Who the Heck Am I?

Boss Lady Montana

No seriously, who do I think I am?

Because really? Who am I (or anyone really) to be telling you how to run your business or how to build your life?

The biggest tenent of being a Boss (or a CEO or a CFO or whatever C-Suite you want to call yourself) is that YOU get to define what makes a business and a life for you...not anyone else.

However, this is the moment where I talk a little bit about myself, my journey to #BossLadyDom, why I actually started this Boss Lady Business, and OBVIOUSLY how I failed along the way. Because can't have a juicy story without all the terrible falls along the way.

(And if you want to tell your #BossLady Story? Fill out this questionnaire to get featured on the blog!)

The Beginning

I really wanted to start this story with a "long ago and faraway" nonsense, but I'm not one for nostalgia, so let's just dive in.

I grew up outside of a city in Western New York (Rochester to be exact; Pittsford to be...more exact) and literally, the moment I was given free will to leave, I skipped that joint faster than Bonnie and Clyde broke out of the clink.

The only reason I mention where I grew up is that I need to mention my parents: my dad was an entrepreneur most of my life (read: successfully failing at some wrong ideas...and successfully not failing at some right ones) and my mom was not (which was great because that meant we had food to eat). Mama Caselli also had an insanely strong work ethic which was helpful, because I probably would watch way more Netflix now than I actually do if not for her genes running through my veins.

(Seriously, the woman is more productive in a Sunday than I was in the first six months of this year).

Spoiler alert: I did NOT grow up with dreams of being my own boss. I did not have a lemonade stand, I didn't draw pictures and sell them to my friends, I didn't have dreams of opening my own pizza shop. 

I simply have an enormous ego. That does not an employee make. Go figure.

THE LESSON: You don't have to WANT SO BADLY TO OWN YOUR OWN BUSINESS YOUR WHOLE LIFE. You can simply not enjoy any of the other working options presented to you and just start doing your own thing. Your mileage may vary with that one, but know that if you're getting bogged down by the fact that you're not completely sure entrepreneurship is your bag and has been your bag for your whole entire life? Don't worry about it. I'm certainly not.

The Middle

After I graduated with good grades and a bad attitude (I was a saucy 18-year-old, let me tell you), I hightailed it for Georgetown University to major in English and to become the world's next Connie Chung with better hair (hand to God).

Spoiler alert: It didn't work out. I decided I liked being in positions of leadership and planning things and hosting/attending parties way too much to ever devote entire evenings to the news cycle.

At the end of college, I got a student position planning our Senior Parents' Weekend, and nearly doubled our revenue (no word on costs because I couldn't see the budget, but likely profit doubled too) by instituting some really simple procedures like offering an early bird discount and increasing prices two months out from the event (because DUH, but also, why did no one think of that in the previous years?).

I also struggled with our web developer at the time and came thiiiiiissss clooooose to creating my own website. I wish I would have; it would have saved me literally HOURS of my life and I could have jump started website building in 2006 instead of waiting until 2008 to build my first site.

THE LESSON: Notice your strengths (and don't take any shit from the web guy).

If you don't want to watch the news and instead want to host 12 people for dinner, turn that into a job. Also, learn how to use Squarespace and never fight Todd the aggravating web developer again.

The Middle End

After college, I went to NYC and worked for a boutique high-end wedding planning firm in Manhattan (literally stumbled into that one) and worked for celebrity clients, all while making no money and working 80 hours a week. Do you know what the inside of the New York Public Library looks like at 4am on a Sunday? I do.

I quit and pursued strategic marketing and client events at a law firm (really I just didn't want to work on Saturdays at 4am anymore), and REALLY loved it.

Until the economy crashed and I went from being 23 and a hard-working busy bee to 23 and working like 7 hours a day and not even knowing what to do with myself.

Cue four years of self-doubt, extreme highs and lows, binge drinking, binge traveling, binge running, binge everything -- because I was 23 and didn't do things in moderation -- and trying to figure out my life's purpose (been there? I bet you have).

After five years in Manhattan and being in the same job that I had been in since I was 23, I decided that soul searching within the confines of the world's most insane city was not going to do it for me. So I took a sabbatical to India in March 2012 and then a job in Montana JUST FOR THE SUMMER. And then I would find my life's purpose and return to one of the coasts to live my fulfilled life of being a strategic event planner and making millions of dollars to travel around the world.

You can guess how that turned out.

THE LESSON: Your 20s matter, but if they sort of suck and you're trying to do everything you can to make it out alive, then keep going, lady. I would do ANYTHING I possibly could not to do my 20s all over again. Arms, legs, whatever I have to sacrifice. That shit was hell and thank God for being 30.

Also, everything happens for a reason. Your job is to take failure and ask yourself "What am I supposed to learn from this?"


So in 2012, because I had met a dude (which, to this day, even though it hurt letting him go, I attribute almost everything I have right now to that seemingly ridiculous decision to move to MONTANA for a guy I barely know) and because PBR was $2.50 and not $6, I decided to settle down for a few months instead of moving one more time.

And that's when I started my first service based business as a copywriter and marketing chick.

(Well, actually my sister basically yelled at me over the phone about how I better start that business that I kept talking about starting, and then I hung up on her and cried and then went in my bedroom and built a website for my business. It was awful, but it led me to a client a few months later.)

And it took me eighteen solid months of building and having part-time jobs and switching focus about 100 times and hating my life and hating what I was doing and being unsure and crying into my pillow before things got a little bit easier.

(Which is a whole separate story for a whole separate blog post.)

And then, about a year ago in the Fall of 2014, I finally committed to Bozeman, I took a huge leap and quit all my part-time gigs, and dove head first into Lauren Caselli Events. And it was still hard, but because I had those panic-inducing moments of "maybe I'm not good enough" and "maybe this isn't how it should be".

If you're having those moments? You're on the right track. No one gets to success feeling 100% confident all the time.

THE LESSON: Every move, every missed opportunity, every client that you say NO to, every client you say YES to...is preparing you for the moment that you feel successful in your business.

And while I didn't dive deep into the mission of the Boss Lady Bash on this go-round or how I build my business from nothing to...more than nothing, I hope this gives you a little insight into how hard it can be to be a business owner, how many twists and turns you have to take before you actually get to the place that you want to be.

Ya dig, #montanaboss?

Good. Now it's your turn: