When Should I Hire Help? Pros and Cons of Being a Solo-Prenuer

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Are you at full capacity in your business and find yourself wondering…

“Is it time to hire help?”

If so, this video is for you!

We’re going to discuss the PROs and CONs of outsourcing…

  • 3 signs that you’re definitely ready to hire a team…
  • The first hire I recommend every business owner make FIRST…
  • Plus make sure you stick around until the end because I’m going to talk about the #1 thing you MUST consider before making any hiring decision.

Hey, Posse! What’s up? It’s Alex. 

Coming at ya this week with a blog for all my freelancers, small business owners, and solo-preneurs wondering when the heck (or IF the heck) they should start expanding their one-person team. 

But before we get into it – make sure you’re subscribed to my newsletter to get all the latest in entrepreneurship, marketing, copywriting, social media, and more…

Now let’s get right into it with some cold hard facts… 

  • 99.9% of businesses across the US are small businesses.
  • And over 80% of those small businesses have no employees.

But that doesn’t necessarily mean they don’t outsource help or hire contractors…

When you hire an employee, that essentially means you agree to pay that person a set wage for a set number of hours worked – regardless of whether there is work for them to do…

When you hire a contractor or outsource tasks – you are paying someone for a contracted period or project…

And this is a great place to start.

In fact, 37% of small businesses outsource at least one business process – that could be marketing, VA, writing, web development, design, HR recruiting, or a whole host of other jobs. 

And whether you know it or not, you’re probably already outsourcing one or two things in your business…

Like legal, accounting or bookkeeping!

But when do you know when to hire your first contractor? What do you outsource? And you need to outsource in order to be successful?

Well, the answer is no, but that all depends on what success looks like to you.

I worked as a freelance copywriter and marketing consultant for 8 years – making over $300,000 a year – and I did it completely solo

No team, no outsourcing. Just me. Ok and my accountant.

And I loved it. It worked perfectly for me.

I traveled the world with nothing but my laptop in tow… had VERY few expenses and basically zero dollars in overhead.

It wasn’t until I started The Copy Posse that I decided it was finally time to outsource and hire help. 

I just didn’t have enough time, energy, or mental capacity to do it all myself anymore. 

I wanted to take my business to the next level and knew I needed help to make it happen. 

So how do YOU know when the time is right for YOU?

3 Signs You Should Hire Help

Here are 3 signs to look for… 

#1 You’re working too many hours.

If you find yourself working long hours…

8, 10, 12 hour days…

Not taking weekends off…

And you’re STILL struggling to keep up with everything…

It might be time to start outsourcing some of your work.

#2 You’re getting overwhelmed.

If you’re constantly feeling overwhelmed and stressed out by the amount of work you have to do…

Or you keep missing deadlines or important things like admin tasks or inbox management are falling through the cracks… 

Then it may be time to start delegating tasks…

#3 You’re missing opportunities.

Finally – if you find yourself turning down work or missing out on opportunities because you simply don’t have enough time or resources, to make it happen…

Then it may be time to hire help. 

Now if you’re like: “OMG that’s totally me. I need to hire someone ASAP!!!!

Hold up, hold up. Just wait a minute…

Because while it can definitely sound enticing to save yourself time, take on more clients, make more money, and be less overwhelmed

The reality is…

Hiring a team or outsourcing work isn’t necessarily going to solve all those problems for you. 

So before you decide to hire some help, first let’s consider the pros and cons…

Pros of Hiring A Team or Outsourcing:

Now, let’s first talk about all the reason outsourcing is great for your biz.

#1 More time to focus on your strengths.

The very first hire I made was a virtual assistant. 

And it’s the reason I recommend EVERY business owner hire a VA before they hire anyone else… 

Someone to take over the time-consuming, but critical administrative tasks like invoicing, making appointments, scheduling tasks, bookkeeping, etc. 

You’d be surprised how much time business owners spend on admin tasks like these.

So if you can hire a VA to do this stuff for you – you’ll free up quite a bit of time and can focus more on the high leverage revenue-generating work ONLY YOU can do. 

That way, you’re still getting some help and relieving some stress – but you don’t have to worry about training or overseeing quality of work – because you’re still doing all the creative work yourself. 

#2 Increased productivity.

Now obviously, with a team to help you, you can theoretically get more done in less time. 

This means you can take on more clients or projects and grow your business faster.

But be warned… this increase in productivity doesn’t necessarily come right away. 

In the beginning, there will be training and feedback and extra time needed while your new team members learn the ropes. 

In fact, you might find yourself being LESS productive at first

But eventually, as your team members get trained and up to speed, you will get to a point where you no longer have to oversee every little detail and it will allow your business to be more productive and take on my clients/projects. 

#3 Access to new skills and expertise.

This is probably one of the coolest reasons to hire a team. 

The fact is: you can’t be great at everything. You just can’t be

So when you’re a solo-preuner, and you’re doing everything yourself…

…you’re the designer, the writer, the project manager, the social media manager, the sales rep, etc…

Not all of those things will be areas that you thrive at. 

So when you hire a team, you gain access to a larger range of skills and expertise. 

Which means the quality generally improves, because you’re hiring pros to take on tasks that you were previously attempting to do on your own. 

When I hired my social media manager, the quality and value shared in my social media channels really improved. 

Because while I was a great writer and loved design… 

I wasn’t great at consistency or repurposing content in a way that made sense. 

So hiring her really up-leveled my social presence. 

Alright, now those are some pretty promising PROs… But we also need to consider the CONs…

Cons of Hiring a Team or Outsourcing:

Now, there are 3 major cons to keep in mind when outsourcing to a freelancer.

#1 Cost.

Hiring a team can be expensive, especially if you’re just starting out. 

So this is a BIG one to consider. 

When you hire a team, you’re taking on a lot of responsibility. You’re now paying someone – and they are relying on you for that money. 

And depending on what kind of busuiness you have, you might not just being paying them a salary…

You might also be paying benefits, insurance, office space, etc…

So it’s very important here to sit down with your accountant and take a look at your revenue to discuss if you can realistically afford it. 

Remember to base it off what you’re making NOW – not what you *hope* you’ll be able to make once you hire them. 

#2 Management.

Managing a team can be challenging, especially if you’re not used to it. 

You need to be able to step into the CEO role – delegating tasks, keeping your team members motivated and responsible, encouraging ownership, maintaining a positive and healthy workplace dynamic, and probably the hardest of all….


As the boss, it’s really up to YOU to set the bar and precedence for the type of communication and atmosphere your team will have. 

Making sure everyone on the team is on the same page and deadlines are being met…

All while encouraging a positive experience and ensuring your people feel seen, heard, and validated. 

A team that feels respected and valued is the key to a successful team. 

And the truth is – that can be a lot of work! 

That’s why it’s so important to do your due diligence when hiring – making sure the people you bring on are on the same page as you and value the same things is SOOOO IMPORTANT. 

#3 Quality control.

This is another big one that holds business owners back from hiring out. 

When you’re a business owner – your business is like your baby – right?

And it can feel so scary to release the control and allow someone else to step in and take over… especially because there is no one who knows your business as well as you do. 

So there is this feeling that the quality of your work or business might suffer. 

It’s a valid fear. I totally get it. 

But again – this risk can be greatly reduced if you do a thorough job during the hiring process. 

Don’t cut corners and hire the cheapest and the fastest just in the name of getting something done. 

At the end of the day, everything your business puts out is reflective of YOU

So if you can’t afford to hire someone qualified – then it’s probably best to keep doing the work yourself until you can afford someone qualified and reliable. 

When you outsource work, you may have less control over the quality of the work being done. You’ll need to make sure you’re hiring qualified, reliable people who can deliver high-quality work.

#4 Security risks.

I know, I know… This feels like yucky one to talk about – no one likes to think about “worst case scenario”. 

But the fact is: when you outsource work, you’re likely sharing sensitive information with people. 

Which is an obvious risk – right?

So again… I know I sound like a broken record here… 

But it’s important to protect yourself by vetting hires through a robust hiring process – use contracts, ask for references, and have other security measures in place to protect your data. 

And there are plenty of tools and safeguards out therepassword managers, multi-factor authentication, and more –  that can help you share logins and other sensitive information in a safe and secure way.

Now that’s all A LOT to consider…

So I’m going to make it real simple for you… 

THIS is the #1 most important thing I want you to consider… 


Unfortunately, I’ve seen a lot of freelancers and small business owners fall into this trap of thinking they “have” to hire a team and grow their business into an empire – in order to meet this false narrative of what it means to be “successful”. 

But what happens for some of these business owners is that they end up super unhappy because that’s not actually what THEY want. 

THEY don’t want to scale a big business and hire a team…

All they really want is to pursue their passion, make a decent living, and spend more time with their family or travel or what else – right? 

So what they *think* they need to do in order to be successful is directly contradicting what they *actually* want. 

And they end up unhappy. 

Now I’m not saying either way is right or wrong. 

Both are amazing options as long as it’s in alignment with what you want.  

So please, please, please don’t fall into comparison trap. 

I recommend taking an inventory of every single task that you do in a week. For every task, at the end of the week, label it as either do, delegate, or delete.

  • Do = The task that only you can do. And you should continue do.
  • Delegate = The tasks you can outsource to make your life a lot easier.
  • Delete = The tasks you’re doing and you don’t even really know why you’re doing them.

Then ask yourself, is there anything on the do list that you really can delegate?

Your delegate list is the perfect place to start when you’re ready to scale your business and grow your team…

Just remember – quality over anything else. 

It’s so important to take your time during the hiring process, vet your hires, and invest some time and energy into training them properly. 

And if you’re a business owner looking to hire an awesome copywriter, I’ve got great news for you…

You can hire a Posse-trained writer to help you with your copy, content, and marketing! These writers have been through (and successfully completed) my 8-week copywriting program…

They have learned my proprietary copywriting processes, along with proven frameworks and formulas…⁠

And they have been trained by me in writing compelling sales copy, brand storytelling, direct-response methodologies, email marketing, crafting hooks, and so much more.⁠

So if you’ve been looking for that “hidden gem” of a copywriter…⁠

You know… one that’s talented, dedicated, and excited to work with a brand long-term…⁠

Then the Posse just might have the perfect writer for you. 

Click for more info on hiring a Posse-trained writer! 

I hope you found this video super helpful. 

Until next time, I’m Alex – Ciao for now! 

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