I am currently working at a software-development job I'm not fond of my salary (which is below the industry average), benefits that I do not need, and there are no career advancement prospects. I would like to search for a different job, but various commitments in my personal life make it difficult for me to find much free time I can commit to the job-search.

I am considering quitting my current job and using the time that has been freed up for my job search, but my friends who are not in the software industry, strongly advised against this. When I asked why, they gave a nebulous "It's easier to find a job while you have a job" response without giving specific reasons. This brings me to the crux of my question - will quitting my current job make it harder for me to find a new one? Are there any other issues with quitting my job that I am not aware of?

Some things I am not concerned about:

  • Appearance of 'job-hopping' - This is my first job and I have it for a couple of years
  • Lack of income - I have almost two years' salary saved up and I've kept my living expenses low
  • Contract-related problems - I'm pretty sure my contract does not include any non-compete clauses or anything that makes it more difficult to quit
  • Not finding a new job immediately - It took me a couple months to find my current job after I graduated college, and I'm fine spending two or three months unemployed. If I don't find a new job immediately, I plan to dedicate some time to personal projects, online classes, and building up a small github portfolio.
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    If money isn't an issue, my advice would be to free up some time by taking non-paid leave, depending on what's possible in your region. That way you're still technically employed... – Laurent S. Dec 3 '18 at 9:43

Being unemployed while searching for a job confers a number of disadvantages:

  • You don't know how long you'll be unemployed for. You say you're fine spending 2-3 months unemployed, but what if it was double that? Exactly how long you'll be unemployed for is a bit of a black box so it's a gamble. You say you're personally fine with this but it's a sticking point for many people so I feel it's still worth highlighting.
  • Employers can take being unemployed as a sign of desperation and attempt to lowball you on salary negotiations, since they figure you 'need the job' and, if you're on month 5 of your planned 2/3 months unemployment, you may well be.
  • It's unusual to leave a job without another one lined up, so I feel they are more likely to scrutinise your last job and what you have done since. Why did they leave their last job without another one lined up? Were they forced out? These questions generally don't arise if you're already employed while looking.

Anecdotally, however, it's entirely possible to do so and twice now I have personally found jobs in software development after stints of unemployment. It entirely depends on what position you're going for, what your skills/CV looks like and how desperate the company is to hire. In my case I have a strong CV and the local area has a significant lack of people with my skills, so periods of unemployment were largely glossed over.

It's not a great answer, but unfortunately 'it depends' is closest to the truth. On balance, being unemployed during a job search does disadvantage you, but the difference may be minimal if you work in a field where candidates are in high demand and you have a good CV.

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