The Entrepreneur's Guide to Outsourcing With Ease (and Growing Your Business Fast!)
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The Entrepreneur’s Guide to Outsourcing With Ease (and Growing Your Business Fast!)

Usually, when you start your freelance writing business, you wear all the hats. You not only complete writing assignments for clients, but you also conduct all marketing and administrative tasks, from blogging to bookkeeping.

If you hope to develop your dream writing business, however, you must outsource some tasks at some point — and not just once in a while. This goes beyond using apps to manage your business yourself to hiring other humans to help.

For many, this is a scary prospect because of the potential to make hiring mistakes, but it’s doable with the right guidance. So, why, when or how do you outsource or subcontract some tasks to paid vendors and which tasks should those be? Here’s everything you need to know.

Outsourcing: Why should entrepreneurs do it?

Why outsource?

If you hope to grow your business so you can pursue larger, more interesting and lucrative projects, you can’t do it alone.

If you hope to grow your #freelance business so you can pursue larger, more interesting and lucrative projects, you can’t do it alone. What's the answer? #Outsourcing | #Entrepreneur Click To Tweet

You must regularly outsource tasks necessary to sustain business operations, but not for you to do yourself. Those tasks may include administrative tasks like billing and bookkeeping and professional services like quarterly tax accounting and legal support.

It’s especially important to outsource when the hourly rate for those vendors is less than yours — transcribers are one example. As your business grows, use them to take on tasks that are more costly for you to do. Ruthie Bowles of Defy The Status Quo Marketing in Baltimore, MD agrees. “I was growing my client base, but I was spending a lot of time on routine tasks that weren’t high value, or they were high value but fairly simple.”

The desire to use her skills to provide the most value to her clients pushed her to outsource tasks that didn’t do that. “It also helped me get more business development, marketing and sales done,” says Bowles.

When should you outsource?

The more complex or busy your business becomes, the more likely you must hire external vendors to handle certain business activities. If you want to maintain satisfied clients, especially by completing assignments on time, delegating tasks to reliable paid vendors facilitates that.

Outsource when you have more writing assignments than you can complete yourself or your needs for more sophisticated professional help grow. For Bowles, this happened when she went from part-time to full-time freelancing.

Changes in your personal life also can mean outsourcing tasks. “I had my second baby and moved across the country last year,” says Ana Reisdorf, MS, RD, a registered dietician who has a team of writers. “My business also really started to take off and I couldn’t do it all, so I knew I needed help,” she continues.

It’s wise to outsource before you become too overwhelmed to maintain exceptional client service and work-life balance.

How to outsource to grow your business.

How to outsource?

Much depends on your business and personal goals, your writing niche, and your personality. There also are legal and accounting issues to consider, including as they relate to your business structure. Hiring outside your country of residence can present challenges, too, as does managing a remote team.

“When a business owner uses a contractor (vendor), they should interview them carefully to determine if it will be a good fit,” says Gainesville, VA CPA, John Wall. “It is important that the business owner knows what skills the potential vendor has, and what the cost will be,” adds the public accountant with 32 years of experience.

6 Tips to outsource with ease:

1. Establish business and personal goals.

Once again, it’s ideal to begin the subcontracting process before you need extra help so you’re ready when you do. Evaluate your business reasons for beginning to outsource. Is it to grow your business in a particular way?

For example, do you want an agency model or to remain a solopreneur book author, speaker, or blogger with no team identified on your website? Are you pursuing larger client projects? Do you want shorter workweeks?

Do you detest certain tasks, know you do some poorly or put off important ones like collecting on invoices and keeping accounting books up to date? Bowles says, “There are things I outsource I could do myself, but I just don’t have the time, which means they wouldn’t get done at all.”

Also, consider your personal reasons. This can be anything from wanting to travel more or spending more time with your growing family to getting more training or education. Reisdorf says of her subcontractors, “They are available to jump in when kids are sick, or I have other obligations.”

“Mine have given me more time to pursue personal projects and spend more time with my family,” says Bowles.

How to outsource like a pro: Find contractors who specialize in your niche.

2. Find contractors who specialize in your niche.

It may seem less costly to hire inexperienced subcontractors. But the time you spend to train someone to execute the content demands you and clients in your niche have will offset any savings.

You can’t maintain efficiency correcting their mistakes while managing other vendors and working on the business. So, it’s best to hire professional writers or other contractors who specialize in your niche and pay them reasonably.

Reisdorf agrees, saying, “I have a team of other registered dieticians who want to be writers, too.” That makes her small agency a specialty firm, and that helps her generate more revenue.

Both women carefully vet writers and other contractors before hiring them. “I offered a paid trial to everyone who applied [to work with me] and spoke to them on the phone,” says Reisdorf. After one experience where she didn’t, Bowles now also offers a small, paid trial project to help determine if a contractor’s performance lives up to their marketing.

“It’s not that people are trying to trick you, but there is a lot to learn at the beginning of the relationship,” she says. “It’s better to make a small change to an outline than it is to fix a fully written piece of content, for example,” she adds.

3. Determine how you like to work.

Your personality will determine how you work best with others. Often, how you prefer to work with your clients is how you’ll work with vendors.

Do you like lots of face time and virtual collaboration or are you someone who wants to give instructions and have your subcontractors work entirely independent of you?

Do you want to manage a team of remote subcontractors and have the skills to help them thrive working for you?

The idea is to make your work more efficient. So, outsource to those whose personalities and work styles sync best with yours or meet business requirements.

How to outsource: Decide what you need help with and when.

4. Decide what you need help with and when.

While both Bowles and Reisdorf have regular subcontractors, they also hire some on an as-needed basis as well. Bowles, for example, maintains contracts with two virtual assistants, each of whom specializes in specific tasks like social media marketing or bookkeeping.

She also has editors and other writers. “I have a small group that I work with consistently, and I bring in new people as needed,” she explains.

Reisdorf says, “I have five other registered dieticians who work with me regularly.” Each also runs their own enterprise but acts as a part of Reisdorf’s firm’s team.

You can subcontract out transcription, website development and maintenance, appointment setting or many other tasks, too. Make a list of what you need and how often. Then set about finding the right help.

5. Find subcontractors from reputable sources.

Both Reisdorf and Bowles found other freelancers on Facebook, Reisdorf in an industry-specific group. “I posted the opportunity in the group and had about 30 apply.”

There are many other platforms like LinkedIn and Fiverr that offer you ways to connect with talent for hire, including legal and accounting help. Look for those platforms that allow previous service buyers to rate or rank those who provide services and carefully read reviews or recommendations. Get referrals from others who’ve outsourced, too.

“I wrote up a detailed job post to give respondents an idea of what I was looking for,” says Bowles of this important step.

How to outsource: Address legal and accounting considerations.

6. Address legal and accounting considerations.

This is where you get professional help like that of an attorney or a CPA like Wall. While blog posts, articles or other content can be informative, providing insights at no cost, they are no substitute for licensed professional legal and financial help.

To avoid legal and accounting mistakes and their consequences, it’s wise to get that help when you start your business. Outsourcing makes it more imperative.

Acknowledging, however, that most small business owners manage such issues themselves, Wall provides some accounting tips for outsourcing.

Make sure you maintain your books. Wall says, “The biggest problem that I see freelancers and business owners running into is not keeping up with their accounting.” If you will do it yourself, be sure to use CPA-friendly accounting software. That should be one with files you can share with your bookkeeper or accountant to help you manage when you hire one to make sure your books are accurate and tax authority compliant.

Wall also instructs freelancers hiring others not to forget to complete and distribute 1099s annually. “For compliance, U.S. law requires business owners to issue their vendors an IRS form 1099 by Jan. 31 of the following year,” explains Wall.

You send them to unincorporated freelancers you paid $600 or more the prior year. You must include specific information on all 1099s and be certain the IRS gets a copy, too. Make sure you know how to complete and issue these properly to avert tax compliance issues.

The good news is payments to vendors are tax-deductible for you. “The correct way to deduct them is dollar for dollar,” Wall says. “For example, if you paid a vendor $5,000 for the year, you deduct $5,000 as a business expense,” he adds.

But, he cautions, “The exact amount of taxes that a business owner pays depends on what kind of entity they are — sole proprietor, LLC, S-corp., C-corp., etc.”

While Reisdorf has relationships with vendors who live in the U.S., Bowles has some who don’t. Of that, Wall says, “Using vendors outside the U.S. is fine, but besides interviewing them, the business owner needs to make sure there are no security issues such as unauthorized access to sensitive data.”

Wall recommends you also understand the differences between an independent contractor and employee when outsourcing. “If a business owner will supervise and control most of the work that the vendor is doing, they should hire the person as an employee,” he says. “The IRS and states have specific definitions of who qualifies as an independent contractor and who must be an employee.”

Despite its challenges, there are rewards to outsourcing, including higher revenue. Reisdorf, who’s been writing for six years says, “Not only has it really decreased my stress level, it’s allowed me to grow a 6-figure business this year.”

Why should you #outsource, when should you do it, and how do you get started? Here's everything #freelancers need to know. Click To Tweet
Dahna Chandler

About Dahna

Dahna Chandler is an award-winning business and finance journalist with 20 years’ experience writing for top media outlets and top blogs. She is passionate about helping wealth-minded freelance writers thrive financially by reaching their wealth objectives. Visit her site at Get Money Moxie, and follow her on Twitter and Facebook.

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