Short version: I'd like to hear people's insights on how true it is that it's much more difficult to get hired at a new job if you're not working in a current one.
Some more detail: Work in nonprofit fundraising and event planning. Ready to leave as soon as I can find a job in my preferred field (been looking for several weeks now). That might come in three weeks, or in several months. However, my "busy season" in events is about to pick up in about a month or so, and will continue until the summer. I'd really like to be out of there before it all starts, as I don't look forward to that part of my job anymore, and I might get a new offer elsewhere during the season. I really don't want to leave in the middle of all the planning and executing all this stuff, because I have a good relationship with my boss and coworkers and don't just want to leave them in the lurch.
So I'm considering quitting some time in the next month, giving them time to find and onboard someone new in my position, and in the meantime continuing my job search and hope that something comes down the pipes sooner than later. What gives me pause is the common wisdom that hiring teams prefer to hire people who are currently working (I guess that reflects better on an applicant?). So I do worry that I could be making this more difficult for myself than it's worth by taking such steps. I do have enough saved to cover probably 6 to 8 months of unemployment.
TL:DR, It's roughly a choice between continuing to work and job search until I have a new one, but risk hurting my relationship with current employers if I have to then leave abruptly in a busy time for them, OR setting a sooner, definitive departure date that will probably keep a better relationship, but may be a detriment to my chances of getting hired if I go unemployed for too long. I'd love to hear people's insights on how bad that detriment can be. Thank very much.
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