I've been working at my job for 1.5 years now. Right after I was hired, my coworkers told me horror stories about the 'early days' when they all took pay cuts/furloughs to keep the company afloat. Although they acted like these stories were in the distant past, there have been several red flags that the company is still on shaky financial ground. Most recently, my boss (very unprofessionally, imo) told me in casual conversation that he didn't know if he could make payroll this month. It's odd to me because two people have quit since I started and they were both making significantly more money than I do so that overhead is gone...shouldn't we be OK financially? To top all of this off, company morale is terrible. My boss can be very combative and difficult, even in casual conversations. The work is highly stressful and we often work nights. This is my first job out of school and I think it's safe to say I'm completely burned out. I've been looking for other jobs but haven't had any luck so far. I'm honestly panicking at this point...I'm living paycheck to paycheck and am really reliant on a steady income...mainly as a result of my significant student loans. I guess I'm wondering if anyone out there has dealt with a similar situation and has any advice.
If you find out that you might not get paid, then you update your CV and apply everywhere to find a new job.
The way you describe your boss, that's not just something that makes it unpleasant to work for him, that's also something that makes it unpleasant to do business with him, so his income will tend to dry up, which explains why he cannot make payroll.
And looking for other jobs isn't based on luck. Take your CV to someone who is good at writing CVs (ask around in your family or ask friends, or have it done professionally). At the very least, look at your CV and ask if you would hire that person. If not, then rewrite your CV with the attitude "I'm great and you should hire me, and here's why...".
We obviously can't tell how your company is doing, but going on the information you've provided:
You are describing my previous job almost exactly (except for people quitting, in my case they were let go). I'll echo other answers to update your CV and get back out looking for a job.
1: Your boss can't pay his staff and you have to work (presumably unpaid) overtime? This suggests he doesn't have a viable business.
2: Stressful work? You don't go into detail here, but if it's anything like my case: unhappy & demanding customers? Everything going wrong and you're run off your feet trying to fix it? Possibly even you might have to deliver products / services that might be out of your company's established skill set. Stressful work is part of a job, but it should only be occasional (e.g. important deadlines approaching), not a constant of the job. If it's continuously happening then it's a sign the company is struggling, and has dug itself into a hole that is very difficult to get out of.
Most customers don't get unhappy for no reason. It's usually because your company is in over its head and so can't provide the products/services that they agreed to provide with good enough quality.
3: Difficult/unapproachable boss, bad morale. I'm making a few assumptions here (small company, he represents the majority of management) but it sounds like bad management within the company.
4: Your personal sanity is suffering. This alone should be enough to make you leave.