How to Outsource Your Lifestyle Business Without Hiring Full Time Employees

Outsourcing Business

Tell me if this sounds like you...

  • You want to scale your business but don't want to bring on employees.
  • You want to earn more and achieve more and know you can't do it alone BUT you've worked hard to design a lifestyle business that you love and you don't want to lose it.
  • You're afraid that hiring employees will add stress to your life and make the lifestyle business you designed less rewarding. 

If any of the above describe you, you likely value lifestyle freedom over money.

Keep in mind, most people don't prioritize lifestyle in their work life. This is where you and I are different. 

You started reading this article after all right? 

If you're still with me, great! 

Enter your text here...

I promise you that you're going to love this article.

I'm going to show you exactly how to grow your lifestyle business without sacrificing any part of the lifestyle you worked so hard for!

Two Truths of the "Lifestyle Business"

Most "lifestyle businesses" are ran by one man or woman (although this is certainly not always the case). It's often synonymous with "solopreneurship."

I learned a couple of things during my pursuit of business growth WITHOUT hiring traditional, full time employees (synonymous to me with losing freedom). 

First, it is very possible to achieve amazing results, without hiring traditional, full time employees.

It is very possible to achieve amazing results, without hiring traditional, full time employees. #solopreneur #lifestylebusiness

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Thanks to 3rd party services, freelancing (contractor) networks and various softwares, I can achieve growth while maintaining the freedom I love.  

Keep in mind, if I hit my head (on one of my seasonal vacations perhaps) and my opinion changes and I decide I now want employees, I can always add them later. 

I promise you, it is infinitely easier to hire employees than it is to fire them. If your business is just starting and you don't know for absolute certain that you need and want employees, I highly recommend you check out the services and resources I'm going to share in this article before you do any hiring. 

Secondly, not having employees doesn't mean that you have to do everything yourself...

I outsource a massive amount of work each week using monthly services (which I'll cover in detail in this post).

This article is going to showcase services that will allow you to outsource:

  • Basic website issues (in WordPress)
  • Design work
  • Bookkeeping
  • Content promotion
  • Content creation
  • Odds 'n Ends (also known as bitch work as some of my old bosses lovingly coined it when I did it).

Oh, the cool thing?

You Won't Have to Pay High Rates

The services I share give you affordable options. When hiring contractors, you'll be able to negotiate rates and will not need to pay additional taxes on the labor. 

You Won't Have to Worry About Keeping Employees Busy

You will still need to feed these services work and manage projects for contractors, but the cost is far less and you won't have someone standing idly by at all times. Your business will be lean and efficient.

You Won't Have to Worry About Employee Taxes

You'll work through contractors, agencies and softwares so there is no payroll to handle. Of course, talk with a CPA or tax professional to make sure your situation applies. 

You Won't Have to Conduct Frequent Interviews 

You will only need to conduct interviews for larger projects (if necessary).

You Won't Be Limited by 9-5 Hours

You'll be able to get work done 24/7 (for the most part) if you outsource to services and contractors. 

Ok, let's cover just a couple of things before we even hint at the idea of hiring anyone.

This Isn't the "4 Hour Work Week"

Outsourcing for outsourcing's sake is inefficient. One of the biggest mistakes I see is entrepreneurs trying to outsource too soon just to avoid doing work.

I hope this article isn't misleading you...I still work my ass off. I enjoy working my ass off. I'm no Gary Vaynerchuck, but I regularly work 12+ hours a day.

Many people have fallen victim to a misunderstanding of the concept found in the popular book "The 4 Hour Workweek: Escape 9-5 Live Anywhere and Join the New Rich" by Tim Ferriss.

Note: Although a lot of people were misled because of their own misinterpretations of the book, this is still one of my most highly recommended books for entrepreneurs who are seeking lifestyle businesses.  

The idea that almost everything can be outsourced and we can get by with 4 hours max per week is not realistic for 99% of people who read the book. 

People get outsourcing backwards.They try to outsource the business before there is even a solid business to outsource! You often need to do a lot of the grunt work upfront. It pays off when it's time to outsource. 

People get outsourcing backwards.They try to outsource the business before there is even a solid business to outsource! You often need to do a lot of the grunt work upfront. It pays off when it's time to outsource. #outsourcing

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They avoid putting in the grueling work at the beginning and are too focused on the "how soon can I delegate all of this except for the money counting," part.

First, become aware of your actual needs and how much time you are spending.

Try to be totally aware of the time you spend messing around with WordPress. If you do this long enough, you will know whether or not you need any of these tools and services I am about to mention.

Second, understand that you will need to be very clear in describing your needs. 

I will show how I do this later in the article, but the low-cost services I use are only as quality as I make them.

Questions to Ask before Outsourcing Tasks

Before deciding whether or not to outsource anything, you should ask yourself the following questions.

#1 "Is my time better spent somewhere else?"

This may be a task that you should do yourself if it is easier than explaining to someone and if it is only a one time fix. Don't be afraid to get your hands dirty from time to time. There is a huge difference between effectively outsourcing tasks and outsourcing for the sake of outsourcing.

Basically, don't spend 20 mins explaining a 10 min task you could do yourself. This seems like common sense, but once you develop the mindset of "I have to outsource or I am being inefficient," you may not notice logical errors like this.

If it is a repeating task, you should outsource if your time is more valuable than the rate paid to a freelancer.

#2 "Is this task flexible enough to risk losing time if the service or contractor fails to deliver as expected?"

Unfortunately, many times outsourcing fails. You may end up spending much more time trying to get someone else to do a task than if you just did it yourself. 

This is part of the process, do NOT use this as an excuse to continue doing things yourself!

You are not a hero because you do everything. It is a lazy habit

Now, if you have a task with a pending deadline that you can't miss or that needs a certain level of quality that you don't have time to explain, you may need to get your hands dirty from time to time. 

#3 "Is this something that could be detrimental to my business if it's done incorrectly?"

Some tasks like SEO (search engine optimization) and brand management should never be done on the cheap. Often times, amateurs claim to be able to do these tasks and end up damaging their client's search rankings or even worse, their brand's credibility. Your brand is worth the extra expense of a professional and falling out of grace with Google can be crippling. Use discernment here and be careful who you trust and with what.

Always be careful when outsourcing SEO and make sure that you whoever you hire is practicing white hat tactics only. 

You should only pay a trusted professional for this. Although many SEO fixes are simple, doing them incorrectly can be crippling to your ranking in search engines.

#4 "Is this task detailed and easy to explain?"

How much time is it going to take you to explain this gig? Consider how much time will be involved when you inevitably have to explain the task again if it's done incorrectly. Don't hire until you are completely certain what you really need and how it needs to be done.

#5 "Is this task something I am going to need very infrequently?"

If this is a task that you will need frequently (at least a couple times a week) you may be better off learning how to do it yourself and then hiring someone to do it regularly at a set rate. I use for tasks like this (I discuss it more later in this article).

I recommend that you learn how to do it yourself first because it will make it much easier for you to understand what to expect, how long it should take and what you should pay.

There is a fine line of course, you don't need to learn iOS programming before you outsource app development, but you should learn how to set up DNS servers properly if you work with a lot of new websites.

#6 "Is this something that will improve my brand?"

I know it can be difficult for people to assign value to tasks in terms of dollars, but you should get use to this. If this is something that will not build your brand or make you money, don't buy it. That is pretty simple right?

You Should Never Buy Subscribers, Likes or Shares

These are not just a waste of time from an earnings standpoint (think about it, are these fake subscribers going to participate and potentially buy your product or service?) but they can easily be spotted as SPAM and can affect your rankings in various platforms or even worse, destroy the credibility of your brand. Build your following the right way. Organically and at a reasonable pace.

Monthly Services for Lifestyle Businesses

Here are the services I pay each month to avoid the need to hire an employee or spend hours doing monotonous tasks on my own that can be done better by someone else.

Fancy Hands to Replace Administrative Task (Bitch Work)

I have a challenge for you…

Write down everything you do tomorrow and I mean everything. I guarantee you that there will be a list of random, one-off tasks that you weren't expecting to do.

These tiny little tasks can throw us off our groove big time and take us away from doing the higher level things that matter most. Fancy Hands is where I dump a lot of these tasks and avoid these productivity potholes.

Click here to see a host of example questions you can outsource with Fancy Hands

Why I like Fancy Hands

I hate doing monotonous tasks! There are so many things in my day that could be done by a 14-year-old, but they need to get done or I will be screwed.

Fancy Hands makes sure I don't get screwed and that I don't have to do them.


Who is this for?

  • Anyone who has considered hiring a personal virtual assistant.
  • Anyone who has repetitive tasks that they can schedule in advance.
  • Anyone who travels a lot and wants help booking hotels and flights (my favorite part honestly, as I always mess this up if I do it myself).

Alternatives to Fancy Hands

There are plenty of alternatives to FancyHands.

I have not used these services personally, I just did the research and found what appeared like comparative options. 

Design Pickle to Handle Your Simple Design Tasks

Design Pickle is a blogger's dream come true.

I actually enjoy making designs and graphics for my blog, but I do find that…

  1. I am not amazing at it (Design Pickle's staff are almost always better).
  2. I spend a lot of time on it.

Why I Like Design Pickle

Quality design work is critical for content marketers like me. Design Pickle allows me to write content (what I do best) and they do the graphics (what they do best).

Who is this for?

Anyone who needs designs frequently. Marketers like myself benefit from a service like Design Pickle the most.

If I were to hire someone for each individual design task I needed, I would not only waste tons of time, I would also spend 1,000s of dollars!

Bench.Co to Handle Your Bookkeeping

Taxes are inevitable.

Benjamin Franklin said it best...

"In this world, nothing can be said to be certain, except death and taxes."

Since there's no getting around it (legally or for long anyway) you might as well make sure that your taxes are done properly. 

It's important that you understand 

Bench will provide you with a dedicated bookkeeper for your business. 

Who is this for?

Anyone who doesn't like keeping their own books. While you still need to be very vigilant in your record keeping, Bench is a great convenience and powerful asset to any small business.

Keep in mind, your bookkeeper is NOT an accountant. They don't make tax payments for you and they won't be giving you financial advice. They simply manage your income statements, 

Why I Like Bench

I am terrible at keeping my own books. Seriously, terrible. Any help I can get is so appreciated, it is nuts.

Bookkeeping is one of the most easily outsourced tasks for solopreneurs like us.  

My books are a mess and handles them elegantly. 

I have ....

  • Over 1 dozen different affiliates paying me monthly. 
  • Dozens of affiliates I pay each year
  • Many profit splits 
  • Tons of random business expenses (travel, suppliers, mortgage, etc)

I love dumping all that mess onto Bench's shoulders.

A note on pricing with Bench. The price you expect to pay is likely underestimated. I ended up paying over $250/month when I expected to be in a smaller package. Keep this in mind and don't be shocked if you require a bigger plan like I did. 

How to Get the Most Value from These Services

When sending a request, use a screen capture tool to snap a picture of the area needing attention.

  • Use an annotation software to make markups on the image. I use Techsmith's Snagit but there are free options like Skitch by Evernote.
  • Be clear in your description. They are humans, not robots. This is part of why the service is so awesome, but they can't read your mind. Be clear and you can get your tasks done without any additional correspondence.
  • Note the date, time and task request in the email subject. This will make it easier for you and the support team. You may want to reference the changes they have made later if you have future questions, and good email titles help for quick recall.

Ok, I wish you the best of luck and hope that you find these services as helpful as I have!

Hiring Freelancers for Your Lifestyle Business

Almost any job that you could hire a full time person to handle could be outsourced to a freelancer (also called "contractor").

There are a number of networks that help place freelancers with employers. The pricing varies depending on task, experience and other factors at play. 

Let's start with the cheapest option:

Fiverr for Simple Task Based Work

Fiverr is Awesome

Fiverr is a very commonly used outsourcing network that can be a fantastic use of your money OR an absolute waste of your time and energy. 

I didn't say waste of money (because you can get your money back if a gig is not up to par), but you cannot get the time and energy back. I think that is worse. 

When I started growing my first business, I was a huge fan of Fiverr. A lot of this had to do with the fact I couldn't afford much else and didn't know about many other options. It was pretty cool nonetheless.

Fiverr Gigs Ordered

After purchasing dozens of different gigs ranging from logo design, voiceovers, transcription, data entry, image editing, website design and even hand drawn caricatures of myself (don't ask), I have a rounded understanding of what tends to work and what doesn't on Fiverr.

I even sold gigs on Fiverr writing comedy, so I have seen both sides.

I have wasted a lot of time on Fiverr gigs, and I want to help you avoid this.

Fiverr is great, but it is far from perfectDue to its affordability and easy startup, many bootstrapping entrepreneurs attempt to use Fiverr for everything.

They want logos made, websites launched, copywriting crafted, sales pages perfected...unfortunately, Fiverr is not the best option for all of these things and you may very likely end up paying more money in the long run and wasting a lot of time.

Fiverr is...

  • A great place to find a wide array of basic jobs or ones that require very specific technical expertise.
  • A good option if you have time-consuming tasks of low-level importance.
  • A good option if you have a clear job description with details, timelines, and examples.
  • A good option for one-time or infrequent gigs.

Fiverr is not...

  • A place to outsource every task you have and save money.
  • A good option if you have very important tasks and deadlines that aren't flexible.
  • A good option if you have open-ended gigs that require a great deal of ingenuity and self-guided work.
  • A good option for ongoing jobs or ones you need daily

Fiverr Pros and Cons

  • Simple PayPal ordering
  • Refunds are easy
  • Affordable (generally)
  • thumbs-o-up
    Many pre-existing gigs
  • thumbs-o-up
    Some protection from scams
  • thumbs-o-up
    Mobile app
  • Many subpar gigs
  • Strict rules
  • Many misleading orders
  • thumbs-o-down
    Some sellers push bad affiliates
  • thumbs-o-down
    Not as easy to post requests
  • thumbs-o-down
    Mobile app needs improvement

Whether you decide to use it a lot or just occasionally, I highly recommend that you create a free account on Fiverr.

Upwork for More Skilled Tasks and Large Projects

Upwork Logo

Upwork is a platform that connects contractors and employers.

It makes the process of hiring much easier since it shows past work history, employee reviews and desired wages.

Tasks to outsource on Upwork

You can outsource just about anything on Upwork, but here are a few tasks that I have used them for in the past. 

  • Software and Web Development
  • Design Work
  • Proofreading/Editing
  • Content Creation
  • Accounting
  • Spreadsheet Support
  • E-commerce Support (Order fulfillment, Refund management, etc). 

The total list of work categories is very large. 

Upwork Subcategories

I haven't hired in each category, but the process is the same across the board. 

Upwork Pros and Cons

  • Large pool of talented contractors
  • Employee work history and reviews
  • Easy payment options
  • thumbs-o-up
    Hire task based or hourly 
  • thumbs-o-up
    Easy to get started
  • thumbs-o-up
    Mobile app
  • thumbs-o-up
    Easy communication with contractors
  • thumbs-o-up
    Tasks are refundable if they aren't completed properly
  • Not all contractors are qualified
  • Fees for hiring
  • Some job postings won't receive many bids

Upwork has really been a lifesaver for my business and I love referring them to friends and readers. 

Creating a job post is very easy. You choose your category, desired success rate and desired hourly rate. 

Hire on upwork

Upwork has you covered for anything you can think of (ok, almost anything). 

Final Words on Outsourcing for Your Lifestyle Business

I've given you the services and networks that can help you grow your lifestyle business without hiring full time employees, now let me close the article with a few tips.

Tip #1 Don't Be Cheap

It can be tempting to hire the cheapest labor possible for each task. Trust me when I tell you that going cheap isn't wise in the long run. 

Many unskilled administrative tasks can be outsourced at very low rates, but other tasks deserve better wages. 

For instance, you can pay $4/hour for data entry work but you shouldn't pay $8/hour for web development. Use common sense and don't let yourself get burnt trying to save a few bucks. 

If the task is worth outsourcing it is worth outsourcing right. Understand what the financial value of a task will be to you if it's done properly and pay accordingly. 

Tip #2 Be Extremely Clear

Outsourcing is an art. Some people can do it well and others can't. 

As a blogger and former warehouse manager, I'm use to explaining things in easy to understand ways. I'm able to delegate tasks well because I am very clear and I don't leave much room for interpretation. 

​Make your tasks as clear as possible. Some ways to do that include...

  1. Making video recordings of what you need done. 
  2. Creating annotated screenshots when appropriate. 
  3. Encouraging the contractor to ask questions. 
  4. Providing examples of what you want completed. 

Clarity is king. 

Tip #3 If It's Not Broken Don't Fix It (Rehire the Same Employees)

The hardest part of outsourcing is creating the posting and reviewing candidates. 

Once you do this once and once the person performs well, don't overcomplicate things, just hire them again. Build rapport with them, let them learn what your business is about and you'll get consistent results that should be completed better and faster over time. 

Tip #4 Don't Outsource Things That Don't Need to Be Done to Begin With

Peter Drucker said it best...

"There is nothing so useless as doing efficiently that which should not be done at all."

It doesn't matter if you're doing it or paying someone to do it...Tasks that don't move the needle forward should be ignored. 

Tip #5 Document Your Processes 

You should always be building a library of repeating tasks that you perform. By doing this, you make it much easier to step away from them and outsource them later. 

If you hire someone and explain a task to them be sure to document it and save the instructions for later in case they fail to perform, leave the industry, aren't available or you need to hire more people to complete the same task. 

I recommend tools like Camtasia and Screenflow 8 for recording videos and simple Google docs for this. Save them in a folder and keep adding to the stash whenever you find time. 

There are also services that allow you to store your processes in an employee portal. They aren't cheap and I don't find them to be any better than free options like simple files and folders in Google Drive.

Note: This is not a comprehensive guide on virtual outsourcing. I highly recommend reading Virtual Freedom: How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business by Chris Drucker if you're looking for something more comprehensive.

What do you think? Did I miss any resources you recommend for freelancing? Leave a comment and let me know!

About the author

Nate McCallister

Nate is the founder and main contributor of He is a lifestyle entrepreneur who spends his time building businesses and raising his two kids Sawyer and Brooks with his beautiful wife Emily. His main interests include copywriting, economics and piano.


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