Hiring Contractors: When to Outsource for Online Business

Last Updated on March 8, 2023

Wondering when to start outsourcing help and hiring contractors for your online business, and when to try to save money by doing it yourself? You’ve come to the right place! It can be overwhelming figuring out what is actually worth spending your time and money on. I answer your questions (and more) in this guide for knowing when to outsource for your online business and when to invest in learning skills yourself.

When starting or growing any new business, entrepreneurs always have to answer the age old question: do I have to spend money to make money?

In my opinion, the answer is a wholehearted YES!

The caveat: you MUST have clear goals, take a strategic approach to what online business expenses you want to invest in, AND when to outsource and delegate the endless tasks that come along with being a blogger, entrepreneur and business owner.

Many people and ‘experts’ out there may disagree and take a more conservative approach to growing a business, and I get that. In fact, I definitely do NOT advocate spending tons of money you don’t have and going into debt.

Yet for me, as someone who wanted to grow my business as quickly as I could, I felt like there were some smart investments I could make so that I could get where I wanted to go. From hiring contractors to knowing when to outsource, thinking through the online business expenses that had high ROIs were a strategic part to growing my business.

At the same time, I’m all about keeping things simple and sustainable, so learning how to outsource and delegate has been one of the biggest areas I’ve focused on these last couple of years to grow in a way that works for me. 

What’s the point of building a business that you can’t keep up with and adds major stress to your life? Having a business should be empowering and allow you create the life you dream about–not be your next slave driver.

If you’ve been struggling to make choices about hiring contractors, what and when to outsource, where to spend money, how to delegate the myriad tasks of your business, then this post is for you.

Let’s get started!

Hiring Contractors

When it comes to hiring contractors, it is important to be clear on the difference between contractors and employees. A contractor is a self-employed worker who has a set of skills that they offer to businesses. They are contracted to work on specific projects for companies pertaining to those skill sets that they already possess. You have no responsibility in training a contractor. Good news!

Hiring contractors is different from working with a firm or company that provides specialized services. For example, you can hiring a contract SEO blog writer, or you could work with a firm that provides that service.

There are many ways to find contractors to hire, from Indeed and Linkedin to other sites like Fiverr, Upwork, and 99Designs. Plus, you can ask around and get word-of-mouth recommendations.

When to Outsource + What to Delegate?

Ultimately, it all comes down to this: what are you good at, and what do you enjoy doing?

That is my critical strategy for deciding what and when to outsource.

Keep in mind: just because you can do something, doesn’t mean you should. I’m sure you’re very competent and skilled at many things, but perhaps you don’t enjoy those tasks, that work isn’t what lights you up and fulfills you in a deep way…if that’s the case, perhaps you shouldn’t be spending your time and energy on those tasks.

If you really want to get to the next level–whether that means having more free time, making more money and/or more of an impact, or all of the above!–then I highly recommend focusing on your areas of joy and genius, and outsourcing the rest, as you’re able to.

In the book The Big Leap by Gay Hendricks, he defines your ‘zone of genius’ as those things where there is no one else that can do exactly what you are doing, in the way you are doing it. It’s where you feel in the ‘flow’, excited and energized, where you utilize not just your skills but the full spectrum of your gifts.

If you can get to a place where you’re living and working in your zone of genius, you’ll not only enjoy your life more, but your business is going to operate better and thrive when you have the right people in the right places.

Click here to download a fillable spreadsheet to help you determine where YOU should spend money, time and energy in YOUR business. This simple formula is the same one I use to decide on outsourcing tasks. 

For me, my zone of genius is in business development. I feel most fulfilled, energized and successful when I’m thinking of new ways of doing things, coming up with new business ideas and marketing strategies and analyzing what’s working and what isn’t.

I also feel in my zone of genius when I’m writing blog posts on topics that I’m truly passionate about, subjects that I feel are important and will really help my readers with a problem they’re struggling with, posts that I feel will really make a deep impact in others’ lives.

What’s not in my zone of genius: social media. photography. mindless admin tasks. bookkeeping. tech-heavy website issues and design.

And so you know what–since I’m not good at those things and I hate doing them, I outsource them all.

Small Business Expense Categories: Online Business Basics, Setup + Launch

First, let’s talk about getting started with a business. What can and should you outsource in the beginning?

Should I Outsource Website Install + Design? 

As a new entrepreneur, getting your website set up is obviously the #1 thing you need to do. This is so important, as it’s going to be your ‘home’ for hopefully years to come.

If you have no tech experience, this is undoubtedly going to feel intimidating and overwhelming. It’s tempting to hire someone for this task, but, actually, I’d strongly advise against it in most cases. Why?

1. Money:To get a high-quality site, it’s going to cost you a lot of money. Even though I believe in spending money where it makes sense, you still have to gauge where to best put your precious resources, and you can’t spend money on everything, especially in the beginning. Hiring a web developer/designer will cost a pretty penny (we’re talking upwards of $2,000-$7,000), and I personally think it’s too much of an upfront cost. Eventually–once you’ve made some money–you can hire someone to make tweaks and upgrades to the functionality and aesthetics of your site, but in the beginning, you just need to your skeleton up and running.
2. Understanding: It’s important for you to understand how your site works, especially as a blogger since you’ll be on the back-end side of your site A LOT. While there’s a big learning curve, in the long run it’s important for you to at least understand the basics of building and operating a site in WordPress. In this post, How to Start a Blog (That Actually Makes Money!) in 6 Easy Steps, I show you how to actually get your domain name, hosting service and content management system (aka the basics) set up and running. (I used Bluehost when I started out as my hosting company, and then later upgraded to Cloudways once I had more traffic to justify the higher cost per month.)
3. It’s Easy: Ultimately, one of the main reasons I recommend DIY-ing your blog in the beginning is because it’s so easy. Especially if you go with Bluehost, which gives you your domain name for free, has automatic WordPress install and 24/7 help available. Simply purchase a theme, some plug-ins and make a few simple tweaks and you’re ready to go. In the beginning, it’s more important to focus on creating killer content and keeping your design clean, simple and easy to navigate, than it is to have some fancy logo or complicated design.
4. Educate Yourself: From there, I HIGHLY recommend my mastermind, the Success with Soul Incubator, which will teach you ALL the ins and outs of online business, from building your site to accounting to PR to SEO, and so much more.

Should I Outsource Writing Content?

For most websites, especially with blogs, you’re likely going to want to be the one writing the posts, especially in the beginning. If you’re starting a blog and you don’t like writing, I’m not totally sure why you’re starting a blog, ha!

Creating content is THE MOST IMPORTANT thing you’ll do for your blog, so enjoying that process is super important.

Being yourself is 10x more powerful when it comes to blogging compared to having an English degree, and a lot of bloggers simply write about their own experiences and day-to-day lives.

There are plenty of exceptions to this. My business website for example, has some of my personal life splashed in and certainly speaks in my own voice, but the content is more educational, informative and resource-based than personal musings. The blog is not my diary.

Another example would be if you’re creating more of an aggregate media site–for example an online magazine or a website with multiple authors. In this case, it’s possible you’d want to hire freelance writers to create high-quality content for you, or at minimum find some bloggers who would be interested in guest posting in exchange for exposure (though I’ll warn you, you get what you pay for!).

For the majority of small to medium-sized blogs, though, the blogger behind the brand is who people connect with, so sharing your authentic voice is key.

I wasn’t sure if I’d ever outsource my blog writing (especially as a former proud freelancer!), but I’m pleased that my assistant has learned over time how to match my voice and create on-point content, so she now helps out with a lot of writing.

Then, I simply come through to make edits, add some personal connection points and ensure the entire piece fits with my mission. I love this system because it frees me up to focus on other tasks in my zone of genius, and just work less in general. (Yeah, I’m all about the 4-hour work week!). 😉

Should I Outsource Photography?

I knew photography was going to be a key part of branding for me with a food and healthy lifestyle blog, but I quickly realized that this task was NOT for me. I tried to take the photos myself few times, but honestly didn’t have the patience, skill, or desire or time to learn how to take and edit gorgeous photos.

In fact, taking my own photos made me incredibly anxious and took hours, and I was never pleased with the end result. No skill and no enjoyment? OUTSOURCE IT!

I decided to hire my friend, Heidi Geldhauser (a professional photographer in Atlanta whom I’d worked with many times before) to do my photography for my former blog and have never looked back! It’s a perfect arrangement for me and I absolutely love the work she delivers–the quality is way better than anything I could do on my own (totally HER zone of genius), and other than planning and attending our bi-weekly photo shoots, I don’t have to take any time to process and edit photos.

What took me dozens of hours before now just takes me about 8 hours per month. And the finished product is more beautiful than anything I could ever do myself.

This decision is going to be different for everyone and most of you will likely opt to try your hand at photography. In fact, some of you probably want to start a blog because you love photography! If this task is something you enjoy–or think that you might–I totally recommend you give it a try and save yourself the money, especially when first getting started.

Small Business Expense Categories: Maintenance Help

Once you’ve got the basics of your blog designed and set up, next comes the day-to-day tasks of actually operating your site. Here are just some of the things to consider when deciding on where you can and should spend money.

Should I Outsource Website Support? 

For website support, again, you need to ask yourself the question: Does this category lie in my zone of genius?

For me, it’s a HELL NO. I don’t enjoy tech talk, jargon, code–it’s like a foreign language–I’m certainly not skilled or educated on best practices, and I’d really rather not deal with it. Some people, on the other hand, have a background in web development or computer science and love this stuff (or have a willing and competent husband/friend/partner who is happy to help).

I 100% recommend at a minimum getting a tool like Vaultpress, a plug-in that regularly backs up your site automatically and protects again spam. Our sites are vulnerable and can sometimes crash, so just in case, it’s worth the $39/year for the peace of mind and avoiding total devastation.

If the budget allows, I also completely love and recommend Andrew and his team over at Nerdpress, who I pay monthly for basic tech support. If an issue comes up, I shoot them an email and they’re so helpful and quick to reply. It’s crazy how much little things come up on a regular basis, and without a trusted tech person on your side, this part of the business can certainly get overwhelming.

Nerdpress has also helped me with many tech issues, like securing my website from spam and hackers, boosting site speed, image optimization and SEO, making updates to plug-ins, installing security certifications (SSL and https, for example), switching hosts and servers, and much more!

Having these kinds of worries off of my to-do list has been so liberating and helpful!

Should I Outsource Social Media?

I have taken a personal and business approach to eliminating social media from my life. In the past I invested in hiring contractors to keep up Success with Soul social media, but now I just let my Instgram page live without updating it. You can read more about my reasoning for this approach and how you, too, can build a business without social media.

One of the reasons that I stopped investing time and money into social media was because after my engagement plateaued, I posted less content and my followers started to drop. My reach and engagement suffered. Instagram was only showing my posts to 1-2% of my followers (the people who have chosen to follow me!). The truth about social media is that you are competing with an algorithm to try and get content in front of people that they will end up scrolling past.

For this reason, I encourage my clients to invest more time and energy into improving their website SEO, starting blogs, and pursuing other communication and marketing methods.

Should I Outsource Accounting?

Let’s be honest: very few of us got into blogging or online businesses because we love doing our taxes (unless maybe you’re a financial blogger). However, it’s a necessary part of being a business owner, especially as you grow, and you’ve just gotta take care of your cash flow, books and paying Uncle Sam. Managing all of those online business expenses and financial matters is something you don’t want to get wrong, though.

This year, I finally decided to hire for my bookkeeping, payroll and taxes, after filing as an S-Corp. I highlyg recommend my CPA, Steadfast Bookkeeping. And my bookkeeper and money coach, Kelly Marshall, saved me! It was just too complicated to figure out payroll and stay on top of all of the forms and taxes you have to pay as a corporation (being a sole proprietor was much easier, though not cost-effective after I reached a certain income level), so outsourcing this made the most sense for me. I even did an interview with her about How to Change Your Money Mindset that you can listen to here.

Another great podcast interview I did was with Dondrea Owens all about Money Management Tips to Scale to 6-Figures & Beyond that you can listen to here.

Before I was an S-Corp, I managed all of my own books (I’m a spreadsheet nerd at heart so this wasn’t difficult for me), but I still hired an accountant to do my annual taxes.

Unless you’re a total tax pro or accounting whiz, I highly recommend you at least find a CPA who can help you file your taxes each year and maximize your deductions, cause let me tell you–self-employment taxes ain’t cheap! Outsourcing help with managing my online business expenses was one of the best investments I made.

Small Business Expense Categories: Investing for the Long Run

Should I hire a Virtual Assistant?

For me, hiring my first virtual assistant (VA) was key. She was actually a friend of mine who was on maternity leave so it was a great fit for awhile. She supported me with various time-consuming tasks like finding and pitching sponsors I was interested in partnering with, negotiating the contracts and then managing those relationships.

Many entrepreneurs hire out VAs to help them with tasks like social media curating and posting, Pinterest pinning/scheduling, uploading posts to WordPress, creating graphics, managing emails, submitting to food sharing sites, and lots of other admin tasks.

I highly recommend this practice because, guess what? You really can’t do it all, and that’s okay. You shouldn’t have to–running a business is A TON of work and knowing when and where you need help is key to your success.

My current VA–who I actually call my Business Manager, as it sounds more professional to me and she truly does play a much bigger role on my team that just handling admin tasks–has been with me for over a year and does all the tasks above and more. Some of her most important tasks in addition to sponsor management, managing our affiliate programs, writing email copy and supporting me with blog post writing (as mentioned above).

I really think hiring a VA was one of the best things I ever did for my business, as we can get so much more done together, and it allows me to really focus on what I love.

Plus, running your own business is solitary, isolating and (I’ll just say it), downright lonely. It’s a lot of time spent alone at your desk and it’s really nice to have someone on your team to bounce ideas off of, brainstorm strategies, get feedback and just chat.

You can start small–maybe hire someone for a few hours a week to help with your most pressing tasks–and as you grow, allow their position to grow with you.

I recommend you listen to this great episode I did with Micala Quinn about How to Hire or Become a Virtual Assistant + Work at Home and take a look at this other post I did all about 10 Tips for Hiring Your First Virtual Marketing Assistant.

Should I Outsource PR? 

My guess is that most bloggers don’t actively pursue PR and media opportunities, and I think this is a mistake. When I say PR, I’m talking guest posting for big sites, being a guest on podcasts, collaborating with other bloggers, getting link backs to your blog on big publications, etc.

This is another area that’s perfect for a VA, as you likely won’t make time for it yourself, and IMO it adds a layer of professionalism to have someone else pitch your expertise. It can be a little awkward to pitch yourself.

For example, I’ve been a guest on 23 podcasts in the last two years, 19 of which are because my VA pitched me to the show’s host. This provides such great exposure for my business, as people who listen to you for an entire 45 minutes on a podcast are starting off by really getting to know and trust you, and are likely going to want to visit and follow your blog, social media, and emails, etc.

I cannot recommend enough Selena Soo’s Impacting Millions to boost your publicity and PR strategy, too! Selena is the queen of PR and knows exactly how to put you in front of big names like Forbes and Rebecca Minkoff’s Superwomen podcast! I joined and it was a game changer for me! Here’s my honest review and take on it! I would also recommend listening to my interviews with Selena Soo herself and Lynya Floyd where they talk about the importance of outsourcing PR within your business.

Click here to download a fillable spreadsheet to help you determine where YOU should spend money, time and energy in YOUR business. This simple formula is the same one I use to decide on outsourcing tasks. 

Should I Invest in Advertising? 

I’ve had mixed results getting traffic to my site from ads–even when I’ve outsourced this task to ‘experts’. I’ve worked with Facebook ad experts, Outbrain, a Pinterest ad expert, and am currently testing out Google Ads.

I’ve tried running ads to gain traffic to blog posts, and even though we did get traffic, the bounce rate was so high and the engagement so low that ultimately, I didn’t feel like it was worth the money since the visitors weren’t converting.

On the flipside, I’ve had some success running ads to lead magnets that get people on my email list where I sell them something.

But here’s what I do know: I am not an ads expert. I have no idea what I’m doing. And though a couple experts I have hired didn’t work out, I do think if I were to invest in ads in the future, I would outsource it to a trusted pro OR I would invest in myself or one of my team members learning how to effectively set up and run ads.

Because ultimately, very few businesses are successful without doing some kind of advertising or marketing. And there are plenty of people who have seen the power of ads and swear by them.

Stay tuned–if I ever find a great solution, I’ll be sure to share here!

You can learn more about how you can create Facebook ads and how they can work for you by listening to this episode I did with Monica Louie!

Should I Invest in Blogging Courses + Education?

Shameless plug time: 100% you should! I sold my own blog in order to invest all my time and energy into building Success with Soul, a business that helps other female entrepreneurs gain the tools they need to build their own businesses. Specifically, the Success with Soul Incubator is a holistic mastermind empowering female coaches to make money sustainably!

Just like I encourage others to invest in courses and education, I have taken some great online business courses like Marie Forleo’s B-School and Melyssa Griffin’s Blog to Biz Hive. These are expensive trainings, yet I find them an invaluable investment in the success of my business. Of course, I’ve mentioned Selena Soo above, but I cannot stress enough how she basically changed my business’s publicity life. And for the best in online business education, I cannot recommend Amy Porterfield’s Digital Course Academy enough.

I do think there’s a tendency, though, for many of us to be perpetual course takers and yet rarely actually follow through on what we learn. So, while I encourage you to educate yourself to improve your blogging business, it’s not worth the money if you’re not going actually going to implement what you’ve learned.

This quote from Abu Bakr sums it up: “Without knowledge action is useless, and knowledge without action is futile.”

Should I outsource SEO?

Implementing good SEO on your website and blog is the #1 way to generate organic traffic to your website. It is a MUST for any online business.

It took me several years to improve my understanding and implementation of SEO for my own blog and business. Pretty early on I worked with an SEO expert who did a complete site audit on my first blog . It was very thorough and I slowly made my way through his advice–there were literally DOZENS of actions I needed to take.

Even though it was hard work, learning how to implement an SEO strategy was a skill I wouldn’t have wanted to outsource. Now, I teach SEO best practices inside the Success with Soul Incubator so that other entrepreneurs can also improve and learn to master the art of SEO.

While you can listen to podcasts, follow SEO blogs and the like for free, I do think it’s worth it to get personalized SEO support for your specific brand.

However, for entrepreneurs who want to outsource SEO, there are many agencies and contractors that are experts that can take your SEO to the next level. I would recommend Meg Clarke from Clapping Dog Media, who I have had offer workshops to Incubator clients. We also recommend Foodie Digital, especially for food bloggers.

Should I outsource Branding?

Finally, having a consistent and memorable brand is key to success. If you are just starting out, I would recommend using a premium WordPress theme and installing it on your site, which are easy to customize by yourself.

Plus, Canva is changing the world of graphic design, making it so much easier to do in-house design work.

If you are an established business looking for some rebranding or branding updates, I would recommend then outsourcing for help (unless you are a coding wiz!) In the past, I worked with 99 Designs for designing my logos and worked with Pinegate Road to redesign this website.

Again, this shouldn’t be a priority over creating helpful and valuable content that people truly connect with, but as you grow it is important to place more attention on these types of details that create a cohesive, easy-to-navigate and memorable experience for the reader.

Frequently Asked Questions

Summary Hiring Contractors: When to Outsource

Whew! I know that was a lot, but I hope it helped give you insight into how to decide where and how to spend your money in order to create a successful business and life you love.

If you want to go further and get personalized support from me, I invite you to join me in the Success with Soul Incubator, where you can learn how to implement many of these yourself.

Click here to download a fillable spreadsheet to help you determine where YOU should spend money, time and energy in YOUR business. This simple formula is the same one I use to decide on outsourcing tasks.