Don’t Love Your Job? Teach Yourself A New One

This is the story of how one woman became a designer without going to design school. Karen Cheng’s experience offers valuable insights for anyone itching to do something different.

Don’t Love Your Job? Teach Yourself A New One

I got my job as a designer without going to design school.


I wanted to change careers and become a designer, but I didn’t have four years and $100,000 to go back to school. So I decided to teach myself. At first, I had a lot of doubts about whether someone could teach themselves well enough to get a job.

If you’re wondering the same, the answer is yes.

I hacked together my own design education in six months while working a full-time job. I didn’t think I was ready but started applying for jobs anyway –and got a job at a great startup, Exec.


I’ll admit, I’m nowhere near as good as many design prodigies that come out of a four-year education at an elite school. But I’m definitely good enough to do my job well. I design a pretty wide range of things – for the website, iPhone app, emails, social media, and print.

Maybe you want to change careers. Perhaps you are, like me, looking to become a designer full-time. Or you just want to learn some basics for your startup or side project.

This is how I did it–and how you can, too.


Step 1. I learned to see.

The biggest mistake for someone like me is jumping into Photoshop too fast. Learning Photoshop does not make you a designer, just like buying paintbrushes doesn’t make you an artist. Start with the foundation.

First, I learned how to draw.

You don’t have to sit in a room with a bunch of other artists trying to draw a naked woman.


You don’t even have to get that good at drawing. Just learn some basics so you can be comfortable sketching with a pen.

In fact, for me I only had to do one thing to learn how to draw: Get the book You Can Draw in 30 Days and practice for half an hour every day for a month. I’ve looked at a lot of drawing books and this is one of the best.

Then I learned graphic design theory.

I started with the book Picture This. It’s a story book of Little Red Riding hood, but it taught me the foundations of graphic design at the same time.


I learned about color, typography, and designing with a grid.

I learned some basics in user experience.

There are a lot of books about user experience. I started with these two quick reads to get in the right mind-set:

The Design of Everyday Things


Don’t Make Me Think!

I learned how to write.

I didn’t fill my mockups with placeholder text like Lorem Ipsum. Your job as a designer is not just to make pretty pictures – you must be a good communicator. I thought through the entire experience, choosing every word carefully. I wrote for humans, not in the academic tone used to make one sound smart in school papers.

I read Made to Stick, one of my favorite books of all time. It will teach you how to suck in your readers.


Voice and Tone is a website full of great examples of how to talk to users.

I learned to kill my work.

This is the hardest step in this whole guide.

Be prepared to kill everything you make. In my case I had to be prepared to violently slaughter my precious design babies. The sooner you can embrace this idea, the better your work will become. When you realize your work isn’t good enough, kill it. Start again.


Get another pair of eyes. Don’t know anyone in the field you are aiming for? I didn’t either, so I made some designer friends – and went to designer meetups and events.

I also sought out the opinion of people who don’t care about design, too. I showed my work to people who would be my users and asked them to try what I’d designed. Don’t be afraid to ask strangers – I once took advantage of a delayed flight by asking all the people in the airport terminal to try out an app I was designing. Most of them were bored and happy to help, and I got some great usability feedback.

Listen. Really listen. Don’t argue. If you ask someone for feedback, they’re doing you a favor by giving you their time and attention. Don’t repay the favor by arguing with them. Instead of arguing, thank them and ask questions. Decide later whether you want to incorporate their feedback.


Step 2. I learned how to use Photoshop and Illustrator.

Hooray! Now I had got a pretty solid foundation–both visual and UX. I was ready to learn Photoshop. Actually, for would-be designers I recommend starting with Illustrator first and then moving on to Photoshop after. Illustrator is what designers use to make logos and icons. InDesign is good for print design like flyers and business cards.

I learned Illustrator.

There are a ton of books, online tutorials and in-person classes to learn Illustrator. Here are the books I found especially helpful to learn the basics of Illustrator:


Adobe Illustrator Classroom in a Book–It’s boring, but if you get through at least half of it, you’ll know your way around Illustrator pretty well.

Vector Basic Training–This book teaches you how to make things in Illustrator that actually look good.

Now for the fun stuff! I followed these online tutorials and was impressed by what I could make. Here are two of my favorites–a logo and a scenic landscape.


I learned Photoshop.

There are a million and one tutorials out there. A lot of them are crap. Fortunately, there are sites with really high quality tutorials. PSDTuts by TutsPlus is one of them.

Here’s a good Photoshop tutorial to make an iPhone app.

Here’s another good Photoshop tutorial to create a website mockup.
I carved out an hour or two every day to go through some tutorials, and was happy to see how quickly I made progress.


Step 3. I learned some specialties.

I had to decide: Do I want to design mobile apps? Websites? Infographics? I explored them all and picked the ones I enjoyed to get better at them.

I learned Logo Design.

I had to learn how to make a logo that doesn’t suck: Logo Design Love.

Then I learned to create a consistent brand–from the website to business cards. This book, Designing Brand Identity, was incredibly helpful.

[h3I learned mobile app design.[/h3]

I started with this tutorial to get my feet wet in visual design for mobile apps.

I also read this short but very comprehensive and well-thought out book on iPhone design: Tapworthy. It taught me how to make an app that not only looks good but is easy to use.

Meanwhile, I geeked out on the apps on my phone, and critiqued them. I asked: What works and what doesn’t?

I learned web design.

I read Don’t Make Me Think to learn how to make a website that people find easy to use and navigate.

And I read The Principles of Beautiful Web Design which taught me how to make a website look good.

I made a list of the websites I think are beautifully designed, and noted what they have in common. I found some great examples on SiteInspire.

Step 4. I built my portfolio

You don’t need to go to a fancy design school to get a job as a designer. But you do need a solid portfolio.

How do you build a portfolio if you’re just starting out for the first time? The good news is you don’t need to work on real projects with real clients to build a portfolio. Make up your own side projects. Here are a few ideas I came up with:

  • Design silly ideas for T-shirts.
  • Find poorly designed websites and redesign them.
  • Got an idea for an iPhone app? Mock it up.
  • Join a team at Startup Weekend and be a designer on a weekend project.
  • Enter a 99 designs contest to practice designing to a brief.
  • Do the graphic design exercises in the Creative Workshop book.
  • Find a local nonprofit and offer to design for free.
  • Resist the temptation to include every single thing you’ve ever designed in your portfolio. This is a place for your strongest work only.

Steal, steal, steal at first. This was a valuable lesson. I didn’t worry at first about being original–that will come later, once I’m more comfortable with my craft. When you learn a musical instrument, you learn how to play other people’s songs before composing your own. Same goes for design. I stole like an artist.

Step 5: I got a job as a designer.

When I first started learning design, I went to a job search workshop for designers. I walked into a room full of designers who had much more experience than I did–five, 10, 15 years experience. All of them were looking for jobs. That was intimidating. There I was, trying to teach myself design, knowing I was competing with these experienced designers.

And yet less than a year later, I got a design job. There was one key difference between me and many of the other designers that gave me an edge: I knew how to work with developers.

As a designer, the biggest factor to boost your employability is to be able to work with developers. So I learned some interaction design. Some basic HTML and CSS. Designers in the tech industry (interaction designers, web designers, app designers) are in extremely high demand and are paid well. That’s where the jobs are right now.

No matter what kind of work you are looking to break into, this is extremely important:

Go out and make serendipity happen–tell everyone you know that you’re looking for a job as a designer. You never know who might know someone.

Research companies and agencies you might be interested in. Look on LinkedIn for second- and third-degree connections to people who work at those companies and ask for intros. The best way to get a job is through a connection. If you don’t have a connection, there’s still a lot you can do to give yourself an edge.

Once you’ve got the job, keep learning.

I’ve been at Exec for a year now and have learned a ton on the job. I seek out designers who are much more talented than I am, and learn from them. I find design classes (good online ones are Skillshare, General Assembly, Treehouse, and TutsPlus). I work on side projects. I geek out at the design section of bookstores. There is still so much to learn and to improve on.

Keep your skills sharp, and always keep learning.

Questions? Say hi at @karenxcheng. If you decide to start learning design and want to seriously commit to practicing everyday, drop me a line at karen (at) danceinayear (dot) com. I’m running an experiment to help keep you motivated.

Karen X. Cheng is the co-founder of 100. She learned to dance in a year. Say hi at @karenxcheng.

[Image: Flickr user Ian Sane]