Every 20-Something Should Read This

Let's face it: Most of us aren't going to be topping any "30 Under 30" lists. It would be nice, but in reality, it's more likely you'll spend your 20s just trying to figure out what the hell to do with your life. Major kudos to the badass women who do make those lists, but this story is not for you. This story is for the rest of us.

I've always considered myself a bit of a late bloomer (I'm not going to tell you how old I was when I had my first kiss), and that has kind of applied to my career as well. I love what I do, but it wasn't until I hit my early 30s that I finally believed I actually knew what I was doing. I'd suffered through some bad bosses, bad jobs, and some career confusion. At 34, I don't have all the answers, but I feel pretty confident in my future (not cocky, mind you, I still recognize how hard it is, whether you're 25 or 35 or 55).

Ahead, 30 things every woman should do for their career before they hit 30. As with every list like this, pick and choose what is applicable to you. The most important piece of advice I have is to learn to believe in your own abilities — and many of the directives here will encourage that. Trust in yourself, don't be afraid to make mistakes or ask for help, and go out and do your thing. Maybe it will land you on a "40 Under 40" list. We can all dream, right?

Opener photo by Erica Gannett.
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Illustrated by Abbie Winters.
This is simple advice that's really hard to achieve. What constitutes career happiness and success is different for everyone. For some, it’s getting a big paycheck, for others it’s about creative freedom, or cool coworkers, or job security. It’s not necessarily something you understand when you're beginning your career, but by two or three jobs in, it starts to become clearer.

Let’s be realistic, though; just because you like your job, that doesn’t mean there won’t be bad days, annoying colleagues, or setbacks. That’s why you get paid to work. If you wake up every morning and want to cry (I’ve been there), or you’re bored — or worse, you feel you’re being taken advantage of by your boss — it's probably time to move on.

Also worth pointing out: Once you have a job you like, that doesn’t mean you should stop looking for a new one. It’s always useful to keep an eye on the listings and go on interviews from time to time, just to keep those skills up to snuff. Which leads to point two…
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Illustrated by Abbie Winters.
Updating your résumé is kind of the worst — not as bad as doing your taxes, but not very pleasant, either. But there are a few reasons why it’s important to keep it up to date. Firstly, if you edit your résumé every three to four months, you’ll remember more of the cool stuff you’ve been doing at work. If you rarely take time to record your achievements, it's more likely you'll forget all the details of that project you managed that was a huge hit and brought in big money.

Secondly, you never know when you’ll need an updated résumé to send out to a potential employer — even when you’re not looking for a job. If you take the time to revise every quarter, it will be ready to go whenever you need it, whether or not you’re looking for a new job.

Need some help perfecting your résumé? Check out this post for more details.
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Illustrated by Abbie Winters.
On every street corner, in every bar, restaurant, and coffee shop, people are complaining about their shitty bosses. Really. Next time you’re out, just look around, and you will see two women having an intense conversation about a bad manager. Even if you have a job you like, there’s a good chance there’s someone in senior management you don’t love. But there is a secret to being successful even when you have a bad boss, and that’s managing up.

Truly, before you learn to manage your own employees, it’s important to be able to manage your manager. We’ve written about this in more detail here. Master this skill, and not only will you have more success at work, you'll have more job satisfaction.
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Illustrated by Abbie Winters.
This is one of the more intimidating items on this list. Asking for a raise is hard — and it’s especially difficult for women, who worry about coming off as too aggressive and, as a result, often end up leaving money on the table. A LinkedIn and Citigroup survey from 2014 showed that only 27% of women had asked for a raise that year — but a whopping 84% of those who asked got one. With women still making less than men, one of the surest ways to close the gender-wage gap is by asking for more money.

I know how hard it is. I spent the whole of my 20s avoiding any conversations about compensation, no doubt to the detriment of my savings account. It was only this past year that I worked up the nerve to ask for more money. It was scary, but in the end, I got what I felt I deserved — and that felt good.

This is an enduring truth that will pop up again and again in your career: Rarely will you get handed an opportunity/promotion/raise if you don't speak up.

For advice on how to negotiate, check out this story. Yes, it’s terrifying, but it’s also empowering. You can do this.
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Illustrated by Abbie Winters.
Everyone knows it's important to dress appropriately for an interview (seriously, one time I didn't hire an intern because she showed up in jeans), but even more important is donning an outfit that makes you feel confident. You don’t need a wardrobe filled with interview outfits, just two that look and feel good. You don't want to be pulling at your skirt or fiddling with your straps when you're supposed to be presenting a calm and collected demeanor to your potential boss.

Naturally, R29 has lots of advice on picking just the right outfit. You can look here or here for starters.
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Illustrated by Abbie Winters.
There are a million organization apps out there, dozens of systems for categorizing your emails, and seemingly endless schools of thought on the best way to stay on top of things. They’re all great, but only if you stick with them. By 30, you should have found the best way to keep your shit together. That might be a menagerie of apps on your phone and computer, or an old-fashioned notebook. The important thing is finding what works for you.

It’s also worth revisiting your organization methods from time to time, to mix things up and try something new. This is one area of your work life that can get super stale after a while.
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Illustrated by Abbie Winters.
Do you hit the snooze button 10 times and then rush to get out the door? Do you struggle to pick out the perfect outfit and then miss your train? The Bangles knew what they were talking about when they sang "Manic Monday."

Developing a morning routine can prevent some of this stress. If you like to press snooze, set your alarm a little earlier. If you struggle to find just the right outfit, spend some time the night before deciding what to wear. If you can, squeeze in a workout before you head into the office. Similar to systems for organization, everyone has a different idea of the perfect morning routine. It’s up to you to find the one that makes you happiest, but even a small shift (waking up 15 minutes earlier so you can enjoy a cup of coffee in bed) can make a huge difference.
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Illustrated by Abbie Winters.
You can’t read any kind of career advice without seeing this suggestion, and I’ll admit that it’s somewhat misleading. You can’t ask someone to be your mentor, just like you can’t ask someone to be your best friend. You’d sound like a huge nerd. But you can actively seek advice from women (and men!) who are doing jobs you'd love to do one day. Email them and ask them for coffee. Really, this works! (Follow this simple email template if you're unsure what to say in your initial ask.)

While it’s important to seek outside counsel, it’s even more important to have an advisor where you work. Unfortunately, finding this in-office mentor isn’t as easy as sending out an email and asking for a coffee. These kinds of relationships take time to develop, but they are worth the effort and can be hugely helpful in propelling your career.

The important thing is to be less concerned with the label “mentor” (or worse, that oh-so-elusive “sponsor”) and more focused on the quality of the relationship. And don't expect your direct boss to be your mentor. It doesn't always work that way — though it's awesome when it does. If you don't connect with your manager, look around the office for someone else who might fit the bill.
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Illustrated by Abbie Winters.
You might be thinking: I’m too young to be a mentor! I know NOTHING! Not so! If you’re out there in the working world, making waves in your badass way (I see the awesome things you’re doing), then you are ready for a mentee.

There is nothing that will boost your work confidence like spending 30 minutes talking with a college student, intern, or younger colleague about what you do. It's similar to a job interview, in that you have to parse your work responsibilities to a few sound bites, but without the same pressure. You have a lot of experience and knowledge, working with a mentee is a great way to show that off — and recognize it for yourself.
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Illustrated by Abbie Winters.
This might be the hardest thing on the list after finding a job you like. In my early 20s, I had no problem saying everything I thought — almost to the point of having no filter. Six years into my career, I swung to the opposite side of the spectrum and rarely opened my mouth to share my opinion, even when I knew I was right.

Women often hold back during meetings, but it’s crucial that our voices are heard. Even former Secretary of State Madeleine Albright has talked about how hard it can be to speak up — especially if you're the only woman in the room. But it's part of your job to have opinions and come up with solutions. Remember when that junior coworker was so impressed with your skills? Channel that confidence the next time you want to share your opinion on a controversial topic. You’ve got this. You know what you’re talking about.
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Illustrated by Abbie Winters.
Who are you and what’s your deal? If you had three minutes in an elevator with your dream mentor/boss/venture capitalist, could you answer those questions with confidence and clarity? An elevator pitch isn’t just for businessmen trying to sell a product; it's for anyone who wants to sell themselves (yes, you!). So, practice getting your story into a tight, entertaining anecdote you can share at networking events and interviews alike. You never know when you’re going to have the opportunity to sell yourself. This easy how-to offers good advice on upgrading your pitch.
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Illustrated by Abbie Winters.
Your 20s are all about working your butt off and taking every opportunity that comes along, even if it seems scary (or worse, boring). If your boss is looking for volunteers, raise your hand. If you see an opportunity that looks promising, speak up. You just never know where these opportunities will take you, but chances are you’ll learn something — and that’s invaluable.
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Illustrated by Abbie Winters.
Yes, I just told you to say “yes” to everything, but you also have to learn to say “no.” Both are important to success and happiness at work, but “no” is a hard word and should be used carefully. From a manager's perspective, it's really frustrating when an employee simply says, "No, I won't do that." You need to learn when and how to say it — and always have an argument to explain why you want to decline something. Your boss is more likely to consider your opinion if you express it calmly, clearly, and with purpose.

But — and this is key — if your boss comes back and says, "Sorry, you have to do this," then you need to suck it up and do it. Take satisfaction from the fact that you stood up for yourself and trust that your boss has some bigger end goal in mind (or just needs you to get the job done).
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Illustrated by Abbie Winters.
Seriously, nothing will annoy your boss more than telling him you won’t do something because it’s not part of your job description (it's even worse than a "no" without reason). Plus, with that kind of attitude, you might be missing out on some awesome opportunities. Sticking to a narrow job description prevents you from taking on new tasks and growing in your job.

That’s not to say that you should take on unnecessary menial tasks or get stuck with grunt work that no one else wants to do (unless, you are the one hired to do said grunt work, in which case, sorry, but that is your job). But if you look at your career with a wide lens, you’ll see that job descriptions are crazy limiting, and that taking on new challenges will keep things interesting. Not to mention that mastering a skill that’s not in your job description will give you more leverage the next time you want to ask for a raise or promotion.
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Illustrated by Abbie Winters.
Don’t be a scaredy-cat! What’s the worst that could happen when you take a risk? Someone could say no, or laugh at your crazy dream, or maybe yell at you. And you will be sad or angry, and maybe you'll cry. Any of those reactions is okay. It’s not bad to face setbacks and disappointments when you’re developing your career, in fact, it's inevitable. It builds character, of course, but it also helps you recognize what's important to you in your work life.
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Illustrated by Abbie Winters.
We’ve written about the good and bad aspects of this relationship before, but we’ll focus on the good here. It’s really important to find a friend or two at work who you trust and genuinely like. These people are the ones who will understand when you vent about Barb in marketing in a way that your other friends won’t.

It’s also important that you don't just focus on the bad stuff when hanging out with your work wife — avoid spending all your time in a full-blown bitch session, which can be counter-productive. Don't underestimate the importance of celebrating small wins and boosting each other's confidence.
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Illustrated by Abbie Winters.
The human resources team and dozens of managers are shooting me dirty looks over this suggestion, but truly, it’s necessary to take a break sometimes. I’ve found I'm happier with work when I feel my home life is a priority. In our 24/7, always-on culture, this is especially important.

I'm not suggesting you do this all the time — or even that you take a full day. Maybe it means sneaking out a little early to catch a movie or to see your friend’s new baby. Maybe it means taking a morning off to stay in bed and catch up with your significant other. Your career is important, but your personal life is, too. And having a happy home life will make you a better employee. Don't underestimate that.
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Illustrated by Abbie Winters.
Remember when I said that you need to play hookie once in a while? That's true; but if you're gunning to get ahead, you need to put in the long hours. Get in before your boss and work until after she leaves. You don’t have to do it every day, but you do have to do it sometimes. It’s especially important during key moments in your career development: when you're beginning a new job, gunning for a promotion, or working for a new boss. Putting in long hours can show your dedication (though we don't suggest you fake it, like these guys).
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Illustrated by Abbie Winters.
You don’t need to check your email on vacation. Trust me. Once a year, it’s so important to take a few days (or a full week!) and really cut yourself off from work and from technology in general. That means not just avoiding work email, but turning off Facebook and Twitter, too. Put down your smartphone and look at the world around you. The therapeutic power of this detox can be so invigorating. You will be fully engaged on vacation, and come back inspired and rested and ready to dive back into things at the office. You might even find that you missed work. (Well, if you have that job you like.)
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Illustrated by Abbie Winters.
Everyone needs a friend who they can cry to when things get really, really bad at work (because they will sometimes). It's important that this person isn't a colleague, though — while it's good to have work friends, sometimes you need a little separation of church and state. Seek out someone who will listen without trying to offer advice or spout unhelpful platitudes. And once you've cried it out...
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Illustrated by Abbie Winters.
...then it's time to call on the friend who kicks your butt into high gear and tells you (oh-so-nicely) put on your big-girl pants and get over it. Work sucks sometimes; if you don’t like it, change it. These straight-talking friends are the ones who help pick you up, dust you off, and rebuild your confidence when it's shattered.
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Illustrated by Abbie Winters.
Everyone has different goals and dreams for their career, and that’s totally cool. As they say, some people live for work and some people work to live. By your late 20s, you'll probably have sorted out which category you fall into, and then you can start adjusting your work-life balance accordingly. Maybe that means finding a solid 9-to-5 job that never requires you to put in extra hours. Maybe you don’t mind working 50-plus-hour weeks, but you want a gig that lets you travel. As you build your career, take note of the things that make you happy and seek out the job that helps you achieve them.
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Illustrated by Abbie Winters.
This is so important, because you are going to fuck up. At my first real job, I sent something to the copy shop to be printed, and racked up a $1,500 bill. I immediately realized my mistake and called the copy shop to see how I could fix it. (I cried, and they knocked $500 off the bill.) Then I told my boss what happened. He was super impressed that I didn’t try to cover up the mistake, and I realized from that moment the power of telling the truth and being up front about mistakes as soon as they happen.

Most of us don’t work in life-or-death careers. The world won’t end when you screw up, but owning up to mistakes early gives you (or your manager) more time to fix things. That doesn’t mean you won’t get in trouble, but a calm apology can go a long way.
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Illustrated by Abbie Winters.
Some people are all about the five-year plan. I’ve never had one. In truth, they've always seemed super limiting. There are a lot of awesome opportunities out there, and I never want to miss out on one because it didn't fit into a delineated life plan.

But it’s good to have at least a vague picture of where and how you want to grow. Is there an opportunity at your current job that is appealing? What skills do you need to get there? Do you want to move to another city some day? What are the steps you need to take to make that change? You don’t need to map out your whole life, but you should always be working toward something new.
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Illustrated by Abbie Winters.
When we were kids, my mom used to say there were three things you always need to do: eat, sleep, and bathe. If something was out of sorts, chances are you’re hungry, tired, or in need of a shower. All three will fix almost any problem.

I’d add exercise to this list. Making time to work out at least a few times a week makes spending all day at a desk much easier. It’s a proven stress reliever that can also be a great way to unwind, get inspired, or zone out.
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Illustrated by Abbie Winters.
I always joke that the longer I work, the more I realize how much I don't know. You might be done with college (or graduate school), but it’s so important to keep learning. Just think about your Aunt Kate who can’t understand Twitter, or your boss who can't figure out how to download an attachment (really, I worked for someone like this). You don’t want to be her one day.

As you move into your 30s, you won’t be the wunderkind anymore, but that doesn’t mean you should stop improving your skills, understanding new technology, and working on your weaker areas. Learning doesn’t just help your career, it makes you a more interesting person.
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Illustrated by Abbie Winters.
Sheryl Sandberg writes about this in Lean In, and it’s something we all need to keep in mind. Always sit at the main conference table, never take a seat along the wall. If you want to get ahead, you need to be seen and heard, and that's much easier when you're sitting in the middle of the action.

Along these same lines, always show up to meetings on time and don’t wait for someone to tell you the meeting is happening. Be there and be ready to discuss whatever is on the agenda.
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Illustrated by Abbie Winters.
Did I say that saying “no” is the hardest thing on this list? I lied. It’s asking for a favor, and that's because you have to set aside your ego and admit you need help. But that's okay — it's totally cool to need help sometimes. Showing a little vulnerability is a good thing. It will help you connect with coworkers and encourage them to reach out to you when they need help, too.
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Illustrated by Abbie Winters.
There's a lot of power in a handwritten thank you note. You should always send one after an interview. You should also send a thank you email. I would argue there's no such thing as too many thank yous.

The importance of saying "thank you" isn't limited to just job interviews. Every time you ask someone to do something for you (whether or not you're the manager), don't forget to say "thanks." It's amazing how far expressing appreciation can go.
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Illustrated by Abbie Winters.
Do you want to be a CEO, launch your own business, or be teacher of the year? That's awesome. Own that. Do you have smaller goals? That's cool, too. You might not be able to be whatever you want to be (I will never be a prima ballerina in the New York City Ballet), but don't be afraid to aim high. Embrace your ambition, and don't think of it as a bad thing. Ambitious women might get a bad rap, but things are changing for the better, and part of that is because women are learning to speak up, own their successes, and be total badasses who inspire future generations.

You might just be starting your career, or making a job change, or struggling to get people to pay attention to you, but don't underestimate your skills. Follow some of the advice I've offered in this story, and you'll make some strides. And, on the bad days, count on those friends and work wives to spur you on.