Lifestyle Engineering

The Ultimate Guide to Outsourcing: The Mindset, The Processes and Examples

Original Post from Lifestyle Engineering


As an ultimate Lifestyle Engineer™ you should be able to build scalable processes around your own life and professional hustle. Outsourcing has been perhaps the most valuable skill in my arsenal.  

I have hired hundreds of freelancers and saved myself and my companies over $100k and a lot of time doing this.  

Imagine getting on-demand top talent at a fraction of the cost. This means that you do not have to hire full-time personnel and pay outlandish salaries, besides dealing with insurance and other paperwork. Your risks and expenses of hiring wrong full-time people are minimized.

Eventually you’ll want to develop your own army of trusted freelancers who can help you build almost anything when you need it.  You can build an agency doing “service arbitrage,” start a tech product or just free up your work load.

Above all, mastering outsourcing means that you’ll become the owner of a business/system, not it’s workhorse.

Building a successful team of freelancers will be one of the greatest assets in your business and beyond.  But you must learn both how to hire and manage them effectively.

I had to learn outsourcing the hard way. I’ve lost money and time. I have tried and failed tens of times outsourcing various work task to glean the experience and knowledge in this guide.

This guide will show you everything you need to know about the art of outsourcing,  from understanding how freelancers are wired to writing project descriptions and managing your remote team effectively.

Learning outsourcing can take a lot of time to master, but this guide will speed up your learning curve and potentially save you months and thousands of dollars.

Reading Time: 20 minutes

Feel free to bookmark or email yourself the link to this guide, so that you can dive into it when you have more time.

Big Picture

The Why: Focus

“Focus On Being Productive Instead Of Busy”
-Tim Ferris

As a lifelong learner, you should eliminate repetitive tasks so that you can focus on what your core skill areas are to step up your game every day. Spreading yourself thin will never get you to become world-class at anything.

I see many entrepreneurs often fall this trap. If you can do something, it does not mean that you should do it. It can be tough for a lot of entrepreneurs to put their egos aside and say, “I know I’ll get better results by hiring someone to do this task for me. They do it daily, have a genuine talent for it and are passionate about it.”

That’s where founders try to be designers, developers, fundraisers and everything in between all at once. Those guys rarely succeed. It’s simply not scalable and the quality of work suffers.

Outsourcing will give you FOCUS to practice and develop the skill you are exceptional at.

To escape the rat race, you have to be the owner of your hustle, not the irreplaceable piece.

The tedious and mundane work you simply hate doing is in many cases someone else’s livelihood and they are not only good at it, they relish performing the task.

If you begrudgingly do the task yourself,  the quality is probably not going to be as good and it will most likely take you twice the time an experienced and skilled freelancer would. So if the opportunity cost of your time is $100/h, you should not try to save every penny for your business by doing everything  yourself.

Finding Your Ikigai

If you haven’t found your ikigai [生き甲斐] that generates you hundreds of dollars an hour for the work that you love, this matrix will help find it:

More on that in the next blog post.

Why outsourcing fails

Before we dive into outsourcing itself, you might ask yourself why so few people actually actively practice it. Because most of us keep making the following mistakes.

Here are the most common mistakes:

Problem #1: The outsourcing objectives are not clear

Problem #2: Expectations are not set correctly

Problem #3: There is a lack of communication

Problem #4 Hiring the wrong people

Following this guide will show you how to avoid these mistakes.

What can you outsource?

The first things you should outsource:  

  1. Something you really hate doing
  2. Something you simply aren’t very competent at doing.
  3. Tasks that are absolutely needed to be done, but the  cost of your time spent elsewhere is too high. [High opportunity cost]

Ask yourself:

  • What  have I been putting off for a while?
  • What 20% of things cost me 80% of my time?
  • What 20% of things create 80% of anger / unhappiness / stress?
  • What tasks do I enjoy but a freelancer would do better and save me valuable time?

This is a good starting point to find what you should consider outsourcing.

After answering the above questions, ask yourself these additional questions:

  • Elimination

If I eliminate that task, can the project still exist?  What if I simply eliminate this task?

  • Alternatives

What are the alternative jobs I can be working on instead that will yield better outcomes? Is the alternative job more valuable and important?

  • Importance

How important is this task? Does it need to be done in this specific time frame?  Will it affect the outcome of the entire project?  Will the time it takes me to do it negatively affect the timeline of project completion?

  • Experience

How much experience do I have in this area? How well can I perform this task compared to the good enough for this project.

  • Cost

How many hours times estimated hourly rate would it take to do the job compared to delegating it to a freelancer? Will outsourcing save or lose me money?

Things I outsource:

  • Admin Support and Clerical Work

Project management, Account management, Web research, Data enrichment, Cleaning data, Transcription, Personalized mass email reach out [can be used for PR and lead gen]

  • Business Development and Marketing

Email marketing, Social media marketing [SMM], Sales and marketing strategy [funnels and lead generation]

  • Creative work

Web Design, Logo Design. Mobile Applications Design. Banners and Ads Design. Video Editing. Photo Editing.

  • Writing

Editorial work & proofreading, Research, Compiling data to back research, Ghostwriting [could be based on your notes and research]

  • Development

Websites, Mobile Apps, Chrome Extensions, Automation tools [especially the marketing ones], Desktop apps

There are many other things you could outsource, but the above five categories are the most popular ones.

What not to outsource

When I read Tim Ferriss’ The Four Hour Workweek I immediately thought how great it would be to have a number of superhuman virtual assistants that can work around the clock.
Initially, I outsourced almost everything I could possibly think about: scheduling meetings, researching fun stuff to do, following ups after events. I delegated practically everything in my life including things I didn’t need to do at all or should have been doing myself.

By now,  I’ve  hired over 100+ freelancers, and not a single person on my outsourced team is currently  a personal assistant.

The reality is I was delegating unimportant to-dos instead of eliminating them because they didn’t support my overall objective.   

From my project management experience, I learned that my most important “productivity” skill is the ability to set priorities correctly.

So now, if I don’t  find time to handle a particular personal life task, I simply eliminate it.  Why outsource something that will yield a negligible benefit?

When in doubt about what you should or should not outsource, simply go back to the outsourcing decision tree above.

Quick notes on setting priorities

Below is the Eisenhower Decision Matrix. Use this matrix as a guide for each task you want to outsource. It would help you immensely in categorizing the “priority” tasks from the “trivial”.

Also recall the the 80/20 rule, aka Pareto principle! You’ve got to identify the 20% of work that will glean 80% of the results. This way you will be able to be able to accomplish 4 times as much.


Mitigating risks is one of the most crucial components when outsourcing. Always keep in mind that “Murphy’s Law” will apply here.

“Anything that can go wrong, will go wrong.”

Do not fully rely on given timelines and don’t expect stellar quality work every time you outsource something. This especially applies when you do not have much project management experience or experience working with the freelancer you hired.  

Remember that you’re always dealing with humans as freelancers. No one is infallible. Not everyone is going to be 100% “on their game” with every freelance job.

Copywriters aren’t always going to write that exact copy that can send a potential customer over the edge to buy on the spot, and graphic designers are going to have days when they put together 12 different designs for an ad and all of them look like they were done by a freshman college  student in “Art 101”.

You should never outsource things that are crucial components of your business or dependent on the overall outcome of the project. If you’re planning to build and scale a software product for example, outsourcing is rarely going to cut it.  You’ll probably need to build an in-house tech team.

The “How” of Outsourcing  

Safe Bet: Hire a Project Manager

The easiest way to outsource an entire project is to find a project manager who has done it successfully many times before.  This is “outsourcing your outsourcing”. Clever, right?

If you want to save yourself as much time as possible, your best bet would be to hire a project manager. Good project managers can interpret what you want to get done and assemble a team around your task/process.

Your project manager is likely to have a network of freelancers him/herself. This means that the difficult freelancer-recruiting process can be avoided. If you are super lucky, your project manager may have people across different industries and specialities.

One thing to keep in mind: if you are a bad manager, don’t expect amazing results and getting exactly what you want on the first try. You will be managing a manager. If you are bad at it, you may be the weakest link in the system.

Hack: Consider hiring a great project manager as a coach or mentor who will teach you the outsourcing game. These guys do outsourcing professionally and can lay out all their processes to you and explain in detail why, what and how they do what they do.  

If you find really good ones, grab them and pay them whatever they want! (if you can afford it.) Learning this skill alone can pay huge dividends down the road in saving you time and money in building businesses and accomplishing projects.

The Structure of Successful Outsourcing

By now I’m sure, if you’ve never used outsourcing as a viable business model for more productivity and better quality of work on a project, you’re  probably starting to see the huge benefits outsourcing can bring. So if you see outsourcing as something you may want to do on a daily / weekly basis in order to fast-track your project or business, then you should certainly learn how to do it like a pro yourself.

Here are the fundamentals of outsourcing:

  • Writing job descriptions [JD] and project descriptions [PD]
  • Hiring
  • Overseeing and Managing
  • Communications

Understanding Freelancers

Before we dive into writing project descriptions and hiring, you need to know your target audience. How do they “operate”? Why do these guys freelance in the first place? What do they care about?  What motivates them?

Useful Facts about Freelancers:

  1. 60/40

Most freelancers spend 40% of their time on landing gigs and only 60% actually doing what they are good at. Most of them  win under 10% of jobs that they apply to.

 2. Long-Term Gigs

Freelancers prefer building a long term relationship and getting repeat projects as opposed to one-off projects.

  3. Timing

Freelancers often wait a long time [a few days to a few weeks] until they actually win a project.

Most freelancers are continually chasing gigs, so timing is a big issue in getting top talent. You’ll want to catch them during a slow time in their workflow.

  4. Getting more business

Your rating, review and project in their portfolio will help freelancers land future gigs more easily. This is your value proposition to them outside of cash. You’ll want to communicate what you can bring to the table for them up front.

  5. Treatment

People can often treat freelancers in a demeaning way. Freelancers rarely get the sense of belonging and social connection.  Treating them respectfully and fairly goes a long way in motivating good freelancers to want to work with you.

Leverage the above to get their interest and stellar results:

  1. 60/40 & Long Term

If you give a freelancer a project and are happy with them, communicate an interest in developing a long term relationship with them. 

Giving freelancers an opportunity to do work that they are passionate about, as opposed to looking for gigs,  will make them happy. The more you work together, the better quality work they will deliver.

  2. Timing

If possible, mention that the project is available “NOW” to spark their interest. This “scarcity” tactic can work to motivate a freelancer who may be on the fence about sending a proposal or working with you on a project.

  3. Getting them more business

Promise freelancers a “5-Star rating” on the hiring site and a great recommendation upon successful completion of your project. New freelancers respond to this, as they are looking to build a track record, will want work with you more.

  4. Treatment

Be fun and allow your freelancers to be free creatively. Treat them like experts. I often say:

“I am here to make this project as exciting and enjoyable for you as I can. You are the professional, whereas I am here to offer guidance to add the extra 10% so that we can  produce stellar results together.”

When freelancers feel they have creative freedom, they don’t feel like you’re looking over their shoulder continually and are free to create their best work.

Ask them for feedback. You will get great insights on what will make their job easier and you will discover the major roadblocks in their way. Freelancers feel more connected with you as a result.

Double their brain power by doubling their responsibility.

Most freelancers prefer to work with a client they like and who are happy with their work.  This is very motivating to them,  especially when some of their clients can be difficult or hard to please.

For the most part people want to produce work that they can be proud of. Treat people as equals, even if you end up paying them $3/h. In return, you will get the best work out of your freelancers. Being nice and likable will save you time and money--- I guarantee it!

Pro Tip: Rethink management -Dan Pink’s TED Talk: The puzzle of motivation


Never think of freelancers as those who could do everything superbly.

Developers usually make really bad designers. Good designers are often terrible copywriters.  Copywriters can be poor marketers.

Often times it makes sense to separate a project into different sections based on the unique skill sets required. Or you can just work with agencies that have already figured out the mix.

Job Description [JD]

Job Description vs. Project Description

A job description is similar to an executive summary of your whole project. The project description on the other hand, is a much lengthier version of the job description that goes into detail about specifications, frameworks, communication preferences, overall scope of the project, and much more.

Job Description Headlines:

I usually separate every job description into the following parts:

1. WHAT do  you need to get done?

2. WHY do you want the job done?

This will help the freelancer to better understand the objective of the project and get him/her excited.

3. Specifications

4. Your HOW can go here.

Any technical specifications and examples go here.

5. Perks.

What’s in it for the freelancer? What will they get out of it besides money? Prestige of working on a really cool project? Being aligned with a “rising star” in an industry?

6. Job application expectations

You should always say exactly what you want to see in the job application. Make sure to determine what you are looking for in a “perfect” candidate - metrics. These are proof of how well their work contributed to the outcome of a project from other clients. Having this data will help you qualify / disqualify candidates much quicker.  

This will also help you determine how much time your applicants actually invested thinking about your project.

Good length for the Job Description → 1/2 - 1 page

Avoid lengthy job descriptions.  Job descriptions that are longer than one page can be very overwhelming to freelancers.  You should be able to outline the overall project and outcomes clearly and succinctly in the above stated length.

Freelancer Job Titles

Titles are extremely important. They will determine the click-through rate.

Here are some tips to get better response:

  1. Be specific about the type and expertise level of a freelancer. “Senior Quality Assurance Engineer pro at Python 3.6…”
  2. Use comparisons to similar projects “... an app like Uber”
  3. Name your industry. “... for Real Estate brokers”
  4. Many freelancers will send a proposal based on past work in a particular industry.
  5. You can list the project as “FAST” or “SIMPLE” for smaller projects.
  6. Be positive about the project to get freelancers excited about it.
  7. Mention “Long Term” or “Repeat Work” so they will give you better pricing as well as realize that you could possibly become a steady client, thus cutting down on their time sending proposals.
  8. “NOW” and “URGENT” works incredibly well in getting the most amount of proposals from most freelancers at all skill levels due to the urgency of the request.
  9. “5-Star Feedback” - this can be a big incentive for newbie freelancers who are trying to get their feet wet.

URGENT: FB Ad Copywriter for a Crowdfunding Campaign [long-term available]

Project Description

Creating a good project description is probably one of the most important things you need to learn to master the art of outsourcing.

Length: 1,000-10,000 words [2-50 pages]

A good project description will explain to your freelancers exactly what needs to be done. And it all comes down to communication. Unfortunately people cannot read your mind, so you need to hash out your project and all the specs upfront, clearly and succinctly.

In my early days of outsourcing, I crafted very poor project descriptions. Not surprisingly, many of my projects got delayed and flopped and, consequently,  I lost a bunch of money.

Pro Tip: Also avoid describing all your project specs over the phone. They need to be on paper, so that you can reference them in the future.

What to include in a project description [PD]:
  • Project Overview
  • KPIs, milestones, deadlines, timelines.

What will be considered success for a particular task? Milestone?

  • Specifications.

Design expectations, programing language / stacks, APIs, etc.

Examples of similar companies / products.

  • Communication expectations.

Set very clear rules on communication. Try to have fixed call dates on the calendar for at least a few weeks ahead for bigger projects.

Ask freelancers to give you progress reports on set dates.

Mode of communication. Skype? Phone? Email?

  • NDAs and portfolio allowance

You can use for contracts.


  1. Steps and Criteria to write PDs.
  2. Project Management Plan

Finding Freelancers

Now you have a killer job and project descriptions and it’s time to get it in the hands of freelancers.

There are many ways you can find freelancers. The most typical one is “asking around.” However, this method will limit you in many ways. You want the ultimate flexibility, scalability and risk mitigation.

Almost all freelancers I’ve ever hired came from online freelancing platforms. It’s nice to have your friends refer freelancers. But the odds are that your friends are not experts in outsourcing and haven’t had a large enough pool of candidates to choose from.  

In addition, most of the referrals from my friends are usually very overpriced. I usually get freelancers online for 40% of the cost for the same quality work.

Online you will get the buffet of options at a good price.


Make sure to try out different freelancing platforms, before you stick to one. You are most probably going have a difficult time finding candidates in the beginning. Every platform attracts a unique audience and style of doing business.   


Upwork is, by far, my favorite platform. It’s good for anything and everything.  Here you can find people charging as little as $3/h and all the way up to a few hundred dollars an hour for experts with decades of experience.

The main reasons I prefer Upwork to its competition:

  1. Quality of candidates
  2. Quality of proposals
  3. Large pool of freelancers
  4. Your money is protected in escrow [Freelancers are the ones who are risking the most]


Simple way to get anything designed. Crowdsourced content.

Behance can help you find some of the top designers and creatives who might not be on the market. Emailing these guys can help you hire the top 1%!


  1. ProBlogger


  1. Crossover
  2. TopTal
  3. Gigster


FirmList - Use FirmList to find local outsourcing platforms and agencies.

Other Platforms


Fiverr is a great platform for hiring freelancers for small projects and on a low budget.  Although I almost never use it due to low quality and the difficulty of developing longer term relationships.

Two reasons to use Fiverr:

  1. Cost. Most freelance “gigs” (that’s what they’re called on Fiverr) start out at $5 (although they don’t have to). For smaller or short-term projects this a fine platform to find talent. People on Upwork would usually not even talk to you at that price point.
  2. Certain Types of Creative Work. I use Fiverr for voice work from time to time. Other than that I’ve never been satisfied with any other type of work on Fiverr. is also a very popular platform for outsourcing. My experience there has not been very pleasant however. Most freelancers blindly copy and paste their job cover letters, leaving you go through piles of bad applications. The quality of proposals is consistently low. And the user interface is clunky. It’s not even close to the ease and professionalism of finding  talent on


First glance at the applications:

  • Speed of response
  • How specific his/her messages are related to the job you’re posting.
  • Does his/her profile description match the job you are hiring for?
  • Reviews and overall success rate of work.
  • Similar types of project under their profile.

You can archive candidates that are not a good fit. Upwork Example.


  • Ask if the person did the project him/herself and ask for specifics. You’d be surprised how many people claim ownership to projects they did not actually do.  
  • Ask for a process break down. What goes into doing this project successfully?  Ask “why” and see how they respond.

Hiring Practices:

  • Don’t hire right away. The more time that elapses,  the higher chance that the person will be good. I prefer to wait for at least 24h for bigger projects. It’s ok to hire quick for MVT [next section]
  • Ask freelancers to repeat back what they need to do to be sure they are clear on the specifics of the project.

Works extremely well over the phone.

  • Ask candidates how they would tackle the problem / process.  

Hourly breakdown per section of the project.

  • Look at examples of past work.

If people do not attach examples, that’s a red flag. However, if a person sounds knowledgeable and gave you a personalized cover letter, it may make sense to message them asking for examples of their work. I have hired some great freelancers for cheap, because they did not know how to sell themselves, but could do the work really well. That strategy is more time-consuming and risky, but can save you a little bit of money. Remember that if people don’t know how to sell, the odds are that they may not have as many projects done under their belt and are, therefore, less experienced.

  • How specific is the person’s cover letter to your job? Did they answer questions? Did they address the points?

Job Re-Posting Method

And remember, if you do not find anyone within 12 hours, always feel free to simply repost the job again. It’s free.

80% of all of your applicants will come within the first 12h most of the time. You’ll want to cover a variety of time zones to get some diversity in your applications/freelancers.  This happens due to the fact that most freelancers do not like applying for gigs that already have a lot of applications. Their applications can be at the bottom of the pile, so they do not even bother.

I repost at least twice, before I make a hire.


The speed of hiring is extremely important as it will determine the duration of the project. Some folks take weeks to hire freelancers for their projects, which is simply not practical. In fact,  good freelancers will not want to chat for extended periods of time about your project. They want to get down to business.  After all,  if they are that good, they can find gigs pretty easily.

Once communication is initiated with them, try to have an active conversation and request all the information that you need from them.

Minimum Viable Test:

Before putting all your precious time and resources into one candidate, I almost always “date before I get married.” See what you are signing up for. This is especially important if you have long and expensive projects.

For example, instead of hiring a person to do a design of 5 web pages for $1,000, you can ask them to create a banner ad for your company or design a one pager. When you are ready to hire a particular person, ask them if they would be open to do a paid test project. This “paid test project” will do several things:

  • Tests communication between you and the freelancer as well as their understanding of the project.
  • Showcases their work.
  • Shows how long it takes to get things delivered.

You can even give the same test project to multiple freelancers and see who produces better work and is more pleasant to work with.  Such experiments may cost you anywhere from $20-$100, but it is absolutely worth it!

This cheap experiment will eventually save a thousands of dollars and a lot of time and headaches.

Price Negotiation

When you’ve found a person you want to hire, you need to maximize your quality/price ratio. Freelancers typically want to make as much money as possible, whereas you try to save as much money as possible, keeping the quality really high.

Remember that you should have ideally gotten your quotes in cover letters. This number will give you a good bench mark. If quotes from your top candidates are too high for your budget, you might want to bring up the pricing conversation sooner rather than later.  You will save a lot of time as a result.

Tip #1: Engage your freelancer before discussing price.

You want to put you and your prospective freelancer in an environment where you and they feel the most comfortable.

Engage them in positive conversation about the project specs, timelines, etc. Near the end of the conversation you should address the compensation.  I love discussing price over the phone. By the time you pop the pricing question, most freelancers will not have thought about it much.

Their thinking process will be: “I do not want to lose this client by naming a price that’s too high.” So they will usually start with a lower price than they would have otherwise given you if the conversation was over email, for example.

It’s also much tougher to be bold when naming a high price over the phone.  

Tip #2:  Don’t name the price first.

This is probably the most overused technique in negotiation. Some freelancers may ask you “what do you have in mind.”

It’s important that you don’t drop the ball and steer the conversation. You could ask, what was the freelancer’s most comparable project. First ask about the specs [similarities and differences] and then ask how much they charged for that project.

If the price is lower than they quoted you, perfect. You have a new benchmark to work with.

If the price is higher, you can outright say that it’s pricey for you. Use silence to your advantage.

Tip #3: Do your research

Before chatting about the price, you need to know the market estimate for your project. You could simply Google it or check on the freelance site where you found the freelancer and check similar or past projects.  

If you asked for the hourly project breakdown, do the math and see how it compares to the quote they’ve given you. Question how much time a subtask will take. Feel free to ask freelancers to give you more info on each subtask. Sometimes you will see inconsistencies. But that’s not necessarily because people want to get one over on you. It’s usually because they are probably bad at estimating price on a project.

Tip #4: Be likable and state all the benefits of working with you.

Here is where you can save a lot of money. If people love working with you, they will be willing to take lower fees.  This is not to say that the quality of their work will go up, it just means that they enjoy working with you.

Always remember what most freelancers want primarily: well-written specs [this will save them a lot of time], good communication, repeat work and a 5-star rating with a great testimonial.

If you restate the above when talking about the price, you can many times  get a better deal. Don’t forget that you will actually need to pull through on your promises.

Tip #5: Competition

Ideally you should have at least 2-3 candidates to choose from. When negotiating about fees, you can say:

“To be honest, I am talking to a few other candidates at the moment, and they’d take this project for $X… [Silence]”

Remember an old sales adage: “the person who speaks  first buys the product”. This means that you should not say ANYTHING after you make the above statement.  Wait for the freelancer to respond first.  

Then reassure them and mention all the reasons you’d like to work with them instead.

You can be creative with the amount, but be ready to have them call your bluff.

Overall, this strategy works like magic.

Other Tips

  1. Speak less, listen more and use silence to your advantage.  
  2. Don’t low ball. Freelancers interest level in working with you will plummet, and it will be hard to recover.

Overseeing and Managing


Never be afraid to give people feedback and ask for revisions. Don’t be afraid to offend your freelancers by asking for improvements.  It’s your money and project on the line and they are working for you. You hired them for a specific task with a specific outcome and you should it expect nothing less.  At the end of the day, you want superb quality work, and many freelancers need your guidance.

Often times freelancers are very capable of doing what you want [if you hired the right ones]. They just need some detailed constructive feedback to give you exactly what you want.

Since most freelancers have more than one job at any given time, it’s important to stay in contact with them and remind them of timelines and project due dates. It can very easy for some freelancers to stray from your project if you don’t stay in communication with them.

Continue to motivate them by doing what Ken Blanchard recommends in his seminal book, “The One Minute Manager” : “Catch people doing something right”. Remember that freelancers are like anyone else.  They like to know that their work is appreciated and valued on a project.  Their fee is important for sure. However, it’s a basic human need to feel wanted and needed--even on a work project--so if you can tap into this and satisfy it, your freelancer is more inclined to be more focused on your project and do their best work.


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