are costing you precious hours that could be used for billable work, outsourcing is definitely an option to consider. Also, if those undesirable tasks are costing you creativity and causing your other work to suffer, you should give it some thought.

Think of an up-and-coming, talented chef whose craft beer-infused, farm-to-table chicken pot pie makes celebrity chefs swoon and critics give out hugs. Let’s say she adores working on main dishes, but doesn’t give a damn about salads… but the people still want salads. What should she do? Should she soldier on through those tedious greens while the pot pies suffer in quality, or hire someone who’s as skilled in salad-crafting as she is in comfort food?

Where do you find freelancers for hire?

This answer could easily become overwhelming, so I’ll try to be clear and simple. The fact is that the pool of freelancers is huge, varied, and full of differing skill levels… and they can be found just about anywhere.

Certain websites like Upwork (formerly oDesk and Elance) and Freelancer are frequently used and oft-recommended due to their payment protection systems and the ability to browse profiles and portfolios of competing freelancers. These websites are designed to create a competitive marketplace for freelancers who need work and the people who want to hire them. Surprisingly enough, Craigslist can also be a wealth of work opportunities, providing that you research any prospects you find thoroughly (always ask for a reference).

All of these options provide a unique opportunity: the chance to utilize offshoreoutsourcing.

The topic of offshore outsourcing is a hot one. It can be intimidating to think about dealing with someone overseas. You’ll likely have a lot of questions: What are theoutsourcing pros and cons of hiring workers out of the country? Should I or should I not hire someone offshore?

Due to cultural and language compatibility, outsourcing to the Philippines has become a popular offshore option, but, in all honesty, geographic location is not the main point to take home here.

Here’s the deal:

There are good and bad workers everywhere, and the only way to find the good ones is via thorough interview processes.

You want to make sure that you can communicate effectively with the person you hire (verbally and in writing), regardless of their native language. You want to see examples of their previous work, and you want to communicate with some of their references to make sure that deadlines were met on time, and work quality was satisfying. If you’re hiring for creative work, ask for a paid trial project that will give you a real-time idea of what it’s like to work with a specific prospect. This is a process that should be used in any hiring situation, stateside or no.

Your other option is to look locally and consult your contacts. You know thatconference you’re going to next month? The one you’re hoping will score you some industry knowledge and potential clients? You should also add “scope out outsourcing possibilities” to your to-do list. A conference or other networking event is a rare opportunity to actually meet possible hiring options in person, chat with them about what they do and love, and get a feel of their personality and work ethic. It’s practically a mini-interview, but with free coffee and a few hundred other people hanging around you.

Be ready to hit the ground running.

Your new hire’s first day on the job is not the day to come up with a plan and get your documentation in order. Do you think that famous comfort food chef would toss a new salad-maker into the kitchen without first discussing the restaurant’s menu, her personal cooking style, and the rules of the kitchen? Would you expect success from a new team member who has only half-formed instructions and minimal documentation to work from?

I really hope your answer is “no” here.

Outsourcing requires thorough communication, explicit documentation, and crystal-clear expectations.

This means that you need to have contracts drawn up and signed before any work is done. This means that you need to know exactly which duties you’re hiring this person to perform, and you need to provide him or her with any instructions that will help get the job done properly, such as account login information and important due dates. Be sure to schedule progress meetings so that you can work on the effectiveness of your new working relationship.

Make workflow smooth for all parties.

The point of outsourcing is to free up your time so that you can focus on what you love… not give you extra work to take care of. A chef who is constantly hovering over her newly-hired salad preparer is not a chef who is experimenting with exciting new ways to incorporate bacon into a meal.

Set boundaries and expectations for work times, and methods of communication so that work isn’t intruding into the time you’ve dedicated to personal pursuits or family activities. If you’re working in different time zones or countries, discuss deadlines, appointments, and anything else that is time-sensitive with a world clock in front of you. Don’t assume that your new virtual assistant or logo specialist knows that “9 am” means “9 am your time.”

Another good way to keep your new outsourcing life organized is by utilizing project management software. Trello, Basecamp, and Asana are all highly popular and helpful options for product management that will keep both you and your new hire on the same page.

Be prepared. Be organized. Invest in a planner. Something. Anything.

So maybe you’re not the most organized person in the world. Normally I’d say that, as long as you’re meeting deadlines and paying your bills, that’s okay. When we’re talking about outsourcing, though? It’s not okay.

If you can’t be prepared, thorough, and explicit with the person you’ve hired to help you, you’re going to end up costing yourself more money and putting out more effort than you were in the first place… and your original product will surely begin to suffer.

I think we can all agree that, on a list of freelancing pros and cons, that’s considered a “con,” right? We don’t want that for you. We want you to evaluate your need for outsourcing, put forth a conscious effort to hire a solid prospect, and show up with enough material to turn you and your new outsourcing gem into a productivity powerhouse.

Now, if that outsourcing gem can make a mean salad on top of making you more money? All the better.

Over to you!

Thanks for reading! Got some killer wisdom you want to share? We’d love to hear from you below!

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Originally published at approveme.me/freelancing on

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