Freelancing is fantastic. You’ve probably heard that 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 cat’s pajamas 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?

What kinds of tasks can you outsource?

While our super-hip chef will clearly be hiring a salad expert, what about you? What kind of freelancer do you need to hire? The options are surprisingly vast, and the possibilities of the time that can be freed up is genuinely exciting! (And, yes, I used an exclamation point there. I don’t care if it looks tacky; this is pretty sweet.)

Social Media & Marketing

Many freelancers offer a product or specialize in a service that isn’t marketing. The thing is, though, if you want people to actually pay for that product or service, you’re going to need to do some marketing. Luckily, some of the most popular outsourcing options available right now are social media management, SEO optimization, and marketing.

Imagine getting to focus in-depth on exactly what you love to do, each and every day. Meanwhile, an experienced remote worker (who checks in with you on a regular basis) takes care of your social media posts, google rankings, and marketing strategies so you don’t have to. I don’t know about you, but that sounds like a frolic through a unicorn-laden meadow to me.


If you actually create a product and sell it online, you’ve got a whole ‘nother bag of freelance potatoes to deal with. By hiring an eCommerce specialist, you’ll have someone to create product descriptions, provide customer service in a timely manner, and manage your account. These tasks can take a lot of time out of your billable work, and with proper communication, can be easily transferred to another experienced worker.

General Business Management

Think of the things you have to do each day to keep your business functioning smoothly. Between email communication, scheduling, invoicing and bill pay, website updates, and contract generation, there are certain days where my business management can eat up an entire morning. By hiring a virtual assistant, you can get those mornings back.

Content Creation

Does the thought of writing a blog post or a personal bio make you want to hide under a desk? Here’s a secret: you don’t have to write anything if you don’t want to. For real. There are people who will do that for you.

These are just a few of the options available for outsourcing. FreeeUp has a more extensive list; you should totally check that out.

Be ready to hit the ground running.

A 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 worker 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. Keeping in touch and monitoring progress is key: if something’s not working, address it. Schedule times to meet and discuss process, progress, and problems. If you constantly work on the quality of your outsourcing relationship, you’ll be much happier in the long run.

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 a 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 a new hire on the same page.

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

Now, usually, when it comes to organization, I don’t get too worked up. A messy desk and a wall covered in post-its is fine, so long as it works for you and doesn’t cause anyone else problems. If you’re paying bills on time and meeting your deadlines, what’s the big deal?

When you’re talking about outsourcing, though? Being disorganized in terms of communication with a new hire is not going to work.

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 the newfound  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.


Connor Gillivan


Connor Gillivan is the author of Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, a serial entrepreneur, and the CMO and co-founder of When he’s not bringing together hundreds of freelancers and business owners, he’s mentoring entrepreneurs through his site, He currently lives in Denver, Colorado.


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3 thoughts on “The Ultimate Guide to Outsourcing as a Freelancer

  1. Its like you read my mind! You appear to know so much about this,
    like you wrote the book on it or something. An excellent read.

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