When I was 21, I moved to New York with almost no money but lots of nerves and excitement. Over the next fourteen years, I worked a bunch of different jobs and learned so much—sometimes the hard way! For career week, I’d love to share 10 things I’ve learned during my career…

If you’re curious, here’s a short recap of my (scribbly) career path:

* As a teenager, I tutored math, made pizzas, shoveled driveways, delivered newspapers, waited tables and babysat (for $2.50 an hour!).

* In college, I did research for professors and worked at an awesome coffee shop. During the summers, I interned for a publishing house in New York and a law firm in D.C.

* In my early twenties, I moved to New York to intern at Cosmopolitan Magazine, and taught Kaplan LSAT courses at night to pay rent. The next fall, I went to NYU law school, but was miserable and left after a year. I felt totally lost! Then I got a job at a boutique editorial and marketing firm, where we wrote and edited small custom magazines. After a few years, I was promoted to be the editor in chief of a start-up magazine called Bene. In the evenings, I kept tutoring the LSAT and also started a blog on the side, just for fun. My little brother helped me set it up and named it Cup of Jo. :)

* In my late twenties: When my blog got bigger, I left my full-time job and went freelance. I contributed to Cookie, Budget Travel and New York Magazine, where I wrote my favorite story of all time about people who wear only one color. I freelanced for Cookie Magazine’s design blog. I worked hard on my own blog and then landed a job at Glamour Magazine to launch their relationships blog, Smitten.

* In my thirties: When I turned 31, and was pregnant with Toby, I decided to leave Glamour (where I had been for two years) and focus on Cup of Jo full-time. That’s where I am now! (Here’s more about blogging as a career.)


So, here are ten things I’ve learned through the years and wish I could go back and tell my 21-year-old self (and I’d love to hear if you agree!)…

1. Everything takes forever. As efficient and awesome as you are, everything will take 2x-10x longer than you expect. Factor that in.

2. Always take notes. When your boss is giving you instructions—or you have a genius idea in the shower—write things down. You think you’ll remember but you won’t.

3. Don’t worry if you don’t love your career right away. You’re not really supposed to like your job at the beginning; you’re supposed to like your industry. First jobs are often frustrating, stressful and hard, with long hours and grunt work and volatile bosses. When you work your way up, generally after a few years, it gets more fun and rewarding—with more perks! I think it’s actually reassuring to realize that because then you can stop worrying about not liking your job and just work hard and put in your time and move up to the good stuff. So, at the beginning, stay very positive and hungry and trust that it will work out.

4. Work is still work. Generally jobs do get more fun and rewarding as you move up, but they’re still work, at the end of the day. Pinterest is peppered with quotes saying things like, “Do what you love,” “Love what you do,” “Find your passion,” etc. Although I agree that it’s great to enjoy your career overall, those kinds of quotes can be misleading and make you feel like if you don’t LOVE your work all the time, if you don’t LOVE every moment, you’re somehow failing this goal. But work is work. That’s why you get paid to do it. It’s okay to have bad days.

5. Network up and down. Many people get turned off by the term “networking” (read: a bunch of suited-up people at happy hour) but I just think of it as a fancy word for making friends in your industry. When you email someone about a project, ask about their dog. Tell them about your vacation. Send a card when they have a baby. Be real with them. Help people. Stay in touch. Tell friends about job openings. Meet for breakfast, or send a short note saying you loved their recent article or project.

6. Be solution oriented. Never say “that wouldn’t work” without having a solution or alternate idea to follow up with. Things often fall through, so always have back-ups, alternates, a plan B, and get the job done.

7. Be gracious and positive. Be very appreciative when people help you. Write glowing thank you notes. Be excited about your work. Say things like, “Absolutely,” “My pleasure,” “Thrilled to be working with you,” “Can’t wait to get started.” Generally, be a pleasure to be around. THIS IS NOT THE SAME AS BEING A DOORMAT; you’ll still ask for what you want, but you’ll ask nicely. You’ll stand up for yourself, you’ll get promotions, you’ll be a leader—but you’ll be warm and gracious and polite and supportive of your team. Many decisions people make are subjective; it’s helpful for you if they like you and want to help you. “The person who gets the gig is the person who knows how to hang. Nobody hires you because you’re the best musician.” —Larry Legend.

8. Take your vacation. My friend Jason told me this early on in my career. Vacation days are part of your salary. Don’t feel guilty, you’ve earned them—go have fun! Have a life outside work; this might sound obvious, but now and again you might find yourself sucked into work so much that you feel like it’s all you do; so shake it up and host a big dinner party; start a movie club; buy a skateboard; learn to knit; plan a road trip. Studies show that four in 10 American workers allow some of their paid vacation days to go unused and expire. Here’s a great quote from entrepreneur Seth Bannon:

Professional runners take long breaks between marathons. They make no excuses for this, and no one judges them for it, because everyone knows that rest and recuperation is an essential part of being a pro athlete. The same is true for entrepreneurs (and everyone, really). Preventing burnout is part of your job. Staying well rested is part of your job. Sleep and exercise help, but occasional extended breaks are essential too, and their benefits on creativity, productivity, and happiness are well documented. It’s time we stopped making excuses for rest and relaxation. Doing so is not only bad for you, but sends the wrong message to the rest of your team. So next time you’re planning a vacation, announce it with pride.

9. Get good at making decisions. The higher you get up in your career, the more decisions you have to make. If you’re the boss, you make a LOT of decisions all day long—for yourself and other people. Get good at it. Try not to obsess or overanalyze. Make decisions confidently. When I was promoted at my old company, my role turned from writer/editor to full-time decision maker. It was exhausting, but you just have to power through. (Although I have to say, at the end of the day, I was like, I cannot choose what I’m having for dinner, I’m spent!)

Says Vogue editor in chief and Condé Nast artistic director Anna Wintour:

“I think possibly what people working for one hate the most is indecision…Even if I’m completely unsure, I’ll pretend I know exactly what I’m talking about and make a decision.”

Writes New York Magazine about actress, writer and producer Mindy Kaling:

Since the start of Mindy’s production, Kaling’s job as a showrunner has turned into that of “a professional question answerer,” she says.

Writes Vanity Fair about President Obama:

At play, the president wears red-white-and-blue Under Armor high-tops, but at work it’s strictly blue or gray suits. “I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make,” he tells Lewis. “You need to focus your decision-making energy. You need to routinize yourself. You can’t be going through the day distracted by trivia.”

10. Ask for raises!!!!! Ask for a raise. Every year. Make a list of your accomplishments over the past year. Phrase it by saying you’ve “earned” a raise (not that you “deserve” one). I’ve read studies that women don’t ask for raises nearly as much as men, because they worry that they’ll upset their bosses; don’t! Just ask! You’re a great employee and you’re making money for your boss and will continue to grow the company! Most companies work raises into the budget. They will not be surprised or put off. They will see how valuable you are. Even if your boss doesn’t end up giving you the raise, she will respect you for asking. My friend, who works in human resources, says she always wants to tell people to ask for raises—half the time, they’re already approved! If the company’s budget is tight, consider asking for vacation days in lieu of money. And don’t just ask for raises, ask for everything: promotions, bigger assignments, more responsibility. If you’re enthusiastic and hard working, you will be amazed by how often you hear “yes.” (As Don Draper said, “I don’t believe in fate. You make your own opportunities.”)

BONUS: Work very, very hard. And know that every successful person has also worked incredibly hard to get there. If it feels like everyone else got it easily or had it handed to them, it’s simply not true. Even “dream jobs,” like a food critic or a travel writer, are actually really hard jobs. After all, the hardest thing in the world is to make something look easy. Good luck!!!

What have you learned in your career? Do you agree or disagree with any of these? What would you tell your 21-year-old self? I would LOVE LOVE LOVE to hear…

P.S. Blogging as a career, and 15 career tips from smart women.

(Photo taken in our office by the lovely Caroline Donofrio)