The Freelancer’s Secret to Learning Any New Skill

by on 23rd April 2012 with 28 Comments


As a designer, developer and all around creative person, there are some skills that likely came very naturally to you. The learning experience just sucked you in and you enjoyed yourself enough that you picked up this new talent in an impressively brief timespan.

Other skills however, prove to be more difficult. Sometimes you can feel like your brain is simply full and that there’s no more room for this old dog to learn a new trick. How do you overcome this mental block and force yourself to learn that new skill you’ve been wanting to pick up? There’s a secret that many freelancers know well that is a sure fire way to learn almost anything new in your given field. Read on to see what it is!

The Problem


Let’s say you’re a great designer and have some impressive HTML/CSS chops, but can’t write a line of JavaScript to save your life. “No problem” you think, “I learned all of that other stuff, I can do this!”

So you fire up, start watching some video tutorials, and then remember that you should definitely tweet about how great Lynda is for learning new stuff, which leads to a solid hour of messing around on Twitter because, let’s face it, those videos had you bored out of your mind.

No matter, what you really need is a book. A good old paper and ink lesson doesn’t have all the distractions of your computer. So you head to Amazon, buy the best manual you can find, then take a break for a few days while you wait for it to arrive. When it does arrive, you block out a few hours, find a nice comfy chair in a quiet spot, crack open the book, then awake an hour later to find your face cemented to the pages with drool.

What’s the matter with you? Have you suddenly become educationally incompetent? Why was learning so easy at the start of your career and so difficult now? Should you keep searching for alternative learning techniques or does the problem lie elsewhere?

But I’m Normally So Productive!


For me, and I’m sure a ton of others, the problem in situations like these turned out not to be so much the method of education as the circumstances surrounding the education.

I’m a workaholic who juggles at least three jobs at any given time, often several more. At work, I strive on stress and leverage my psychological need to meet deadlines at all costs to stay productive. If we remove that stress from the equation, I’m not really the same person.

When I’m casually attempting to learn something in my free time, I don’t feel pressured to produce. Consequently, I’m prone to distraction, procrastination, and all other manner of avoidance that leads to my ultimate frustration at my inability to pick up a new skill. This effect is exponentially worsened by all of that work-related stress, which leads me to drop the education attempt in favor of simply using my free time to work more.

Necessity Is The Mother of Education


I recently had a revelation regarding my ideal environment for learning. It all started with a job offer. Someone approached me and asked me to take on a huge project that involved producing over a dozen professional quality videos.

Let’s be clear, I’m a designer and a photographer, but I’m definitely not a video guy. I’ve always been fascinated by the lure of video, but have never really had the time to jump in and master the art. In fact, I had never really done any video work at all, even on a personal, home movie level. I know there’s a “record” button on my beloved 5D Mark II, but I had never used it.

The time requirements for this project were beyond what I could really commit to, the deadline was sooner than I wanted it to be and the requisite skills were way out of my ballpark. I literally had no idea how I would deliver what they were asking me to produce. My answer: “Sure! I’d love to!”

The Missing Ingredient


Right away I found that I was in over my head. I quickly realized that I needed more equipment than a camera (microphones, backdrops, lights, etc.), and that getting the setup that I wanted would be costly, time consuming and frustrating. I also realized that I didn’t possess the software necessary for such a feat, nor did I have any experience with any video editing software. In short, I was screwed. My stress indicators lit up like a Christmas tree.

And there it was. My secret serum for education was finally present. Faced with the fact that I had promised to deliver a product, I realized that I had given myself no out, no room for slacking off or getting distracted. The situation I had created was strictly sink or swim. I was staking my reputation with some important people on this project so I took the only available course of action that I could see: I worked my butt off.

I did a ton of research, decided on some equipment, created a project outline, filmed what I needed to film and spent ages on an outdated Mac that’s horrible for video, chopping it all up and piecing it together in between spinning beach balls and progress bars. Eventually, I had my first video. The process was brutal, but I had done it. The fruits of my labor were clear as day. That little victory was so incredibly encouraging that I pressed on. Video two was even easier! After that, I really hit my stride and things became much smoother.

The Secret To Learning Anything


The moral of this story is clear: if I want to learn something, the best way for me to do it is to get a job doing it. Looking back over my career, I could suddenly see that literally all of my notable skills had evolved along similar lines.

I landed an amazing print design gig at the age of 18, despite the fact that I didn’t know how design worked in the least. I had to learn, and quick, so I did. Similarly, I wasn’t able to make the jump to web design and coding until I landed a job that required me to pick it up. Photography was the same, I knew how to take a picture but didn’t really understand my camera on a deep level or learn about professional post-processing workflows until a friend asked me to help him shoot a few weddings.

I would wager that I’m not the only one who tends to learn under duress better than in a casual, no-stress environment. Even formal education applies these constructs through homework with tight deadlines and difficult testing procedures. In college I pulled a 4.0 not because I was particularly smart, but because I felt pressured to do get my work done to the best of my ability.

Find a Gig That Challenges You


My message here is simple: if you want to learn something new, find someone who will pay you to do it and commit to a deadline. Nothing will push you to greatness quite like the fear of failure and embarassment.

It’s probably one of the more intense methods of self-forced learning that you can find, but you’ll find that once you pull it off, you’ll have an immense amount of pride in what you were able to produce, not to mention an awesome new bullet point for the skills section of your resume!

Results May Very

I fully realize that it’s not possible to paint every creative on the planet with such a broad stroke. There are no doubt plenty of people out there who fold up like origami under stress and are more prone to miss the deadline and/or drop the project than complete it.

Though I question your choice of profession if this describes you, I do think you can be helped by my story as well. Focus on the part where I examined the situations from my past where I was able to pick up a new skill and looked for a common thread. Perform this analysis on your own skill set. The circumstances that successfully worked for you in the past will likely work again, you just have to manufacture a similar situation. Your goal is merely to find your particular learning style and exploit it. Mine is a crazy kamikaze death dive where I pull out at the last second and somehow walk away unscathed and better for the experience, yours might be something much more relaxed and stress-free. Though I do recommend that you give my way a shot at least once, because it really is quite effective.

How Do You Learn Best?

There you have it, I have single handedly broken down the wall standing between you and expanding your collection of professional skills. You’re welcome.

On a serious note, I’d love to hear what you think about all this. Do you find that the best way to learn a new skill is to take on a job that requires it? Why or why not?

Awesome stock images provided by BigStock

Comments & Discussion


  • Ruari

    Amazing article! Any chance of the vids being open to the public soon? I’m no video guru, never worked with them at all, just interested in the work!

  • Bless Quarshie

    Amazing piece! It’s like you are talking about me.

    This is so true, and frankly, this is the exact same advice that a friend of mine gave me. He’s a web developer, and it works for me. Best way to learn a new skill – do a project with it. Give yourself a deadline. That’s what he said.

    Yours goes a bit more nose-deep into the dive. Get a PAID project which already gives you a deadline. That works for me – and I’m reminded again to go pick up on all the great skills I want to learn that I’ve not yet been able to pick up yet – the most notable bieng JQuery and Python.

    Thanks for this!

  • Jason

    It was as if you unlocked the diary I don’t have and copied and pasted it here for your article. You were in my head man, and that is exactly what I face, as a matter of fact, I was just recently attempting some JavaScript tutorials on and treehouse only to get distracted because I have no deadline breathing down my back to learn JavaScript more thorough at the moment. I’ve often thought if it weren’t for deadlines I’d never get anything accomplished. Great piece!

  • Andrew

    How did you know how much time the project would take to complete and how much to charge if this was something new to you? I can understand the principle and it makes sense but in practice are you not opening yourself up for a potential large fall?

  • Joshua Johnson

    Andrew… YES! No guts no glory :)

  • Nina

    Great article, and it totally reflects what I’ve just recently gone through. I’ve done the whole watching JavaScript videos on as well (I did get through the majority of it), but I feel it wasn’t as useful as it could have been because I had no reason to use it in my work.

    I kept on telling myself that I would go look for work after I work on my skills in PHP, Ruby, Rails, SQL, graphic design, project management, business, etc. Eventually, I realized that I just need to get over my fear of failure, believe in my ability to learn and do what’s necessary, and just throw myself out there!

  • siggi

    great article, you hit the nail!

    i wouldn’t go that far to take an entire project from ground up with a new technique or language as a “learning session”, but you are absolutely right.

    as a fulltime programmer in various languages, i learned most of them in similar situations. i had the best learning results when i had a pre-existing codebase.

    one day a existing customer of mine called with an project in java, wich was “almost finished” (40-50% done), but “our inhouse developer left”. i had done nothing before in java but said i’ll try my best. after playing with the existing code for 2 days i could manage to finish it in less than 2 weeks, where a experienced java developer might have done it in 5 days.

    in the end, i neither will nor want to be a great java programmer, but i learned most of the do’s and dont’s of the language, my customer was happy with his finished application and the billing amount was fair for both parts.
    that’s what i would call a classic win-win-situation.

  • alx blmn

    :) tan claro como el agua…

  • ethan danstrom

    “are you not opening yourself up for a potential large fall?”

    We all want to succeed, but I know that I lack the bricklaying dedication to take all the tiny small steps to get there. That 3am buzz of finally getting it RIGHT is a painful itchy eyeball way to do it, but damn…you really get better.

    This is a great story, and I hope it give somebody a productive shove down a perceived flight of stairs.

  • Mayan

    “If we remove that stress from the equation, I’m not really the same person.” — This is sooo me. I’ve actually thought of doing the same thing. And I’m glad to hear that it works for you. I’ll definitely give it a shot. :D

  • Think360studio

    Hi. After reading this article i feel that i was not the only person who stressed while learning something new. As a designer i feel that nobody in this world want stress. Your article is awesome

  • BadCircuit

    I realised this quite a while back about myself, although not in the inspirational way you did.

    I used to slack off on projects till there was almost no time left. I would then reluctantly have to switch off my gaming console and graft my butt off to meet deadline.

    The lazyness coupled with the need to impress and deliver a successful solution or great design resulted in some really awesome stuff and new skills aquired in record time.

    I always do my best under pressure. It’s almost like my brain is sleeping when I try to give myself enough time to do things. So what I have done is kept that pressure at a constant high. Take on more projects, give myself tight deadlines and even take on work that is out of my comfort zone.

    I leave the gaming for the odd weekend here and there just to cool down the grey matter.

  • J Hornbuckle

    I am often in the exact same boat. I try to pick up something new and can’t stay focused. When I was learning C# this happened. Then a chance came along to develop a program to automate an FTP process. I volunteered to make it happened. The next thing you know I was pretty proficient in C# and the program was a huge success.

  • Intime Designs

    I couldn’t agree more. I can’t tell you how many times this has happened to me. Great article.

  • Frank Waive

    Great article and comments, i may not be weird after-all, am not the only one in this boat!!! thanks for sharing.

  • ilithya

    :o it was like i was reading a profile of myself. Crazy! But completely true to me and to my experience. I do not produce if i’m not under stress.

    Thanks for an inspiring article.

  • Manuela

    So true. Reading all comments, I realize it’s all soo true for most of us. I begin to read books, begin to watch videos…and don’t finish at all. Just feeling pressure push me on the right way :)
    Thanks for your post, I finally feel me no more alone in my way :)))

  • Bharat Chowdary

    I’m a freelancer and I always try to find some time to know new things but end-up with nothing. Have to be more productive and have to improve skills.

  • Marina

    I noticed that if you are trying to do something on your own you will need support and some luck. I started as a rookie webdesigner and now I earn my money with that job. The bad thing is that I need resources for my activity, for my clients and I need free resources, cause if I pay for it than I will be unemployed instantly. As long people here has sort of experience, can someone recommend me some websites with free assets? Some big collections…please it will really help me. Thanks!

  • Gabriel Dubois

    @ Marina,

    Since you have been in the game for some time now, you probably know that there is no Holy Grail of resources – there is no site that offers it all to everyone. There are some great repositories, like Envato (for general assets) or Dafont (for fonts). But big, well established sites usually have little packages for free.
    Try searching for the newcomers, since they are usually giving everything for free, just to make an impact, get some publicity.
    Me, for example, I’m looking at, a new sharing portal, where all the ~4000 files are free right now. They are growing, slowly, but growing. And they’re offering the files mostly free for commercial use, and the rest are only personal use.

  • Marina


    Thank you very much for the website that you recommend. It is very helpful, I hope in time it will grow with the resources. I felt that you were mocking me with the Holy Grail or maybe I’m insane, anyway, have a wonderful day!

  • TN Pas Cher

    where all the ~4000 files are free right now. They are growing, slowly, but growing. And they’re offering the files mostly free for co

  • JuanJo

    This article is so true, A couple of times happened to me.
    I think, the main reason to learn a new skill is the mix of the necessity and the rewards you will apply to that new skill. The reward is not necessarily money, it could, be just the feeling to achieve a new personal challenge or win a competition. Maybe, is the psychological effect of any kind of reward what makes you focus and be interested in learning new things.

  • Adverse

    Great article, the best way is to challenge yourself. Wise words

  • AntoxaGray

    I failed my first ever coding project that I was paid for.

  • stephen

    You know, I never got anything less than an A- on a term paper back in the day at college – AND I never started those papers until a day or two before they were due. I guess I’ve been a “stress monkey” my whole life! The times I tend to stress deadlines the most is when I have too much time and not enough work, as BadCircuit says it makes me lazy. When the stress isn’t there and then I tend to underestimate how much time it will take to overcome the obstacles (not usually the work itself, the obstacles) like the beach ball, the dreaded repair permissions, the emergency friend who calls and needs a lift, the once in a lifetime power outage, the “OMG I need toner to print this proof,” etc. … the list goes on and on. I am at my best as you say when I’m jammed from dusk till dawn and then even learning something new tends to happen a lot faster – because it has to.

  • Frank

    Nice article.

  • Rohit

    nice article bro..
    while reading the article i found it similar to wat i think while learning anything new…
    currently m working for my new house design website ( )…
    your article was useful…thnx.. :)


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