When it comes time to outsource work in your business, you know those itty bitty tasks that take all day, do you freak out? Are you a self-confessed control freak like me?

Do these words run through your mind at the thought of outsourcing parts of your business…?

“No-one’s going to be able to come up with blog post graphics that are like my brand.”

“My followers on social media will know it’s not me sharing content.”

“Argh, why can’t I just find another me?!”

Ah, yep. Those are the true signs of a control freak.

And guess what? There’s absolutely nothing wrong with this at all.

Sometimes, you can do things better because you’re in your business, you are your business, right?

But if you want to grow your side hustle into something that’s amazing and awesome, there are going to be things that you need to remove from your plate and onto someone else’s or something else’s…

Sometimes, you have to loosen the control strings and learn to delegate. Otherwise, you’re going to be a ‘sad Suzy' that no-one wants to play or work with.

Here’s what you’re gonna learn in today’s blog post:

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  • What does outsource mean for you and your business?
  • What is outsourcing – really?
  • What can I outsource?
  • What tools can I use to automate processes?
  • Plus so much more!


*There are some affiliate links throughout this blog post. This means that if you click on them and sign up via that link, I'll get some form of payment for this. This doesn't cost you anything but means the world to me, so thank you 🙂

What Does Outsource Mean?

Outsource can lead to freedom in your business

Before we move into the ‘meat and potatoes’ of this post, let’s talk a little about what outsourcing means for you and your business.

Right now, I bet you’re overwhelmed with the number of tasks you’ve got to do in your business. In fact, I’d bet that you’re busy all the time, but feel like you’re not achieving any of the stuff you want to.

Instead, you’re busy with all the minutia… the stuff that doesn’t make a difference to your bottom line, but still has to get done, right?

Yeah… I hear ya. I was like this for the first 12 months when I started freelancing. I always felt so busy, so pushed for time, but felt like I wasn’t moving that far forward in my business at all.

This, my friends, is where outsourcing can make a huge difference to you and your business.

Imagine being able to just sit down and write or design or chat with a client.

Without having to worry about creating blog post images, formatting the blog post and scheduling it.

Not having to worry about sending out the hundreds of emails you need to make sure your clients are briefed and on task.

Imagine if all that stuff was taken care of by someone else!


Now that you’ve got a sense of euphoria, let’s see how you can let your inner control freak simmer down enough to hand the reins over to someone else.

7 Ways to Outsource Work in Your Side Hustle When You’re a Control Freak

How to outsource work in your business when you're a control freak. Including strategies for automation too. Click through to read more.

#1: Make a list, check it twice

I’m sure you’ve heard this before, but have you sat down with a pen and paper and written down all the stuff that you do in a week in your business?

What’s a day in the life like for you?

I want you to write everything down that you do in a day. Include all your personal stuff, like picking the kids up, grocery shopping, putting fuel in the car etc.

Break it down into 30-minute blocks, so that you’ve got a clear idea of what’s going on.

Label things so you know what they relate to. For example, picking the kids up would get the label “family” while writing a blog post would get the label “business”.

Use labels that make sense to you – you’re the only one going to see this.

Once you’ve done this, leave the list for 24 hours and then come back to it and see if you missed anything. Update it as needed.

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Your Task: For the next 7 days, write down everything that you do in 30-minute chunks. This might work best inside a diary that has time blocks shown, or you could do it in your Google Calendar as well.

Time Commitment: An hour or two each day. Although if you’re smart, you’ll already have a pretty good idea of this stuff already and it will only take you a few minutes each day to make sure you’ve got everything covered.


#2: Write it down

Now that you’ve got an idea of all the stuff that you’re doing, it’s time to figure out what you can comfortably delegate.

I know you’re freaking out, because you don’t feel like you can delegate anything, but you can. I’ll hold your hand.

Here're some of the things that might be on your list that you could delegate to a VA or automate with a tool:

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  • Blog post image creation
  • Blog formatting, proof-reading and scheduling
  • Loading up your social media platforms with share-worthy content (creating images as needed)
  • Updating your WordPress blog plugins each week
  • Scheduling client meetings
  • Updating your calendar availability
  • Filtering emails for you
  • Placing your grocery order for you (all you have to do is pay for it online!)
  • Sending out personalised gifts to friends and family
  • Tracking business expenses


There is a ton more that you could add to this list and I’m sure you’ve got even more specific tasks written down.

Now that you’ve got an idea of some of the tasks you want to outsource, it’s time to figure out how best to do that.

And it all starts with writing down the steps you take to complete each task.Write ideas down first thing in the morning

If the thought of writing down a whole bunch of processes bores you to tears (like it does me), then record the actions you take to complete the task instead.

I do this for all the tasks I outsource to a VA. I use screencast-o-matic to screen share and record videos of what I’m doing.

This way, I’m ensuring that nothing is missed. What I find happens, when I sit down and write a task out, is I tend to miss a small step, that is essential to the task being completed the way I want it done.

This doesn’t happen when I’m recording a screen share of my computer screen!

Plus, it takes less time to record a screen share than it does to write it all down and I’m all about working smarter 🙂

The point of doing this is to make it so that anyone could step in and do this task for you.

WARNING: Make sure that this task doesn’t need your input to be completed. If it’s something that you need to be involved in, then it’s not a task that can be outsourced. Parts of it might be able to be delegated, and that’s what you need to figure out BEFORE you go down this path.

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Your Task: Identify 2-5 tasks that you can outsource right now. Record the processes that you take to complete each task. Either write these down or record a screen share video.

Time Commitment: Approx. 2-3 hours depending on how many tasks you’re planning to outsource.


#3: Train them

Now, just because you’ve given your VA these processes, doesn’t mean you can just walk away and leave them to it.

Very uncool.

Think about when you start a new job or when you first started your side hustle — how uncomfortable and out-of-your-depth did you feel?

Well, guess what? Your VA is likely feeling the same way.

Spend some time bringing them up to speed on what it is your business does, what you stand for and how you like to communicate.

If it helps, and it will, set up a welcome board in your fav project management program. I’m talking Trello, Freedcamp or even Slack.

Add things like:

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  • a link to your website/blog,
  • any templates that they might need access to,
  • login details for software like Canva (or add them to your Canva for Work profile) and Gmail.


Make them feel like they are part of the team and you’ll get the best out of them too.

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Your Task: Create a project in your fav project management program and add all the bits and pieces that your new VA is going to need access to while they're working for you. Add a welcome board/task so that they know where to get started. This is where you'd add all the training videos too.

You'll also need to spend some time with them 1:1 to go over everything, make sure you schedule a call to do this.

Time Commitment: Approx. 1-2 hours depending on how much stuff you need to provide and cover.


#4: Check-in regularly

If you don’t want to have heart palpitations every month because you’ve got no idea where your VA is at with everything, then set up regular check-ins.Check-in regularly with your VA

This could be a quick email each week from your VA, letting you know what they’ve done. It could be a 10-minute chat on Skype or Facebook so that you’re in the loop.

You could set up a Slack account for your business where you communicate with your VA(s) on a daily basis. Then nothing is left to chance and your inner control freak is left feeling like you’re back in control.

You should also be providing feedback to your VA to let them know how they’re doing and what they might need to change.

If they are managing customer service for you, you could ask them to CC you in on communications so that you can check their language and make sure they’re on point with your brand.

This should NOT be used as a way to undermine them, though. Keep feedback constructive and then when ready, remove yourself from seeing what they’re doing.

It’s all about trust.

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Your Task: Decide on how often you want to check-in and then setup those as repeat appointments in your calendar.

You'll also need to spend some time with them 1:1 to go over everything, make sure you schedule a call to do this.

Time Commitment: Approx. 1 hour.


#5: Provide clear expectations

This point kinda ties into #3. You should be upfront with what you expect from them. In fact, you should make this clear during the interview stage.

To be clear on expectations, you first need to know what you want.

Think about the following:

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  • How often do you want to check-in with them?
  • Should they ask you questions when they come up, or would you rather they batched them into one email a day?
  • Do you have specific times of the day you want them to be working, or doesn’t it worry you?
  • Do you want them to take initiative? And if so, do they need to check with you first?
  • Do you have specific deadlines for each task?


By being clear on what you want and what you expect from them, you provide a clear path for your VA to follow.

You’re setting them up for success, rather than failure. And that’s the end goal, right?

You want them to be successful so that you can happily outsource more tasks to them as needed.

#6: Say thank you often

Ever heard of positive reinforcement?

Don’t be one of those entrepreneur’s who only speaks up when something is wrong. That’s such a douche move.

Instead, thank your VA often for the great job they are doing.

Of course, I’m not saying you shouldn’t speak up with something is wrong — just don’t let that be the only thing your VA hears from you.

If it is, they are going to dread hearing from you and eventually, they’re gonna get the heck outta Dodge!

And then, you’ll have to train a new VA. Not exactly the smartest use of your time, right?

Say thank you, let them know when they do something awesome, and you’ll see a big difference in how they get the tasks done.

#7: Can you automate it?

Now this one is for the major control freaks out there.

If the thought of handing off a task to another person just doesn’t float your boat, but you know you can’t do this by yourself, then you should consider automation tools.

I’ve just started implementing some of these myself and I have to say, I’m loving how awesome they are.

What the heck am I talking about?

Here’s some of the tools you might be familiar with, not realising they were automation tools:

The last two are the powerhouses when it comes to proper business automation.

IFTTT provides a ton of recipes you can use to automate small tasks, like backing up your contacts list or sending out a tweet as soon as a blog post goes live. You can even automate some of your personal tasks too.

If you want to learn more, my friend Brittany Berger has written a great post on 14 IFTTT Automation Recipes Solo Business Owners Can Use.

Zapier provides even more options, allowing you to create multi-app automations. I’m just starting to use this now and will be writing a blog post about how I’m using this in the next few weeks.

Needless to say, you can reduce your control freak freak-out by using automation tools instead. You still have the control, but the actions are automated.

Now it’s Your Turn

Now you know how you can outsource some of those tasks in your business that take up time, but don’t need you to do them… the question is, will you take action and outsource them?

Or will you continue as you are, busy without really being busy?

Do you have any tips to add to this? Maybe you’re using some automation tools already… let me know in the comments below.

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Lise Cartwright
Lise Cartwright

Founder of Hustle & Groove and your creative business strategist. If you want to get notified of new posts just like the ones you see here, then make sure you join the awesome H & G community — Join Now!

    4 replies to "7 Ways to Outsource Work When You’re A Control Freak"

    • Amy

      Thanks for this post! I’ve been toying with outsourcing for MONTHS but can’t stand not being in control. I worry that if I hire a VA it will take more time to train them and then I’ll constantly be checking their work. I’m starting with automating tasks…baby steps.

      • Lise Cartwright

        Hi Amy. I know the feeling well! I started with automating tasks too… once you get that sorted, hiring a VA doesn’t seem so scary 🙂

    • […] it feels impossible to delegate any of the work you do, it’s time to train fellow workers to […]

    • Seema

      I also need to outsource. It is not possible to do everything efficiently

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