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Shannon and Businesslady: From College to Career (Part 2 – Your Questions!)

To read Part 1 of this series, click here. As a refresher, I sat down with Courtney C.W. Guerra, aka Businesslady and author of Is This Working?, an “entertaining and witty” career guide. I asked her to don her Businesslady cap once more to answer some of your original questions about working and finding a job after graduation. Questions are grouped by the names, majors, and years of those who asked them. 


Jake, Sophomore, English Education, Hank, Senior, Biochemistry and Psychology Double Major, and Lilo, Junior, Cinema & Screen Studies:

  • “My biggest concern is that with so many more people getting their Bachelor’s degree nowadays, this won’t be enough on its own to secure a job. It seems like all of my friends have ended up getting positions because of their connections rather than their qualifications and it’s discouraging as someone who doesn’t feel like they have much networking experience. I feel like I won’t be able to attain even an “entry level” position in my field.”

As this question is the most common that got asked, along with the most comprehensive, Courtney’s advice for this is thorough and detailed, as well as realistic. As she states, “I think that the first job out of college is often the toughest because you aren’t likely to have an office-type experience. Because it is an entry-level position, you are competing against everybody else who’s got a similar set of credentials, and in that case, I’ll be honest that networking and having an ‘in’ can be really valuable.” 

However, Courtney stresses that networking isn’t exactly what you may believe it is: “To the extent that you are able to do networking, that is something to pursue. I talk about this in my book, but you hear networking and you often think ‘ew.’ Networking feels exploitative in a sense of, ‘I’m gonna pretend I care about someone so that they can help me!’ I think it is totally valid to not want to do that.” As Courtney explains, it is not the manipulative thing it has been cast as: “Really, though, what networking is is considering the people you already know and seeing if there is any alignment with what they do for a living and who they know, and the type of career you hope to pursue. Things like informational interviews, which are not like, you meet with a person and they magically find a position for you—it’s not an actual interview—but it is a way to learn more about the types of skills and job duties that are part of whatever field you hope to be in. Having just one conversation with someone in a field that you want to break your way into, that’s going to help you in an actual interview in distinguishing yourself against someone who’s just kind of guessing, ‘I think I know what a project manager is,’ ‘I think I know what a communications manager does.’ If you do make those kinds of connections, they can turn into job leads—maybe not right away but down the line—so keep in touch and join LinkedIn, so you don’t lose track of people. If a position does open up at a company that you are qualified for, then the fact that you do know someone there can help you. Even if they can’t vouch for your work, they can still say ‘I’ve had a conversation with this person and they seem sharp,’” and that does go somewhere.”

Speaking to this question and some others further down, Courtney also addresses pigeonholing yourself right out of college, “If you know there is a particular industry you want to work in, or a particular set of work duties that seem suited to your talents, by all means, try to land there and pursue jobs that fit that. But, I think I would be cautious about being too limiting in saying ‘I want to work in this field and I’m only going to pursue jobs in this field’ because a lot of things are really transferable. This is especially true if you’re not having success. For example, ‘I want to be a graphic designer for a non-profit that is addressing homelessness’ is a wonderful career goal, but there are only so many jobs that fit that description. Maybe you find a job doing graphic design at another nonprofit, maybe you find a job at a nonprofit addressing homelessness but in a general communications job and you’re not really doing graphic design, but maybe you can incorporate that more and more into your portfolio as you go on. Once you have a resume—once you’ve established yourself in the working world—it’s easier to translate that experience to a new position.” 

As we discussed in Part 1, Courtney once again brings up the value of a Humanities degree in this regard: “A cover letter or resume is repackaging your experience to make the case that you are a good fit for whatever job you’re pursuing. You do a ‘project manager reading’ of yourself as a person who can do XYZ in the job.” 

In conclusion, Courtney makes the case that your first job out of college is not the decider of the rest of your life: “You can have a different sense of what a job entails before you actually hold it, so you should also be flexible and be prepared to realize, ‘Oh, I thought I liked this type of work, but it actually involves a lot more spreadsheet organization than I realized and I hate spreadsheets,’ or maybe it’s, “Oh, I thought I wanted to be a writer, but I really love creating work plans for complex organizational initiatives, that really excites me.’ I’m not saying that you think you want a job in your field but it doesn’t matter what kind of job you get and you’ll find a field eventually, cause it’s not that simple. But, I think there is a lot of value in feeling out what is of interest to you as you step out into the working world and being creative in terms of how you take the skills you’re developing and apply them to positions.”


Bridget, Senior, Business Administration, and Erin, Senior, Adolescent English Education:

  • “I am most concerned that there may be no positions available in the location I want to live. I am also nervous about hunting for jobs in an area that I don’t live in now, even if I do want to move. I don’t want my hometown connections to leave me stuck in my hometown; I want to branch out.”

Courtney is very confident about the ability (and flexibility) of being able to choose where you live, “I think that this is the thing, in the long run, the pandemic will kind of help. Folks will be more amenable to remote work. Historically speaking, local candidates have an advantage in that they don’t have to deal with complications of relocating. I think, if it’s a position that can be done remotely, that is less of a risk. If the relocation falls through, the employment can still continue.”

She continues, “With a lot of these questions, you sort of have to pick the thing that’s most important to you for the job search, and then let other things fall to the status of ‘nice to have.’ So, if you really want to work in a particular industry, you don’t get the exact job you want but you get a foot in that industry. Or maybe you want to do a particular type of job, but don’t do it for the type of company or organization you hoped for. Similarly, if you really want to be in a particular geographic area, then you have to be willing to cast a wider net in the first job you take in that area. Whereas, if you’re willing to live anywhere, but you really want to work for example, an animal welfare charity, you can look in any city that has one and you get a much broader spectrum.”

Courtney once again emphasizes networking, “If you have any connections local to where you’re moving, definitely tap those. This is a case where your school’s alumni organization can be useful. I didn’t understand those resources as being available to me when I was graduating college. The worst answer you can get is a gentle no. Ask Career Services, ‘Hey do you know anyone working in XYZ industry in [A] city that’s an alum that you could put me in touch with?’ Maybe they’ll say no, or maybe they’ll say they can’t do that and you’ll have to poke around on LinkedIn. If I got an email like that, I would be more than happy to talk to that person, and maybe there are organizations that I can brainstorm that might be a good place for them to work because they don’t live here yet.” 

In conclusion, Courtney’s advice is similar to the others in terms of being flexible, networking where you can, and prioritizing. As she shows, there are plenty of avenues for relocation (whether or not you want to).


Dylan, Senior, English Literature, and Palina, Junior, Zoology:

  • “My biggest concern is generally not being prepared, either for an interview or having the right skills for the job even if I do land it.”

“This is kind of like the impostor-syndrome question below, and aligns with what I was saying about finding the “professional world” version of yourself. Even the most experienced candidates need to do some on-the-job learning when they take a new position, because every workplace is different. It’s not your responsibility to tackle a new role flawlessly from day one, or identify every potential shortcoming for your interviewer. All you need to do is present yourself in the best possible light, be honest (but positive!) about your abilities, and trust that if you get hired, it’s because you were indeed sufficiently qualified.

“One great way to prepare for an interview is to come prepared with stories about how you tackled a particular project or problem (ideally in a way that’s relevant to the position you’ve applied for). You want to give the interviewer insight into how your mind works and the types of decision-making they can expect of you as an employee. Things like Microsoft Office proficiency or how to use specialized database systems are much easier to train people on than ‘be a good problem-solver.’”


Mo, Senior, English Education:

  • “My biggest concern is wanting to avoid feeling like an imposter and instead feeling confident in my abilities; does this make much of a difference when it comes to finding a job or is faking it ‘til you make it really the golden ticket?”

Courtney has a very relevant (and popular) catchphrase for this question: “Carry yourself with the confidence of a mediocre white man.” 

She, of course, has some caveats to this, “People who are marginalized for various reasons struggle with this in a way that white cis het men do not. Not to say that they are immune to insecurity, or never have imposter syndrome themselves. However, the messaging of ‘Be accommodating, don’t intimidate people! Are you sure someone else doesn’t have a better idea than you?’ is easy to internalize if you are, for example, a woman. This often does not work in your favor in professional settings. On the flipside, there is a rhetoric of ‘Women apologize too much! Don’t apologize! Be aggressive!’ That kind of cheerleading can be good, but I’d also stress that being considerate, thoughtful, and owning up to your mistakes aren’t negative qualities, especially because they’re associated with a more feminine affect. There is a big difference between apologizing for having an idea—which doesn’t help you—and apologizing sincerely to your colleague because you made a mistake or you’ve now created work for them.” In conclusion, Courtney emphasizes that there is a balance needed between complete insecurity and complete confidence. 

She continues, “It’s tough, because if you walk into a job as an entry-level person, and start demanding they restructure everything, people are going to rightly tell you to slow your roll. However, one of the hardest things in terms of leveling up your career is developing that confidence that you know what you’re talking about if you think you have something to say. Again, you have to be willing to be wrong. With my own work, if I just sat there and waited for someone to tell me that ‘We have placed the crown of You Know What You’re Talking About on your head, like feel free to start leading these meetings now,’ that was never going to happen. I had to just listen, learn, and absorb, and then just say what I thought. There were times where I proposed something and it got shot down, but more often than not, it was like, ‘Yeah that makes sense, you are the authority on this, you have learned what you needed to learn to be in this position.’”

Courtney advises you shouldn’t overclaim or be dishonest on job applications, but learn to present the person who you are as honestly and in the strongest way possible (another Humanities strong-suit). “My general rule with imposter syndrome is that if you think you need to overcome it, you should. People who are overconfident in a way that is a problem do not struggle with imposter syndrome, and so if you’re constantly second-guessing yourself, and worrying you’re not good enough, it probably means you are good enough. The more you can try to push past it, the better served you will be.”


Mary Kate, Senior, Business Admin and Creative Writing Double Major with a Minor in Medieval/Ren Studies: 

  • “Aside from the current pandemic, I think my main question would be in how to make oneself essential despite lack of job experience. Many new employees have been let go due to the pandemic and are always the first to go when layoffs come around. Is there anything one can do outside of work ethic to help maintain good relations and increase the chances of not being expendable at a new job?”

This question’s answer is similar to the first one in the advice that Courtney gives: “Work ethic is always important, but so are personal connections. Even if they can’t save you from a layoff, they provide you with a network of people who can help you find a new position.”

However, Courtney also elaborates on the importance of your own skills and growing into your career: “This also dovetails with my advice to be on the lookout for ways to expand your role. The more you can take on (without overextending yourself), the more indispensable you’ll be. And once those skills are on your resume, they’ll make you more employable when you want (or have) to take a new job.”


Sara, Junior, English and Creative Writing:

  • “I don’t do well in completely remote environments. How should I go about finding an in-person job in my field even after COVID?”

Courtney, as someone whose job has been remote well before the pandemic (and the only one in her organization to be remote before COVID), understands the difference between the remote and in-person work and preferring one to another. However, she is also a bit more encouraging about life after COVID: “There will always be a value in in-person interaction. There is a big difference between the pandemic and now. Before the pandemic, I was seeing people for three days a month nine months out of the year, and that was definitely a transition to not seeing any of my coworkers in a year. Zoom is great, and there is value to the flexibility of remote work— it’s environmentally friendly, you don’t have to spend time commuting, things like that. But depending on what your home situation is, there are definitely advantages to having an office with a door you can close, where you pets and children aren’t in—that they will never be in—so I understand that. For people that don’t find it to be to their taste to work remotely, I think there will always be office jobs.”

In the end, Courtney keeps it simple: “I’m confident that in-person work will still exist after the pandemic, and I anticipate that those jobs will be very vocal about being NOT REMOTE. So just pay attention to the listings and apply for positions that will bring you into an office.” 


Mattie, Sophomore, Cinema & Screen Studies:

  • “Some job areas don’t have a huge demand for people right now, if not ever. What are some things to do to ensure that you can find a decent job in your field, knowing not a lot of people are successful in doing so?”

“‘A decent job in your field’ might be hard to get right out of college, but ‘a decent job in an adjacent field’ or ‘an annoying job in your field’ is probably more attainable. Or, at worst, ‘an annoying job in a mostly unrelated field.’ That last one will at least help you stay motivated to keep looking, and you can use it as a chance to burnish your resume—what videogamers refer to as ‘grinding’ (doing lots of less-fun battles to level up your character, get better weapons, etc.). It’s great to have high standards and ambitious long-term goals, but don’t let them discourage you if you have to spend some time doing a job that’s less exciting or aligned with your interests.”


Mal, Senior, Theatre (Acting/Directing): 

  • “My biggest concern is that theatres will still be shut down due to the pandemic. I’m also scared that I’ll get out of college and there’s going to be such a surge of people looking for jobs that it is going to be impossible for me to land any type of job let alone in my field.”

Courtney has a bit more optimism, but also some caution about mindset that ties back to Mattie’s question as well: “From what I’ve heard, the theater industry is actually starting to come back, so that’s encouraging. But the ‘surge of new grads all trying to get jobs in a competitive field’ issue is evergreen—as is my advice: if you can’t find a position in the industry you want, try to find one that will help you develop skills that are relevant to what you have in mind (or vice-versa, a job where the day-to-day work isn’t exactly what you want to do long-term, but develops your connections within your chosen field).”


Jordyn, Senior, Biology and Creative Writing Minor:

  • “My biggest concern is trying to find a job that actually fits me and what I want to do in the future. I don’t really know the right steps to get to where I want.”

I will simply let Courtney elaborate here: “A while back I was looking at a baby book my parents put together for me, in which my grandparents answered questions about their early lives. My grandpa’s answer to what he wanted to do after high school was ‘Get a job—any job. It was the Depression.’ And while that last part is pretty specific to its historical moment, the first part is, as they say, highly relatable. It can be hard to even know what you want to do for a living when you’re fresh out of college, let alone how to find your way there. But not knowing is okay! If nothing else, it frees you from some of the anxieties your peers are facing (see all the worries about field-specific job opportunities above). Even a terrible position can be useful by teaching you exactly what you don’t want to do 40 hours a week. And it’ll still give you something to put on your resume as evidence of your experience.

There’s nothing wrong with taking a job because it’s the only offer you’ve gotten and you have to pay rent somehow. There’s nothing wrong with staying in a job because you don’t mind the work and your colleagues aren’t actively awful. It’s good to keep checking in with yourself to make sure you’re still satisfied (do you want more money, more responsibility, more flexible hours, different duties, or some combination thereof—or to move to a different industry?), but if you’re not yearning for a change, don’t arbitrarily upend your professional life to chase a vague notion of advancement.

Of course, the entire universe of available jobs can feel overwhelming if you don’t have any parameters to help narrow your search. So allow me to suggest some. Are you passionate about particular causes? Look for positions at nonprofits that work on those issues. Is there a particular type of work that you love? Try to find jobs that will allow you to use and develop those skills. Do you want to live in a particular city or neighborhood? Find organizations with a convenient commute. Or just spend some time trawling job-search sites—after a while, you’ll start to recognize keywords that help you identify (or rule out) places where you might apply.

I have a lot of friends in their late 30s or older who are settled into established careers, but hardly any of them had a clearly defined idea of what they wanted to be doing when they graduated college. Even those who have stayed on a fairly linear path have veered off it slightly. And again, that’s not to say it’s wrong or foolish to be pursuing a specific goal! It’s just to point out that something can feel like a failure or setback in the moment, but ultimately be part of a longer arc that gets you into a fulfilling career you might never have considered otherwise.”


On that beautiful note, thank you Courtney for joining me for this article once again, and as well, thank you to the students for submitting their questions! As you already know, you can (and should) 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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