design principles - How would I know how good of a designer I am?

To me my designs looks good, at least for some months. But to others not so much. I want to go freelancing but I don't want to be a bad designer. So how do I find out if my logo/website/business card/backgrounds are good, and if not, what is bad about them?

Answer

This old quote from US broadcaster Ira Glass puts it really well. It's something I believe is true for every creative profession:

Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work.

Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.

Feeling conflicted about your own work is healthy - it's a sign of high standards and of pushing yourself.

For you, it sounds like it's not those months where you don't like your work so much that you should worry about. Pushing yourself is normal and healthy. Being satisfied with everything you produce is not a sign of being a good designer - quite the opposite. Maybe you're going too easy on your work in those months where you're perfectly satisfied with it.

It's very hard to judge your own ability, because it's healthy and normal have a certain amount of dissatisfaction with your ability from always aiming slightly higher each time your ability gets slightly higher - what web comic Cyanide & Happiness called "The Creator's Curse":

...and it is pretty neat because it keeps people improving - if you don't have it, you might be stagnating. It's easier to cope with the constant frustration when you know it's for the best... (or at least, that's what I keep telling myself).

If you like charts, here's another neat illustration, by the painter Marc Dalessio. Obviously it's not scientific... but it perfectly matches my experience with all types of skill development, and judging by the comments and the image going viral, it resonated with many others, too.

Note the periods after you improve, where you think you're better than you really are; then you slowly realise you aren't that good yet, your critical skills improve, you get frustrated, and it's during that frustration that improvements begin.

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It's not easy to assess your own ability objectively - you're biased. A pair of questions which help assess it objectively are: "Are my clients (or boss) happy, paying, and recommending me to others?" and "Am I improving - is my work and skill set really, actually better than 3 months ago?". If you don't have clients or an equivalent source of impartial objective feedback yet, or if you feel you need more, get it using some of the suggestions in plainclothes' answer.

A few design-specific tips for better assessing yourself and your work:

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  Find ways to look at your work with fresh eyes - make temporary changes that mean you don't recognise it as that thing you've spent hours on, forcing your brain to process it a little more like you would if you were seeing it for the first time. Tricks include:

  
  
  
  
  
  • Unfocus your eyes
  
  
  • Literally step back (or, zoom out if, like me sometimes, you're feeling too lazy to stand up... but stepping back is better!)
  
  
  • Flip horizontal (or use a mirror if it's a physical drawing).
  
  
  • Dramatically change the hue / lighting.
  
  
  • Remove or simplify the colours.
  
  
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    Run it through a photoshop effect (or if it's a physical drawing, I've heard of people using tinted glass)

    
    
    
    
    • If it suddenly looks imbalanced or wrong the moment you see it without recognizing it, there's a flaw you didn't see before because you'd grown accustomed to it.
    
    
    • Expect to be surprised. I often react immediately like "HOLY HELL the right hand side is SO unbalanced and the title's getting lost and the centre is FAR too busy and too dark relative to the whole image. Is this really my design? It looked fine seconds ago...". Then you hit undo, focus your eyes, sit back down, etc etc and see that, yes, it really was like that all along. And now you know better how to improve it.
    
    
    
    
    
  
  
  
  


• There's no easy technique to become able to be impartial and emotionally detached about your own work while still being passionate about improving it, you just need to develop this kind of discipline, and it takes time and effort (plus lots of experiences of being forced to bin and move on from ideas you love by clients you won't release were actually right all along until 10 months later). The closest I've ever known to a technique to get a prompt boost of impartial thinking when needed is, put it to one side, come up with an alternate concept, and develop that, treating your last work as the rival you have to beat.


• Show it to people who know nothing about what you're trying to do, and ask them to talk you through what they see - where their eyes fall first, where they look next, how they react to each element. Give no clues or prompting, seek out people you can trust to be brutally honest and encourage them to be more brutally honest. Expect to be surprised most of the time and expect people to initially say, "Yeah, I get this, it's good", then slowly reveal that they actually interpreted it in the opposite way to what you wanted, and expect people to turn out to totally miss or misunderstand the last things you'd expect. If you're not surprised like this, you're probably influencing them and/or they're not being brutally honest enough.


• Do everything Lèse majesté suggests to improve, sharpen and keep fresh your aesthetic eye. (actually, maybe skip be careful with design competitions - except for the best ones, the feedback is usually bad, who wins is usually near-random and they're usually horribly exploitative. But if you've got nothing else to do on a Sunday afternoon, I guess entering a few with low expectations can't hurt)


• Read DA01's awesome answer, and know which phase you're in and how far through that phase you are. If you don't vividly remember the painful transition from phase 2 to phase 3, if even thinking about that soul-destroying period doesn't make you shudder a little (or laugh, if it was enough years ago), you're probably in phase 1 or 2. There's no shame in being in phase 2, everyone goes through it. Just don't linger there.