Are these red flags or just quirks, or, Should I quit a new job?
April 15, 2016 8:44 AM   Subscribe

I was recently hired for a part-time (two days/week) position as an assistant at a small employment services company. After two days of training/work, I feel very uncomfortable about the position and the work environment. I'm considering not going back (I would call/email, of course, I'm not planning to just not show up). However, I've had a really rough year, and don't fully trust my perceptions and decisions. I'm trying to separate new-job-discomfort from this-situation-is-genuinely-weird discomfort, and would love some outside perspective. Additional backstory/context and plenty of details within!

Some backstory that may be relevant/useful: up until February, I spent 2.5 years working for a medium-sized nonprofit. The commute and pay were terrible, and the work itself was often boring/unfulfilling, but I cared a lot about the mission, and the people were generally kind and dedicated. Last fall, I went through a major personal crisis that left me deeply depressed/near-suicidal. I convinced myself I had to change everything about my life and ended up quitting the nonprofit right after they offered me a different, full-time position that would have been more fulfilling (still with the awful commute and pay, though). I had waffled on leaving for a long time pre-crisis, and then my life blew up, so I guess I decided to blow it up even more.

I've regretted the decision a great deal, but have also appreciated the time off to recover and work on healthier life habits (therapy, exercise, meditation, all that). Frankly, I think I needed the break, but I probably should have asked for a temporary leave instead of quitting outright. It just didn't occur to me that that might be an option until it was too late. I panicked. I feel like I was lost/sleeping for six months, and quitting made me wake up and see what a mess I was in. Anyhow: the mess is made. I have to move on. I've been working to turn this major life upset into an opportunity, building up my writing career (I have a few steady freelance gigs, and it's what I most want to pursue) and trying to figure out what I want my rebuilt life to look like. I'm very fortunate and grateful to have some family help to supplement my freelance income, so I haven't been in real danger, although I want and need to have more, and more steady, income again.

The new part-time job is close to home (I can walk there! nice!) and pays almost 2x/hour as my previous position. Half the time for almost the same amount of money was very appealing, so I applied, interviewed, and accepted the position. But now I'm really struggling with whether to stay or not. I don't want to give too many identifying details (hence going anonymous) but here's a brief (okay, not-so-brief) list of the stuff that makes me want to run screaming. This is all from two days of work/training.

1. It's a very small business (one owner, two associates) and there seems to be a constant level of drama between the people. The majority of my "training" so far has been advice on how to manage personalities. For example, one of them can be texted questions, the other one hates texts and won't respond. The outgoing assistant and owner spent an hour talking about how best to speak with one of the associates about some missing money. Another example: I was instructed to call the associate who hates texting to ask if she had set up a service that was assigned to her; she was very strange on the phone with me, and then emailed the owner to say, "I feel uncomfortable being put in the position of talking to someone I don't know about something you and I are still discussing." I saw the email right away because I have access to the owner's inbox, which this person knows. Every interaction between them is weirdly coded/loaded. There seems to be a constant ballet of passive-agression and walking on glass to keep everyone happy, but it means nothing gets done. It's just a whole lot of DRAMA to walk into in the first week, and I'm very uncomfortable with it.

2. The job was described as being an administrative and communications assistant for the business, but in reality it seems to be more of a personal assistant to the owner, and a lot of the work is managing their business AND personal finances (which was not disclosed in the interview process). They have an office for seeing clients, but the two days I work are from their home, working on my own laptop while they work on theirs. I'm not confident in the business practices...there's been a lot of talk about moving money around between accounts to make sure certain things get covered, and it's not clear whether business accounts and persona accounts are separate. The outgoing assistant told me that they always gets paid, whatever else is going on...but it felt very strange that they had to emphasize that to me. Like, "This stuff is a MESS, but don't worry, you'll get yours."

3. The owner conducts all of their business through a single gmail account that is also their personal account. All of the work for my position is conducted through the same account -- I have constant access to their emails. In the first two days, I saw several VERY personal things that I would really prefer not to know about my boss. I also saw some discussion of me as a potential hire, abd check-ins with a friend about "how it's going with the new assistant," etc. This is all just sitting in a stuffed inbox, and according to the outgoing assistant, there's not much room to change these systems. It is what it is, this is how they do business, my job is to keep up.

4. The outgoing person has been working as a contractor; the owner wants to hire me on as an employee, but had nothing in place to do so. The outgoing person has been working to set up all the necessary paperwork (including getting an EIN for the owner, finding someone to do payroll, etc.). It looks like I'll essentially be in charge of hiring myself. This feels really uncomfortable and strange, but I don't know if it's common in very small businesses?

5. There are more little examples of general weirdness I could share; I guess I'm most concerned about the whole feel/atmosphere of the business. It's an employment services agency providing career counseling and resume coaching to professionals, but so far it's a shockingly unprofessional work environment, to the degree that I would never recommend them to a friend seeking employment advice. It feels shady, to the degree that I wouldn't be surprised if something illegal was going on. I'm not generally paranoid about stuff like this, and I worry that I sound crazy...I don't know if I'm explaining it well, it just FEELS so strange. Bad vibes all around.

Does this situation sound weird, or am I being unreasonable/overly-sensitive? Is this just how it is in very small businesses? If I quit, of course, there's no guarantee that I'll find another job soon, and it feels crazy to pass up a job that on paper should suit my situation well...but in reality it's SO WEIRD. I am very tempted to quit and keep trying to find something that's a better fit. Am I being crazy?

Thank you for reading this novel and any advice you may have.
posted by anonymous to Work & Money (27 answers total)
I wouldn't blame you for not going back, but so far it mostly sound like the organisation is chaotic rather than that it's an unpleasant environment to work in. Maybe give it a bit longer and look out for (a) if they start dragging you into their dramaz and making you take sides, (b) if they ask you to do something that's clearly financially dodgy, (c) they're going to sink and you won't get paid. At that point, leave for sure.
posted by crocomancer at 8:56 AM on April 15, 2016

That sounds very wierd. I'm a pretty dedicated worker, but that situation throws up lots of flags. I'm sure you could handle it for a while, if you need the money, especially since it's only two days a week, but wow... Those personalities and drama sounds horrible.
posted by hydra77 at 8:57 AM on April 15, 2016

I think there are some people who are really good at working at places like that - it's a very niche culture, though not terribly unusual for small family businesses - and the rest of us are not and it can often turn into one of those frog-boiling situations where two years later you suddenly realize "I don't have to do this."

I personally would stay while looking for the next thing, but I would wrap some safety features into my life (check-ins with my work-wisest friend, standing talking point with therapist, etc) to make sure I don't get Stockholm Syndromed before I can escape.
posted by Lyn Never at 9:01 AM on April 15, 2016 [13 favorites]

It sounds bad, but probably not dangerous bad, and part-time leaves you plenty of time to look for work while maintaining an income. You've might have some room to change things going forward (like getting separate email accounts, oy) but it does sound like this guy hasn't got his shit together at all.

Personal assistant work for an incompetent person sucks, especially when it's not clearly supposed to be personal assistant work. Depends on how badly you need the money and how likely you are to find something more stable soon. And yeah, watch out for the frog-boiling stuff. It's easy to get sucked in and then you've got some fun times rebuilding your mental health afterward.
posted by asperity at 9:04 AM on April 15, 2016 [2 favorites]

Is this just how it is in very small businesses?

I guarantee you there are small businesses that are not some the sort of Game of Thronesian microcosm you're describing but plenty are. This is just part-time though, so keep applying for other stuff and decide for yourself what the last straw for quitting will be in advance (once you get the lay of the land, I mean) and stay vigilant.
posted by griphus at 9:04 AM on April 15, 2016 [5 favorites]

I think your red flag detector is spot-on. That said, given the pay and the two days a week... I might keep it a bit longer? As long as you get paid, don't ask you to do anything illegal and they don't try to drag you into the drama. (Cash those checks immediately.)

If drama is one of those things that gives you hives (metaphorical or otherwise), it's okay to quit.

The suggestion to have check-ins with a good friend and/or a therapist is a good one.
posted by purple_bird at 9:07 AM on April 15, 2016 [1 favorite]


None of that is "fairly normal." Those are deeply crazy dysfunctional people with some money to burn on looking like they have a business. They are playing, and they will play with you. They will use you. There will be giant blow ups, you'll get blamed because their business and finances are messy -- just no no no.

This is not a healthier environment! Run!
posted by jbenben at 9:07 AM on April 15, 2016 [6 favorites]

It does sound weird, so you have to decide whether the pay is sufficient to cover the weirdness for you, for now. Obviously the other person reached their limit/found something better and departed, and you certainly could too, at any time. Going in for your next shift doesn't mean signing up for life, after all.
posted by teremala at 9:12 AM on April 15, 2016 [1 favorite]

You are part time but will be contacted constantly outside of your work hours because they're a mess. You will be on-call just like all personal assistants are.
posted by jbenben at 9:14 AM on April 15, 2016

Being asked to work outside of paid working hours is a super good last straw.
posted by griphus at 9:15 AM on April 15, 2016 [14 favorites]

You know, the more I think about it, the more I think you should leave. Trust your gut. There are all kinds of red flags here and you are right to pay attention to them. There's value in honoring those emotions--they're what keep you safe and sane. Good luck.
posted by purple_bird at 9:28 AM on April 15, 2016

In some small business cultures, there's an unspoken part of the job description which is "be my personal assistant and yes-man and hired friend and manage my personality problems and social maladjustments".

I've had that job before and balked at all the emotional labour because I didn't expect the drama going in, and as it crept up I felt taken advantage of. But perhaps I could have mentally re-framed my responsibilities to realize that the drama was part of the job, in which case perhaps I could have accepted the extra work before I got irrevocably jaded by it.

If you re-frame your job responsibilities now, you may feel differently and be able to handle the tiptoeing. One thing to remember is that these people you're working for would probably make more money within a larger corporate structure, but some people are just too persnickety for that culture and need a small self-made customized culture that supports their weirdness, so they started their own culture, and you are being paid fairly well to fit into their specific ways. It's up to you to decide if you can add those extra emotional jobs onto your actual job description and if once all that's considered, if you still think the pay is worthwhile.

It can take a specific kind of personality to work well in ego-driven environments like this. In my old workplace (which had a high-drama, hard-to-placate emotional toddler manager at the top of the chain), I noticed that people who were very conciliatory and diplomatic, nurturing, forgiving, soft about deadlines, easygoing, feel-it-out type people really did well. Employees who were efficiency-oriented, protocol-following, naturally critical (even in a constructive way), and/or get-it-done-now type people hated it.

Maybe make a list of both your hard and soft responsibilities:
Answer phones.
Remember that Bill prefers chatting in person, and Lisette prefers to get the cold hard numbers by text.
Buy Bill's birthday cake and then give it to Lisette to give to Bill as if she bought it.
Flatter Lisette before client meetings, praise her after.
Ignore inappropriate emails in group inbox.
Prepare final report deck.

Once it's all on paper, if all these jobs still feel ok for the salary, it may be easier to stay (but maybe keep looking? My sense from your question is that you just may not be the type who will enjoy all of this even if you add it to your mental job description- and that is totally ok, because this kinda work is kinda bullshit!)
posted by pseudostrabismus at 9:29 AM on April 15, 2016 [8 favorites]

This sounds really sketchy, BUT. It doesn't sound like you feel like you're in physical danger, and it does sound like they're reliable about making payroll. Having a job as opposed to being unemployed can be a big plus in getting hired elsewhere, and at two days a week it sounds like you'd have plenty of time to continue your job search. I would keep this job FOR NOW so you can pull in the money and also be able to say you are currently employed, but also keep looking for a different job so you can move on as soon as possible - it sounds like it would be really frustrating to stay there long term.
posted by rainbowbrite at 9:30 AM on April 15, 2016 [13 favorites]

I'd say be actively looking for a different job. It sounds like the only good this job will do for you is (probably) give you a paycheck. From my experience being a personal assistant, you really need to have the right personality for it and/or have similar values to your boss. That wasn't me, and I also just felt awkward working in someone's home (it was like being a guest, but for a whole work day). Maybe something to think about!
posted by Baethan at 9:32 AM on April 15, 2016 [1 favorite]

I think it sounds disorganized, and maybe dysfunctional, but I wouldn't leap to the conclusion that they're doing anything illegal. So what if you have to organize the paperwork to get yourself in as an employee--knowing how to get an EIN number could be useful in the future. Moving money from account to account isn't unknown for people who have small businesses or are self-employed. If they were washing money for the mob, they wouldn't have US bank accounts.
You could suggest to your boss that a separate email account for you might make things easier for him.
Yes, trust your gut, and all that, but unless you've got some other likely prospects, I'd say that doing this gig for a while and keep looking for a better fit.
posted by Ideefixe at 9:39 AM on April 15, 2016

It's only two days a week, so stay for now, but start looking for another job immediately. Because this is one major clusterfuck.
posted by MexicanYenta at 9:42 AM on April 15, 2016 [3 favorites]

I would stay, but maintain clear boundaries, and start looking for a better job. You have nothing to lose by putting your foot down about things like being contacted outside of work—if they ask why you aren't responding to texts or emails or whatever outside of working hours, just say "That's not in my job description. If you want to negotiate an on-call arrangement that covers things like that, we can do it but I'll expect to be paid." Basically, do no more than the minimum required by your job description or whatever was discussed in your hiring interview (if you have no official job description) and refuse to budge on being asked to do more without being paid more.

You are there to collect a paycheck and so that you can tell future employers that you are currently employed. You are not trying to make friends, build a career, or burnish your resume. You owe your current employer nothing more than to fulfill your basic duties, and you should expect nothing more than a regular paycheck. Do what you must, two days a week, to be able to keep collecting that paycheck until you find a job at a better-run organization. They don't get free extras from you. This is a business relationship. Compartmentalize it and be strict about your boundaries.

If they don't like it, they can fire you, which would be no big loss to you. You're on the fence about staying anyway, so being fired would force your hand but that's all. Even if that happens, you'll have the money that you made and the head start on a new job search, so you'll come out ahead compared to where you would be if you quit today. They probably won't though; it's usually easier to let an employee scrape by on the bare minimum.

What they don't get to do is yell at you, harass you, undermine you, or insist that you do work that's outside the scope of your job as described when you were hired without having an agreement in writing. If they try to pull any of that crap, you can quit. You can quit on the spot, if you so choose. Don't be afraid to do so if they refuse to respect your boundaries. You owe them nothing outside of the basic time-for-money trade described in your contract.

So I say stay, look for another job, and do no more than the absolute minimum. That is a perfectly acceptable way to approach a crappy job at a dysfunctional company.
posted by Anticipation Of A New Lover's Arrival, The at 10:04 AM on April 15, 2016 [7 favorites]

1. It's a very small business (one owner, two associates) and there seems to be a constant level of drama between the people. The majority of my "training" so far has been advice on how to manage personalities.

This is how far I got before I decided that I would walk away were I in your shoes. Nothing you wrote after that convinced me that my first impression was wrong.

Granted, I've pretty much always worked for big, fortune 500 corporations but everything about that company seems totally weird.

You might not be able to trust the degree of your perceptions but you can certainly trust the direction. And I really don't think you're over-estimating the degree to which this stuff is weird either.

I'd at least proceed cautiously and assume that you're going to leave unless things improve.
posted by VTX at 10:05 AM on April 15, 2016

Does this situation sound weird, or am I being unreasonable/overly-sensitive?

It sound like your current need for high structure and this low-structure seat-of-the-pants kind of job are not a great fit.

You're in an office that sounds like the far end of the one-off, just do it and don't care about process kind of positions where results are all that matter. It's impossible to say if they're currently doing anything specifically illegal, but it does sound like the place where the edges may well be skirted on a regular basis. Some people love this free-wheeling environment. It can provide a lot of freedom and allows for a lot of creativity, but, as you note, that requires a lot of personal reserves and the capacity to deal with a lot of crap from others, bosses and co-workers.

I think you need, and should seek, a job that doesn't make those demands of you, one that provides a stable routine, detailed job descriptions with a formal working culture. That likely means large corporation, organization or government.

I'd treat this as a short term gig until you can find more permanent work that suits you better in a lower-intensity, more highly structured environment.
posted by bonehead at 10:07 AM on April 15, 2016 [2 favorites]

I work in something kinda similar... a lot of ego massaging for the bosses, being asked ridiculous things, dealing with them freaking out over nothing. . . and while at first I found it absurd, overwhelming and stupid, I actually find it has given me a lot more interpersonal confidence to know how to deal with any type of personality and not be intimidated by people. It helps build assertiveness and is forcing me to learn how to better express myself since I'm naturally timid but not a pushover. So that is a benefit.
As long as it doesnt negatively impact your health
posted by winterportage at 10:08 AM on April 15, 2016 [3 favorites]

It doesn't sound like it's set up to run professionally, but nothing you mention sounds unethical (although the moving-money-between-accounts might border on that, depending on the details). It sounds like they are seeking to get more professional (the EIN). And wherever you go, managing personalities and knowing how someone's communication preferences and how best to get a reply from someone will be part of your job.
posted by salvia at 10:38 AM on April 15, 2016

I moved from a corporate job to a small individually-owned business and the adjustment was hard. But after a while, I found that I really did enjoy the new job. There was the much more casual atmosphere, the stronger emphasis on personalities, and blended boundaries. The openness was uncomfortable at first. I was used to having a personal life and a separate professional persona, with not a lot of carry-over. I found that after the initial adjustment, I was much more free to be myself, to be self-driven, and to be able to make changes on the fly. For me, it was a better Life-work balance, more creative and engaging, and more fulfilling.
posted by raisingsand at 10:45 AM on April 15, 2016

I was sort of on the fence about most of what you mention and was going to nth sticking around just long enough to find another job. Then you said this:

...a lot of the work is managing their business AND personal finances (which was not disclosed in the interview process)....the two days I work are from their home, working on my own laptop while they work on theirs. I'm not confident in the business practices...there's been a lot of talk about moving money around between accounts to make sure certain things get covered, and it's not clear whether business accounts and persona accounts are separate."

When it comes to possibly sketchy business and accounting practices, I'd be reluctant to manage administrative and accounting tasks on their computer system. There's no way in hell I'd do it on my own laptop. I strongly advise leaving now.
posted by _Mona_ at 10:45 AM on April 15, 2016 [5 favorites]

Since part of your big question is should you quit, there is one aspect that I don't think anyone else has pointed out yet:

...ended up quitting the nonprofit right after they offered me a different, full-time position that would have been more fulfilling (still with the awful commute and pay, though). ...

...I've regretted the decision a great deal...

If you liked the former job and many of the things that you wanted (and it sounds like new tools to move forward), contact them again. Right now. Is that position still available or a similar one? It might solve your entire problem.

I'm not sure if the job you are in now has red flags or not (for some people yes, other people no), but my concern more is about you, OP. From your description, you are starting on shaky grounds from what you have gone through, and it might not be healthy for you.

The good thing is sounds like there is lots of down time to look for another job.

Also, one more thing that I see in your post. If you are looking to eventually do freelance writing - can you look for a job that includes significantly more writing? For myself, this was what made the transition much, much easier (from professional samples to having contacts). So you could hold out until you get such a job if it is present (or maybe grant writing, anything that you can be hired for eventually on a freelance basis if that is what you are looking for as an end game.)

Good luck.
posted by Wolfster at 11:04 AM on April 15, 2016 [4 favorites]

See if you can push back on some of the most critical stuff (like the bring your own laptop crap.) They may be willing to professionalize things enough to where your job is a lot more comfortable.

I will tell you that my experience with non-managerial types leading offices makes me think they'd probably run a business in the way you describe. I've also had to work sorting out someone's invoices and other paperwork (years of them) in their bedroom. She paid the agency for six months of full-time labor and then I got through it all in a few weeks because she had no idea how much time the actual tasks were supposed to take, presumably because she simply never did it at all.

Anyway, I'd give "pushing back" a shot before quitting. Heck, you could be the savior of their operation!
posted by SMPA at 11:09 AM on April 15, 2016

The using your own laptop thing is a non-starter all by itself. When this shit-show blows up, your laptop could end up being evidence for forensic accountants or law enforcement. No, this is not the likeliest of scenarios, but neither is your taking their financial records and publishing them on the web. Either is *possible* in the current regime, and either is bad.

Yikes. Just a big old bottle of no.
posted by Emperor SnooKloze at 1:15 PM on April 15, 2016 [3 favorites]

there's been a lot of talk about moving money around between accounts to make sure certain things get covered, and it's not clear whether business accounts and persona accounts are separate.

For me, this is a red flag. If you're helping manage their personal finances, and either the IRS or your state tax board comes calling, what's to keep them from putting the blame on you, and throwing you under the bus?

Also, frequently moving money between accounts sounds like a pretext to you either not timely receiving your paycheck, or having it bounce.
posted by invisible ink at 5:43 PM on April 15, 2016 [1 favorite]

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