Musings + Essays

The Dotted Lines.

By: Jen Shoop

I recently had a long catch-up with a girlfriend struggling through some personal turmoil, and she mentioned something that has lingered with me in the days since our conversation.  She said that she’s not particularly happy with her current job, but that she’s also grateful for it, as its flexibility with working from home and somewhat lax work hours have given her the space to attend to herself during this bumpy personal time.  She said something like — “I know I’m supposed to feel bad about not being personally defined by my job, but right now, that’s just what it is: a job.”  She added that this New Yorker article by Toni Morrison had helped her come to this perspective, and to feel OK about it.  In the article, Morrison explains that she had come to dislike a job she’d had owing to its unexpectedly and increasingly difficult demands, and when she returned home and complained to her father, he replied plainly:  “Listen. You don’t live there. You live here. With your people. Go to work. Get your money. And come on home.”  Morrison explains that she interpreted his straight-forward reply as follows: “1.  Whatever the work is, do it well—not for the boss but for yourself.  2.  You make the job; it doesn’t make you.  3.  Your real life is with us, your family.  4.  You are not the work you do; you are the person you are.”

I’ve been turning this over in my mind since our conversation.  I was intrigued by and empathetic to my friend’s seeming reluctance to accept Morrison’s Baby Boomer-esque approach to work, wherein (dramatically oversimplifying here) work was perceived as a financial imperative rather than a mode of personal expression.  Work is work, home is home, and never the twain shall meet.  Nowadays (again dramatically oversimplifying), those of us in the millennial set are led to believe that work should be meaningful, self-defining, fulfilling.  Workspaces have evolved to look and feel like homes, with couches, ping-pong tables, open kitchens, and even, in some cases, nap “pods” (beds at work!)  And do any offices have a dress code anymore?  You can roll right out of bed and into your cube — or open workspace, more likely — without raising any eyebrows.  The subtext is that we should be our true selves at work, and that the old distinctions between work and play have dissolved.  Many of my friends have absorbed this new mindset readily, hungrily, possibly unquestioningly.  They take it as a point of pride when they are stuck at work until 11 p.m., or when they need to duck out from dinner to take a work call, or when their bosses are texting them on a Sunday morning.  I’m not saying that they aren’t expected to participate in those interactions — it’s not feigned, and I have been required to do the same during various parts of my career — but that it’s done with flourish, with showmanship, a sort of “look at me; I’m important!”  This, to me, is the unhealthy aftermath of a dramatic change in the way our generation views “work.”

But there is something else.  There is a falsehood that our generation has absorbed that suggests that all work must be meaningful, important, and magically aligned with our truest passions from the minute we graduate from college and somehow polish ourselves up to appear borderline respectable in an office setting.  I’ll never forget when a college-aged intern of mine came into my office one afternoon, heaved a sigh, and said that she just didn’t like the work she was doing right then.  “Honestly, it’s boring,” she intoned.  “Can I do something else?  I want to do something that matters.”  I was simultaneously pleased with myself for currying her confidence as I had never had a boss that had seemed to care about “my personal journey” and baffled by her perspective.  “But it does matter,” I replied.  And I explained how her seemingly menial work checking online courseware for various standards and requesting permission to republish certain works from authors were ultimately enabling us to provide free educational opportunities for those in need.  She didn’t buy it, I don’t think, but it was a bluff anyway, if I’m honest.  While it is true her work was contributing to a greater mission, my most authentic self wanted to say: “Yes, it’s menial.  That’s because you’re an intern and I’m the director.  Someone needs to do those things so that the higher ups can tackle the strategic work.  But if you do your job well, you will move up quickly.  Do you know how many hours of brainless data entry I did for $8/hour for four consecutive summers of my life?  A lot.  Like, a lot a lot.  Everyone pays their dues.  Even though data entry was the intellectual equivalent of writing “I will not be late again” three hundred thousands times in a row on a chalkboard, I learned how to set myself apart.  I was pleasant, punctual, polite.  I learned keyboard shortcuts and hack-y ways to navigate the clunky software more efficiently.  I challenged myself to complete my daily workload as fast as possible.  I was noticed.  It’s the way of the world.”

Setting aside my crotchety “when I was your age…” musings, upon reflection, I realize that I have toggled between both perspectives (we’ll call them “baby boomer” and “millennial” for the sake of simplicity) at various times in my career.  There have been jobs that I treated as pure work, completely separate from my own interests and ambitions, a paycheck when I needed it.  There have been other jobs that have been “more than,” that have shaped my identity, kept me up at night and woke me up in the morning, felt so deeply personal and so aligned with my passions and interests that I’ve had trouble separating “work time” from “personal time.”  And it may come as no surprise that those jobs tended to pay less and require more.  And you know what?  It’s OK, I think, to switch between perspectives.  I think there can be courage and strength in muscling through only-a-paycheck kinds of jobs, especially when they are undertaken to make ends meet or afford a better lifestyle or help us up a ladder.  And I think there can be serious growth and self-illumination that comes from jobs that challenges us and enable us to work on meaningful problems.

I realize the irony of my writing this piece right now, as I am decidedly out of the working world, spending half my week as a stay-at-home mom — and yet I am contributing to our household income and building a business, while refining a craft I have been practicing since I was a child.  I am straddling the lanes of “passionate hobby” (dare I say “art,” in its own way?), “entrepreneurship,” and “homemaker/mother,” and the concerns of my friend feel so distant from my own at the moment.  But hearing her thoughts on the topic of work versus real life brought me right back to the intensity of the many situations in which I found myself during my 20s and early 30s.  It made me realized that of course we’d all love to have jobs that pay well and empower us to be our best selves, all while solving a meaty world problem.  But the truth is that if a job is any one of those things, I’d probably consider it seriously.  And I might prioritize certain elements over others given the circumstances of my personal life at a given time.  For this reason, I found Morrison’s formula oddly comforting, a panacea I hadn’t quite known I’d wanted; she says: “I have never considered the level of labor to be the measure of myself, and I have never placed the security of a job above the value of home.”  It comes as a reassurance to those of us feeling like our work worlds are all-consuming, or that conflicts or stressful tasks or long hours in the workplace are sucking us dry, or that we should feel guilty for some reason for not being as obsessed with our jobs as everyone else in our generation appears to be.  You are you first.

What do you think about the dotted lines between work and personal life?


+If I had to dress up for work, I daydream about wearing an all-white/all-cream look, something demure but fashion-forward, like this blouse and these trousers (or tucked into this chic skirt!).  I also love the scalloped edge on this chic LWD (extra 40% off!), this ladylike polka dot dress (on sale for under $50!), and the unexpected two-tone chic-ness of this under-$100 dress.

+OK, I am absolutely DROOLING over this tote.  It looks like it’s Celine or something — but it’s a fraction of the price.  I love its roominess and versatility (note that there’s an extendable shoulder strap!).

+Have you ever had to break up with a friend?

+I’m still wearing my Tory Burch pearl mules all the time, and though they’re now on sale (even cheaper in certain colorways!), you can get the look for even LESS with these beauties.

+These Vejas are super chic and very heavily discounted (extra 20% off!)  If you don’t want to invest in a pair of expensive, trendy GGs, these are your ticket!

+One of my best friends just raved about this book.  Added to my list!

+Flowers, or the shape of restlessness.

+In my roundup of button-centric dresses, I neglected to include this splashy style from Tibi.  So chic!

+Love the idea of serving appetizers on Williams-Sonoma.

+Even on sale, these are pricey — but how GROWN UP AND CHIC!??!?!

+This would be a super cool gift for a wine lover.

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22 thoughts on “The Dotted Lines.

  1. I’m late to comment and a lot of what I planned to say was already tackled by others in this space — but I love this post. Toni Morrison is a national treasure (I’m biased; I wrote my high school thesis on her!) and I love this article, the sentiments you unpacked above, and the general idea that one’s work identity shouldn’t override their personal identity. It took me a long time to learn this myself, and as a previous commenter said, I definitely learned the hard way — years of working 12+ hour days (in a creative industry that pays a relatively low wage) left me completely burnt out and mentally/emotionally compromised. I’m glad to say that I learned the importance of setting boundaries at work and now that I’m back in that same industry, I make sure to end work at a reasonable hour, manage expectations in terms of when I’ll answer emails/texts after hours, and make sure to take my allotted vacation days. It makes a wooooorld of difference! And it’s important, as others said, to cultivate a life outside of work. This has been so important for me.

    To put it in your terms, I am (literally) an older millennial who aspires to be more like a baby boomer when it comes to work, I think. 🙂

    1. Hi! You know what’s interesting — it seems like there could be something age-related about this, and not from a generation standpoint. Maybe we all hit our 30s and beyond and suddenly feel like we want more balance and have a greater sense of perspective. (We probably also have more complex and long-standing family relationships that need tending to — whether that’s children, spouses, ex-spouses, elderly parents, etc.)

      Thanks for writing in. Glad you’ve made yourself more of a priority over time!!!


  2. I, too, loved this post as I’ve thought a lot about this subject, and have learned (probably the hard way) that it is so important to have some separation from work and real life. If you find work that incorporates your passions, you can count yourself blessed. But even then, your identity is not in a job, another person, etc. I think we are better employees, as well as the other roles we occupy, when we have real interests and passions that are outside of our 40+ hour work week.

    I also am not sure it’s a generational thing; I am actually on the younger side of Gen X, I guess – I’ve worked with both Boomers and Millennials. While it may seem like Boomers have had more longevity with one company, I think that’s a function of the business landscape when they started working, and the fact that more of them had 9-5 jobs where they clocked in and out, and didn’t have the devices as their constant companion the way we do today. My parents often don’t understand how I can’t just log-off or leave work at a certain time. I also found quite a bit of similarities between my Boomer co-workers and Millennial co-workers. I think each valued their personal time, and they really got along well. It was interesting to observe! In terms of feeling like you must find meaning or not doing menial work in your job, I blame the universities, haha. I jumped around a lot in my twenties, too, and thought working would be like it was in school – you get good grades, you excel. It’s not really like that in the real world. I also think what we overlook in the corporate world is mentorships – some organizations have great programs, but I think we can cultivate more tenure within organizations if employees have a clearer career path they can work toward, and have someone to guide them through it.

    Anyway, I went on too long here, but really a thought-provoking post!

    1. So, so much to comment on here — such good points and interesting observations. I hadn’t thought about how the Internet and cloud have made it far more difficult to draw lines around “work time” and “home time,” but it’s so true, and has further obfuscated the distinctions. I’m also interested in your comment about how working hard / getting good grades doesn’t necessarily mean you will excel in the real world. Why is that, do you think? More people (and relationship dynamics) are involved in the equation?

      Lots to digest here and will be mulling over your points for the next few hours I’m sure!

  3. I can’t speak to the more traditional/ linear careers like law and medecine but for those of us with a bit more space or randomness in our paths (raises hand), I think cyclical is a v fine shape. Just as farmers let the corn fields grow fallow one season and the soybeans the next, it’s rejuvenating to do so with different aspects of our lives. (If we have the privilege.) I’m getting abstract but tldr is yes! If you can, let a job just be a job while an entrancing tiny human is your entrancing tiny human, or your side project is giving you all the flutters. Later on, something or someone else might hog the spotlight—but really, as long as there’s _a_spitlight, you’re doing alright.

    1. Hi Claire! I like that visual, and I agree. Your comments brought to mind the mania around achieving “balance” in all things — and how it often sets us up for failure. I personally feel that I’m always trying to juggle five balls: family, career, exercise, sleep/self-care, and friends. (Maybe there’s a sixth category that I’m not thinking of right now…#mombrain) I can truly only be good at three of those things at any given time; something has to give in the other categories. Accepting that has made me a much happier, more sane person. And so it makes sense that in some periods of my life, career needs to take a backseat to other priorities, whether that means treating it like a paycheck or sort of going through the motions. I’m not in the zone right now, of course, but I’ve certainly been in it in the past, and always carried guilt around while doing it…

      Thanks for writing in about this! xo

  4. Chiming in on the conversation. I stayed with a company for 11 years – I think the longest of any of my peers. I also did menial and quite physical work at the start, but my skill set grew from there and I became an EXPERT in the systems, in the technology, and in the company systems and it made me a very valuable employee. I’ve wondered a lot about millenials and if this moving around jobs and constantly searching will make many great generalists, but we will lose experts ?

    I’ve wondered if this inability to “put in the hours”. Is more than just putting in the hours, but also like playing scales and practicing the piano to able to master it?

    1. This is such a fascinating point, Laura — I certainly feel like I was in a lane where I was going to be a generalist vs. a specialist. I was “specializing” more in the industry rather than the skillset/position (I jumped around from content to product and a couple of other blurry categories). In fact, Mr. Magpie and I have often referred to ourselves as “the jack and jill of all trades, master of none” and looked on with envy at those of our friends who have put in time in honing a specific kind of expertise. There must be something so reassuring and empowering about being really, really good at something really, really specific that you can’t just shortcut into. For sure the “millennial” mentality is playing into this!


  5. Jen – I absolutely see and understand the divide you’re talking about. I think another manifestation is in career continuity – baby boomers often worked for a single company forever, whereas I hardly know anyone still with his or her initial post-school employer. Our generation is constantly searching for something better and more meaningful (not to mention we are more geographically mobile), which is likely related to seeking fulfillment from work more generally.

    1. You are so right! I just commented to one of my friends the other day that I am the only person I can think of that has been in the same job for over 5 years (when I graduated law school). It’s crazy! Maybe I was meant to be a baby boomer….

    2. Yes! That is so true! I have a few friends that have had like 8 or 10 career changes since college! I wonder why a sense of loyalty to the company has eroded over time — maybe it is because we all have a sense that we should “look out for number one” in our professional lives, or at least that’s the sense of competitiveness that seemed to circulate in some of the schools I attended. Really interesting point!

  6. I think that there are certain professions, that fall into your baby boomer category, that you really need to keep personal separate from work. For example, as a family law lawyer I had to learn to separate my work and personal and not think about or communicate with clients at home, otherwise I’d be worrying about my clients all the time and drive myself crazy (literally used to keep me up at night). I expect it’s the same for doctors and teachers. I think if you establishes these boundaries early on, clients respect and understand them

    I also think that to some extent the “baby boomer” professions will always require dress codes and a certain amount of in office presence. I think the law is one of the last professions where you need a private office. Clients are paying a lot, employers are paying you a lot and a lot of trust and confidentiality is being placed in you. You are expected to be there, look nice and have a nice, private place to keep their confidential information. I think it is much the same with banking/finance and I don’t think this will change as the rest of the world starts working from home and wearing yoga pants, jeans, etc. every day.

    Final thought, it’s called work for a reason but I think it is important in every job to feel like you have accomplished something every day and many people need to learn, like your intern did, that this doesn’t mean saving the world. It can mean helping a customer find the perfect pair of pants in a store, finishing a set of data entry, greeting all your customer’s with a smile, etc. I think putting this in perspective helps you enjoy work more.

    1. Jen — !! There is soo much here to unpack, but I found your comments about the innate qualities of professions like law and medicine that lend themselves to specific office structures and dress codes super interesting. Do we think this *might* be because, in those trades, you are coming face to face with clients who expect one-on-one care, so presentation is de rigueur — whereas companies in which the “clients” or “customers” are behind a screen or maybe even virtually invisible have led to much more lax environments? The only exception is – possibly – finance (?). I know many friends who worked behind screens and rarely saw customers but were still expected to dress up every day. I don’t know, my wheels are spinning a bit here but you really made me think a lot about the “structure” of certain kinds of professions, and why they might be that way.

      And, I completely agree with your final point. I would never want to feel like an automoton, just punching in every day, grinding away, and leaving, though I know there are many, many, many jobs that entail that kind of monotony and probably require a level of grit and mental toughness I don’t have. But even in those kinds of line jobs, I agree with you — I so deeply admire people who can make the best of any task by trying to be the best they can, leave a good impression, and do a good job, full stop. In writing this, I’m actually thinking about an office admin I had many years ago who was probably the hardest working person I have ever met — she greeted every task, no matter how small, with a positive attitude and a desire to go above and beyond. I need to be more like Izzy…


  7. I love this so much! My identity in work versus my personal life is something I think about constantly. Some days, I get so frustrated with the nature of my job (lots of playing the busy game or “I stayed here until 1 am last night…” said with a really obvious sense of pride ) and I frequently think to myself “nothing is that important” when it feels like my personal wellbeing is at stake for the sake of work (which is often in the age of 24/7 email). I take a lot of pride in my work, and it’s important to me to do a great job, but it does irk me that we are expected to give up autonomy over our lives sometimes. I also fully acknowledge that I’m really guilty of giving in to the feeling that some work related things are the be all end all and I know I’ve been that friend at dinner too many times. I have so much trouble reconciling the two feelings. I also struggle with the feeling that I’m dedicating so much time and energy to something that doesn’t really work on any of those big picture issues, especially with the state of our world these days. One of the most comforting things for me is that you can still be kind and do good, no matter the setting – it doesn’t have to tied to income. Being a good friend/sister/daughter/partner/etc matters. Working hard matters. Being kind and giving people the benefit of the doubt matters. Similar to what you said – you are the same you 100% of the time, so that is what’s important more so than the specific job you do. I feel like I could talk about this forever – I really loved the way you wrote this!

    1. Keep talking!! I found your comments honest and strikingly similar to many of the emotions my friends and I have shared with one another from time to time. I think a lot of us have trouble “reconciling the two feelings” you’ve outlined. Personally, when I try to unpack why I would occasionally mention with a certain smugness that I had to work late or miss something because of work, I think that it was because I liked my friends to know that I was respected and important in the workplace; it was part of my identity and it was an easy way to share or suggest my workplace persona with them? Maybe? I’m not sure…

      Anyway, your takeaways are right in line with my own: being kind and hard-working are going to be a good look on you no matter what arena you’re in.

      Thanks for writing!!!


  8. Such a well-written post with so much food for thought! I love that I never know what kind of thought-provoking yet still entertaining topic you’ll choose to tackle on a certain day. You’re a talent! Interestingly I do have a dress code as an in house lawyer- and I find it a relief not to have to come up with cute, work appropriate casual outfits.

    1. Yes – I think most lawyers have to adhere to a dress code! Now I dress in business attire (dresses or pants/blouses), and even in my prior office which was business casual, all still had to look professional. Significant segments of the economy are still run by people dressed in business attire in a traditional office format, though often forgotten about by millennials working for start-ups.

      1. Hi Leah! You are so right; I am speaking from a rarified set of job experiences (exclusively non-profit and start-up) and those are not representative. Good call. Still, I wonder whether you relate to or have observed the other distinctions between millennial and baby boomer in terms of mindset around what work means, even in a more traditional corporate environment?

    2. Thank you, Daphne! Glad to hear this. I’m curious whether, as a lawyer, you relate to the millennial vs. baby boomer divide? Maybe it’s different in more specialized trades where you have so many years of required education/training? Thanks as always for reading along and sharing your thoughts…!

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