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7 Time & Money Investments It Took To Secure My First “Grown-Up” Job

Not long ago, I leveled up by securing a job that could actually be considered a career. I had stepped out of the freelancing, writing for crumbs on the interwebz world, and into an office, a large salary, and health benefits.

I know many of us have or will or currently are going through the process of finding a job. A grown-up one. When I was applying, I obsessively read everything that was out there on the process, trying to decide what was normal and whether or not I was ultimately doomed. Now that I’ve gotten the job, I’m writing my own guide for those of you that may be just as scared as confused as I was. Here’s the breakdown of the career caliber job hunt, by the numbers.

1. Four Years of Education (No More, No Less)

There are some that say that the Bachelor’s degree is the new high school diploma. At every turn, as I was growing in my education, I was being urged into grad school. Told that it was 100% necessary to securing a good job and a competitive salary. I graduated from my Bachelor’s program with a double major, a minor, and a thesis. Pretty hefty accomplishment, compared to some of my peers. But I told myself that going to law school would be the best thing for me, and I dove right into law school, not even sure if I wanted to be a lawyer but convinced that the “JD advantage” would be invaluable.

Let me say it loudly, for the people in the back: DON’T PURSUE A GRAD DEGREE JUST BECAUSE, ESPECIALLY NOT F***ING LAW SCHOOL!! Of course, there are some dreams that require a Master’s or a Doctorate and so on, but be real with yourself and what you actually want instead of just assuming that a more advanced degree is the right thing for you.

I got hired for a job that only required my four-year degree. If I’m being totally square, I got hired based off of one of my two majors and a handful of specific classes. Guess what? It’s a job that pays just as well as what I could have made, as a lawyer (let’s be honest: I was never destined for Big Bucks Big Law). Education is a wonderful thing, and I wish all of us could soak up as much of it as humanly possible. But education is also a huge cost and, honestly, a luxury item in many ways. Get what you need and get out. No more, no less.

2. Four Years of “Experience” (And Why That Was the Bitch of It All)

The cruel, running joke of the ambitious millennial is the trend of non-entry-level experience being required for many entry-level jobs. Having the perfect collage of experiences and skills is damn difficult and extremely hard to navigate when considering how much of our limited energy goes into our schooling and working the kind of jobs that just keep a roof over our heads.

I threw my effort into being a Jaqueline-of-all-Trades in early 2014. I wanted to be a writer. Actually, that’s not true. I knew I was good at writing and wanted to get some exposure to my name on the off-chance that it would be helpful in the future (Spoiler Alert: it was). So, I started generating clickbait for a large online magazine. No pay. By that point, I had already set the goal of sexy attorney out there and was serving as a law clerk at the local, very small, very overwhelmed prosecutor’s office. Also no pay. Over the years, I would “level up” the caliber of publications that I would submit to. I branched out from plebian horoscope breakdowns to more practical subjects.

The only paid gigs I managed to secure, this entire time, was a brief position as an editor for a small, local humor paper (and when I say paid, I mean it was literally beer money) and the remote copy editor position that nobody but me took seriously, which was singlehandedly responsible for opening all the doors.

The bitch of it all is twofold. On the one hand, I realize the immense privilege that came with my ability to take any gig, unpaid or not, because of the financial safety net provided by my parents’ help in paying my tuition. And I shudder to think 1) how screwed I would be if I hadn’t had that option and 2) how unfairly screwed many of my peers are because nobody should be doing meaningful work for free, and many don’t have the option to consider whether or not they would.

The second side of this double-edged sword was that my varied experience was both my greatest asset and a weight around my neck. I had worked in a variety of industries and gained expertise on a variety of subjects. Working on the Internet gave me an in to such things as social media trends, understanding demographics and increasing readership, and the nuts and bolts of just writing good copy. Working in traditional settings, like a law office, taught me how to manage stress and timelines and how to serve real people in a variety of situations. My skillset was strong but it was a crapshoot in terms of whether potential employers would look at the collection of hats I’ve worn as a testament to a diverse background of experience or as evidence that I was all over the place. My greatest advantage, being good at a lot of things, was keeping me shut out of some offices. But, ultimately, my experience would be what catapulted me from “I just need a job” to “Here’s a job that is actually a step in your career.”

3. Three Months of Searching

I started my job search right after Christmas, on the pitiful hope that the new year would equal new hires. I wasn’t exactly wrong, as January is one of the most popular months for hiring. *Sigh* It sucks. Searching for a job totally fucking sucks. There is the waiting and the applying and the waiting and the rejections and the waiting and then maybe someone interviews you and then you wait and you wait and fill out more applications and wait.

To say that I was a wreck during this time is an understatement. Even with the good fortune of having a lucrative side hustle to fill my time (and my coffers), the pressure and the fear is something incredibly real. I think we often forget how long these things take. We know there’s gonna be a lot of interviews and a lot of rejection. But we rarely talk about the fact that you can have an interview and it can go well… and you’ll still wait two weeks to see if you’ve advanced to the next round. Fuck it all, my dudes.

4. Two Major Reevaluations of the Self

Job hunting has a way of bringing out our absolute worst insecurities. At many points in my journey, I felt worthless and afraid and like nobody wanted me and that it would never happen. I questioned my abilities. Panicked over what would happen if I couldn’t find a job that would truly pay the bills. My inability to land a job convinced me that I wasn’t capable of functioning in any capacity.

It’s okay to mourn. It’s okay to be disappointed and even a little fearful. But rejection is a part of life, and the fact that you weren’t a fit in one place does not negate all the skill, education, and personal touch that you bring to the world and to future workplaces. Remember that and, should you fall off the wagon and have another meltdown along the way, keep remembering it.

5. 60+ Job Applications

I shit you not. Filling out job applications became my job. I was fortunate to be searching in a city that is experiencing a lot of growth and opportunity. Where the market is good and hip, startup type companies are coming in alongside corporate giants who like the vibe. There were a lot of applications to fill out, and I filled out every last one of them. It’s exhausting, and I think the worst part is that you get excited about the possibilities, which makes the crash of never hearing back or being turned down so much harder.

Finding a job can sometimes feel like actually searching for a needle in a haystack. Dive into that haystack, y’all. It’s time-consuming, but the needle is in there somewhere, goddammit.

6. 17 Interviews

That number is much less than the 60 applications, did you notice? I have a love/hate relationship with interviewing. On the one hand, I’ve always been comfortable in conversation, and with my mixed bag of experience, it always helps to be able to talk it through and break it down, per the situation. I hate it because it’s fucking scary.

Phone interviews — they’re awkward and never seem to happen at the right time and you’re trying to say enough without saying too much and your dog always decides to bark as soon as you connect.

The first round of interviews is, in my opinion, the worst. You still have plenty of time to fuck this up and have them not call you. You have no idea how they feel about you, yet, so you get nervous and, if you’re like me, you ramble. Ugh. I had a total trainwreck of an interview (that a friend had set up for me!!) where I got excited and just barreled through the process. I was a verbal bull in the china shop of that opportunity. It did not go well.

7. Two Heartbreaks

Searching for a job is a lot like dating. You’re out there. Single and ready to mingle. Suddenly, a vision appears across the room. You’re smitten. You saunter up, give them your best line, and leave them with your phone number. And they never call.

Or, maybe they do call. You go on a date. Maybe you only get that one date and it doesn’t work out. But even worse is when the date goes well and you go on two more dates and suddenly their engagement announcement to Not You appears on Facebook.

Okay, so maybe that’s a bit of a stretch in illustration, but I’ve had my heart broken on the job hunt. The first time was “The One That Got Away.” A position opened up at the headquarters of a local brand that I was crazy about. I had been a huge fan of the company for years, they were so cool and the culture was hip. I was so stoked to even maybe have the chance to interview with them. I got so hyped on the possibilities and rode that high for weeks. Before the rejection came. Ouch.

The second one was definitely a blow. It was one of those job postings that ticked off every box. The location was good. It was a position within an industry that I had worked in before. I seemed to be exactly the candidate that they were looking for. They thought so, too, because I made it through three rounds of interviews. I was in the final two candidates. In the time that I had been going in, I had really fallen in love. When that rejection came, it was hugely disheartening. I had no clue what I could have done differently. It instantly made me fearful for the rest of my search, because if I couldn’t get this job that my experience was so perfectly tuned to, how was I gonna get hired anywhere else?

Just like in actual dating, heartbreak is important because it’s an opportunity to get real with yourself and evaluate where you are while also setting you up to fully appreciate it when “the right one” comes along.

Finally, 1 Awesome Opportunity

It’s cliché, but it’s true: things had a way of working out. One of the last places I applied to and interviewed for ended up being the one. Not only did they give me a job, they gave me the best salary of anyone else I had spoken with, they offered flexible hours to make the commute more tolerable, and the culture is rad.

To wear out that tired dating comparison, sometimes it’s the breakup that sends you into the arms of someone that is good for you. Love is patient and you should be patient with yourself and with your job search.

Caitlin is a lean, mean writing machine based in Austin, TX. By day she is a mild-mannered content marketer, by night she is a freelance copy editor, and (when there are hours left in the day) she writes for the adoration of faceless online readers, everywhere! When she’s not writing, Caitlin annoys everyone around her with her obsessive love of podcasts, movies, and coffee.

Image via Pexels

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