Which Career Battles Should You Fight And Which Should You Drop?

It can be tricky figuring out how to advocate for yourself, and when it’s worth the fight. From getting more meaningful work to suspecting discrimination, here’s when to speak up.

Which Career Battles Should You Fight And Which Should You Drop?
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Kaleigh Moore had been working for an Illinois nonprofit as a PR manager for around two years when she asked her boss to work remotely once a week. “I was mostly doing email and phone outreach or writing work when I wasn’t traveling,” Moore recalls, and “the 100-plus miles on my car each day and gas money were significantly cutting into my earnings,” which weren’t that high to begin with.


But Moore, who now works for herself as a writer for tech companies, was only 23 at the time and one of the least senior people in her office. She felt it was risky to ask, “but I was getting to the point where I was going to start looking for something new or quit if I couldn’t find a way to increase flexibility within the role,” she explains. Moore’s boss said yes, and despite picking up on murmurs of resentment among some coworkers afterward, she says she never regretted it.

It’s not easy advocating for yourself when you’re starting out in your career. You don’t have a ton of experience navigating workplace politics, which can make it tough to know how to be tactful, and which types of concerns will earn a positive response. You probably don’t have a ton of power, either. Not to mention, there are sometimes real consequences to sticking your neck out. Here’s how to weigh those and other factors while deciding which issues to raise and how to raise them.

When You Want To Do More Interesting Work

“A lot of people I work with struggle with the discussion around ‘more meaningful work’ because they don’t want to be labeled as a ‘needy millennial’,” says career strategist Linda Raynier. “So many feel unfulfilled and aren’t able to express that. They feel they can do more and offer more, but due to age and title they feel like they don’t have the credibility to speak up.” Millennial stereotyping in the workplace is real and counterproductive, both for its subjects and its perpetrators, but it doesn’t need to doom younger employees to a purgatory of grunt work and condescension from higher-ups.

Your best ticket out? “Old-fashioned hard work is still the best path to building credibility,” Raynier explains. As Humu CEO and former Google HR chief Laszlo Bock wrote for Fast Company recently, employees who consistently make small, ‘above-and-beyond’ contributions are hard for managers to avoid rewarding eventually.

So before you ask your boss for more inspiring work, make sure you have something to show for yourself–nail the details of your job description, and start showing how you can make an impact beyond it. (Not sure how? Here are some tips.) In addition to credibility, that should also give you the confidence to ask for greater responsibilities.

When You Have An Idea For A Change Or Improvement

When you’re low in the ranks, you may worry that suggesting a change elsewhere in the organization will be seen as overstepping. But you may have more options than just “tell your boss and hope for the best” or “shut up and deal with it.”


“Part of the challenge is that a person may be stuck in their own thoughts and may need someone else to help provide perspective,” says career coach Simone Wilson. Rather than working up the courage to approach your boss about it (and shouldering the risk), ask a colleague or someone more senior who’s at a safe remove from the issue to weigh in–even somebody at another company.

Wilson recommends running your idea past “someone who can serve as a sounding board [and] who can help you work through your approach so that you can share your concerns in a succinct and confident manner.” First, see what they say about your proposed solution. Then, if they agree it sounds solid, ask how they’d suggest tactfully raising your idea.

When You’re Being Discriminated Against Or Victimized

The recent flood of sexual assault and harassment allegations across dozens of industries has shed light on the many reasons so much misconduct never gets reported and why so much that does never gets properly addressed. Among them, women and people of color in particular rightly fear personal or professional repercussions for filing HR complaints about sexual misconduct as well as sexism, racism, ageism, homophobia, and other bias-driven behavior; the worst that can happen for speaking up, in many cases, is definitely not just hearing “no.”

But even though being younger or low in the hierarchy compounds these risks, Raynier believes that “some of these issues are showstoppers” and warrant addressing rather than silently suffering. “It’s important to remember that you are the one that’s in control of your career”–or deserve to be, at any rate–and that anyone who’s victimizing you in the workplace is hoping you’ll doubt or forget that. While there’s no single easy way to decide how, when, and even whether to report abuse or discrimination at work, there are steps you can take to find the best solution–like these, for starters.

Raynier points out that it’s the job of employers to create “an environment where their staff can feel encouraged to express their opinions and values and be heard, and [where] challenging current practices is seen as constructive and not a personal criticism.” So no matter what type of issue you’re considering going to bat for, keep in mind that your boss (or an HR officer) has a responsibility to hear you out and take you seriously.

But broadly speaking, Moore says her successful request for a more flexible schedule has taught her to err on the side of communicating. “If you’re on the verge of quitting, but there’s something you really want or need within a job, tell your boss. They’re not mind readers.”


About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.