Caroline Vazzana is a freelance stylist and media consultant, the founder of the site Making It In Manhattan, and the absolute archetype of a boss woman. I recently had the chance to talk with her a little more about her experiences striking out on her own after working for years in a traditional 9-to-5 editorial career. She shared some great insights into the world of fashion freelance.
Give some background about yourself (i.e. where you’re from, what you studied, your interests, etc.)? When did you come up with the idea to freelance and what made you decide to strike out on your own?
I’m from Staten Island originally, so I was lucky that I grew up so close to the city and the magic and lure of the city inspired me… there was always something there for me. But funny enough I wound up going to college outside of New York because I didn’t want to be too close to home and wanted the experience of living on my own. I went to a small liberal arts school in Pennsylvania and I studied a general fashion and merchandising major. I first thought that I wanted to be a designer and I quickly realized that I wasn’t good at sewing, so I knew the best way to figure out what to do is by doing internships.
My first internship was with Anna Sui–I was in the production department and interned there over the summer. I also was able to take a little hiatus from school and come back to work there during fashion week which was completely different and a whirlwind. After that experience I wanted to explore the editorial side of fashion and I interned at Marie Claire magazine, which, I guess you could say, that internship is what really solidified my interest in the media side of the industry because I got to learn so much and be so hands on and see that it was so creative and you get to work with so many designers rather than just one. I fell in love with it.
I’m from Staten Island originally, so I was lucky that I grew up so close to the city and the magic and lure of the city inspired me… there was always something there for me.
From there, when I graduated I got a job at Teen Vogue, at first only in a temporary role which was to help out with two projects on the marketing team, and then a position to be the assistant to the fashion editor and the senior fashion accessories editor opened up and I quickly jumped at the role, thinking “This is what I’ve been dreaming of!” I got to do requests for photoshoots, help out when Teen Vogue would do segments on the Today Show and things like that, it was really exciting.
Eventually I was seeing everything shifting to digital so I knew I needed to learn everything about digital if I wanted to stay in the game, so I started writing for TeenVogue.com, and eventually got a job at InStyle writing for the digital team so that was when I really got to learn how SEO works, how to form an editorial calendar, and all of those great skills. From those two experiences I learned so much! The best part of working at a magazine is getting to do a little bit of everything. It brings together all of the things I loved about the industry into one place.
The idea of being my own boss and working freelance was always in the back of my mind and I would see friends of mine who were bloggers and influencers and thought it looked incredible to be able to forge your own path and leave your own name. While I was at InStyle, I started my website Making It In Manhattan because I saw a gap in terms of fun and relatable career advice for people wanting to go into fashion. I could remember what it was like when I was first starting out and no one in my family had ever worked in fashion, many are doctors, so I felt very lost and didn’t know where to go or who to ask.
I got great reactions once I started and my readership was going really well right from the start, in part because of my knowledge of SEO and digital content. Also while still at InStyle I began freelance styling as well. It can be hard to really see those ideas through though if only able to work at night or on the weekends with a full-time job. Eventually it gets to a point where it’s a now-or-never kind of deal and you need to take a leap of faith. If it doesn’t work you can always go back and find another job but if you don’t take the leap you’re always going to have the voice in the back of your head saying “what if?” From there, the rest is history and it’s still being written.
…if you don’t take the leap you’re always going to have the voice in the back of your head saying ‘what if?’
What were the steps you took to bring the blog and a freelance career from an idea to a reality?
When I first came up with the idea to launch my own business and begin my freelance career, I wrote all of my ideas down, asking myself “What’s the name going to be? What is it going to be about? What is the message going to be and what can I add to the conversation that’s happening in the digital world that isn’t already being said?” Once I felt like I had a grasp of what I wanted the site to be about it was then a matter of design. I hired a graphic designer to build out the site. Before it went live I’d already written several articles so that it wasn’t just one article on the site. I was always keeping in mind SEO and keywords that people might be searching, making sure they were throughout the site and in the articles.
Now where I’m at, I’m looking to do a redesign and I’m working on amping up content. I have a bunch of freelance writers who work for me as well. It got to a point where as much as I wanted my voice on the site, I think it’s important to have other people’s points of views. I see the site becoming its own place in the industry, like a Man Repeller, with a roster of writers working for us and pumping out content on a daily basis. It’s always a matter of bettering yourself and continuing to work. Every day I’m learning and the initial steps I took helped me to set a good foundation and now I’m trying to perfect it every single day.
It’s always a matter of bettering yourself and continuing to work.
How do you think your previous professional experience has helped you in what you are doing now and in your freelance career?
I definitely feel that the site wouldn’t have been nearly as successful if I hadn’t first worked for Teen Vogue and InStyle because I learned so much, even about basic things like how to write a digital article, word count, format and headlines, layout, writing request emails to publicists… things I wouldn’t have known if I hadn’t worked there. All of those foundational skills I gained while working in the editorial world and it helped me so much to make it as professional as possible from the start.
Is there anything you wish you’d done differently since starting? What things have you learned from the experience of launching the site?
I always say that your mistakes are what lead you to where you are, so I can’t say I wish I’d done anything differently, per se. I’m really happy with what I’ve learned along the way. If I had to say one thing, I wish I’d made my Instagram more professional years ago. I use it a lot to market and get my readership up so if I could have known how impactful it was going to be I wish I had jumped at building it up strongly. Some people don’t even have sites anymore, just Instagram.
I always say that your mistakes are what lead you to where you are
Who have been your role models and why?
Leandra Medine, for sure, because I really admire what she’s done with Man Repeller. She’s taken it from being solely a blog to a digital site. Emily Weiss is another one who, as the founder of Into the Gloss and Glossier, is such smart businesswoman and every day I’m trying to get better with the business aspects of a freelance career so I really look up to her for that. And personally, my mom is such a great role model. She’s so positive and believes in me so much and encourages me to fearlessly chase my dreams and pursue my passions. She is an incredibly hard worker and helped my dad start his business and is now helping me. Having that kind of support, especially when trying to do things on your own, is so important.
What would you say are your main points of advice to girls looking to freelance creatively, especially in New York City?
My general advice is just go for it! You might question yourself but if it comes to a point where all you can do is think about it and you have so many ideas and you know this is meant to be, just go for it and take the risk. If you are passionate, you are going to work hard. And you will have to work really hard because you’re no longer going to have a boss or team to pick up the slack.
If you’re going to work freelance, be ready to work really hard, focus a lot of time and energy into it because you’re pretty much working 24/7. Also be nice to people. You don’t know where people are going to end up, how your paths are going to cross. If you work really hard and you’re nice to people, you will be successful because you have to be. Karma will make its way back to you. I also like to remind myself, no just means not right now, because in a couple of months or years you could go back and have whole new experiences under your belt and get the chance, so never get discouraged. No one else is you and that’s your super power. What you bring to the table, no one else can also bring to the table.
If you work really hard and you’re nice to people, you will be successful
What current projects are you working on and hope to do more with? What do you look for in new freelance projects?
I’m now working with Flower Eyewear, which I’m really excited about, as one of their brand ambassadors and I obviously love my glasses. I don’t go anywhere without my glasses so I’m really loving working with them on a long term basis. Longevity is something I look for in new projects because you and the brand can really grow together. This kind of partnership entails wearing the product, posting about the brand, showing how I style them and how they fit seamlessly into my life and wardrobe.
I always try to make sure that each project is “on brand” for example my style is quite colorful and eclectic and I wouldn’t accept a collaboration that was all black and very serious. I want to be authentic and wouldn’t want my followers to see something and feel frustrated thinking I was only posting because I was getting paid. If I’m working with a brand, I really like the product and would use it in my life.
What is your favorite part of working freelance? Is there anything you miss from a more traditionally structured job?
I enjoy getting to be so creative–I get to come up with all sorts of crazy creative ideas and if I want to put all of them into motion, I can. There’s no one telling you no and you get to decide it all, from the articles you write to the jobs you do. If something succeeds and does really well, you know that you did that.
I guess the one thing I would say I miss are coworkers because I’m working alone a lot. But I also love that I get to meet so many incredible and inspiring people on a daily basis and I love building a network of these incredible women I can turn to if I need something and who I can talk to and bounce ideas around with. I may not have “coworkers” anymore but I have this network. I may not have gotten the chance to work with many of these people if I were still in the traditional 9-to-5 world.
Where do you find your inspiration?
I always have my eyes open and I’m always looking for inspiration. It could literally be as I’m walking down a street in New York City and I’ll see something or see someone wearing something. There are so many women with amazing style in the city and I see so much just looking around. It could also be found scrolling through Instagram, you never know when inspiration might strike.
I always have my eyes open and I’m always looking for inspiration.
Personally I like to write things down so I’ll carry a notebook and pen in every single purse I have so I own a million notebooks because if I all of a sudden get some great idea and think I’ll remember it later, I never do. So I try to always jot a note and then can revisit them later when I get home. When I was at InStyle I got used to pitching as many as five stories a week so I was always finding ways to jog my mind.
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