Putting my persuasive skills to use for rehiring - advice?

Do not apply for this job if you do not plan to stay with it through the black-out holiday period. Because if you get it, and leave a third time during the holidays, those bridges will be more burned than a really really burnt thing.

Go ahead and ask, but accept in your heart that this job means you aren't seeing your parents for Christmas. If you can't accept and be ok with this, then you shouldn't try to go back to this job. They are very clear about this rule, and of course your availability during peak times should play a factor in rehiring. "Technically" they can (and probably should) fire you if you leave during Christmas this year, regardless of when the flights were booked. Plan on an early December or late January family get together instead (and if there are other siblings or whatever involved get them to agree now -- there's nothing special about the date, it's about everyone getting together, so find a date that works. Bonus: everything (flights + gifts) is way cheaper after Christmas). As for what to email, I don't think you need to be super persuasive/salesman-y, but you might want to explain why you left, and why that's no longer an issue now (and while I wouldn't lie or completely make something up here, you also shouldn't feel obligated to tell the whole truth here... find some aspect of the truth that is also a good story), and say you are interested in coming back and prepared to stay and work through the Christmas season and beyond, and ask if there are any openings available.

You should definitely go back! I was given the recommendation from a current employee (subordinate) to email my former boss (aka, the store general manager) instead of taking the roundabout routes I took (as mentioned in [c] above). Yes, I agree with the current employee that you should email your old boss and ask if you can come back. If you were a good worker (which it sounds like you were), she'll probably be able to get you a re-hire (which is sometimes easier than a new hiring, depends on the company). As a data point, I did this with a large restaurant chain and it worked out really well. I was moving out of the area, left under kind of a cloud because I ended up not being able to put in my full notice period (moving stuff got overwhelming and I had to put in extra hours there, so couldn't work my last couple shifts), but I had been a good worker overall and when I reached out to my old boss she was happy to have me back. I reached out to ask about being rehired by calling my old restaurant and asking for an appointment to see my GM. I showed up for the appointment in interview-ready clothes with a sorta cover letter saying how much I wanted to work at the restaurant again and a resume, and straight up asked my GM my old job back. She was very easygoing about it (way more so than I expected) and everything was great. Being (officially) a re-hire rather than a new hire meant that I didn't have to get knocked back to square one in terms of have to re-do the orientation, or in terms of other bureaucratic issues related to "benefits"/privileges, etc. I pretty much got to step back in where I had left off when I quit the first time. However, I did have to prove myself again to a certain extent because in a business like that, with massive turnover, I was going to back to a staff that had a large percentage of newbies who hadn't worked with me before (though I was only gone about a month!). I'm also not sure if it's a good idea if I go ahead now and book flights for Christmas vacation. No, don't book flights for Christmas vacation. If you are working for a company that blacks out leave during the Christmas season, you DON'T HAVE a Christmas vacation. You can take a vacation at other times but ABSOLUTELY PLAN TO BE WORKING OVER CHRISTMAS. That's just the nature of the beast if you're working in retail. There are pretty comparable situations in other industries, too, if that makes you feel better -- accountants in the US can't have "spring break," for example, because that's the height of tax season. Some industries just have a heavy season when companies make a huge percentage of their money and workers in those industries have to accept/adapt to that, and retail is definitely one of those industries. If that's not something you're willing to deal with, then you can't work for this company (or probably in retail), which doesn't allow leave over Christmas. Even though it's a "job" rather than a "career," this will be how you're making a living, and you have to be willing to prioritize and adapt to that to a certain extent.

It would be resigning then, just maybe not entirely by your choice. It is 100% not an option for you to have this job & see your family then. The fact that you may have spent $xxx on plane tickets is not relevant to your employer if they have a Christmas blackout rule, and a jaguar says probably even asking would be a bridge-burning fiesta.

It's one thing for a totally new employee to say "oh, but I already have tickets for Christmas" because then it is at least feasibly something they didn't know, it's another thing for someone who used to work there and knowing the blackout took extra time one year then resigned the next year. I'd really appreciate your help and advice on how to best navigate this to get the results I want. If you work there again, you'll be working there over Christmas. The results you want -- to be hired there but also to be across the country over the holidays -- are not possible to get. You might be able to get rehired, but when you speak to your ex-boss you will be saying "and I know that there is a blackout date, and I have already told my family that I will not be leaving DC in December". And then you need to follow through.

I've worked retail (national chain). I've worked holiday periods (they suck, overtime notwithstanding). If you buy plane tickets and don't mention it and they hire you, they can absolutely withdraw the offer or fire you once you tell them you have plane tickets and want whatever days off. There's nothing illegal about it, and given your last holiday-related experiences with this, I don't understand why you don't understand that retail-worker holidays blackouts is how it works. You have to choose; your potential future employer does not have to keep you on staff just because you bought tickets.

Look, you basically have a history of screwing over this retailer due to your vacations. You should not ask this particular store for any consideration of any of your vacation plans while asking them for your job back, because you will demonstrate that you are once again prioritizing your vacation schedule over their needs. As a human being, you certainly should prioritize your own life over a crappy-ish retail job, but you are not coming to them as a human being, you are coming to them as a potential employee. Retail employees with vacation-related strikes against them do not have leverage to ask for additional vacation-related considerations. If you want to work retail, are willing to work over the holiday season, and need to take a week in October, I'd recommend applying for a job at a totally different retail store. If you want to prioritize spending time with your family and friends (which is absolutely a valid choice), then temp work or some sort of office job might be a much much better fit.

When I first started reading this Ask, I was inclined to be sympathetic. I left a long-term, stable position at a good retail job a couple of years ago, myself. Like you, part of the reason I left was burnout, which doesn't seem as bad in the proverbial rear-view mirror. I still have friends working there who are happy to see me (a trip to the store can take over an hour, just saying howdy), and on days when I'm feeling unsure about my current path I sometimes want to pursue slotting back in. I may yet. I'm not going to laugh at your desire to return. I am going to laugh ruefully at your assumptions and your approach to making that happen, though. Bear with me: I'd really appreciate your help and advice on how to best navigate this to get the results I want. The result you want is to get your old job back, but you also want a fantasy version of that job. You won't be able to navigate anything until this is resolved. It seems like you don't grasp how the retail world functions. You need to really examine whether you fit in that type of work, or even the service industries in general. At this point, without a significant adjustment in expectations, I suspect your request to re-up will be laughed at, thrown in the trash, and that trash can burned with fire. Retail workers -- at all levels -- just work during holidays. It's not fair. But it's the reality of the work, even at the best of employers. This one did you a kindness by allowing you time off for family reasons, which you proceeded to disrespect significantly (like, firing offense significantly). This was surely irritating and somewhat embarrassing for the manager who probably pulled strings/cashed favors to make it possible. Not only that, but you inconvenienced your coworkers, who had to work harder during an already stressful time; I wonder if any of them had sick relatives? Then, just one year later, you quit in order to visit your family again (and because all your friends got to visit theirs?). The message you've sent them so far is that, while you may be a high-quality employee when you're there, you aren't willing to actually be there. No surprise that you didn't get a pleasant official response to your resignation letter, and no surprise that they haven't eagerly responded to your renewed interest. They may positively love you as a person, but you've given them every reason to be wary of you as an employee. If you really want this job back, my advice is to completely forget about vacations for at minimum six months. When you talk to whichever manager you think might be willing to give you the time, make this absolutely clear. And I don't mean you saying, "So I'll just take my Xmas vacation in February, right?" I mean, "I know my reliability has been an issue, and I'm committed to improving. You'll have me through the holiday period, no question. Seeing my family is important, but we can revisit that during the slower months." The priority should be on demonstrating your willingness to step up, not on trying to secure a specific vacation window before you've even been rehired. Who knows -- it might work; my former retail employer hired people back, but only if they'd either been extremely dependable during their previous tenure, or had made concrete and sincere efforts to change problem behavior. Larger picture, this tension between personal freedom and the needs of the employer is simply something that you'll struggle with in any line of work. White collar, service, what have you. It's possible that retail work (with its tight margins and tighter labor budgets) won't allow you the flexibility you want. Something that isn't as dependent on specific employees doing specific tasks during specific times may be a better fit.

You don't want the job enough to give up holidays with your family. It's a retail job, and they treat employees as a commodity, so for the most part I'd say 'screw 'em' regarding taking the holiday off. But it does put a burden on the coworkers who have to cover that time. Plus, if there's any time off at all, it should be someone else's turn. I think you have a blind spot about the reality of working retail - for most retailers, the Thanksgiving - Christmas season is a huge percentage of their business. They schedule staff to make sure sales are optimized. If you can't work at Christmas, you should consider other employment options.