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I'll have to admit that I try to get away with as little sleep as possible. It's not that I'm trying to be a hero or show that I'm macho, I'm doing the whole nights and weekends thing to work on my product because I'm driven to make it successful and it feels absurd to trade off progress for sleep.
I'm well aware of the potential consequences health and otherwise but I see it as a short term cost for a long term benefit.
I'm in my early 30s now, and I've noticed among my friends that the folks who aren't regularly getting enough sleep have seemed to prematurely aged. It's not one big noticeable thing, but it's lots of little things, like how good their skin looks, how much gray they have, what there energy level is.
Don't ask for sources, because I don't have any, this is just an anecdote and a hunch. :)
I'm in the fortunate position now of being able to set my own work schedule. I almost never use an alarm clock, but I still get up around 8am, which is my personal indicator that I'm sleeping enough. I've also found that I have no problem working 12 or 14 hour days, much more than your average worker, but when I do so, I never take the time away from sleeping, but other activities instead.
You would probably make even more progress if you allowed yourself a good sleep schedule. If you "try to get away with as little sleep as possible", it is very likely you are sleep deprived, which leads to bad decisions and more frequent mistakes.
It's reasonable to assume I'm hurting my productivity but like I said I'm doing the whole nights and weekends thing, a couple extra hours of less productive work is better than none.
As far as grogginess/tiredness after you wake up goes that's related to where in your sleep cycle you wake up. I use one of the numerous iPhone/Android apps that use the accelerator to detect and wake you up at the end of a sleep phase.
What about the productivity costs of sleeplessness? It might be that you're actually hurting both your health and your product by shaving off a few hours of sleep.
8+ hour sleeps every night is probably the single life rule I strictly abide by. Wake up not groggy, but refreshed, ready. Entire day you're just a power house.
My main issue is that I want to avoid needing to customize my resume to the company every time. I already spend a bunch of time writing cover letters to companies, and most of the time you never even hear back. (I'm applying to internships)