top of page

4 Signs It’s Time to Outsource or Hire

Feeling overwhelmed? Need a helping hand? As a solopreneur, it’s difficult to juggle all the day-to-day tasks in your business, let alone create new products and programs. That’s where outsourcing comes in!

If you’re not sure whether it’s time to outsource, read on!

Is Outsourcing Necessary?

You’ve probably heard that every solopreneur reaches a point where they need to outsource in order to scale. While I don’t think that’s true for every single small business, it’s definitely been the case for mine.

Your business’s potential really comes down to time. Even if you worked 12-hour days (which I don’t recommend), you’re still limited in what you can accomplish. And in order to prioritize your own wellbeing, you have to find ways to get more done without burning yourself out.

When it comes to outsourcing, it all depends on what success looks like to you. If you’re happy with the size of your business, your amount of take-home pay, and how much you work, keep doing you! But if you want to make more, work less, and scale your business significantly, building a team is the best way to do it.

How to Know If It’s Time to Outsource

Not sure whether or not to take the next step? Here are some signs it’s time to outsource.

1. You end most of your days with an incomplete to-do list.

There’s nothing as disappointing as reaching the end of the work time and moving all your incomplete tasks to the next day. And chances are, you’ll end up doing the same thing the next day, and the next, and the next. It’s frustrating, overwhelming, and a surefire way to burn out.

If you can’t eliminate the tasks, outsource them. Whether you hire an online business manager to keep the wheels turning while you do the creative work or contract a VA to manage your emails for a few hours a week, a helping hand will pare down your own to-do list and help you focus on what matters most.

2. You spend too much time on tasks you hate.

How much time do you spend working in your business versus on your business? All those admin tasks–answering emails, sending invoices, posting on Instagram, updating your website–take time away from your creative work. The more time you spend on tasks you don’t enjoy, the less you’ll love your business. Over time, that turns into resentment.

Before it gets that far, outsource those pesky administrative tasks! Not only will you enjoy your day-to-day work more, but you’ll free up tons of time in your schedule for focusing on client work, brainstorming new products, or just straight up relaxing.

3. You’ve reached the limit of how much you can make.

When you’re your business’s only asset, you inevitably reach a stopping point. There are only so many hours in the day, and you only have so much energy to give. If you can’t raise your prices any more, the only way to make more money is making more time, which means hiring.

If you’re not sure whether or not outsourcing can help you make more money, check out this blog post to learn how to calculate your hourly rate.

4. You know you’ll have to outsource in the next few months.

If there’s one piece of advice I would share with every small business owner in the world, it’s this: Outsource before you have to. I cannot express how much this tip has helped me in scaling my own business and minimizing my stress.

If you wait to outsource until you absolutely have to, it’s already too late. At this point, you’ve got a full calendar, an overflowing to-do list, and no extra energy to spend on hiring, training, and managing a team member. But if you hire before you reach this point, you’ll be able to create a seamless onboarding process for your new hire and save yourself a lot of headaches.

So if you can see that “uh oh” point in the distance, hire now. You’ll be glad you did.

Ready to outsource? Here are your next steps.

Once you’ve decided it’s time to outsource, you’ll need to do some prepwork.

STEP 1: Decide which tasks you want to outsource.

Spend a week or so paying close attention to your to-do list. Which tasks could be outsourced? Which could be automated? Which could be eliminated altogether? A stronger understanding of your day-to-day operations will help you determine what work requires your personal attention and what could be done by an employee or contractor.

STEP 2: Decide how you want to hire.

Speaking of, you’ll need to decide whether you want to hire an employee or a contractor. This decision depends on how involved you want this person to be in your business and how much control you want over their processes. Do you want them entirely entwined in your business, or do you just want to send them work on the side? Do you want to train them on your processes, or do you not care how the work gets done? Do you want to provide benefits, time off, and stability in return for a more dedicated employee, or are you willing to be just one client on a contractor’s list?

The Pretty Penny team consists of both employees and contractors, and they each play different roles. If you’re not sure which route to take, check out this post on hiring employees and contractors.

STEP 3: Create an onboarding system.

Before you hire, make sure you have a system in place for training and onboarding your employee or contractor. The exact process will depend on what kind of work they’re doing and in what capacity, but the beginning steps are the same across the board:

  • Write a job description. Whether or not you post it anywhere, this will provide clear expectations for your new hire and yourself.

  • Record your processes. For the tasks you eventually want to outsource, record them with a program like Loom or write the steps out in a good old-fashioned Google Doc. That way, your new hire will have somewhere to turn when they have questions.

  • Set a check-in time frame. Maybe you’re hiring a social media manager, and you want to check in with them in three months to make sure you’re seeing results. Set this time frame, create a list of desired results, and communicate these with potential hires.

Hire the Right Way!

A lasting business relationship starts with a strong foundation. Check out my Outsourcing Toolkit for tips and tricks on hiring the right way.


Want more tips like these? Be sure to subscribe to the newsletter! (and don't forget to follow along on IG @prettypennyaccounting)

Feeling unsure or worried about the accounting side of your business? Download this free guide with 3 steps to financial confidence in your business.

Ready to hand over your accounting? Download my services guide and let's work together!


bottom of page