An Advice Columnist Roundtable Featuring “Ask A Manager” and Businesslady, Continued!

Part II of II: in which the columnists reflect on column-ing, service and retail jobs, and more

Central Intelligence, and also how every advice columnist feels

Check out Part I of the chat, with Alison from “Ask a Manager” and Ms. Businesslady, now of the Billfold, here!

An Advice Columnist Roundtable, Featuring “Ask A Manager” and Businesslady!

BUSINESSLADY: Thinking about workplace missteps dovetails with one of the things I wanted to ask Alison about, which is keeping benefit-of-the-doubt in check. I’m always trying to read letters through the lens of, “How much is this person trying to spin things in their favor?” I want to believe everyone has pure, conscientious intentions, so when I first started out, I had to remember to ask myself, What if this person is secretly a clone of my worst, most slacker-y coworker?

ALISON: I think about this all the time! By definition, we’re only getting one side of the story, and it’s possible that if someone else involved wrote in, we’d have a very different take on it. But I think that’s okay, because whatever the rest of the story is, the audience is so much broader than that one person. So it’s providing useful info for other people who are in similar situations, even if it turns out that the letter-writer is entirely delusional.

A couple of times, I’ve actually been contacted by coworkers of a letter-writer to say “Uh, this is not an accurate version of the situation.” Which is of course fascinating.

ESTER: Ooh, yes, controversy! Can you tell us more?

ALISON: Once I was contacted by someone who said, essentially, “Everyone in our small community knows who this letter-writer is, she’s alleging things that didn’t happen, and it’s causing problems for us,” and I actually took the letter down, which I don’t think I’ve done other than that one time. A couple of other times, it was just “I know this person and I want to tell you the other side of the story but don’t print it” — which is great for feeding my curiosity, but I’d love it if I was ever allowed to print those counterpoints.

What I would really love is a situation where both people involved in a situation decided jointly to send in their sides of the situation and would let me print both together! I think Carolyn Hax once did a call for that sort of thing but I never saw it happen, which maybe indicates no one will do it.

BUSINESSLADY: I’d love that too! Like mediation. I feel like Dan Savage did that once but I may just be making that up. Then again, if the people are putting that much joint effort into describing the problem, it would probably lead to some kind of resolution without a columnist getting involved.

ESTER: I was struck by the way the intern in their letter to Ask A Manager mentioned that this gig was their first ever because their focus had always been on studying. Presumably the intern never had to work at Mrs. Fields.

about those interns fired for petitioning for a more casual dress code… – Ask a Manager

Did you have service jobs like that, Businesslady, or were you one of those kids whose parents told you your job was to do well in school?

BUSINESSLADY: I absolutely had service jobs! I feel like those are much better preparation for the “real world” than people give them credit for. Because the same skills you use for cranky customers will serve you well when dealing with equally cranky clients/coworkers who still have to maintain a pleasant rapport with. I never waited tables, but I was a sandwich-maker at a (non-Subway) local chain, and I was a cashier at Kohl’s and Borders (RIP).

I didn’t ghost when I quit Borders, but I was a few hours late to my final shift, and everyone was so impressed by my diligence, because most people didn’t show up at all their last day. Which, on the flip side, is one key difference between retail and more professional jobs: it’s easier to be cavalier when you know you probably won’t need a reference.

ESTER: What unsolicited advice would you give the 22-year-olds who are about to start their “real world” jobs in September?

ALISON: You don’t have to know everything! It’s okay to fess up to not being sure what your boss wants you to say in an email to a client or the right way to act at a staff meeting. Ask! It’s actually very disarming when people ask stuff like that, and a good boss will be excited for the opportunity to fill you in (and excited that you’re not just plunging in and making the wrong calls). No one expects you to come in perfectly polished and already knowing exactly how to operate.

BUSINESSLADY: Yes! And, pursuant to my echoes of long-ago workplace shame, to forgive yourself. If you’re a perfectionist, it’s easy to feel like every little mistake is an indictment of your abilities, but it’s so unlikely that a junior person could make a truly horrible error.

ALISON: Yes! You’re going to make mistakes, and that’s usually fine. Don’t keep making the same mistake, and don’t make mistakes borne out of not listening to people, but otherwise you’re probably good.

ESTER: Making mistakes the right way is like fighting the right way: an art. It’s something some people are born knowing and the rest of us must learn over time.

BUSINESSLADY: True. I think that’s the other side of it — whether it’s due to shame or a misplaced sense of self-righteousness, it can be tough to soul-search after you’re called out about something. But if you don’t take the opportunity to learn or improve, you’re just setting yourself up for more heartache down the line.

ESTER: From whom do you two get advice? Who do you turn to when you’re unsure of what to do, in or out of a business setting?

BUSINESSLADY: I’ve been lucky to have some really incredible mentors who’ve helped me learn by example. And then since I read (other) advice columns constantly, I feel like I kind of absorb all their wisdom by osmosis. Plus I have a partner who’s a really good foil for talking through complicated situations — he knows where my blind spots are and can play devil’s advocate in a way that’s productive instead of infuriating.

ALISON: I make my mom, sister, and BFF give me advice all the time on basically everything. My husband, who is more diplomatic than I’ll ever be, is really good in situations where I want to make sure I don’t come across like a jerk. And I’ve been reading Carolyn Hax since the day of her first column in the Washington Post, and I feel like she has permanent residence in my brain as a result.

Carolyn Hax

ESTER: Me too. I started reading Carolyn Hax in print at my kitchen table when I was a teenager and her column was specifically targeted “at the under-35 crowd.” Now I myself am almost 35.

ALISON: ME TOO. On the kitchen table thing, not the age.

BUSINESSLADY: Same here! I think I’ve consumed her entire archives. Glad to know we’re all right-thinking Carolyn Hax fans.

ALISON: My undying loyalty is with Carolyn. I do think she really shaped me from a young age and she is responsible for who I am today.

ESTER: She gave a piece of advice once that I think about a lot: that, in any relationship, the point is not for each party to give 50% but for them both to give 100%.

Another piece of advice that has stuck with me came from a friend: when you begin to overhear someone talking about you, close the door. (Meaning, just don’t listen; you won’t hear anything good.) Is there any piece of advice that’s really stuck with you like that, as a guiding principle?

ALISON: Carolyn Hax instilled in me that you have to just be who you are, warts and all, when you’re dating, because that is how you end up with someone compatible and in a relationship that’s easy. And that you can’t insist that people change. You can only tell them what you’d like and see how they respond and then make your decisions from there.

Also, I always remember how she handled it when she announced in one fell swoop that she had divorced her husband and was pregnant with twins with someone else. She clearly knew that people might take potshots at her, in a “Who are you to be giving advice when your life is in chaos?” kind of way, and she handled it really well. She was like, “Here’s what’s going on, I feel good about what’s happening and here’s why everyone involved is in a good place, and I’m going to do a whole online chat to answer questions you have about my personal life.” It was the greatest example of calm transparency.

BUSINESSLADY: I think that Carolyn Hax anecdote also demonstrates the power of owning your own perspective. I’m often too invested in achieving an “everyone is happy, yay!” outcome, even when that’s pretty much impossible, so I end up over-clarifying and over-explaining. There are definitely situations where, in retrospect, I should’ve adopted a more “here’s the deal” approach. Which, ironically, I’m better at doing in my column than I am in real life.

I can’t say I got this from any one source, but I feel like a guiding principle for me is to avoid feeling regret. Which (obviously) isn’t to say that I don’t look back at situations and think about how I could’ve handled them better/differently, but I like to consider every experience, no matter how negative, as important and inevitable.

And, to Ester’s point, I have definitely learned the “don’t let yourself overhear things” lesson the hard way, several times over, and that is excellent advice.

ESTER: Any last thoughts, and/or questions for each other?

ALISON: Businesslady, I am dying to ask you this because I wonder it all the time and never have anyone I can ask. Do you ever just feel weird about writing an advice column, when you are presumably a normal, flawed person who doesn’t conduct your own life with unreproachable perfection all the time? I definitely have moments, lots of them, of “Who the hell am I to be answering all these letters?”

Oh, and also, I want to know whether you have trouble getting out of advice mode when you’re with friends and family, because I totally struggle to turn that off now at times.

BUSINESSLADY: Oh my gosh, yes! It’s been especially funny lately, because a) there’ve been a bunch of changes at my office, and I keep being like “I wish someone could advise me about this … oh wait” and then b) because I’m officially writing a book, I’ve started outing myself to people I know in real life. But it still feels like I’m making it up, and I don’t know how to get comfortable with the fact that it’s an actual thing.

I actually wish more people would ask me for advice in real life. Maybe they will once I’m less anonymous. But I definitely have that “Ooh, a problem — can I fix it?” thing, which isn’t always the most fun for people who are just looking to vent.

ALISON: Yes. I’ve become terrible when people just want to vent. I WILL SOLVE IT FOR YOU, possibly against your will.

BUSINESSLADY: Ha, just like your tagline!

There have definitely been times when I’ve asked myself, “What would my advice be if this were happening to someone else and not me,” and that’s been a useful tool in sorting through my own minor tribulations.

I know we’re wrapping up, but since this is the Billfold, I wanted to get Alison’s thoughts about the “people’s livelihood” aspect of workplace advice. So many answers boil down to “either deal with this or find a new job,” but of course the latter isn’t always realistic. I’m never entirely sure of the best way to acknowledge the economic realities that letter-writers are dealing with, since I can’t exactly go down a decision tree of “depending on how much you have in savings/what the job market is like in your region/etc.”

It’s often a lot easier to tolerate crap bosses and crap jobs if you’re really clear-eyed about the reasons you’re there.

ALISON: It’s interesting you raise that because I used to be a lot quicker to tell people, “Get out!” I’ve started trying to steer away from that more, or at least to caveat my advice with something like “depending on what your options are.” I lean hard on the idea that you don’t have to leave but you do need to be realistic about what it will be like if you stay. And actually, it’s often a lot easier to tolerate crap bosses and crap jobs if you’re really clear-eyed about the reasons you’re there — the trade-offs that you’re making, like, “Yes, this boss sucks but I’m staying because I need the paycheck/stable job history/whatever.”

BUSINESSLADY: Yeah, it’s tough because I basically just want everyone to be happy and fulfilled, but sometimes that’s just not possible, and it’s hard to chase your dreams if you’re going into debt or worrying about how you’re going to make rent. But you’re right, I think it’s often helpful to people just to hear, “Yeah, you’re right, you’re in a sucky situation.” As my dad always says, the worse the experience, the better the story.

ALISON: I think it’s okay for people not to chase their dreams through work anyway! Work doesn’t always have to be about that kind of fulfillment. It’s okay for it to be about supporting yourself and your family and not a lot more. I want people to feel okay if that’s their situation. It’s not failure!

BUSINESSLADY: That’s a good point too. I guess I’ve always accepted that my working life would be some balance of personal passion and pay-the-bills necessity. But a lot of people grow up imagining that they’ll achieve a dream job someday and then work won’t even feel like work! Sometimes you have to be the bearer of bad news in that regard.

It’s hard to chase your dreams if you’re going into debt or worrying about how you’re going to make rent.

ALISON: I’m going to argue it can even be good news. Sometimes people are actually relieved to realize that it’s okay to not love their job or derive that kind of fulfillment from it. I think for the socioeconomic portions of the population who are raised hearing that they should follow their passion (because it’s not everyone who gets taught that; as a society we’re apparently totally fine with huge swaths of kids never hearing that), it can be really upsetting to feel like you’ve failed at that, and kind of a relief to see it as a perfectly okay thing.

BUSINESSLADY: You’re right. Especially because the kind of “dream jobs” that people get really passionate about are also usually super demanding, or at least it’s easier to let them take over your life if you’re personally invested. I mean, when I think back on the Borders job, I didn’t make a lot of money, so I don’t miss that, but I do sometimes miss the “show up, do what you do, go home” aspect. I never woke up in the middle of the night worried about some outstanding project.

And yes, of course, “follow your dreams” is also very classist in terms of who receives that message. It’s also classist in terms of who’s even able to act on that message, regardless of where it comes from — not everyone has the option of calling in a few family-friend favors and/or living off parental support for a while. So it’s important to recalibrate the conversation around what “success” looks like.

ALISON: My new tagline will be “crusher of dreams.”

BUSINESSLADY: I prefer “adjuster of dreams.” You’re like a chiropractor for the human spirit.

ALISON: You have made my month.

BUSINESSLADY: Which has in turn made my month. 🙂

ESTER: You’re both amazing. Thank you so much for stopping by!

Questions for Businesslady? Send ’em our way to Questions for Ask a Manager? Send ’em to While we’re at it, if you have questions for Rambling Man, send those my way too, to! Let’s get Josh back to work.

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