I’m interested to find out from business owners, freelancers or company owner types, if they ever go a night without sleep? Obviously this is not a desired thing but some times there is that big client that wants that project done now for a very nice fee? Do you put sleep on hold for that extra money for your holiday or do you always get your 8 hours of rest? How many times have you stayed up for 24+ hours?
I am a night owl and an insomniac to boot, once I went 5 days without sleep and got a lot done in that time I can tell you… though I was starting to go nuts from the deprivation. In regards to sleepless nights, I don’t really have any because I just sleep when I’m tired and work when I’m not - most of the time (freelancing). 
I used to be an insomniac and work late (a longggg time ago). The older you get, the more it will take a toll on your health. Nowadays, the only thing that gets me up at night is if our toddler needs me.
I would say about 20 days out of the month, mostly weekends. It is hard to stay to a schedule when your are trying to make things happen
Gotta have my 8 hours. I can stay up, but I hate not being able to think clear, sit it a meeting and try not to yawn etc. So 8 hours of sleep it is!
Oh, it shifted and changed over the course of my life. I have often worked through the night, I have often worked 14 to 16 hours a day for many years, no weekends either. Then I had times to smell the roses for weeks on end, just do idle things but getting the itch to get back full steam. Careers changed and new requirements came along with that.
I am glad I had a life like that, I can not stand sameness. A 9 to 5 life would have killed me.
Many years ago I had a high tech job in oil exploration that frequently involved days on end without any sleep. It’s something you adapt to, so that 24 or 36 hour shifts without sleep are completely routine, and even longer periods become possible too. I think it permanently threw my body clock out of kilter, because I don’t take much notice of what time it is even now, and my routine varies throughout the week. On the plus side, this means it’s very easy to buckle down and work quite obsessively for long periods without suffering ‘jet lag’ later. On the minus side, keeping strange hours sometimes plays havoc with communications with clients, who quite reasonably expect to be able to talk during normal business hours.
I have to say, I enjoy the peace and quiet of night time working. 
Right now it’s 06.00 in the morning in the UK, and I’ve spent the last few hours talking to clients in China, where they’re hard at work right now, and before that with my business partner in the USA. Another messed up night!
Paul
It happens on occasion maybe once every couple of months- dependent on project currently working on.
I can only work 8-10 hours in an 24hr period or I get burned out. Sometimes I do get caught up in work and go for 14-16 hours for a few days then the burn out creeps in and lasts for weeks. So I really have to keep it to 8 hours.
Work is just a way to make a living Not a living.
Unless you do what you love and make a living from it 
Even then, a balanced life is important.