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The Uncomfortable Reality of Having a Younger Boss

I recently started a new job at a large advertising firm. The company is well known, and the position came with good benefits. There wasn’t much of a learning curve in terms of role responsibilities, but then I was hit with the emotional sucker punch: a younger boss.

I made an assumption that my boss was older than me by at least five years, based primarily on the differences in our demeanors (she’s generally more serious and alternates between saying “raise the roof” like a dad in a 1990s teen movie and “back in my day”) and her penchant for Ann Taylor Loft. After careful investigation (i.e., social media stalking) I discovered that I’m older than her by a few months. All of my previous supervisors have always been my seniors by at least a decade. Here then comes my second assumption in a single paragraph: Bosses are typically older than their workers because they have more experience, and as a result, more authority.

According to a CareerBuilder study released in 2012, however, my younger boss is becoming increasingly more common. In fact, roughly 34 percent of workers now report to a younger supervisor. The intergenerational workplace is a new, fascinating phenomenon that comes with its benefits (tons of ideas and perspectives, eclectic Spotify playlists) and challenges (old people hitting “reply all” to every email, awkward Tinder conversations). But while the statistics reassuringly remind me that I’m not alone, they don’t ease my day-to-day insecurities. Needless to say, making the best of it has been more challenging than I thought.

It seems common in many workplaces for similarly-aged employees to gravitate toward each other and become friends. Not saying ageist gangs are the gold standard of office culture, but there’s something to be said for generational relatability. It’s different, though, with power dynamics in play. “I haven’t heard this song in years. How old were we when it came out?” my boss asks as Third Eye Blind’s “Semi-Charmed Life” floats out of her computer speakers. As I leave her private office and retreat to my dingy cubicle, I feel little daggers prodding the tender spot in my business casual soul. For the record, we were 11; at that point, we were both on the same level. She wasn’t approving my timecards.

My boss held my position for a year, and only recently got promoted to her current role when they hired me. Based on her LinkedIn history, I know it’s her first time managing someone. She tries to either be the “cool boss” or put as much distance between us as possible. Which version I get depends on the day. One morning, she’s talking non-stop about her Tarot reading (lingering Tumblr witch tendencies); the next, she’s reading my performance review in a monotone voice punctuated with a clammy handshake. She converses easily with coworkers who aren’t her direct reports, but I’m an awkward stumbling block. “I don’t know what to do with that situation a lot of the time,” I overheard her telling a coworker not that long ago.

I’ve always had a great relationship with past bosses; they’ve been wonderful mentors who have helped build my skills and confidence. But it’s weird to have a younger supervisor try to build rapport by offering me unsolicited relationship advice when I feel like she isn’t really my peer or a world-wizened sage offering something I don’t already know myself. It’s frustrating to have her proofread my work and offer no new lessons; more often than not, new typos show up in her edits. To err is human, I know, but in this already awkward situation, any slip-up on her part signifies the illegitimacy of her authority over me.

She seems to like being the boss, and often takes me along as the resistant passenger on her power trip. She’s made me designated note-taker for all meetings, but insisted that only managers can have company laptops. So I get to write all notes by hand, then type them up. It’s kind of like writing “I will not curse in class” 100 times as punishment in middle school. Younger employees sit there twiddling their thumbs as my haggard 30-year-old fingers scribble away. She also constantly makes me collaborate with the 19-year-old intern on projects. I love the intern, but I’m not sure why I even went to school and worked hard just to be flung back to the ranks of a college sophomore at age 30.

All of this begs the question, what did I do wrong? According to U.S. News & World Report, I went to a better school than her. I’ve gotten great performance reviews at all positions I’ve ever held. I’ve made lifelong friends at work, and built strong connections across my chosen field. Yes, I acknowledge that this is an ego issue. I feel like I’m falling behind where I should be at this point in my life. Just interacting with my boss provides a daily reminder that I’ve regressed and somehow wound up stuck at an entry-level roadblock. I’ve paid my dues for years now, put in the hard work and still wound up as the subordinate with the smaller paycheck. (It’s worth mentioning that I entered this new position with some negative feelings already: I’d been unceremoniously laid off from a now-defunct software company a few months earlier where I’d held a mid-level role — and as everyone who has been laid off knows, regardless of whatever niceties are exchanged in your exit interview, it’s hard to keep from feeling incompetent or demoralized by the experience.)

Two roads diverged in a yellow wood; unlike the cheerfully self-reflective Robert Frost, I can’t shake the feeling that I must have chosen the wrong path in the not-too-distant past. My mom tells me life is a journey, and we can’t compare our own road map to someone else’s unique atlas. She also tells me that only desperate people take shots at the bar. Much like tequila, I take her advice with a grain of salt.

There are plenty of articles out there promising to ease the office tension and offer a cheery perspective for those of us singing the younger boss blues, but most of them are bullshit. One suggests that the struggling older employee focus on getting physically fit, or being confident in what you bring to the table. This sort of thinking just exacerbates the issue and speeds up my spiraling feelings of low self-worth and ability. What reason do I have to be confident in what I bring to the table? Whatever I’ve got clearly isn’t enough. Why should I dwell on my level of experience? When I start to think about my background and skill set, I oscillate wildly between either a) feeling overqualified; or b) worrying that I have no viable skills at all. And while I enjoy going to the gym, I can’t literally strong-arm my way into a better position.

The truth is there isn’t any easy-to-follow advice for employees in my situation. The recession might be over, but it’s still hard to find a full-time job with benefits. Plus, I don’t want my resume to resemble a Whack-a-Mole playbook with too many positions scattered over a short amount of time. At the same time, this is my life, and it’d be nice to feel like I had more agency both in the day-to-day experience and general career path.

And so, at best, I’m paying my bills. At worst, I’m checking job postings on my work computer — a desktop, not laptop, of course — while listening to my boss describe her graphic design skills as “ghetto” or email chains as “retarded” and wondering why bosses aren’t required to go to more diversity trainings.

Get me through this semi-charmed kind of life.