It hit me four years into my career—at that point, a sequence of entry-level to associate-level jobs—as I was filing papers for my boss on a Friday evening. The office lights had already gone out, and I was the only person left. I’d had too much work during the week to get to this more menial task. So there I was, on my hands and knees, papers spread around me in the darkness, feeling completely and utterly content.


This was the kind of mundane, “beneath-my-elite-college-education” task that I’d bemoaned in my first job out of school. But I realized that evening, then in my mid-20s and in a managerial position, that I was making my boss’s life a little happier and easier—even if it was the last thing I wanted to be doing on a Friday night. It finally clicked that the grunt work could be as important as the more challenging tasks I enjoyed, the ones I believed I’d been hired to do.

And what unraveled, along with the endless white paper beside me, was the “I”-deology: the fantasy that a job could serve me, instead of the more accurate view that all jobs serve others, from the assistant serving his boss to the entrepreneur serving his client to the company serving its shareholders.

Here is a sampling of other fallacies I believed, and bad advice I received, that left me with unrealistic expectations and mixed-up priorities—and the advice I wish I’d received instead.

Mistake #1: Serve Yourself and “Follow Your Dreams”

Just as many twenty-somethings are told today, I was harboring an illusion that a job was intended to interest me, make me happy, and fulfill my passions. We hear catchphrases like “follow your dreams” and fantasize about a world in which fulfillment is achieved at every level: intellectually, morally, spiritually. Surely the “hard work” of success should be enjoyable, the way it was when racing the clock to finish a paper in college. But hard work can appear hugely disenchanting if you’re shortsighted about it or if you don’t see an immediate goal.

What we are told less often, if at all: Rolling up your sleeves and doing the labor, from the mindless to the manual, has equal value. (I’ll never forget the image of my elegant, high-heeled, well-respected boss getting down on her knees to help me pack books into boxes.) And if your job, at any level from assistant to business owner, can feel on some days miserably monotonous, you are no different and no less royal than the rest of us.

The better advice would have been: Find your road and follow that. Stay grounded. Dreams, for all their shades and variances, can misguide you.

Mistake #2: Play Hardball

As the daughter of an entrepreneur and homemaker raised in the Women’s Lib era, I was taught by both parents to be as aggressive as possible in negotiating for a position, promotion, or raise. It was important to my mother, and reasonably so, that as a woman, I not be taken advantage of where money was concerned. And thus, with blind faith and false confidence, I came in guns a-blazing from first interview to job offer to job. Why wait for a raise? Demand one!

What playing hardball accomplished was to set me apart in the eyes of management—and not in a good way. (I might as well have been wearing a sign saying Watch out for this one!) My tendency to force the promotion conversation prematurely was antagonistic instead of collegial and defensive when there wasn’t a reason to be.

The better advice would have been: Ensure you’re in a formal negotiation conversation before showing your cards.

Mistake #3: Be the Big Boss’s Pet

When the director of our department opened her door to a friendship, I walked through it without a second thought. Because she—I’ll call her Barbara—made personal calls, I thought it was permissible to make my own, right out loud from my cubicle. I figured if I could exhibit a carefree rather than anxious air, I would demonstrate that I’d already outgrown my entry-level position.

I went out with Barbara and her friends, all twice my age, listened and attempted to relate to their weekly rom-coms, even went so far as to set Barbara up with my father—ill-advised for many reasons. There’s a time and a place when bosses and their underlings can become friends, even close ones, but I’ve learned that it should happen when you’re no longer working with each other. My amorphous, mother/daughter, peer-to-peer, boss/employee relationship with the department head made tough professional conversations feel personal. And all the while, I was distancing myself from my co-workers, who saw my behavior as obsequious and superior.

The better advice would have been: Tread boundaries carefully; be aware of their nuances. Make peers your first allies.

Mistake #4: Be Loyal to No One but Yourself

Always looking for job satisfaction, my generation is not known for career loyalty, and the media has helped shape this attitude. Blog “experts” tell us that bouncing from job to job is fully recommended! Where cool, young tech companies are concerned, this so-called diversity of experience is attractive on a resume, the way of the future. On the other hand, career columnists in more conservative news outlets warn of “a smattering of noncommitments” (which is how I’ve come to refer to my own resume).

We must learn most career mistakes on our own, but it was a close colleague in my business who reversed the course of another falsehood. Born of the generation between my parents’ and mine, he worked his way up from receptionist to business partner. There is something laudable in that endurance, and what it achieved was a trust between him and his boss that those of us designed to be more peripatetic may never experience.

The better advice would have been: Do not cling to youth’s wanderlust and see your job as dead-ended. Establish loyalty to someone—not a corporate entity, but an individual—and your perseverance will pay off.

Career satisfaction has more to do with how we co-exist with our colleagues, how well we seek balance rather than resist it. Aiming for competition rather than collaboration, and putting ourselves first, can easily lead us astray. Those who rise to leadership positions are not the ones who alienate themselves from company culture—but the ones who drive it.

Click here to see Rose’s tips for healthy and happy relationships

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