As burgeoning entrepreneurs, we’re taught that we need to “do it all.” That every single aspect of our new (or established) business is our responsibility. That we should be jacks of all trades. 

But do you have a degree in marketing, finance, web development and design, business management, communications, graphic design, AND sales management? 

I’m going to guess your answer is NO.  

So why should you be expected to know how best to do every task and job necessary for your business? The idea is impractical, unrealistic, and frankly, impossible! 

The greatest entrepreneurs and business owners out there are outsourcing everything that they don’t know how to do, or know that someone else can do better.

What is outsourcing, exactly?

Broadly speaking, outsourcing is the delegation of a task to someone other than yourself. 

Sometimes it’s beneficial to hire someone to your team to permanently outsource some of your tasks to, and sometimes it’s beneficial to hire a freelancer to complete a gig – a one time task or project – for you. Hiring freelancers can be especially useful if their rates are lower than the minimum wage in the country you live in.

Who outsourcing is for

You don’t need to be managing a major conglomerate to justify outsourcing work. Every business owner – regardless of the size of their business – would benefit from reclaiming the time that they spend on menial, delegate-able tasks. 

If right now you’re thinking: “Right, but I could never outsource MY work – it’s too specific,” or “it would take me longer to hire a freelancer/delegate this task than it would for me to just do it right now…”

Think again. 

Outsourcing isn’t meant for the Deep Work that helps you push your business forward. It’s meant to help clear your plate of everything EXCEPT the Deep Work. And investing an extra hour or two now to outsource the task will save you hundreds of hours over the next several years!

What type of tasks can be outsourced?

Hiring a virtual assistant is an entrepreneurial standard at this point – someone who manages your inbox, keeps track of your calendar, simple social media management, and more. 

It’s a common misconception that there’s outsourcing can only be done by very specific kinds of businesses – ones that are IT-heavy, ones that require consistent inbox management, etc. But outsourcing can come in handy for a wide range of different tasks – both professional and personal!

Here are just a few creative ways you can use outsourcing in your life and business: 

  • Birthday tracking and outreach; shopping as needed
  • Scheduling events, conference calls, meetings
  • Market research
  • Monitoring Google Analytics monthly reports
  • Graphic design, photoshop/photo editor
  • Branding
  • Blogging (as a ghostwriter)
  • Video editing
  • Boosting social engagement on social media
  • Transcribing video/audio recordings
  • House cleaning
  • Dog walking

Are you scared of relinquishing control?

We get it – your business is your baby. It’s going to be hard to take the first step in relinquishing control of every detail! Especially for us perfectionists. 

But the truth is, there are many aspects of your business that other people are able to do just as well – maybe even better – than you. That’s nothing to be ashamed of! The sooner you embrace that and start outsourcing tasks you don’t NEED to be doing, the sooner you’re going to have the time and energy to work on the big ideas that are going to thrust your business forward. 

Nathan Hirsch – co-founder and CEO of – has an awesome hack for deciding what to relinquish control of inside of your business: 

“Every month, I list out all of the tasks and projects currently on my plate. I go through each looking at the time it’s taking me to complete and the importance with regards to the growth of the business. I then think, “Could someone else be doing this better than me or at a more affordable rate?” If the answer is “yes” to either, I work to delegate it to someone already in my business or I look for someone new to take it off my plate. By following this monthly “clean up” routine, I find that I’m able to keep my time most focused on where I add the most value to the growth of the business.”

How to start outsourcing right now

The first step in building a solid outsourcing foundation is getting clarity on the systems that you already have in place. Block out an hour on your calendar to brainstorm all of the systems you currently have operating in your business and personal life (ie. Facebook marketing, social media maintenance, sales follow-ups, house cleaning/maintenance). 

Then you’re going to rank these systems based on their importance. This helps you gain clarity on where your priorities really lie (some of which may come as a shock to you!). 

Once you’ve ranked them, take your highest ranking system and break it down into a process outline – a detailed walk-through of a core, delegate-able process in your business. On paper (or a Google Doc), on purpose. 

This is a step a lot of people skip over and jump straight into creating a Standard Operating Procedure (SOP). This is a big no-no for us – if you skip the outlining process, you’re increasing the chances of the process blowing up in your team’s face, and wasting unnecessary time in everyone’s schedule fixing it. 

Once you’ve detailed the entire process, you’re going to War Game it. This means you’re going to put it into action. You’ll find holes in your process. You’ll figure out ways to optimize it you’d never thought of before. You’ll consolidate the 30 steps it takes to finish it down to 12-15. It’s a really illuminating process! 

Only once you’ve War Gamed your process can you begin the process of iron-clad documentation and create an SOP. The point of an SOP is to make the entire process so glaringly simple that someone of average intelligence having an awful day can finish your process with 100% efficiency! 

How to find the perfect person or company to start outsourcing

It can be very overwhelming to hire your first freelancer or virtual employee. 

Here are some of tips for finding a good fit online: 

  • is our go-to site for easily hiring a new contractor. They have each of their contractors go through an extensive skills test prior to being allowed on their site, meaning that you have less of a chance of getting a “dud.” Click the link here to get $25 off your first invoice.
  • Start on Googleduh! – but narrow your search by getting creative with your keywords
    • “Uber for __”  – This has become a shorthand for on-demand services.  For example: “Uber for dog walkers”, “Uber for laundry”
    • “On demand __”   For example: “On demand dog walker”
    • Filter your google results to only news outlets by clicking the “news” subtitle right under the google search bar.  This filters out advertisers and unreliable sites.
  • Search on credible websites like Quora, Techcrunch, Crunchbase for freelance companies
  • Use Fiverr for easier gigs, UpWork or FreeeUp for more advanced or long-term projects
  • TaskRabbit is great for in-person errands/projects you need help with

How to onboard your VA

Once you’ve found a Virtual Assistant who could be a good fit, it’s important to set your expectations from the jump! 

One way to ensure that they’re a good fit for your team is to start them in a one-month trial position. 

During the initial chat with the new consultant, establish a strict communication policy. Every communication policy is different, but some of the best ones we’ve seen explain how often you expect to receive updates from them, the channel of communication that you expect them to follow (email, Facebook message, etc.), and your average response time.

Another critical part of our onboarding process is getting new freelancers onto the online task manager that our company operates from (Asana, in our case). We have tutorials and walk-through screencasts ready to send to freelancers to get them acquainted with our system and task-manager etiquette.

How to troubleshoot common issues with your consultants

Outsourcing is not a foolproof process – it requires some trial and error! 

Here are some of the common issues we see clients encounter while outsourcing: 

Communication issues: 

Despite having set forth an awesome communication policy, you may still run into issues. If you’re hiring a freelancer from a country different than your own – and English isn’t their first language – they may have different communication patterns than you. Be mindful of the culture and language that your freelancers come from, and have an open conversation with them if you’re not satisfied with their communication style.

Execution issues: 

It can be a little challenging at first to explain what you want from a freelancer, especially if you’ve been doing everything on your own. You might get pinged back with an “I don’t understand your instructions” after your first few hirings. 

That doesn’t mean you shouldn’t be hiring freelancers, it just means you need to spend a bit more time detailing your expectations for the project. Rather than getting frustrated, recognize that they can’t read your mind and make an effort to explain your project thoroughly.

When outlining a project or creating a screencast, always err on the side of over-explanation. Including too much information in a screencast in order to ensure that the freelancer knows EXACTLY what they’re doing is better than slowing down the progress of the project by fielding a bunch of questions later.

How to know when to let someone go: 

Sometimes the person you hire just isn’t a good fit for you, and that’s entirely okay also. Here are some key indicators it’s time to look for another freelancer:

  • Poor communication: If you’ve laid out a clear communication policy that they’re not following and you’ve had a conversation about being more communicative, it may be time to cut them loose
  • Not receptive to your feedback: If they’re not following your instructions repeatedly and you’ve made your instructions as clear as possible, this is a major red flag 
  • They miss deadlines: If they’re consistently not delivering what they’ve promised in a timely manner, or they always have excuses for why they haven’t finished the project, they may not be worth investing more time into

Are you valuing your time accurately?

There are SO many managers who struggle with outsourcing. And it’s not because they’re incapable, or because their business is so unique that they couldn’t possibly get outside help. It’s solely because we as humans have a tendency to be completely irrational about time. 

Have you (or a perfectionist you know) ever said something like: 

I can’t hire a housekeeper. It’s MY responsibility to keep my house clean…

Outsourcing this task to my assistant would be impossible. I’d just have to redo it afterwards…

No one else can do this. They don’t know my special system…

This is a personal task. I’d feel uncomfortable with outsourcing this to someone else…

Are you raising your hand sullenly right now? That’s ok! Let’s talk about this from a rational point of view. 

Let’s say you work 40 hours per week and get paid $40 per hour. You’re perfectly happy and have plenty of free time.

Now let’s say your boss asks you to work nights and weekends. You start to feel starved for hours. It’s no longer enough to get paid $40 per hour, and you start to grumble. However when your boss offers to raise your hourly rate to $50 for those 20 extra hours, you start to feel like you’re being compensated fairly. You agree to work nights and weekends.

The next week, your boss asks you to work even more – 80 hours per week. Now you’re indignant. This would mean you have no time to watch TV, take care of your kids, or do much of anything outside of eat, sleep, and work.  

…But your boss raises your hourly wage to $100 per hour for these extra hours. It’s not optimal, but at least you’re making lots of money. You agree to work the 80 hours.

Your boss becomes a tyrant, and the next week he asks if you can just start sleeping at the office and working 150 hours. Hell no! You’re just about to quit, but then he tells you you’ll be paid a whopping $500 per hour to work at this grueling pace.  

You think for a minute – this is a tough one. You’re fast approaching your asymptotic breaking point – the point at which there’s no amount of money anyone could pay you to compensate you for your time because your life is so miserable. 

You can gauge the asymptotic breaking point by looking at your time in two different rates – Capacity Hours and Past Capacity Hours. Past Capacity Hours factor in the opportunity cost paid for overwork.

If you’re independently wealthy, then who cares if it takes you 2 hours for laundry? But if you’re working 40 hours a week and then coming home to take care of kids, that 2 hours might be your only 2 hours to have quality time with your kids. You should therefore be valuing that time at a premium.

You get to decide how to value each hour of your time throughout your day. For example, if you work in an office, then time spent at home prepping meals is much more scarce and valuable than someone who works from home, where they can leisurely prep meals throughout the day during breaks. 

You also get to decide how far to take it. Your Past Capacity Hours will be worth more than your Capacity Hours. But how much more is up to you – it’s different for every person. For example, a parent may have a higher past capacity rate than a single person because their time with their kids is valued higher than a single person’s time watching TV. 

When you catch yourself thinking something potentially irrational, look at it with this logical analysis and see if you still feel confident in your direction. Because while cultural and emotional arguments for the value of your time have merit, they are often the reasons your time is being wasted doing low-value tasks that you should be systematizing, automating, and delegating and outsourcing.  

So instead of thinking “I can’t hire a housekeeper.  It’s my responsibility to keep my house clean…” – think “I value each hour I spend cleaning the house at $70. If I can pay a professional to do it at or below this rate, it will be worth it to me.”

And similarly, when you catch yourself thinking “I’m very particular, and honestly it just takes me 5 minutes to do it myself, so I’m not going to delegate it…” you can replace it with “This task is too low-value for me to be doing all the time. It would take me an hour to create a detailed SOP for my assistant, so I’m choosing to invest that time knowing that I’ll see a return on that investment very soon.

What happens when you embrace outsourcing

So many entrepreneurs feel trapped by their success – unable to push their business forward in the ways that they want to because they’re bogged down by keeping their business afloat. Over time, that leads to stress, overwhelm, and burnout. Which can ultimately lead to a loss of passion for your kickass business!

If this sounds like you, it’s time to take the leap. 

We recommend starting small. Find one task that you’re doing on a regular basis that someone else could absolutely do. Create an outline of how to execute that task. Create an SOP (a detailed set of instructions) for it. Hire a freelancer on a trial basis. 

You’ll be blown away by the impact this small step has on your cognitive load! 

Demir & Carey Bentley

Demir and Carey Bentley are the founders of Lifehack Method, WSJ & USA Today bestselling authors, and executive productivity coaches. They've helped thousands of people avoid burnout and soar to their highest level of productivity. Read more about them here.