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Sunday Sermon: Risking Everything For The Sake Of Happiness

Welcome to the Sunday Sermon! I'll be your pastor and the topic of today's discussion is risk, and how scary it can be to take risks in this day and age -- but how rewarding it can be to bet on yourself and win. 

First of all, I want to say, Happy Mother's Day to my hilarious, insanely kind, and super smart mom. She's always pushed me to do more, be more, and for the most part, has supported every creative venture I've ever pursued. She's largely the person I looked to for encouragement and validation -- the one who pushed me to perform music, to make art, to play sports. She's a fucking badass. 

She's also the person I was most afraid of disappointing when I took a major risk and left finance to pursue creating content. At that time I don't even think she had high-speed internet and wasn't exactly on board (for a variety of logical reasons) with this insanely spontaneous, risky move. As a woman who wanted the safest, economically stable path for her daughter, she was extremely displeased with my hair-trigger decision to move to LA without a plan. At one point, things were so strained between us that didn't really talk much and when we did, it was VERY uncomfortable. At that point, our relationship was seriously at risk. As untimely and sad as it was to be on this journey without my road dog, and biggest cheerleader, I stayed the course. THAT was the hardest part of that chapter for sure. 

It's also sometimes the price you have to pay for taking a chance on yourself.

And of course, when I landed at USA TODAY, slowly but surely we mended our relationship. But holy shit at the time it was scary. And it was lonely. Incredibly lonely. But in order to pursue this incredibly improbable dream, that was the strategic risk I felt I needed to take. 

Fast forward into my career at USA TODAY, which (although it might be hard to remember) at one point was a dream destination for many sportswriters and journalists. I was hired to build out our daily video content around sports/culture. I was the only on-camera host for one of the largest national media brands. Because of that, I was the one they sent to be on-camera for every big sporting event, interviewing the highest-profile athletes how I saw fit (which was a blessing and a curse). I was fortunate to be given a talented, brilliant producer who was a true partner from the beginning and by the end, became like family. We planned our content together, brainstormed together, wrote scripts together, traveled to all of the locations together, shit, we even carpooled together to work. Even when the work was stressful, we had fun because we were together. He allowed me to be myself 100% and was EXTREMELY patient when I was fully on my diva bullshit. 

How patient was he? How much on my bullshit was I??? Well, here's a little example. One time when we were traveling to Minnesota, I had a cooler full of food, and the TSA agent took issue with the amount of liquid in my unopened kimchee (sorry not sorry), so much so that in order to take it through security, he and I both needed to be patted down and our luggage needed an extra level of inspection. It was ridiculously stubborn on my part to put him through that bullshit just for some $9 kimchee (it was the principle), but he never complained. Was he mad when I never even ate the Kimchee I dragged from DC all the way to Minneapolis? You better believe he was EXASPERATED. 

Shout out to my guy Collin. As you can see, we had a very comfortable working relationship that I, honestly could have done indefinitely. 

Why would I ever consider leaving a job like that?

That's a fair question. To leave an established job that put me up front at the Final Four, the Super Bowl, and just about every other major sporting event on the calendar, working directly with the biggest athletes in the world, to work for Barstool Sports?

That, my friends, is risk. What's the possible payout for taking a chance like that?

Brand value. Audience. Personal growth. Personal happiness.

After a couple of years, I felt I had stopped learning, growing and unfortunately, the audience at USA TODAY, was a demographic closer to my mom's age than mine. And thus, my social following reflected that. I was being asked to condense my personality into a 60-90 second bite-size videos to be put in the corner of our sports articles. Newspapers and other old media were struggling financially and I didn't think our business model was ever going to change (talk to the Foreplay boys about what it's like dealing with old media). No matter how comfortable and exciting my day-to-day job was, no matter how much I loved the people I worked with, I needed to take another risk to move forward. I needed to go somewhere with a richer brand, a bigger audience, and a company that gave me the freedom to by myself. 

Barstool met all of those criteria in spades. 

Let me tell you. In general, the majority of the female "friends" I had made in media, do NOT like Barstool. As soon as I started at Barstool, I was abandoned by many of those so-called friends. My phone calls? Ignored. Text messages were left on read, and of course, I was either unfollowed or blocked on social media. Not by everyone, but by more than you'd guess.

As soon as I got to Barstool HQ, I was fully aware of how different it was going to be. I for one had to move to New York pretty much immediately. STARK contrast. And an expensive one. That person that I had as a sounding board and creative partner; the person who I could trust to tell me whether my content was funny, the person that kept it 100 with me, was gone. I felt pretty shitty about leaving him, too. He was now without a host. And he was left flatfooted to find someone to replace me a couple of months before the Super Bowl. 

I was going to have to adapt and largely figure out how to create solo. The siloed nature of the company was a stark difference from the collaborative environment I came from. And I knew no one. 

But here's the thing about taking risks. 

What I knew about Barstool is what you constantly hear from Erika, and Dave, and Big Cat, and everyone else -- you get out what you put into it. It's why it doesn't matter where you come from, whether it's a sorority on the Alabama campus or a major cable network or anywhere in between. You'll sink or swim here based on your creativity, your originality, and whether your work resonates with an audience.

And to me, THAT was worth leaving a comfortable, traditional job for the great unknown. Because freedom to succeed (and to fail) is worth it if you believe in yourself. And no place I know of gives you that freedom better than Barstool Sports.

So I took a risk and I don't regret it. Even in spite of the quarantine, I'm doing interesting and rewarding work and I feel like it's just the beginning. 

Listen, I know... Risk feels like shit. Risk brings about fear. Like, will we fail? Will the people in our life judge us for failing? Will we look stupid? Will we recover? 

Also, risk comes with real-life consequences. What may we lose in the process of taking these risks? Friends? Family? The lifestyle we built? All of that is possible and more. 

And because of all of that, it's easy to avoid risk. We as human beings crave safety, security, and comfort. It's embedded in our DNA.

But risk is what is required for growth, risk is what's required to level up. Without risk, we stay the same. Without risk, I'd still be selling mutual funds talking about how great I think I'd be at doing what I see on TV, and never knowing whether it was true (jury is still out). And without taking the risks, you risk (no pun intended) becoming bitter about the life you think you should have had, but never went for. Then before you know it you're that middle-aged boomer squashing everyone else's dreams around you, especially the ones brave enough to take the risks your ass never got up the courage to take.