updates: using time off to nanny, the Secret Santa gift, and more

by Alison Green on May 25, 2020

It’s a special “where are you now?” season at Ask a Manager, when I’m running updates from people who had their letters here answered in the past. Here are three updates from past letter-writers.

1. Can I used my unlimited time off to do part-time nanny work?

I thought I’d write in to your request for updates, since this is an interesting time to revisit the question you answered for me in 2018, when I wondered if I could use my employer’s unlimited time off to do occasional nanny work.

Almost everyone agreed this was a Bad Idea – maybe traveling with them could be ok, but I should steer clear of days off of school, sick days, and pickups/dropoffs. I ended up doing all of it anyway. Honestly? It worked out really well. Reading through the comments, a couple of unique things about my situation weren’t clear from my letter:
• I work at a tech company in San Francisco. It seems like we have a pretty different set of cultural expectations around work, flexibility, and time off than a lot of other places and industries.
• In addition to the “Unlimited Discretionary Time Off” policy, we also have flexible scheduling. My manager, for example, usually works 7-3, and another team member works 8-6:30 Monday-Thursday but hasn’t been online for a single Friday that I can remember. Most people work standard 9-5 ish hours but use the flexibility to make room for doctors appointments, time with their kids, recreational sports leagues, band gigs, a long weekend here and there…or whatever. I don’t even usually know.
• My team is spread across 6 different timezones, so someone is always offline for one reason or another, and we don’t really keep track of why.
• There is almost never a situation where leaving for a day or an hour means someone needs to cover for me.
• The nanny “work” is something I find energizing and enjoyable. I would do it for fun and for free.

Even though I ended up doing the opposite of what you recommended, reading through your advice and all of the comments really helped me think it through and make a clear-headed decision. I did ask my manager about it, because I’m the kind of person who asks permission instead of forgiveness about things like this. She had no problem with it, and was actually relieved that I was planning to use some time off and flexibility. I traveled with them for two trips that first year, one last year, and did several long weekends with them. I’ve done one or two sick days, and left work a little early to pick up their daughter maybe five or six times total since writing in. As I said, my manager leaves at 3, so I don’t think she even noticed, although I did put it on my availability calendar. Only once have I had to say no to a childcare request because of a work priority – it wasn’t an issue. We don’t track so I can’t say for sure, but even with this, and some time off that didn’t include the family, I think I take less time off than most people on my team.

Now in 2020, I’m still at the same company. Two promotions later I think I can safely say this hasn’t impacted my standing at all. I also still have a great relationship with the family. My partner and I are actually sheltered in place with them right now, in an odd twist – they have a second home with a guest house outside of the city, and invited us up to join them when it started, since there’s more space to work from home and safer social distance here than in our apartment building. We’re here as family friends; I’m not doing childcare.

I know this is a weird situation, and I do understand why everyone advised against it. For me, the stars kind of aligned to make it work.

2. Can I put an opportunity on hold for a few years? (#5 at the link)

I delivered a version of your suggested response to them and thankfully I had already been open from the beginning of the process that I wasn’t looking to move right away but was interested in the company. They said they’re open to a longer transition time and moved me forward with the hiring process. Everything went very well and they offered me the job on the condition that I travel once a month to work in person with the team and move next year. After discussions with my husband about our plans, I was happy to accept those terms and started my new job in March! Unfortunately due to COVID-19 the travel is on hold, but otherwise everything is going very well and my new team is finding creative ways to work “together” and keep morale high.

Thank you for your and readers’ advice – seeing it helped me understand how important it is to be up-front about your situation/preferences and also to be flexible if the opportunity is right.

3. Secret Santa gifts with a message (#2 at the link)

I am the high school teacher who wrote in about whether to use a Secret Santa gift as a vehicle for a larger message about implicit racial bias. Thank you so much for publishing my letter and for your thoughtful response and moderation.

I am a white, middle aged female from a racially diverse family that includes German, Puerto Rican, Trinidadian, Italian, Mexican, and Japanese people. I have seen first hand how unfairly my non-white family members have been treated. I teach in a high-profile small career and technical education (what used to be known as vocational) public high school that prepares students for both college and careers in an industry that has been traditionally underrepresented by minorities and women, but is desperate for young talent. Our grads go on to work and study in the field. We are located in Big East Coast City that used to be more diverse but is becoming increasingly segregated.

Some background about why I wrote in: I wrote in the Friday Open Thread about this right after I drew Sam’s name. A spirited discussion ensued, with many terrific titles of books being shared, although the overall advice was to stick to a normal gift. By the end of the discussion, I had decided to get off my soap box and do the normal gift. However, later that night, both my friend who is a teacher and a WOC and my husband, who is of an oppressed ethnic minority (his people are still hunted down in some parts of the world), felt that I SHOULD use the opportunity to make a statement. Then I was all confused and it led me to write directly to you.

To clarify, Sam was defensive and dismissive, as if to say “well of course I do this, it’s not MY fault”, rather than having an “aha” moment. What was not in my original letter is that Sam has said some wonky things before, such as demanding to know what the female chemistry teacher’s qualifications were (on his first day) to expressing disbelief that one of our black teachers was also Puerto Rican and spoke Spanish among other recent bizarre things. Also surprisingly, Sam is in his mid-thirties and has a few years of experience in another minority-prevalent school.

I stand behind my decision to speak to my principal 100%. I will not stand by if there is even a shadow of a question of one of my students being treated unfairly due to race, gender, religion, or ethnicity. I have worked with teachers at a previous school who felt that “THESE” kids only need to be taught enough to fill out a job application at the supermarket and that’s it. These kinds of microaggressions build up and can derail a young person’s life. As for the risk of Sam being fired, we all have a right to due process in the school system I am in, and we are inclined to work to educate each other, not punish. Ignorance is not a permanent state, and my reasons for talking to my principal were rooted in the desire to return to the previous implicit bias training we had before Sam arrived. I felt we needed training like that again.

Anyway, on to the gift! I ended up getting Sam a nice steel travel beverage mug designed with elements from the school’s industry theme filled with chocolates. The organizer collected the gifts and handed them out throughout the day so I didn’t see his reaction when he opened mine. He found me at the end of the day and thanked me, glad that he could now get his to go coffee in a reusable cup. I’m glad I did the right thing and stayed in the spirit of the season.

Unrelated, out of the blue, before the gift exchange Sam asked if he could come and observe me teach some time. It’s odd because we teach opposite ends of the content spectrum, but I told him I had an open door and any time he wanted to come in was fine. Let’s see what happens!

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{ 59 comments }

{ 59 comments… read them below }

  1. Elizabeth*

    Secret Santa – I am so glad this opened the door to future meaningful conversations. You could always leave a book on their box.

    1. Annony*

      I agree. Giving him a book on implicit bias could be a constructive things so long as it is done openly (rather than leaving the book with no note) and not as a gift since it really isn’t meant as one.

      1. Ping*

        You need the relationship before you can initiate the discussion.
        By being kind, the OP has initiated the relationship. This will open up future opportunities for deeper discussion later. It will also allow Sam to put a face and a name to people when they get discriminated against. Instead of “those people” it will be “Mary, Jose, or Tenisha”.

        1. Gruntilda*

          Yes, I think this is the biggest issue for anti-racists: when is the right time to step in? When is our message most effective?
          If OP can build a trusting relationship with Sam, he will be more likely to listen to OP’s message, and it will sink in deeper.
          It takes more patience and kindness and forgiveness to do it this way, rather than “call out/truth bomb drop and write them off/run away” but ultimately I think his students will win out with this method.

    2. The Original K.*

      Me too. I remember the comment/question in an open thread (I think I made a book suggestion).

  2. Observer*

    #3 – I’m glad you used a normal gift, but I also TOTALLY agree that you did the right thing in reporting to the principal.

    Perhaps if you have a different opportunity, you can give him one of the books that was recommended, especially if the training doesn’t happen, or if you have reason to believe that it wasn’t all that effective. That’s a real concern, as there are some good studies that show that many types of training don’t really work the way one would hope.

    1. tangerineRose*

      I’m also glad you reported to the principal.

      And “teachers at a previous school who felt that “THESE” kids only need to be taught enough to fill out a job application at the supermarket and that’s it.” It’s horrible that there are still teachers (or anybody) like this. A society that limits people based on color or gender is a society that is limiting itself, and besides, it’s just mean and unfair.

  3. Madame X*

    1. it sounds like you made the right decision and it worked out really well for you.

  4. Gloria*

    #1: It seems like we have a pretty different set of cultural expectations around work, flexibility, and time off than a lot of other places and industries.

    This is the problem with asking for advice about a really specific situation in a general advice column. Alison’s advice was 100% right; it’s not a good idea to use unlimited PTO to do a second job. The only exception to that, I guess, is if you work in a very casual city for a super flexible employer where people don’t keep track of when other people are working and where coverage is not an issue.

    1. Falling Diphthong*

      And unlimited time off actually means unlimited time off, rather than even less time off.

      1. Kate*

        Would travelling with one’s children and grandchildren count as “time off” for you, or would you rather ban it? I mean one may get left to watch the grandkids in a hotel while parents go to a late show! Heck, would travelling with one’s OWN underage children count as a vacation, really…

        1. Fikly*

          I don’t understand this question at all.

          The issue is about time off from your main employer, not whether or not you are relaxing on a vacation.

          1. Falling Diphthong*

            Yeah, my spouse took time off to help my mother move. It was not a relaxing vacation type thing, but he still had to take time off.

            And yes, I loved traveling with my children when they are small, and would love a future trip with even more grown kids and their children. During which we would offer to babysit–not something we got to do when our kids were tiny.

          2. Kate*

            I think I don’t understand your statement, then. I thought by “unlimited time off mean even less time off” you meant “if you are travelling with a family you are a nanny for then it is not really your time off”.

            1. suprisedcanuk*

              Getting unlimited time off can lead to people taking less time off. It’s hard to know how much time is appropriate to take. If you get 3 or4 weeks of vacation you take it. With unlimited time off it can be tricky.

            2. Fikly*

              There is a common thing where companies that have “unlimited PTO” policies actually have a culture where no one takes any PTO, so it’s unlimited in name only. There is often intense pressure not to take time off, and if you do, you may not only face resentful from your peers and your manager, but it quite often can hold you back from advancing in the company.

              Which is why I like how my company does it – we have unlimited PTO, but we also have guidelines, which is to say, we are told how many days to aim for, and we actually get talked to by our managers if we’re not taking enough (and no one is held to not going over the guideline, either).

              1. JSPA*

                Well, we hear about the ones who do it wrong. Nobody’s complaining about the ones who do it right. Idea jockeys / people whose product is entirely digital and also unconstrained by regulation really can be excellent (and recognized as such) while doubling down on work-life balance–even if “life” includes a nebulous quasi-job / quasi-friendship / quasi-family-relationship that doesn’t fit preconceived molds.

                OP could reframe it as:

                “I see myself, and they see me, as a de-facto adopted part of the family. While they do often supplement my income (and I do call it income, to avoid any tax problems or personal weirdness that might accompany large-ish gifts), the relationship would continue even if no money were involved. Given that they are my de-facto second family, and in many ways my closest family, is it legally problematic to treat “family absences” that involve them the same way I would for flesh-and-blood family? Which, at my job, is completely fine, BTW! If there’s a problem, is it because of bias against “not really relatives,” or is it because they pay me?”

                With that framing (rather than the “working a second job” framing) people might have had an easier time wrapping their heads around the culture, the job requirements, and the closeness.

                But frankly, OP pretty much said all of that; people were just unwilling to hear that there are workplaces that are intentionally configured and run to treat their workers as people first (so long as an excellent job gets done along the way).

                1. Fikly*

                  Given the many studies that have shown workers in the US do not utilize nearly all of their PTO when it’s alloted to them, I do not think it a great leap to think it common that unlimited PTO policies are unlimited in name only.

    2. Carol!*

      I understand wanting to get viewpoints, but OP left out info that could have helped provide better advice. What’s the point of asking for advice when you don’t follow any of it? IMO this is taking advantage of a very generous perk. Abuse it and it could disappear.

      “Two promotions later I think I can safely say this hasn’t impacted my standing at all.” So there!

      1. Gruntilda*

        Yes, this is the problem with advice, especially advice from strangers.
        I’m sure there’s a fable somewhere about this. Like, Frog asks the animals, Should I leave the water and go onto land? Won’t I dry out?
        Elephant says, It’s OK, as long as you go back into the water sometimes.
        Hippo says, Actually it’s better in the water, you should stay there.
        Zebra says, Get out right now! There are crocodiles in there!
        Fish says, Don’t go on land! You’ll die!
        Lion says, Of course you won’t die, that’s ridiculous. I don’t have that problem.

        Ultimately no one knows Frog’s situation so no one can give real advice.

        Maybe the blind men and the elephant is the closest actual fable to this?

      2. JSPA*

        Hm, I didn’t miss her points, and I didn’t think this solution was necessarily impossible.

        Sure, this isn’t a common model. But it’s a basic logic error to move from “I’ve never heard of a job where that would be OK” to “there’s no such job.” There WERE people saying, “it’s rare, but not formally impossible.” There WERE people saying, “clear it with the boss.” There were people saying, “wildly unusual, but great, if it can be done.”

        She CLEARED IT with her boss; how, then, could it possibly be abuse of a perk?

        Why are people so shocked to hear of an open-minded workplace that focuses entirely on, “did you get your work done well, coordinate well with your team, be great to work with and well-worth what we pay you,” and has NO “butts in seats” requirement? They don’t generally become gigantic household names, but they just as certainly do exist.

        There’s a difference between warning people that unicorns are mythological, and insisting that narwhals are mythological, too.

        1. ThisColumnMakesMeGratefulForMyBoss*

          This is beyond open minded though. No matter how flexible a company is, I would be willing to bet that the majority of them that have an unusually flexible unlimited time off policy would not encourage taking your unlimited PTO to work a second job. I feel like this is taking advantage of a situation, and if OP leaves for another company, is going to get hit with a reality check that it’s not even close to the norm.

          1. Swiftly Tilting Planet*

            She’s taking advantage of…the fact her boss said it was perfectly ok to do so?

        2. Tech employee*

          Yes to this! I work at a company with unlimited PTO as well, and I think people could care less about how employees are spending their PTO, as long as they aren’t taking egregious amounts of it compared to everyone else. (I’ve been told the guideline is around five weeks, so as long as you aren’t taking an amount of PTO that is noticeably way above the guideline and are still performing well, you should be fine.)

          1. Tech employee*

            If one person is taking five weeks off to go on vacation, and one person is taking five weeks off to nanny on the side because that’s how they prefer to spend their time off – what is the difference to the employer really?

      3. kt*

        The point of asking for advice is to see if there are things you didn’t think of, things you didn’t weight properly in your initial assessment, etc. It’s to help you through the considerations. In the end, though, we all have to make our own decisions. Asking advice is not “having a stranger decide what you must do”. Sounds to me like the letter-writer used AAM as intended!

        1. A*

          I think the point that was being made is that the original letter did not include some very important contextual info that would have been helpful to know regardless of the question being asked.

      4. Fikly*

        Well, the point is that the advice helped OP to think through and make their decision, as they stated, even if their decision wasn’t what the concensus of the advice was.

        People who give advice and then are annoyed when a person doesn’t follow it and it works out for them – oooh, that’s just making it all about them, not actually the person they claim to be trying to help.

      5. MCMonkeyBean*

        Personally, I don’t think any of the additional info OP provided makes it any more of a good idea with one huge exception: the manager saying it’s okay. It sounds super weird to me, but if her manager doesn’t care then I guess that’s really all that matters at the end of the day!

  6. Contrarian*

    #1, good for you! It takes guts to go against the hive mind around here. You made the right decision.

  7. NeonFireworks*

    Can I just say kudos to Alison for posting updates non-judgmentally even when they involve the OP making a very different decision from what was advised?

    1. Batty Twerp*

      It’s a proper mixed bag of updates! But I’m glad for every one of them that things turned out well for them all.

    2. Glenn*

      I’ve seen her do it both ways — there have definitely been updates where she added an editorial comment about how the OP is still a nutball. But they’re pretty rare! (And I think they tend to be reserved for the people who are totally un-self-aware. This OP clearly did the right thing — if you _ask_ the boss, and the boss says yes, that trumps Internet advice in any event.)

      1. Filosofickle*

        Right, that’s the most important part of this story! She asked her boss, and boss okayed it. Was it risky to even ask? Sure. Most commenters wouldn’t have recommended that. But she took the chance, got permission, and it worked out great.

        1. tangerineRose*

          I thought asking for permission was a better idea than just doing it without permission.

    3. Analytical Tree Hugger*

      Also, AAM has said a few times that she appreciates folks sharing updates even if they didn’t follow the advice, because it’s interesting to hear what they did decide to do and why they did so.

      Also, thank you for updating, LW1! And to AAM for the column and organizing these updates.

      1. nonegiven*

        >because it’s interesting to hear what they did decide to do and why they did so.

        …and how it turned out

  8. Retail not Retail*

    I might have done #1 this summer if things hadn’t gone crazy. We don’t have unlimited PTO but we do have more than I was expecting.

    I got a job at local stadium and I was willing to use a personal or vacation day if there was an important day time event. The boss and people who’d done before said there are no mandatory games, people work which ones they can.

    (Covid note – the day the nba suspended play 40 minutes went by between emails saying “who can work saturday’s game” and “nevermind sports are cancelled we’ll keep you updated.” It’s not for basketball though, more outdoors work.)

  9. juliebulie*

    #3’s husband “his people are still hunted down in some parts of the world” WHAAAAAT?

      1. StrikingFalcon*

        I can’t tell if you’re surprised to learn this still happens or if you’re wondering how this relates to the question, but to give some examples of recent attacks causing genocide or mass displacement: 6.5 million have fled Syria in fear for their lives; the 2016- 2017 attacks on the Rohingya in Burma/Myanmar killed 24,000 and displaced 625,000; and the 2014 attacks against the Yezidi in Iraq killed many and displaced 800,000. There are many other groups – ethnic, religious, or other identities – facing threats on both small and large scales. As to it’s relevance to the question – I‘m assuming it was included to explain why her husband cares about racism.

            1. RebelwithMouseyHair*

              Well mostly to be able to kill them you need to first hunt them down. Speaking as the partner of a former refugee, I can assure you that scenes in films with lines like “I will find you and I will kill you” can strike fear into hearts.

        2. long summer*

          To be honest, I had the same startled reaction as juliebulie. It’s a startling statement!–I had no idea that there existed any ethnicity that is, today, regularly hunted by their presumably-dominant-majority neighbors, and in multiple parts of the world. (To tell the truth, it’s so disturbing that I’ve been wracking my brain over it.)

          In the case of the Syrian displacement, the conflict is not really rooted in ethnicity. As Fake Old Converse Shoes mentioned, albino people are at serious risk of hunting and murder for ‘medicine’ rituals in some places in eastern and southern Africa, e.g. Tanzania–but, of course, albinos are not an ethnic group. There have been accusations of people hunting and eating Pygmies in DR Congo, but Pygmies are such a small ethnic group, and so few of them leave their home regions, that I don’t think they live in more than one part of the world.

          Perhaps an oppressed religious minority is in fact most likely. The Rohingya have indeed been hunted by Myanmar’s armed forces; that is a terrible situation. The Yazidis suffered badly from ISIL. Or, perhaps, in some parts of the world, Romany, or Jews.

          1. Observer*

            The Uyghurs are definitely targeted by the Chinese, and they can be targeted even if they are not in China. In fact on recent security story in the smartphone space was an iPhone hack that was almost certainly done by the Chinese government specifically targeted against Uyghurs.

            So, yeah, this stuff exists.

          2. JSPA*

            I thought of the Royhinga first. The Kurds have been on several nations’ hit lists. And I think one could define at least two, possibly more genocidal sweeps in the greater Sudan area (western Sudan and South Sudan for sure). And then, indigenous peoples are still being targeted very intentionally in parts of the Amazon.

            As we move closer to home (wherever “home” is for each of us) these statements will be seen as “politics” rather than facts, so I suppose I’ll mostly leave it there…except to say, there have been an awful lot of “verb-ing while [member of group]” shootings right in the USA, to the point where anyone of [group] could legitimately fear being hunted during one or another relatively normal daily activity.

          3. Cloudy With a Chance of Meatballs*

            It also startled me (the “hunted down” language specifically), but I have read about asylum seekers in the U.S. who belong to tiny ethnic minorities that have been relentlessly persecuted by the dominant group in their country/region.

          4. RebelwithMouseyHair*

            it can be startling for Westerners. We live such cosseted lives, we have no idea what other people go through.

    2. Fake Old Converse Shoes (not in the US)*

      Albino populations in Africa came immediately to my mind, they’ve been hunt down for ages for ritual purposes.

    3. Black Horse Dancing*

      LGBT people are murdered or hunted across the globe. The statement doesn’t surprise me in the least.

    5. Meyers and Briggs were not real doctors*

      My assumption was albino Africans, but I’m only familiar with West Africa (Guinea in particular).

  10. Vgraham*

    You “planted a seed” and maybe it will take root and change the way one person sees the world! Thank you.

  11. Blueberry*

    #3 — I remember your letter and the discussion very well (I cried over it). I can’t possibly tell you how grateful and impressed with you I am that you care, and how glad I am that you weren’t put off by the naysayers and racism-apologists in the comments. There are kids whose lives have been and will be changed because you’re in their corner; the world is better because you’re in it. Thank you.

    1. Malty*

      Agreed – you are awesome LW3, I’m so glad there are teachers like you in the world

  12. MonkeyPrincess*

    #2 might want to check out the book “The New Kid,” by Jerry Craft. It’s a YA graphic novel (the first graphic novel to ever win a Newbury Award!) that’s basically about racial microagressions in a school environment. I think that it would make an excellent all-staff read at any school.

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