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An Interview With Carly Heitlinger of The College Prepster

The blogosphere is a crowded place, but Carly Heitlinger is in a league of her own. After launching The College Prepster as a college student in 2008, her blog grew from a creative outlet into a booming business. She’s the first to admit the path to becoming a successful, full-time blogger isn't easy, but now she’s living her dream and inspiring millions of readers to do the same.

After a difficult first semester at Georgetown University, Carly felt frustrated and uninspired. College wasn’t all it was cracked up to be and she needed a creative space. At a friend's suggestion, over Christmas break she published her first blog post.

After graduating and working for a startup, Carly made the difficult decision to take a leap of faith and run her blog full time. Since then, it has been full steam ahead for both Carly and her brand. Today The College Prepster boasts millions of monthly page views, over one hundred thousand Instagram followers, and brand collaborations that would set any Prepster’s heart aflutter. The future has never looked brighter for this self-described quirky, passionate Contessa.

Her Starting Point

You started writing The College Prepster while at Georgetown. What prompted you to start the blog? How did you grow a following while still a student?

I started my semester at Georgetown thinking it was going to be the start of the best four years of my life. That’s what everyone said at least! I had first semester jitters but assumed that was normal. Unfortunately, instead of getting more comfortable with college life, I started to crumble from the pressure. It was, in short, a very rough first semester. I miraculously made it through to final exams, but was feeling rather uninspired. A friend suggested that I start a blog, and so I went home over Christmas break and I did!

Growing a following was not really on my mind when I first started. It was solely a creative outlet. But, because blogging was so new and small at the time, I found a great community of similar bloggers and we’d all comment and email back and forth. As social media took off, so did my blog. I really attribute the assimilation of Twitter on college campuses as the first catalyst.

By the time you started your first job out of college at at a startup, your blog had already taken off! How did you find time to write your blog while working full time?

I did not sleep. Looking back, I have no idea how I survived and I realize just how unhealthy I was being. I would wake up at 5:05 every morning, get ready, do a little emailing/work at home, get to work around 7:30 in the morning, and on a good day leave at 7:30 in the evening. I’d eat dinner, try to squeeze in a nap if I didn’t have an event to go to, and work until 1 or 2 in the morning on my blog. I did a lot of blog work on the weekends too. My job was a priority and so was my blog and being the type of perfectionist that I am, I didn’t want to cut back on either… so instead I took unhealthy measures to do it all! Unfortunately that meant my social life, health, happiness, etc., took a hit.

At what point did you know you were ready to quit your job and become a full-time blogger? Was there an “ah-ha” moment for you that lead you to that decision?

I think there was an ah-ha moment, but it took me a lot of months to get there. I wore a lot of hats at my old job and did a very poor job of defining my role within the company. I thought that being a good employee meant saying “yes” all the time, which really just meant that I was being a stressed out employee too afraid to ask for help!

I finally got some relief at my job (long story short, I hit my breaking point and had to ask for help) in the form of an amazing team. While I loved working with my new team, I definitely started to have more time to think about what I was doing. I realized that there was a lot of overlap between what I was doing at my job (editorial, social, etc.) and what my blog was. There was a point when I thought, “I should be focusing my energy on my own website.”

Although I had that thought, I wasn’t ready to pull the trigger on quitting. (I hate that word because it has such a negative connotation, but sometimes quitting isn’t a bad thing!) A couple of months later, I went to out to get lunch and had this very peaceful “Okay, it’s time” thought. I put in my notice that afternoon!

Your blog currently focuses on fashion, lifestyle, your life in New York, and bloggings tips. How has it evolved since the beginning? After over 6 years of blogging, do you ever find it challenging to come up with new content?

I think the evolution of my blog is rooted in social media developing into its own industry, alongside my own personal growth and development. I’ve always shared my favorite shopping picks, personal strides and setbacks, advice, books I’m reading, etc. I think that my consistency of content has been helpful with my blog’s growth and reader engagement.

Coming up with new content is something I stress out about, more than I care to admit, but at the end of the day (literally, around 10pm when I’m writing the next day’s post) it’s not something that I have a problem with. When I’m writing content, I always want to share something I’d share with my best friends. If I’m in a rut, I’ll think…what are my friends and I talking about, what would I text her right now, what books/movies have us all talking, where are we shopping, what are we stressed out or upset about? Then the content just comes much more naturally!

An Interview With Carly Heitlinger of The College Prepster - Her Starting Point

Her Big Break

With so many emails, meetings, and balancing working from home, what are your organizational tips and tricks? What is a typical workday like for you?

Every day is so different. As far a week goes, I always schedule one “only work” day, which is a 100% blank day on my calendar. That’s the day when I sit at my desk and just WORK. Meetings, events, and other outings are part of my job description but it really disrupts my work flow. Those clear calendar days are KEY.

I might have meetings with brands, lunches, coffee with readers, a photo shoot with my photographer, events in the evenings, phone calls, Skype calls, you name it.

Most of my day, however, is spent emailing. It’s my primary form of communication so it’s really important to me to stay on top of it. On a good day, it takes four hours to get through my inbox. I read everything as it comes in, but flag things I need to come back to or respond to (those become my “to-do” list).

Oh, and of course I blog and create other social content.

How do you balance work and personal life? Since so much of your content pulls from personal experiences, how do you draw the line between what to share? Are there any parts of your life that you keep completely offline?

When I was a student and when I had a “normal” job, my blog was my life! It was what I did to blow off steam and it’s what I did in my free time. I loved it, but it was extremely hard to draw the line when it was my hobby.

I actually find it much easier to draw the line now that my blog is my job. On so many levels it makes things more clear cut to me. I know when I’m working and I know when I’m not. It gets a little tricky with Instagram, with what I do and don't share. But I generally know my Instagram calendar/schedule for the day and can differentiate what gets shared and what doesn’t.

There are absolutely parts of my life that I don’t share. I would go crazy if I didn’t! I’ve been doing it for so long- I know when I’m representing The College Prepster and when I’m just going as plain ole Carly. Sounds a little crazy, but differentiating between “which" one I am when I do something helps.

The blogging world can be extremely competitive. How have you learned to deal with criticism and stay focused on your craft? On the flipside, what are your favorite parts of being involved in the blogging community and how have you been able to create friendships with other bloggers?

As I mentioned before, now that blogging is my job it’s so much easier for me to not take things personally. The biggest challenge for me isn’t so much the criticism (I expect it nowadays and so the shock value is totally gone), it’s the lack of privacy. Yes, I share things about my life online, but if I had no idea when I started blogging that it would change my privacy levels in person (that is, beyond the computer).

I’ve had people come to my house. I get stopped in public every day. Certain restaurants/stores are difficult for me to go to. I feel like I have to always be “on” because you never know who’s listening, Snapchatting, etc.! I think these are good signs in terms of the strength of my online presence, but it’s still hard to come to grips with on a personal level.

With that said, I also never would have thought I would make some of my very best friends through blogging. I think the best blogging friendships are the ones that naturally occur. You can’t force a friendship and it’s so obvious when someone invites you to lunch because they want you to Instagram it or something. When it clicks, it clicks! Just like in real life (ha ha), you just know when you have a certain connection or bond with another person.

Ok, we have to ask about your dog, Teddy. He has an Instagram following of over 24k! What do you think are the secrets to Instagram success (for dogs and humans alike)?

25k now (#tigermom)! My boyfriend actually runs his account now because I wasn’t able to put the time and energy into it. Posting frequently is the first trick, but the caveat to that is that it has to be good content. Good is relative here– you have to know both your brand and your audience. What do you want to share, what’s your voice? And on top of that, what does your audience want to see? One of my Instagram mottos is “give the people what they want.” I jokingly say it because I know roughly, based on what the Instagram is, exactly how many likes it will receive. On the other hand, if your audience isn’t responding to something that you want to share you have to carefully cultivate that audience. Sometimes that means losing some followers along the way, but they weren’t the “right” audience anyway.

An Interview With Carly Heitlinger of The College Prepster - Her Big Break

Her Perspective

You have done an amazing job of creating a thriving business out of your blog. How would you describe your personal brand?

Smart, relatable, a little bit quirky, very passionate.

What makes a successful blog in your perspective? What advice do you have for those looking to start a blog?

A successful blog is successful if you define success the right way. If you want to blog as a creative outlet and to share your unique perspective, you will be successful right out of the gate as long as you continue to create and post content. If you think a blog is only successful if it can support you full time and you have 100,000 Instagram followers, you’ll be too frustrated to ever get to that point.

Now, if you’re sticking with creating content and loving every minute of it for six and a half years (sound familiar?), you might make a sizable income from the blog that can support you and you might have 100,000 Instagram followers. But still, the success isn’t in the income/followers, it’s still rooted in enjoying what you do.

You have said you write your blog with the intention of writing what you wish what you could have known when you were younger. Along those lines, what advice would you give to your 18 year-old self?

I really wish I could go back in time and tell myself to relax more and to know everything will work out. I wish she would embrace the hard stuff and know it’s making her better. I would tell her to have a little bit more fun, to be confident in whom she is, and to wear more sunscreen and moisturizer.

And finally, what do you wake up looking forward to? What’s next for your career?

Right now, I’m really excited to see how blogging continues to evolve. I think we’re about to see a major shift in how traditional media embraces digital media. So hopefully there are some exciting partnerships and opportunities down the road!


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