The first commandment of risk-taking: Know thyself

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Or: How to leave your first job when you don’t have a plan

Let’s get this out of the way up front: If you’re the type of person who can make plans on a whim, easily cancel commitments or change your mind without guilt, and try new things without fear, this post probably isn’t for you.

But if you’re like me and you often keep yourself within the confines of a tiny little comfortable box to avoid the risks associated with big life changes (and then 2 years later wonder, “Why am I so miserable?”), listen up. I’m not going to sit here and pretend like I did something truly awe-inspiring or groundbreaking to warrant this unsolicited advice, but somebody out there needs to hear this:

Getting out of your comfort zone and taking a risk can pay off sometimes—as long as you know what you’re doing.

First, some background. Stay with me. I’ve always been the type of person who plans things out in advance. I don’t do well with uncertainty. At the same time, I wouldn’t say I’ve ever had a grand vision of what my life would be like in the future—or, maybe I did at one time, but then I became an “adult” and everything changed. If I had to pin down a dream I once had for myself, it was basically to be Rory Gilmore (until I grew up and rewatched Gilmore Girls and realized Rory is actually the worst).

My senior year of college, I was voted “Most Likely to Succeed” by one of the student organizations I was in, earned a medal for “Student of the Year” in my academic department, and graduated with a 4.0 GPA. I defined myself by my academic success for as long as I could remember, and I achieved almost everything you could achieve in the classroom by the time I graduated.

And then I graduated. And all I could think was, “What the hell am I supposed to do now?”

I found myself, like many graduates, feeling woefully unprepared for the “real world,” despite my achievements. I was so burned out from years of working my ass off that I knew I didn’t want to go back to school, at least not yet. I got a degree in Communication which meant I could do… anything? Nothing? I always loved to write, and it couldn’t be that hard to find a writing job, right?

Like nearly every other recent grad in the communications-media sphere who needs income faster than slow-paying freelancing jobs can provide, I ended up at a marketing agency. I thought I’d be writing, which was partially true, but it turned out that the bulk of the job involved analytical and time management skills. It was exciting at first. I learned a lot very quickly, and many of the things I learned just aren’t taught in school—at least not yet. But because of the culture of my workplace, I managed to convince myself that I enjoyed working long hours (“I take my computer home every night because I want to.”), that I didn’t really like writing as much as I thought (“Google Analytics is just as fun!”), and that my first job could be the one I stay at forever (“Maybe I just got that lucky!”)*.

*If you are older than 25, this is probably the part where you start to roll your eyes—obviously your first job is unlikely to be your last. But if you’re at a similar place in your professional journey, I hope some of this sounds familiar—and that the retelling of the rest of my experience is helpful to you.

I was at that job for nearly two years before I realized how naive I was. I had this epiphany at an industry conference paid for by my company which, ironically, taught me a lot about the industry my company purported to be in and absolutely nothing I could actually apply to my role. I was sitting in session after session, furiously scribbling down notes, thinking, “This is what content marketing actually is? People can actually do this for a living and, like, win awards?”

I went back to my hotel room that night and navigated to Indeed. It would be seven months before I actually quit, but the seeds were planted that day. I didn’t know it, but that’s also the night my quarter-life crisis began. My lightbulb moment had me on a high: I had it all figured out! I could just join a new company with a great content marketing team and my whole life would be better. Easy!

It turns out that two years away from the job search process can lead to selective amnesia about how hard it is—and how awful it can make you feel about yourself. I knew I didn’t want to quit my current job without another one lined up (because who does that?), and I didn’t just want to jump to another job that might not be a great fit. The interview process for the first job I applied for ended in a hiring manager completely ghosting me, and another ended with a kind but devastating email telling me that I was a great candidate and everyone on the team loved meeting me, but the person they went with had more experience.

That second incident left me demoralized. I wasn’t mad at the employer for choosing another candidate—it totally made sense. I probably would’ve done the same thing in their shoes. But I was now exhausted from a months-long interview process and miserable in my job with absolutely no job prospects. At this point, I’d been actively looking for a new role for nearly five months, and it was tough to find the time to apply to enough positions when I was still working 40 hours a week and traveling for various family obligations on the weekends.

So, what is a perpetual planner to do when you have a goal but no concrete plan? I kept looking for jobs that sounded interesting, to little avail. I talked to a staffing agency about potential contract opportunities, just to hear that it would be nearly impossible to be competitive if I insisted on giving my current company two weeks’ notice. Some people might’ve just said to hell with two weeks’ notice when you’re miserable, but my (potentially misplaced) sense of morality told me I couldn’t do that to the people I worked with, particularly on a small team at a smallish company that keenly felt the impact of employee departures.

But I also knew, deep in my gut, that I couldn’t stay. I had been miserable for too long. Was it the worst job in the world? Was I working 60+ hours a week? Were my managers rude or abusive? No. But I could no longer stand to do the work I was doing for more than 40 hours a week, which was more or less required if I wanted to stay. I also knew the structure of the role wasn’t right for me and that the core values of the company did not align with my own. Those I love have always been my top priorities, and my company encouraged work to be the priority above all else, which meant everyone worked as hard as possible for as long as they could stand to without going completely insane. That equation would never equal happiness, at least not for me. I doing the kind of work I had convinced myself that I didn’t like the kind of work I always knew I’d loved to do just to fit in at this company. I wasn’t being true to myself. And it cost me.

While I knew I had to leave, I was still horrified of what would happen if I left without another position locked down. Maybe I’d quit and then I’d never find another job again. Or I’d have to take another shitty job I hated just to make some money. Or… I don’t know? The risk-averse voice inside my head seemed to have many ideas about how the world might end if I didn’t have a job for a few months, despite the fact that people do this kind of thing all the time and the universe still manages to hold itself together. (I am, of course, extremely privileged to even be able to make a decision like this in the first place—to be able to decide what type of work I will do and base that decision off of my own happiness and fulfillment rather than whether I can pay my bills. That is not lost on me.)

I read so many advice articles with titles like, “When to Quit Your Job Without Another Job Lined Up” (spoiler: the advice was usually, “Don’t do it.”). I had talked to friends, my mom, my partner, and myself about the pros and cons of leaving. I fantasized about turning in my notice, but the voice inside my head always crept back in.

“That would be irresponsible.”

“You won’t be able to buy anything.”

“You’ll just end up accepting another terrible job out of desperation.”

Then one day, after chatting with a coworker who I’d clued into my internal struggle over what I should do, a feeling came over me that I couldn’t shake. I had to just do it. I was lucky enough to have the support (emotionally and otherwise) of my partner, who’d been telling me for months to pull the plug. And I knew that if I gave myself a deadline, I’d work harder to find a new job. Plus, if I quit without something lined up, I’d certainly have more time to look once I was, you know, completely and utterly unemployed.

Within the span of about 30 minutes of sitting at my desk and thinking through it, and texting my partner one more time to say, “You’re really fine with me doing this?” and getting an answer in the affirmative, I pulled my boss aside to tell her. I decided to give her plenty of time (until the end of the next month, roughly 5 weeks) so that she could find a replacement for me. And that was it. I had done it. There was no turning back.

I instantly felt relief—also a little fear, of course, but mostly relief. I’d finally taken a step toward being happier, and I couldn’t talk myself out of it now. That was liberating, in a sense. It was a decision that could no longer be debated or discussed or reversed.

Meanwhile, I had applied for a job about five days earlier that sounded great, but I knew there would probably be hundreds of applications and I had, I thought, little chance of even getting an interview. But six days after putting in my almost-unreasonably-long notice, I got an email from the hiring manager asking to schedule a chat about the position. We talked the next day, and I got an email from the CEO three days after that to talk again. I went in for a face-to-face interview a week later, and received an offer the following day.

I almost wish this story didn’t have a happy ending, or that it was more open-ended. It feels like it cheapens the whole spirit of taking a risk, because it worked out so easily for me in this case (after, you know, over half a year of searching). When I started writing this, I still had a little less than two weeks before my last day at my old company, and I’d known for more than a week that I’d have a job waiting for me when I was done.

But I honestly think I’d have written this either way—whether I had a full-time job, went back to freelancing, or spent my days on job applications while sitting in a coffee shop—I’d make this decision a thousand times over, regardless of the outcome.

Because it was true to me.

Because there is never a “perfect time.”

Because you don’t have to do something just because other people do, or because other people think you should.

Because nothing will ever change if you just stay in the same place forever.

Because it’s okay if your definitions of success and happiness are different from those around you.

Because it’s okay to not have all the answers. 

When I graduated from the College of Charleston, I (and all the other graduates) walked out from the beautiful area where commencement is held and under an arch that has this inscription written in Greek:

Know Thyself.

I still have a lot to learn, and I have a long way to go in my professional journey. In five years, I may look back on this period in my life and realize, again, how naive I was. That’s life. But the most important thing I’ve learned in the three years since I passed under that arch is that there is no skill more valuable than knowing yourself and staying true to those values. Maybe I should just listen to this advice I gave to other soon-to-be grads in 2016:

“Keep an open mind, work hard, and do what feels right. Everything else will fall into place.”