Hiring Help in Your Business

I totally understand that the word “hiring” might sound scary to you. But I can say without a shadow of a doubt that hiring help in your business (in some shape or form), is the BEST thing you can do to help your workload and to grow your brand. It might be more within reach than you think! Let’s talk about hiring help in your business.

Hiring Help in Your Business

Hiring Help in Your Business

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Hiring Help in Your Business

Hiring help sounds terrifying… but it totally doesn't have to be! I'm running you through how to know what to hire out, the differences in employees and contractors, and all the things!   Join the Hustle & Grit Club today: https://hustleandgrit.club   Get started with ClickUp for free!

I will be talking about contractors and employees in this post. Preface: I am for SURE not a lawyer or an accountant. I’m going to share what I know about hiring help in your business, but please do not take my legal or financial information for Bible! Definitely reach out to a lawyer or a CPA.

But actually knowing what to hire out, I’m very good at! That’s what I’m hoping to share with you. 

Be CLEAR on what you’re hiring out

Hiring out isn’t as scary as it might sound because of some different options. But to begin with, you NEED to be clear on exactly what you’re hiring out. And to add on to that, you have to hire out what you MOST need help with in your business.

I think that a lot of people hire for the wrong part of their business. You need to hire for things first that:

  • Take up the most of your time
  • You HATE
  • You aren’t the person that has to do them

I want you to make three lists.

  1. All of the tasks you currently do that take the MOST time
  2. Things you HATE doing
  3. All the things that happen in your business that CAN be done by someone else

I want you to be very honest with yourself on all of these lists. You might think you’re the only one who can do your style of video editing, but you could absolutely train someone else to do that.

Now, go through your lists and see which tasks are on ALL THREE of your lists.

My first thing? Customer service and emails. I hated doing it, it took up a lot of my time, and I’m definitely not the only one who can manage my inbox. That’s what I hired out first, and it is the thing I would NEVER go without.

The crossovers on those lists are the things you need to hire for first.

My First Time Hiring Help in My Business

Flashback to baby entrepreneur Jessica in 2015. I was co-hosting the All Up In Your Lady Business podcast with my friend Jaclyn Mellone, and we both owned and contributed to it equally.

I edited the podcast because of my technical knowledge, and it took over my LIFE. My time was dictated by editing podcast. Jaclyn was TOTALLY pulling her weight, but the editing was more responsibility than I anticipated.

Me mutually agreed that, as soon as we started making money, we would hire out editing the podcast. So, we did. And I ended up hiring that person to take over customer service in my business in 2016 when I was not making REMOTELY the money I am now.

Contractors vs. Employees

Again – do NOT take my legal advice. I just want to share my understanding with you.


A contractor can be two different things. They can be a person who either has their own business doing the thing you need help with and will do it for you with their own processes and invoice you. Or, they can be someone who is doing those tasks for you as a freelancer, and you can send them pay based on the hours they work.

You do not pay taxes on contractors – they are responsible for that themselves. If you spend more than $500 on them, you do need to fill out a 1099, but generally they manage their own taxes.

Contractors are fairly easy to find and are the easiest way to get started with hiring help in your business because they require way less commitment.

You can’t dictate when a contractor works. So, if you’re hiring a contractor for 10 hours per week, they can work whenever they want.


You do pay taxes out for employees – state, federal, all the things that are needed.  But you don’t have to pay out health insurance for them or give them a 401k. That’s something I definitely want to grow into as my team continues to grow.

But YOU are in charge of all the things for your employees. Taxes, a W2, getting them their paycheck, etc. You can control the hours that they work and how that works for the company.

Most people will start out with a contractor. But you can totally have a part-time employee instead of a contractor if you’re able to pay taxes on them (that’s the biggest difference).

Different states do have some different requirements – like I can’t have employees in North Carolina if I don’t have some sort of workman’s comp plan, even though they’re working from their own homes.

Hiring help in your business

If you’re new to hiring help in your business…

When I was just getting started with hiring help in my business, I found it really beneficial to look for people who WANTED to start their own businesses to hire as contractors.

I would put out a call on my personal Facebook page describing the job, the hours, and the pay – which is generally much lower than typical contractor pay. I specifically said I was looking for someone interested in building a business with those skills, because in exchange for you working for me for a lower rate, I am willing to show you all the things you need to know to get started.

I’ve done that MULTIPLE times and it’s worked out super wonderfully! It helps me because I don’t have to spend as much on contractors, and it helps the contractor because they learn a ton of skills to go out and start the business they want to start.

The Benefits of Employees

Employees can SOMETIMES be cheaper than contractors. And they’re likely going to be more dedicated to your vision.

It is WAY cheaper for me to give Laura, who is already on my payroll, my videos to edit than to hire it out. Even with hiring someone else for customer service (which we have done). It probably costs me half or even a quarter of what it would have to hire a video editor.

Employees can also be safer in terms of competition. You could get them to sign a non-compete clause that protects you and your business information. But they do require more work on the back end.

Accounting Tip

If you’re going the employee route, you’ll have payroll to think about. I use QuickBooks for my accounting and to manage payroll. It automatically sends out my paychecks and walks me through the forms I need from my employees.

My First Full-Time Employee

As I grew, I needed more than just someone to manage my customer service and inbox. I really needed someone to help me manage my business as a whole in addition to those things.

I went through THREE OBM’s (Organizational Business Managers), who are contractors that take on the role of managing a business. To be honest, I had bad experiences all three times with my OBM’s.

It became way more valuable for me to invest in an employee rather than try again with a contractor. I got way more dedication and way more hours for a similar amount of money each month.

The Hiring Process

I’m not an expert on hiring either, but I have done it a few times! I prefer to hire locally – not so I can meet up with these people, but because I’m passionate about giving local people good jobs.

I have created a makeshift application on Typeform, shared it locally, and hired in that way.

The biggest part of hiring in my opinion is getting REALLY clear on the expectations that you have for this new hire before you even start to hire them. Knowing the expectations you have is crucial to finding the right person. And you need to be able to communicate those expectations with your employee or contractor, too.

I hope this helped you understand more about hiring help in your business!

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