So you’re looking at freelancing and want to know what the most in demand freelance skill is. I get it. You want to do something that people will find valuable and continue to find valuable. Something that will last for years so you can become a specialist and charge well.

PHP is quite popular and not just because of WordPress.

Rust is a language I keep hearing about.

UX design is needed more and more in businesses.

Conversion optimization brings in more sales for clients and clients like bank accounts that are getting larger.

But none of those skills are the most in-demand freelance skill. In fact, the most in-demand skill for a freelancer and the most in-demand skill for an employee, are the same skill.

That single skill is making accurate critical decisions for your job and your clients.

Why Making Good Decisions is the best Freelance Skill

Your clients are not paying your just to type code into a text editor, though they may think they are. They’re not paying you to make a pretty website, though that’s what they may say when they hire you.

They’re paying you to achieve a goal, like more sales or increase site speed. They’re paying you for an outcome, not for the specific skill you have. They view that skill as something that might achieve their goal, but they don’t even know for sure if you will.

What they’re hoping for is that you will be applying your years of expertise in your field to their problem and making smart decisions that achieve their goals.

They don’t want to be bothered by the tiny details, that’s why they hired you. My clients don’t care so much about the PHP version they run; they just hear me say that they’ll get a huge performance boost by jumping from 5.2.X to 7 that they decide to invest in the process.

When you hit issues with their project, you better have an answer along with the problem. If you’re only coming up with problems all the time, then don’t expect to be paid very much or used again as a provider.

If good decision making is the critical freelance skill you need, the next question is, how do you go about building it?

How to Build Your Decision Making Skills

You’re ready to stop worrying about the latest technology and dive into learning to make better decisions, and here is how you do it.

Freelancer’s Need To Understand Cognitive Biases

One of the first things you need to do when building your decision making freelance skill is identify and account for your cognitive biases. While we may think we’re entirely rational beings, that’s not the truth of it. We let our biases creep in all over the place. Understand what your Cognitive Biases are and how to work around them is a key to making better decisions.

A cognitive bias is our tendency to think in a certain way which can lead to throwing common sense out the window and making terrible decisions.

I’ll highlight a few of the Cognitive Biases I see working with freelancers below.

Confirmation Bias

Confirmation Bias is our tendency to find information that confirms our already held beliefs. If you’re on your path towards becoming a master in your field, you must seek out information that contradicts your current opinions.

You must start from the standpoint that the other side is not dumb. They have a point of view that you disagree with, but they’re not stupid knuckle draggers.

In fact, one of the best ways to test your idea is to dive deep enough in to the opposition that you can explain their ideas better than they can. Only when you can do this are you ready to have an opinion.

Availability Heuristic

Availability Heuristic is fairly close to Confirmation Bias. At the very least Availability Heuristic reinforces Confirmation Bias in a virtuous cycle. Availability Heuristic is a mental shortcut where we rely on the most immediate information accessible to inform our decisions.

Falling to Availability Heuristic is how we don’t truly understand the ‘other side’ of an issue. We never hang out with people that hold opposing beliefs, so we don’t have interactions that cause us to question our beliefs.

It’s easier to keep feeding ourselves the diet of things close at hand. Search engines make this natural as well as they try to bring relevant results to us. That means they’re continually looking for information similar to the information you’ve already shown interest in. This exacerbates Availability Heuristic as you find more information close at hand that tells you you’re right.

The Cognitive Bias of Anchoring

The Cognitive Bias of Anchoring has us rely too heavily on a single piece of information on a subject. We act as if this information is the be all and end all on the subject.

Unfortunately, it is also likely the first piece of information we found on the subject. This goes well with the saying “You never get a second chance to make a first impression”.

We use this first piece of information as a filter for all subsequent information and limit the net we cast as we look to make good decisions.

You should be trying to cast the net as far as possible, especially at first, to make sure you understand all sides of a problem.

The Curse of Knowledge

I’m a nerd. Terminal is my friend and don’t even get me started on Vim Keybindings. I know that some of you didn’t even get that line.

The Curse of Knowledge is the curse that we succumb more and more to as we gain experience in our field. We forget what it was like in the early days to not understand the last ten years of developments in the field.

I remember following a coding tutorial that had you open up Terminal and then type vi file.php. Then I was dropped into Vim and had no idea how to edit anything or save anything or…get back to Terminal. The author of that tutorial assumed that you would understand all of those things so skipped them in the explanation.

Now, I use Vim all the time, but it wasn’t always that way.

That’s not nearly all of the Cognitive Biases we suffer from. I could write for a whole year and still not cover them all in detail. A decent place to start your further learning on them is this list of Cognitive Biases on Wikipedia

Next up is Mental Models. They bear many similarities to Cognitive Biases, but instead of being things you should avoid, they’re the models you should be applying to your decision making instead of suffering from Cognitive Biases.

Freelancer’s Need to Build Lots of Mental Models

A mental model is an explanation of the thought process surrounding how something works in the real world. It’s a timeless, universal model of thinking, and there isn’t just one of them1.

This idea, popularized by Charlie Munger, holds that you need a large network of mental models on which to draw. Not only do you need a large number of them, but they need to be fundamental ideas that have stood the test of time. That means that many of them have existed for hundreds of years and aren’t the latest idea found floating around on Facebook.

It’s a common problem to have. We try to keep up with the “new” on the sole basis of it’s “newness”. As if being new makes it inherently more worthy of our attention. Almost all new ideas are a repackaging of a timeless truth. While there is merit in having timeless truths repackaged in to something that makes sense in our current context, far too often we sacrifice learning the timeless part in favour of the newest pop-psych explanation of the idea.

The timeless truth feels harder to grasp, and it might be, where the latest iteration feels easy. When we do this, we’re shortchanging ourselves because we’ll have to learn new aspects of the timeless truth forever since we don’t understand the core principles that are being applied to the present day situations.

When you’re looking at your Mental Models, it’s easy to fall victim to the Availability Heuristic spoken of earlier. In general, if you don’t have at least two models that seem applicable to the problem and are producing useful answers, then you either don’t have enough mental models available, or you don’t understand your client’s problem in enough detail to find a valid solution.

Let’s look at a few mental models that will help you make better decisions. If you want a whole lot more, then dig into Farnam Street’s 113 Mental Models.


The first mental model I’ll highlight is Inversion. This mental model gets you think about the problem backwards. I’ve used it when teaching math to my 7-year-old to great success. When she sees:

__ + 5 = 11

The next step for her is to reverse it to 11 - 5 = __. She reversed the problem and got the answer after struggling with the first versions and growing increasingly frustrated.


This is also called Confirmation Bias and is the tendency to find more information that confirms the beliefs you currently hold. To use this mental model, you must make sure that the conclusions you draw for your clients would be false if the result is not achieved.


If you can’t reproduce a result in your work, then it’s random. Don’t go banking on something that you can’t duplicate because you’re building on a foundation of sand.

A great book all about this is Fooled by Randomness.

Regression to the Mean

In normal systems, most things will tend towards average. If you come across something that’s so far away from average that you’re baffled, then it’s likely an outlier and can’t be trusted.

This is where you can also use the Randomness model and only believe it once you’ve been able to reproduce the result with regularity.

There are more mental models you can use to help make important decisions for your clients. Take the time to do more than scan the list I linked to above. Dig deeper into each one until you could explain it to a 6-year-old. That is the point when you understand how to apply the model.

Freelancer’s Need To Think Like A Business Owner

The next step in developing your freelance skill of making good decisions for your clients is thinking like a business owner. I mean, freelancing is business so you should already be doing this, but you need to apply that business owner hat to your client work as well.

That means when you’re looking at your pricing you think hard about the value that will be provided by the company when you’re quoting on a project. If there is no value, you should be telling your prospect and backing out of the project.

I’ve done this many times, and I’m always the only person that walked a prospect through why I don’t think that the project provides value for them. They are always thankful, and sometimes more than a bit annoyed that no one has brought the value talk up with them. Lots of companies were willing to quote on the work and take money for doing it without ensuring that they are providing value for a client.

Who do you think the only person they will talk to about the next project is?

If you took on a project where there wasn’t a clear value proposition for a prospect, do you think they’d view it as a successful project in 6-months? Would they be lamenting the money they wasted on you?

This type of thinking goes further than when you’re trying to convert someone from a prospect to a client. It goes with every stage of the process.

When you hit a snag in the project and have already come up with a solution, you must also have thought about the value of the solution to the overall project and the client’s business as a whole. If you haven’t done that and can’t advise on the situation from a value standpoint, you haven’t thought hard enough about the problem yet.

Every bit of advice you provide to a client needs to be in light of the single question: “Will this help them achieve their goals and gain more value in their business?”

Awesome Freelancer’s Take Responsibility and Control

The final aspect of making reliable decisions for your clients, and thus developing the single key freelance skill for being a freelancer that stands above the crowd, is that you need to take control.

None of this crap where you report a problem and then toss your hands up waiting for a client to answer your questions. If you’re saying to yourself “That’s not my problem” and then sitting there doing nothing on the clock, you’re on your way to a failed business because no one will want to hire someone like you that wastes so much time.

As I’ve said a few times, a great freelancer comes back with a problem and a solution and a look at how it will address the value the client wanted out of the project.

A great freelancer takes control of their time and makes decisions in the client’s best interests. If you don’t know what their goals are, then you did a crappy job understanding the client. You were never ready to build that proposal in the first place if you didn’t understand the value the client expected from the project2. You’re the crappy freelancer that goes for the clients that don’t know any better, and in the long run, you’re going to fail.

Clients will find you out and the lifeblood of a freelance business, referrals, will dry up.

The critical freelance skill is not anything technical or design. It’s the ability to make decisions. Just because you read this doesn’t mean you’re done learning how to make great decisions. This is a primer on some aspects you need to take into account as you look to build your decision-making skills.

It’s time to put together a plan so that you can make better decisions with less Cognitive Biases breaking your process, and more Mental Models helping you make winning decisions.

Have an awesome day!


PS: If you’re looking to get your business on track join my 8 Week Business Bootcamp.

photo credit: clement127 cc

  1. In fact over at Farnam Street they have a great look at 113 Mental Models which you should read to dive even deeper. 
  2. I wrote a whole book about how to write great proposals and find value for your clients. It’s called Writing Proposals That Win Work