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My question is, should I strongly consider looking for a new job at this point, from what I know?

So today, the owner of our company (about 30 people) announced that a large project (>$1M) we've been working on is really taking a toll on us. The project was probably under-quoted due to this type of project being new to us. At this point I don't know if we'll make a profit at all or if we'll just being making much less profit than expected.

The owner announces the possible cut and he say's he'll probably be firing one of our vendors until next year, an IT company that monitors our servers for downtime etc. This is about $2000 a month. He then goes on to say that we might feel a squeeze, but we may not (alluding to more cuts). I've heard that during the last recession the company did away with mileage reimbursements, which in my own view is like selling your office computers and asking your employees to BYOD to save money. Employees were expected to drive for work, sometimes very long distances with no reimbursement. After that he had to let go of 40% of the workforce. It's only just no picked back up.

Would it be smart to apply for jobs now or does the situation not look too dire at this point?

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    Unfortunately this is out of scope for this SE. Sticking it out versus leaving is a very personal decision that shouldn't be trusted to strangers over the internet. We don't know the consequences of you being out of work for a while or how much you love this job/company or if there would be unreasonable emotional turmoil for you to be laid off. In terms of general advice, always be looking for the next opportunity and assessing it against what you have now. – Myles Oct 3 at 20:05
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Would it be smart to apply for jobs now or does the situation not look too dire at this point?

I like to avoid layoffs when I can. So, for me, I'd be looking for another job now.

I know some folks who don't mind being laid off and collecting unemployment for a while. They would likely just stick around and see what happens.

You get to decide how "dire" your situation really is, and what (if anything) you want to do about it.

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Would it be smart to apply for jobs now?

Yes.

or does the situation not look too dire at this point?

It looks fairly dire to me.

If you want to stick it out, that's your choice, but I'd be looking for another job rather than crossing my fingers and hoping for the best.

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