You finally reached the point where you knew something had to give.
So you hired someone. A VA, a contractor, a freelancer. You handed over a few things - and instead of relief, you felt… frustrated.
Tasks bounced back and forth.
Things got missed.
You spent more time explaining the work than it would’ve taken to just do it yourself.
If that sounds familiar, you’re not alone. We hear this a lot from business owners:
“I tried outsourcing, and it just didn’t work for me.”
But here’s what most people don’t realise:
It often wasn’t the idea of outsourcing that failed, it was the setup.
Why It Feels Like Getting Help Didn't Work
Before you write off the idea entirely, it’s worth asking: what exactly went wrong?
Here are the most common issues we see:
You weren’t supported to delegate properly
You were told to “just hand things over.” But no one helped you figure out what that should be or how to make it work with the way you operate.
The person wasn’t right for the task
They said yes to everything, but they didn’t have the skills (or systems) to back it up.
You were still the project manager
You were chasing updates, clarifying expectations, and fixing mistakes. In other words, the mental load didn’t go anywhere.
And if that’s the kind of experience you’ve had, it makes total sense that you’d hesitate to try again.
What Can Make It Work Next Time?
Here’s what a better setup looks like, based on what we’ve seen work for hundreds of businesses like yours:
Start with what’s slowing you down. You don’t need a perfect plan. You just need a few specific things that are draining your time or constantly falling through the cracks.
Get matched with someone who’s already done it before. A virtual assistant who knows how to manage inboxes, quote jobs, chase debtors, or implement tools without needing a complete walkthrough.
Stay out of the weeds. You shouldn’t need to micromanage. The process should be simple, clear, and give you back time - not take more of it.
So, Should You Try Again?
Maybe. But only if the setup is different.
If you’re still doing admin at 9pm, constantly putting off quotes, or starting your day already behind, it’s not that you need more hours. You need a better way to spend the ones you’ve got.
If you’ve caught yourself thinking, “I could grow this thing… if I just had more space,” - then yes. It’s probably time.
But if the idea of trying again makes you hesitate, that’s okay too. You’re not behind. You’re just cautious, which makes sense when you’ve been burnt before.
The key is this: you don’t need to figure it out alone.
We’ll help you set things up the right way from the start - so support actually feels like support.
