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how i got here *kind of


Chelsea Matson Photography

How did I get here? I was recently asked during a consultation, how did you get into wedding planning? Well, it wasn’t the one-way street you’d imagine. And although I literally dreamed of being a wedding planner when I was in high school, I never thought I’d own my own wedding planning business. Ever.


My dreams of becoming a wedding planner, which began before the 2001 Jennifer Lopez film, were fun while they lasted; but I knew it was an unrealistic path. At the time, I was heading into college with a well-rounded bachelor’s degree in my sights. After studying English and education towards the beginning of college, I ended with an emphasis on marketing and journalism. Also known as, I have no idea what I’m doing.


I’ve always envied my Dad’s ‘career path,’ because he’s been a math nerd all his life, went to college for actuarial sciences, got a job right out of college as an actuary, and still works there, 35+ years later. What could be a clearer, more beautiful career path?


Chelsea Matson Photography

After graduating from Marquette, I worked some administrative jobs at United Way and a cable and wire management company. In those roles, I spent a lot of time working with their HR and Marketing departments. From there, I worked as a marketing projects assistant at a web development agency.


Finally, I found a really nice fit in marketing projects and events at a downtown Milwaukee law firm. I had an amazing events mentor there, and a kind friend (looking at you, Tega). At the law firm, I learned a lot about seamlessly executing professional events. I also learned that that kind of environment just wasn’t for me.


*It was around this time that my cousin was getting married. It was our first family wedding, and we’re Italians, so it was a big, hairy deal. I worked closely with my cousin in planning her wedding, and felt reinvigorated to give weddings (an industry that I’ve always felt connected to) more of my attention.


So, as a fun distraction, I started a blog about weddings in Milwaukee. I’d work all day at the law firm, and come home to blog all night about wedding trends, local vendors and real Milwaukee weddings. Through my position at the law firm, I was meeting a lot of event industry professionals, and some of those people were overlapping with my work on the wedding blog. I was starting to have a lot of fun!


One of the wedding professionals that I met for the blog was Ashley, Owner of Midwestern Bride, a wedding planning company now based in Madison. Ashley and I hit it off pretty quickly because of our similar interests and our experiences with motherhood. After chatting for a few months, Ashley offered me a position as a wedding planner for her company.


Chelsea Matson Photography

So, I took the leap from a corporate, full-time position to a part-time wedding planner. That was terrifying. There were a lot of money fights with my husband, insecurities to work through and feelings of doubt. However, my excitement and total motivation & drive to succeed clouded most of my fears. I’m a people-pleaser; intuitive, observant and helpful by nature. I’m also creative, social, hard working and a problem-solver. These personality traits that I never recognized as professional strengths were really highlighted when I began wedding planning. Ashley’s confidence in my professionalism and skill really laid a sweet foundation for me to work for her for the coming years.


It was really the birth of my second baby that was the catalyst for going out on my own. The time came for me to write my own rules, create well-rounded experiences for my clients, and thoughtfully manage the mom-work life balance that I care so much about.


In years past, I’ve always loved having bosses. Direction never bothered me. Honestly, I preferred it because then none of the responsibilities were 100% on me. Business owning is scary, but I’ve been so warmly supported and fortunate for the relationships I’ve made along the way.


I chose the name Rosewood Weddings because (1) I only want to do weddings, and wanted that to be clear, and (2) my middle name is Rose, it’s a precious family name – but I wanted that mixed with a natural, organic feel.


Chelsea Matson Photography

And the weirdest part? There’s no aspect of my job that I dislike. I’m being serious. Even working in Excel on budgets, or addressing invitations; I even like lying out 300 chargers on reception place settings and working through tough vendor communications. Seriously, even if it’s something that I don’t necessarily enjoy, I am still happy to do it, because I book clients that I love; great people that I care about, and want to move & make proud.


And that’s how I got here *kind of.

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