I've never really had a real low point. I deal with problems pretty well, so I'm able to get through situations without as much trouble as some. I'm going to post one that most people would never consider a low point, but I do a little bit.
Spring of 2005, I'm running my own business
www.sonataweb.net, the local brand, Innovative Media. Business is absolutely great, I've got my own small office with a 4 employees. It's growing at a rate, where literally several months in a row my client numbers were doubling. Unfortunately, what I am I? A guy that HAS almost no business experience, limited knowledge, and a business that operates on pretty small margins, so it's not like I can afford to hire someone. The accounting books are an absolute mess, the services are still great, but that's only due to me working 20 hours a day and some really really devoted employees. As such, I became the business - there was no outside life, I was always irritable, I didn't really sleep because I was always thinking about possible problems. Finally one day I got a job offer from a client to join their management staff, so I went around, found a buyer who was really worse off than I was, but they were willing to fork up some cash. Signed the papers in June and here I am - loving the 9-5 job.