Over the years, many readers have asked about my career and blogging. So, I figured I’d write a post answering the most frequently asked questions (including moving to New York, boyfriends and break-ups)…

Over the years, many readers have asked about my career and blogging. So, I figured I’d write a post answering the most frequently asked questions (including moving to New York, boyfriends and break-ups)…

Why did you first move to New York?
I moved from Michigan to New York almost eleven years ago. After graduating from the University of Michigan, I stayed in Ann Arbor for six months and worked three jobs to save up enough money to move to New York. My first gig here was a full-time unpaid internship with Cosmopolitan Magazine for three months, to help get my foot in the door. I also tutored every day after work and on weekends to make money. I was super broke and had butterflies in my stomach, but was thrilled to finally be in the city.

How broke?
I was almost literally pinching pennies. Every day I’d order a $1.50 bagel with cream cheese for lunch, and I always really wanted to add tomatoes, but for an extra sixty cents, I simply couldn’t afford it. Every night I would walk home from work, since I didn’t want to splurge on the $2 bus fare. My first apartment was a small one-bedroom sublet in midtown which I shared with a guy friend, and he slept in the bedroom and I slept with a blanket on the old sofa in the living room. Now and again we had cockroaches and, even on the hottest days, we never turned on the air conditioner because we couldn’t pay extra on the utility bill. I cannot begin to tell you how much spaghetti I ate for dinner that year, just because it was the cheapest dish I could think of! Now whenever we have spaghetti, it takes me right back.

It was a drag to be so broke, but at the same time, it was exciting. I felt like I was paying my dues. If you ask pretty much anyone who lives in New York, they’ll regale you with terrible apartment stories, crazy roommate sagas, a history of scrimping and saving when they first arrived. It’s a rite of passage.

What was your first job?
Growing up I had a million jobs at restaurants, coffee shops, babysitting, shoveling snowy driveways, etc….but after my first few months in New York, I landed a full-time real job as an editorial assistant at Simon & Schuster (book publishing) for a year.

And then I decided to go to law school.

Law school?
Law school was a big departure. But back when I was graduating from college, I randomly took the LSAT, and when I did well on it, I figured I’d just apply to schools, and when I got in, I figured I might as well send in the deposit. One thing came after another, and it was a bit of a snowball effect. I figured I’d try it for a year. So I applied for student loans and started at NYU School of Law in 2002.

How did it go?
That year was really miserable. Part of it was personal—my college boyfriend and I had broken up, and I was pretty devastated; I lived in a tiny ground-floor dorm that looked out onto crowded Broadway, so I had to keep the blinds closed all day, and there was a hot-dog stand right outside my window, so the whole place smelled like boiled meat. Part of it was law school, itself—I missed working in books and magazines. I felt like I didn’t fit in with the other students and felt lame. I called my mom like 50 times a day. I sobbed on my dad’s shoulder when I went home for Thanksgiving. After finishing the first year, I decided to leave law school. That was actually an easy decision, despite knowing I’d have to somehow repay all the loans (a whopping $54,000 for just one year, zoinks!)

How did you pay back the loans?
As soon as I left law school, I felt flooded with relief. I knew I had made the right decision, even though it was a much, much less secure career path. To help repay the loans, I tutored and taught the LSAT for Kaplan on evenings and weekends, which was actually an awesome job. I made friends with some of the students, since many were my age. During the day, I got a full-time job with a small editorial/advertising firm. It was GREAT to work for a small company because I got a ton of work thrown at me and was just expected to figure it out. The atmosphere was intense, but I loved being trusted to get the work done, and the job gave me confidence that I could do anything. I rose up the ranks quickly (as you can in a small company), and also learned a lot about business, since the owner of the company was an incredible negotiator; I watched her approach big, intimidating brands and basically say, “We are worth this huge price; you should sign with us right away and you will never look back,” and people basically did. She showed me by example that you can ask for the moon and, if you really believe in yourself, actually get it.

What did you do at the company?
My position was an editor, and, over the four years I was there, we worked on some amazing projects. My favorite was launching a magazine called Bene, which was about how to live like an Italian (think: mozzarella, thick sweaters, mama’s boys). It was a dream project and I was asked to take the helm. I worked like a million hours a day, and my boyfriend at the time thought I was the biggest type-A stress case (which I was), but overall I loved it.

When did you start your blog?
Five years ago, I broke up with that same boyfriend and needed a distraction from feeling sad (read: eating potato chips and watching TV). (Funny that now that I’m writing this bio, breakups seem to be at the crux of all my positive life decisions! When a door closes, a window opens, right?) To distract myself, I decided to start a blog. None of my friends had one, and I only read a few—Design*Sponge mostly. Blogging as a career didn’t really exist; never did I imagine Cup of Jo would be anything more than a fun hobby. So I worked on it at night and on weekends. I got really into it and would stay up til 2am working on it. (Here’s my first post!:)

When did your blog start making money?
As I said here, shifting from blogging-as-a-hobby to blogging-as-a-career was a very slow transition and one that I had never anticipated. After a year or so, I started featuring a few ads on my blog to earn some pocket money. And after a couple years, I quit my job to focus on freelance magazine writing (Glamour, New York Magazine) and grow my blog, so it became about half my income. But only about a year ago did I finally realize that my blog had officially become my full-time job—both financially and time-wise. And I was happy and surprised. (Also here’s my work/life balance post, if you’d like to know more.)

What are your favorite parts of blogging?
* Having a close relationship with my beloved readers. Starting the Motherhood Mondays column took the relationship to a new level (do you agree?:), because we started discussing marriage, breastfeeding, depression, infertility, everything. Having these conversations has been an incredible, eye-opening, heartwarming experience.
* I LOVE LOVE LOVE when readers stop us in the street because it’s so awesome to meet readers in person. Blogging can feel isolating sometimes, since you work on a laptop at home, so it’s amazing to meet people. (And everyone is always so nice and cute!:)
* Writing about a bunch of different topics. If we do a bedroom makeover or I read a fascinating parenting book or I’m itching to write a guide to NYC, I can just do it. That’s great, since when you work for a magazine, your “beat” tends to be much more limited. And the great thing is, if I start feeling in a rut, I can just shake things up. It’s a real gift to have editorial control.
* Working with photographers, designers and illustrators. Now and again, I’ve worked with super talented people, like Jamie Beck, Jenny Komenda and Gemma Correll. It’s been such a pleasure and honor. I’d love to do more collaborations in the future.
* Alex being awesome. Alex helps a lot with my blog, not so much in the nitty gritty, but just overarching conversations about ideas, worries, etc. He jokes that I’m the CEO, but he’s the chief strategist, director of communications, personal chef, mailroom guy, and psychotherapist for Cup of Jo. :) And he’s written a couple posts, including 8 confessions of a new dad and his side of the birth story.

What are your least favorite parts of blogging?
Obviously, I feel super lucky to have the job I do, and any negative aspects are absolutely worth it. But I think it’s important sometimes to talk about negative parts of your job, so that other people don’t assume your job is perfect and thus feel bad about their jobs. (It’s like when you’re secretly psyched to read that food critics often get food poisoning:) So here are a few things that can be a drag…

* Negative comments. You know that punched-in-the-gut feeling you get when someone criticizes you? Well, if you have a big blog, you get negative comments pretty much every day, so you have that feeling at some point every day. Sometimes the comments are just from someone cranky (and then this mantra applies), but often they’re from smart readers and thus are really constructive and helpful for growth. I take negative comments seriously and try to learn from them. Criticism helps you grow, as both a blogger and person, and of course I welcome honest comments from my readers. Like I said, though, negative comments can be very tough to read. I’ve always been sensitive to criticism, and I’ll admit, I’ve called my mom in tears more than once. It can feel very personal when you’re writing about yourself and your life.
* Feeling isolated. While working from home, it’s easy to feel lonely without co-workers, especially when you’re working on the laptop on your bed, ha! It’s often fun and social to have a team around you…and sometimes I just want to gossip about The Bachelor the next morning! It’s also tough to never have a sounding board—even just a co-worker to ask, is this idea good or totally crazy?
* Working on vacations/Christmas/weekends/etc. Since I started Cup of Jo five years ago, I don’t think I’ve ever taken a vacation where I didn’t spend some time working—including our honeymoon. Blogging never stops, and running your own business never stops. Since I don’t have anyone else working with me who can take over in my absence, I always have to take time to check in (to upload guest posts, to answer timely advertising questions, etc.). After all, my advertisers are depending on being able to communicate with me, and I owe it to them to have my traffic stay the same even when we’re out of town. I don’t really mind it, though, since I feel lucky to be blogging overall.

Has Toby changed your work approach?
Having a baby forces you (in a good way) to take time off. Whereas I used to take on a million side projects, I don’t anymore. And I love that we have hours built in every evening to go to the playground, sing, play the bongos, make jokes, ride bikes. Apparently the average toddler laughs 400 times a day, and those throaty giggles are totally contagious. Alex is also really laid-back and talented at relaxing (ha), so that has been good for me. He has taught me to stop more often and smell the roses.

Any advice for growing a blog?
People will like reading your blog—and you’ll enjoy writing it—if you’re true to yourself and your posts come from the heart. When you write a post, imagine your mom or best friend reading it. Does it sound like your voice? Does the topic fascinate or inspire you? Is the post clear, enticing and visual? Do you have a point of view that’s different from other bloggers? Write about what you love. I think everyone has an amazing blog inside them, or a story to tell, and I really encourage people to go for it. If you’re starting out, best of luck!

Do you have any tips about starting a magazine career?
I did an interview about my magazine work which might answer some questions. I also love the websites Media Bistro and Ed2010. They have great advice about pitching stories and interviewing; plus, they have job and internship listings. There are obviously many different paths to success, and I would recommend staying very open to opportunities (even low-paying or no-paying ones, at first) and doing all you can to get your foot in the door. Good luck!

What is the biggest misconception about bloggers?
When it’s done right, blogging should look easy—just how magazine articles and books should look easy and fun. But it doesn’t mean that it is easy. I wrote about the behind-the-scenes of running a bigger blog in this interview. There’s so much back-end work, including negotiating with advertisers, redesigning your site, working closely with lawyers when developing contracts, hiring contributors and graphic designers, building a presence on social media, answering hundreds and hundreds of reader emails every day, doing guest posts and interviews, the list goes on. Funnily enough, after a while, the actual writing-of-the-posts feels like only a small part of your daily work (even though that’s obviously the best part!:).

How do you earn money and handle advertising?
For the past six years, I’ve sold most of the ads myself. I’ve worked primarily with small brands, such as etsy shops and jewelry designers. I love working with small business owners and supporting female entrepreneurs.

Now I’ve also decided to work with an ad network that handles banner ads for bloggers. It’s a big step, but I’m excited to free up more time to focus on editorial posts. Starting now, I’ll also be doing a few sponsored posts per month, which I typically sell directly to brands myself. For years, I didn’t accept sponsored posts, but now I’ve seen that they work really well with brands you actually love (such as Pinhole Press and The Honest Company). And I’ll mark them very clearly with text at the top or bottom of the post. So, it will be very clear when something is sponsored; I hope you guys will enjoy the posts, which will help keep Cup of Jo running smoothly.

What do you think about the future of blogging?
I always tell Alex that I’m riding the wave. Blogs probably won’t be around forever (although of course I hope they will!) and you never know how quickly the industry will change. After all, when I started five years ago, I never thought blogging could be a job, and now it is, and maybe it won’t be in the future. There’s definitely not much job security. But I’m grateful to be doing it now, and hope to keep blogging for as long as possible.

If you have read this far, bravo, haha! Thank you so much, and I hope this answered most of your questions (and probably way more:) If you have any others, please feel free to leave them in the comments. I want to reiterate how much I love blogging and how much I love my readers. Thank you again (so much) for everything. Love, Joanna