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Shannon and Businesslady: From College to Career (Part 1)

It is safe to say that if you were born anytime in the last 50 years, you have probably heard from a young age that going to college right out of high school will be the ticket to you landing the career of your choice with a good income. As someone born in ’98, I heard from 1st grade onwards the value of going to college to get a job — and so, here I am, at SUNY Oswego, studying English Literature.  

Since 1998, much of the ideas and language we use to talk about and conceptualize college has changed, as has working. Not only has the value of a college diploma in getting someone into their desired field seemed to shift within the world, but so has the way we even go about looking for jobs. Gone are the days of classified ads and hello Indeed, Monster, and LinkedIn. If it wasn’t confusing enough to try and transition from a college career to a real life one, or understand how to competently do things like write a cover letter, apply for postgraduate study, or move to a different area for work, the pandemic has changed even more of these things within just the past year. Many people, especially both current and newly graduated college students, have had to realign the way they picture their job prospects and career fields. 

As a first semester Senior at SUNY Oswego, and about to be graduating in an era where our society will be adjusting to life directly after a pandemic, I had many of these worries myself. Fortunately, I had heard of someone named “Businesslady,” AKA Courtney C.W. Guerra. Courtney is the author of Is This Working?, an “entertaining and witty” career guide for anyone who’s interested in professional success—but not at the expense of their personal investments. Her advice column, Dear Businesslady, began on The Toast in 2014 and later relocated to The Billfold. She’s also been featured in Inside Higher Ed, Huffington Post, Fast Company, the New York Times Op-Talk, WGN, the Dear Prudence podcast on Slate, and elsewhere.

An expert in lateral and non-linear career growth, Courtney mobilized her early work experience in food service, retail, and data entry—and her dual degree in English and Visual Arts—to work her way up through a series of administrative positions, both corporate and nonprofit. As the Senior Writer & Research Development Director for the UChicago Humanities Division, she crafts compelling applications for faculty research funding. This same editorial perspective informs her work as an advice columnist and career coach, a side project that grew out of her sincere desire to help fellow humanists find their way into fulfilling jobs. Since Courtney not only had achieved career success but knows how to give it out to others, I thought I would sit down with her to try to talk about how one goes about finding a job after college, along with her own personal life experiences.

Getting your degree

Many of us, from a young age, have an idea of what we “want to be when we grow up.” While I specifically remember telling my Pre-K teacher I wanted to be a “Cat Princess,” Courtney relayed to me her dreams of being a high school English teacher. Courtney talks about several reasons why it was easy to imagine herself as an English teacher before getting her degree: “I knew I liked reading books and talking about them, and that I enjoyed writing. So, I thought it made sense for me to be an English major, but people would say, ‘Well, what are you gonna do with an English degree?’ and ‘I’ll be an English teacher’ was a really good way of shutting them down because that completely makes sense. As a high school student, English was one of my favorite classes and it was easy to put myself in that role mentally.” This is a common thread in my own life, with people assuming my English degree will only be valuable for teaching K-12 education. While I know many people within the English degree who are working towards becoming teachers, and I myself had considered it because of the same sorts of thoughts Courtney had, it just wasn’t meant to be. Similarly, by the time it came time to apply for postgraduate study to become an actual teacher, Courtney had decided against it. Why so? “I didn’t want to do more schooling, and I didn’t want to stand in front of a classroom all day. I didn’t know what I wanted to do with my life, but I didn’t think I should go back in to school to become an English teacher. It broke me off into the path of a more professional track.”

Courtney’s words speak to many different things about the educational system itself that prepare us for professional careers, and also the wider world, in terms of how we imagine our degrees to be valuable to our future careers. While there are a wide swath of opportunities available for English majors, even without a Master’s degree, Courtney noted the way in which often our own personal experiences with the most visible career path of those majors (for example, English teachers) dominates the ways in which we select our own career paths, even well into college. If you don’t know about a career field, how can you possibly imagine using your degree to do that thing? Furthermore, if the people around you also cannot imagine any other career path for your chosen major besides the most visible or obvious one, how exactly do you talk to them about something outside of that without feeling on shaky ground?

Our discussion began to focus more and more on the types of ways in which college degrees are conceptualized for the working world, in particular, the humanities. As our world has become more reliant on scientific and technological progress, it becomes obvious then that the emphasis on STEM degrees is directly related to the variety, visibility, and stability of careers in STEM work. However, this has also led to many humanities degrees, such as English, History, Foreign Languages, Philosophy, Art, Music, Drama/Theatre, and countless others, to be much more undervalued. While this article is geared towards those in any discipline, those within the humanities (like myself) can often find ourselves on rough ground in terms of conceptualizing life after college. My friends who study Computer Science can obviously get a job in IT or build computers, my friends studying Chemistry can work in a lab or go on to funded PhD studies, and my friends pursuing Business degrees can start their own company or help manage an already established one. However, the path for humanities majors seems much less defined and much less focused on.

As Courtney tells me, she believes a large part of this undervaluation is within the ways in which humanities degrees are described both to students and the larger world: “It is hard in a pithy way to explain what the humanities does for you as a student. You can say it teaches ‘critical thinking’ but critical thinking isn’t necessarily defined, and it’s easy to be like ‘[this non-humanities discipline] also teaches critical thinking.’ Or, if you focus on individual skills you can acquire as part of a Liberal Arts degree, like it makes you good at analyzing complex problems, well, maybe there are Business degrees that teach you how to do that in a Business context.”

At the end of the day, Courtney lays out exactly why the humanities matter (and why they can be translated into any profession): “Across all disciplines, you are taking a corpus of work that a human being produced, whether its literature, philosophy, historical events, visual art, music, and you are analyzing it critically in the sense of a critic — like a film critic, an art critic. You are looking at how it relates to what came before and after, what it’s doing, how successful it is, what conclusions one might draw from it. In the professional world, you are often doing that same kind of work but basically reading business processes and colleagues around you as a text, in the same way you apply literary theory to a novel. In a business context, you take an organizational goal and lay it against the way your department is currently operating, what it needs to be doing, and find the harmony between that.” 

Relating this all back to her original goals of being an English teacher, Courtney rightly points out that many people in college, despite having some idea of what they might do, still don’t know exactly what they want to be or what they want to be doing. Even if you don’t have a traditional career path in mind, studies in a humanities major—even if branded to be “useless” by others—teach essential professional skills that can be translated into many different fields.

Transitioning from college to career

Well, if you already have the degree, congratulations! As many of my own friends who have graduated would put it, you now have a very expensive piece of paper. As I would put it (and I imagine Courtney would as well), you have put in the hard work and personal development of growing into the person who earned that degree. It can be easy, especially in a world where so many more people are attaining degrees and employers seem to undervalue the work you’ve put in, to underrate your accomplishment. However, you did accomplish something amazing, so be proud. Now, though, it is time to use that accomplishment in the working world!

Most of you already know that you should have a resume (or at least three) and get it looked over by a friend, trusted advisor, and/or the Career Center (which offers services to alumni as well). Along with that, learning how to effectively write a cover letter, how to dress and act during interviews, and to use job application websites are all drilled into our head even before college.  Courtney (as her alter ego Businesslady) has actually already written a column (and once again, a really good book!) detailing the technical aspects of finding jobs online, such as crafting a resume and cover letter, and the actual interview process. If you need help with those mechanics specifically, I highly recommend reading her article.

However, the less talked about (and less defined) aspect of all of this is the fact that going from college to looking for a job is a gigantic life shift that takes some brain reorganization. While most of us have some form of job in college, from summer jobs and internships to being an RA or having a position on the e-board of your student organization, these are often smaller stepping stones to what we see as our first actual “adult” job after college. As Courtney and I discussed, and many of the student questions we got were focused on, a large portion is repositioning how you conceptualize your relationship to not just your work, but to others that now are in your working life. 

While Courtney certainly agreed that finding that first job out of college would be the toughest (and you’re not likely to land your dream job right then), having skills that allow you to branch out and continue growing even with challenges or setbacks was important. One of the things Courtney highlighted was just the ability to talk to other people in your job or field, even if it doesn’t immediately result in a promotion: “So often, feeling comfortable walking up and just talking to people is a hurdle people find difficult to overcome. For the most part, we are social creatures and we respond well when people show an interest and are friendly. If you’re interested in advancing your career, you can find a lot of value in talking to people who are a little bit more senior than you in an organization and learning a little bit about what they do as someone who has a job that you might want to have someday. See if they are willing to talk to you about how they got there, what credentials they have, and what skills they thought were important. They might be busy, or disinterested, but you’ll move on and talk to someone else. For the most part, people enjoy helping out.” Being confident in yourself and your abilities may be the biggest challenge coming from college into the working world, but certainly one step to becoming more secure in your role is simply talking to others and understanding the real world of the field you want to be in.

Courtney and I also discussed another move that recent Bachelor’s graduates can make instead of college, which was postgraduate study. While Courtney does not have a graduate degree—just a “Certificate in Editing” from the University of Chicago’s Graham School—she does caution me a little bit about graduate school (especially PhD programs in the humanities, of which her husband, Dr. Doug Guerra who teaches at this university, pursued): “It’s great if you want to become a specialist in a particular field and you have a plan for paying for your studies (whether it’s through a funded program, manageable student loans, or familial generosity). But especially in the humanities, finding a position as a tenure-track professor is extremely difficult—the supply of candidates vastly outstrips the number of openings, so excellent candidates get passed over all the time—and adjunct instructors often face hardships like low salaries and precarious benefits. Even if you hope to be a college instructor one day, it’s good to have a fallback plan in mind before starting up a PhD program.” 

Dr. Guerra had advised me previously to this through a C19 Podcast, reinforcing the idea that having one specific career in mind when going into graduate school, just as with undergraduate, is not always helpful for your larger trajectory. Though many professions may have requirements of their employees to have certain degrees (such as teaching or medical fields), it is also important to understand that the pressure to go to graduate school to get a “good job” is not always applicable to what you might want to do. At the end of the day, Courtney’s commentary highlights the way in which graduate school is not always the “key” to landing in the field you want to be in. 

Discovering What Works Best

One of the biggest interests in talking to Courtney was her own career path, which ended up including giving career advice out to others. As Courtney describes, her work history prior to and during college was mainly retail (a sub shop and Kohl’s, to be exact), with one office internship helping employees who were relocating to research their new areas. After college, she started off doing temp work along with working at Borders Bookstore (RIP), but her actual experience on her resume was minimal. From there, Courtney got her real experience in an entry-level position at an HR consulting firm where she was able to more or less fall into the position of the CEO’s executive assistant. “I learned a lot of skills through that position, a lot of professional writing skills. Often the way you write for a college paper is not necessarily the voice you want for business communications, which tends to be much more succinct.” Through that entry-level position, Courtney was able to transition to working for the University of Chicago, going from a front desk worker to development (fundraising) and then to her current job: doing developmental editing on faculty proposals for grants and fellowships, and also serving as director of an audio archive.

I was particularly interested in how Courtney came to be “Businesslady.” As she explains, Courtney had also been writing for The Toast (now defunct), which she describes as a “feminist humor” website. It was during this time that another online magazine, The Hairpin, had a series called “Ask a Lady” and “Ask a Dude,” which Courtney found herself inspired by. The “Businesslady” moniker grew out of both Courtney’s desire to be anonymous as well as conveying “a little silliness but also a sense of professional development.” Businesslady has exactly that—while the tone is certainly distinctively Courtney, she specifically describes it as “warm authoritativeness.” From the numerous Businesslady articles I read to get a sense for this article, not only did Businesslady make me believe in her own expertise, but also in my ability to handle the challenges of the professional world—that in and of itself is a feat to be celebrated. 

However, the idea of giving someone else career advice seemed frightening—someone else’s livelihood in my hands? What if I totally screwed it up? Courtney explained to me the way in which your perception of yourself and your relationship to your career changes in a way that allowed her to feel secure in giving advice: “I had weathered a bunch of different transitions, I had weathered a bunch of different bosses, I had been in a pretty wide variety of roles—an admin, fundraising and development, editorial roles, management. I had taken on enough that I had a decent sense of what the scope was of different professional jobs. I had also started working remotely, which was a whole new transition for me that I managed to weather.” 

Going further, Courtney explains the shift in internal confidence and boundary setting that takes place: “There is a transition that happens when you go from your early career to your more established middle career. In the early days, it can be good to have that sense of like ‘Oh my god, my boss wants to talk to me cause I’m about to be fired’ or ‘Okay, somebody gave me some feedback, have to internalize that feedback’ where you’re always trying to prove yourself and go above and beyond to distinguish yourself. That can be valuable, but eventually you want to get to a point where, if you already have a pretty high standard for what constitutes good work, you don’t necessarily need to keep trying to shove that standard high and higher and higher. That is especially true if you find that you’re losing space in your life for relationships and things that you enjoy and nourish your soul. It is important to find a job that makes you happy, but it is dangerous to have your job be the thing that makes you happy.”

One of the reasons I highlight the Businesslady origin story and Courtney’s personal development as it related to how she felt about her career is to give the same kind of confidence that Businesslady gave me while reading her work. Many of the questions Courtney and I received, and many of the questions I saw on the Businesslady articles, simply had to do with feeling secure—how do I feel secure about applying for a job? How do I feel confident in an interview? How do I feel like I know what I’m doing when I actually get the job? How do I advocate for myself for a raise/promotion? While right now may certainly be a trying time for many of us, with remote classes/work, layoffs, entire businesses closing indefinitely, I felt as if Courtney’s story and the writings of Businesslady gave hope to college students (both current and recently graduated) that we can weather the storm and come out stronger. We’re weathering one of the biggest storms in history, and if we can weather this, we can also weather the storm of trying to start and build up a career. Though it may not be our dream job right out of college, there is hope that we can certainly find ourselves through the journey to that dream job (even if that dream changes). 

Stay tuned next week for Part 2 of this article where Courtney answers specific questions submitted by you, the students!

You can connect with Courtney via Twitter, Facebook, her TinyLetter, or her website, DearBusinesslady.com.

Shannon Sutorius was an award winning 23-year-old English major, over 40-time-published author, editor, and former Teaching Assistant who graduated from SUNY Oswego in December of 2021. Shannon was one of the Campus Correspondents for Her Campus Oswego, previously Senior Editor, and wrote the Advice Column, "Dear Athena." Shannon worked with and had been published in Great Lake Review, Medium, and Subnivean. Shannon's awards included the Edward Austin Sheldon Award, Pride Alliance's Defender of LGBT+ Rights in Journalism Award, and the Dr. Richard Wheeler Memorial Scholarship. As well, Shannon was an active member of the Phi Kappa Phi Honor Society.
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