How To Learn And Develop Your Freelancing Skills When You’re Just Starting Out

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As thrilling as making the decision to start freelancing can be, if you’re new to developing your existing skill set or haven’t learned the skill you want to do the freelance work for, it can be daunting. 

There is so much information on the internet on every subject and when it comes to learning your new freelancing skills that’s no different. 

Where to start? Who can you trust? How long should you spend learning before diving in?

All of these questions are completely valid and the fact that you want to develop or sharpen your skills prior to diving in head first is a good sign believe it or not. It means that you’re human and you care about providing quality work. 

Much different than the “claim to be an expert long enough until someone believes me and gives me money, then move on to the next schmuck after doing a dodgy job”. 

When it comes to learning how to build your freelance skills, this article has you covered. 

But first, a trip to the town. 

Why you should develop skills before fully diving in to freelancing

This advice mostly applies to those of you who are completely new to freelancing and may have not even done any work in the field of work that you’re trying to do. 

For those of you who have spent years honing your craft and want to get started freelancing, you should check out this resource instead. 

With that in mind the most crucial reason why you should have someone of a baseline of skill and knowledge prior to starting boils down to one concept. 

Your reputation is everything as a freelancer. 

I repeat, your reputation matters. 

A lot. 

It’s not only important that you’re able to deliver on what you promised to the client and maintain a high quality standard of work, but those first few jobs will also set the tone for you and determine how you feel about yourself and your work. 

This isn’t to say that you need to wait until you’re  a complete professional before doing any sort of freelancing. If that were the case, there would be a lot less solopreneurs in the world. 

My main point is that you should be focused and serious about the work that you’re now putting out into the world. 

Unlike working a corporate job, where sometimes people don’t even have to work and still get paid, when it comes to freelancing you’re only paid as much as the excellent work that you do. 

So before you embark on your journey, developing skill, practicing, and learning are all huge steps in the right direction to ensure you start out on the best foot possible. 

How to systematically develop a new skill

If you’re not used to learning new things regularly or haven’t flexed your new skill muscles in a while, that’s okay. 

When it comes to learning how to do something new, there is clear research that’s been done to help you develop a system that works well for  you and your own personal motivations. 

The key is getting crystal clear on exactly what you want and developing a practice or good habit around what you want so that you aren’t relying on your motivation. 

1. Set a genius goal

Okay, please excuse my terrible attempt at a dad joke, what I meant was that your goals need to be S.M.A.R.T. 

S.M.A.R.T is a well known and successful goal setting framework designed to help you achieve your goals more reliably over time. It stands for:

  • Specific
  • Measurable
  • Achievable
  • Realistic 
  • Time bound

When you set a goal for your learning like “I want to complete 2 graphic design online courses and find a mentor with 2+ years of experience in the next 6 months” it really gives you something to sink your teeth into and look forward to. 

Compare that to something like “i’d really like to learn graphic design” and you’ll see why so many people fall short of their non structured goals so often. 

So do yourself a favor and set a genius goal for yourself right from the start. 

You’ll be glad you did. 

2. Break the skill into small milestones

Learning anything can feel like an overwhelming endeavor, let alone a skill that you want to be responsible for your future income potentially. 

If you view the new skill as one huge mountain that you have to overcome all at once, then your motivation is likely going to dip low when the rest of your life gets hard. 

Instead, it’s better to divide your new freelancing skill development into smaller parts and work on each of them in order, one at a time. Let’s use becoming a graphic designer as an example. 

Here’s a breakdown of what learning to be a graphic designer might contain

  • Understand the basics and get an overview of what’s involved
  • Learn about typography, color, and core UX principles
  • Learn how to edit images with the basic features of adobe photoshop or canva
  • Learn three of the most popular CMSs that you’ll want to help clients with
    • WordPress
    • Squarespace
    • Wix 

And instead of diving into learning everything all at once, you can spend as long as you need at each one of those smaller steps and give it your full attention until you’re done and feel good about it. 

3. Deliberate practice

Developing any new habit or skill takes time, patience, and practice to truly sink in. It’s not enough to learn the theory and intellectually understand something. 

You’ve got to utilize the concept of deliberate practice to really take your skill learning to the next level and help it stick. 

James Clear (a master of habits) describes deliberate practice as “a special type of practice that is purposeful and systematic. While regular practice might include mindless repetitions, deliberate practice requires focused attention and is conducted with the specific goal of improving performance.”

The idea is that you’re not just watching a video or taking  a course to simply check a box. Every exercise, activity, module, or task needs to be taken extremely seriously and done with the intention of having the information sink deep into your memory. 

In the article above, James also describes how you can apply deliberate practice effectively:

  1. Break the overall process down into parts
  2. Identify your weaknesses
  3. Test new strategies for each section
  4. Integrate your learning into the overall process.
  5. Repeat

Doesn’t that sound fun? 

Well, it won’t always be, unfortunately. But if you focus on this type of practice, the results that you’ll experience will be the most fun you’ve ever had. 

4. Stick to a schedule

Related to deliberate practice is the idea of creating and sticking to a routine. If all of your learning is completely random and sporadic, it will be hard for you to retain the information. 

Both children and adults alike tend to be healthier and stick to good habits  when engaged in a set routine so you should apply the same reasoning to your freelance skill development. 

The two most important aspects to get right are scheduling a day and time for when you will focus on learning. It can be a recurring daily practice where you get in your learning prior to going to work, or sessions could be once a week on a saturday evening when you have time. 

The right cadence and time you have to spend on learning is a personal decision that will have to match up to your lifestyle. There’s no shame in not being able to practice for 5 hours every single day. 

That being said, there are limits. You won’t learn that effectively if you’re only studying and practicing for 30 minutes once a month. You’ll want to choose a cadence that leads to consistent progress over time and so at least twice a week or 4 hours a week is a good starting point. 

5. Learn alongside others

Being a business owner of any kind can be a lonely experience at times, freelance or not. 

Just like it’s important to surround yourself with likeminded people in your personal life, it’s crucial that you put yourself in environments that foster joint learning or where you’re learning from someone who’s already been where you’re trying to go. 

When you are moving towards a shared goal or learning alongside others in the same boat as you, it can serve as positive reinforcement. You will have others to learn on, encourage, be encouraged by, and lean on during moments of confusion. 

There is persuasive evidence to support that “cooperative teams achieve higher levels of thought and retain information longer than students who work quietly as individuals.” 

Despite this field of research largely applying to students, it’s fair to say that adults don’t often learn in groups the way that students have the opportunity to and I think there are key takeaways to be understood from the research. 

  • Find mentorship or a coach whenever possible as you learn
  • Learn in a group or alongside another person in the same boat as you
  • Regularly celebrate your wins, voice struggles, and compare notes
  • Share goals and align on objectives as a group

6. Reward yourself

This is such an important step to incentivizing long term skill retention and learning, but it’s something I have struggled with in the past. 

Giving yourself something to look forward to (rather than a punishment to avoid) is an extremely powerful force for motivating yourself to achieve your goal. 

This works because your brain is wired to move towards things and take action in order to achieve a positive outcome. In contrast, when needing to avoid something bad, you and I are wired to stay put and not do much of anything. 

So after you’ve set your goal and broken up your freelancing skill into bite sized chunks, write down or think through how you could best reward yourself after completing each set of tasks. 

Some of my favorite examples:

  • Trip to the spa
  • A solo camping trip without your kids
  • Family night out
  • Two pieces of german chocolate cake
  • A whole saturday binge watching your favorite movies

Choose wisely my friends. 

Best places to learn freelancing skills (for free)

Now that we’ve got some context around why developing your freelancing skill is so important and how to do it, let’s talk about the specifics of where to learn. 

Since you’re starting out on your freelancing journey, I’m not a huge fan of going back to college or paying thousands of dollars for some workshop. If those avenues work for you then by all means I say go for it. 

However, if you’re like me and you don’t have a lot of time, money, or patience as a new freelancer, then these options are  for you. 

Online courses

I’m a huge fan of online courses, especially the free ones. 

Typically, most of the information in these online courses is available throughout the internet. However, the benefit they offer is by presenting the information to you in a structured and carefully thought out way. 

Contrasted with reading a blog post or collection of guides from multiple sources, it allows you to stack your knowledge in a logical way from an expert rather than only reading the information and having it flow right out of your brain. 

What to look out for with a good online course:

  • Get as specific to your desired learning outcome as possible. Rather than look for “how to become a graphic designer” find a course that teaches “the fundamentals of photoshop for beginners”. 
  • Make sure your instructor has credentials. You should be able to find them on linkedin, they should have a portfolio of work, and they should clearly be qualified through their own success to teach. 
  • Action items for the student. A lecture can be helpful in some cases, but the real benefit of online courses is for you to watch along, practice for yourself, take assessments, and even submit work to be evaluated in some cases. That will really help things sink in. 
  • Up to date. Not that history can’t help you  learn a new freelancing skill, but many relevant skills weren’t around or have evolved in the last few years. It’s important that the course you select is up to date at the time you want to learn it. Too many years back and you risk starting off your freelancing journey unprepared. 


It’s been said that as a population, our attention spans are shrinking on the regular, so picking up a book and reading all the way through isn’t for everyone. 

That being said, books are excellent for the same reason that online courses work so well. They are written by a subject matter expert in a way that tells a story and paints a cohesive picture of what you need to learn, in the proper order. 

Your  criteria for selecting a book to learn from should be the exact same as for a good online course. 

Find a community or support group

If it exists, there’s a community group somewhere on the internet for it. 

The tricky part is finding a community of like minded and motivated individuals who are genuinely interested in learning with you and not someone else’s side hustle or a spam forest. 

Here are some excellent places of find community groups:

Best online learning platforms for freelancers

Big takeaway

Learning a new freelancing skill requires you to know exactly what you want, set a clear goal for yourself, use deliberate practice, and use the right tools. 

It won’t always be easy, but it will definitely be worth it. 

You got this. 

Happy learning!

Ken Marshall

Ken Marshall is the Founder of Best Freelancer Tools as well as a husband, former freelancer, recovering foodie, mini Australian shepherd puppy dad, and serial entrepreneur (mostly failures, lots of lessons). He is passionate about helping others achieve their full potential.