Stupid Question 47: In RE to programming, is it normal to feel more stupid the more you learn?

Oh yeah, that's completely normal. Scott Hanselman has written a nice blogpost about it. He also did a podcast about it with Jon Skeet (even Jon feels like a phoney from time to time!).

When you don't know a lot about a subject, you also don't know how much of it you don't know. The more you learn, the more you start understand how much you don't know yet. It's hard to put things into perspective.

Things you don't know before learning something > things you don't know after learning
Things you know before learning < things you know after learning
Things you know you don't know before learning > things you know you don't know after learning

So you do learn and you do know more stuff, but your knowlegde about the things you don't know about yet also grows and unfortunately, that knowledge can overshadow the rest. 

>> Is it normal to feel more stupid the more you learn?
Yes.
>> And if so, is this a good sign or a bad sign?
I personally think it's a good sign as to me it's the realisation that software development is a huge field and you can't know everything no matter how much you may want to.
>> And does this ever pass?
Kind of :-)
>> And in RE to holding conference sessions, do you ever feel ready?
Since I've never spoken at a conference I can't say, but I do know from having attended many that I've never been disappointed with any of the speakers irrelevant of whether their sessions have been "good" or "bad". 

You shouldn't feel stupid - it is just that you now know that there is stuff you don't know.

There is a theory of learning where you go through  four phases:
1) Unknowingly incompetent - you don't know how little you know.
2) Knowingly incompetent - now you know that you don't know everything
3) Knowingly competent - now you know that you know
4) Unknowingly competent - you don't really know that you know. It is just second nature.

For different areas of knowledge you will be in one of those phases. It seems like you stumbled into phase 2 :-)

Don't worry:
1) you know enough to pull it off - just limit your talk to what you know.
2) people know that you have been programming for a year - nobody expects you to be an oracle. 

YES! It's a bit of a cliché, but the statement "the more you learn, the more you realize you don't know"... well, there is a reason it has become a cliché.

I find that you will more rarely find very experienced developers who will stubbornly claim that there is only one true way of doing something (but it happens). The more experienced you get, the more you tend to realize that there are so many more parameters to relate to, than what you might have though about as a beginner. Perhaps you can say that more experienced developers tend to be less fundamentalistic in their views, since they know that every situation is unique. Even though a problem may superficially look very similar to that problem I solved for a client last year, there are differences that makes it not the same.

But don't make the mistake of mixing up this uncertainty with stupidity. Being uncertain opens up for weighing in various possibilities, which may ultimately lead to better decisions. If you mix uncertainty with some experience and self confidence, you probably end up pretty far from "stupid". But sometimes it may be hard to differ those feelings.

I will assume that you have read Scott Hanselman's blog post "I'm a phony. Are you?". If not, do that now. The feeling of not knowing enough is a very human one. Especially when starting to dig into a subject in order to present it to others. You get this feeling that you are barely over the ice, and that everybody else already knows everything you have planned to say, and "who am I to tell them about this?" and all that. It's human, but still a very awkward feeling. 

"But don’t make the mistake of mixing up this uncertainty with stupidity" - nicely put 

I've heard the podcast, and read the blog post. And Scott asked me about this during the podcast he did with me, but I don't feel like a phoney - probably because I never make any claims about being an expert in my field. But, I can imagine, that when you are appointed as an expert and you embrace that title, then strikes of 'dumbness' might make one feel like a phoney. 
Nonetheless, the moments I feel brilliant tend to shrink, as every time I realize how little I know compared to he amount there is to know, I start doubting even the things I can. This, questioning and critizing everything I do, helps me learn new stuff - but quite often also becomes an hinder.
What a paradox! :D 

it is natural and i believe a bit required also.. for when people become super confident is when they start to go astray. 

that said i also feel that we need not be too self critical. there is no harm in stating once in a while that you don't know something and that will get back and 

finally i don't think most people come to judge the speaker. they come to listen and learn and only if the speaker is really really bad, will they switch off and do these other things like judge a speaker. as long as you can hold the attention and make the session interesting, that should be ok. 

This is a sign of intelligence, actually. Some people tend to learn a few facts and think they are an expert - they are not aware of how little they know because they can't comprehend that things are more complicated than they are aware.

Someone who doubts their knowledge is most likely to be more self aware and willing to admit that they don't know everything.

I'm sure we've all worked with people who know very little in comparison to their confidence level of a topic, and it can be quite frustrating.

Also, some people are scared to say 'I don't know'.