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Bet On Yourself

February 10, 2015

I woke up on December 10, 2011, and instead of engaging in my typical run to the beach followed by a stop at Starbucks, I decided to do something different.

Only July 1, 2011, I made a decision that would come to change my life:  I bet on myself.

That day, I decided to start a sports law website,  My goals in starting the website were to show the world my knowledge and understanding of sports law.  I knew what I was capable of, so in starting the website, I was betting on myself and my subsequent ability to land a job in sports.

In the months that followed my launch of, many exciting things happened.  I began networking with industry leaders and executives.  I signed with a broadcasting agent.  Doors that previously had been closed to me began opening.

As more doors began opening, I realized I had to wind down my private practice of the law.  With billable hour requirements, I couldn’t keep up the pace of writing I had been engaging in.  Seeing that writing was my top passion, I knew that I needed more time to pursue it.  Given this, I decided to leave my job at a mid-size law firm in Orange County to become a prosecutor in Colorado.  Doing so would eliminate billable hours from my life and in turn, give me more time to write.

December 10, 2011 fell five days before I was moving from California to Colorado to take on my new job.  It also turned out to be the day that the Los Angeles Angels of Anaheim announced their signing of Albert Pujols–arguably, the most valuable free agent in 2011–in a well-attended press conference.

Earlier in 2011, I met David Cohen, who at the time was the general counsel for the Angels.  When we met, I think that was all of two weeks old.  That didn’t stop me from marching right up to him after he finished speaking on a panel and introducing myself as the site’s founder.  David was kind and generous, in that he said he’d heard of the site.  In the weeks that followed, I’d sit down for an interview with him.  As time has passed, David has become one of my greatest mentors and friends in the sports law world.

When the Angels signed Pujols, I remember emailing David congratulating him and the team on their big get.  We shot a few emails back-and-forth about the press conference.  Seeing that I didn’t know if I was going to be in town, I didn’t secure a credential.

When the day of the press conference arose, I suddenly wanted to attend the conference.  It’d be one of the last chances I’d have to attend a major news event in California, and I wanted to take advantage of it.  I figured I could just show up at the stadium and there’d be a handful of people.  Long story short, I didn’t think it’d be an issue that I didn’t have a press credential.

Once I got to the stadium, I quickly realized how wrong I was.  In the years since that event, I’ve covered countless press conferences.  I’ve never seen as many media and people converged at one, save for maybe Beyonce’s press conference ahead of Super Bowl 47.  Seeing the throngs of people, I knew I wasn’t going to get anywhere close enough to the action to be able to ask Pujols questions, let alone accurately transcribe his quotes.  To make my being there worthwhile, I quickly had to act.  In the moment, I realized I had to bet on myself.

I approached the media area of the press conference and walked up to the security guard managing media credentials.  I introduced myself as Alicia Jessop from and explained my situation regarding my credential.  Luckily, in getting to know David, he had introduced me to the Angels’ media director.  I told the security guard that the media director knew me.  The security director then paged someone over his walkie talkie, talked to that person for a few seconds and a few moments later, I was being led through the ropes and into one of the first rows of the press conference.

When I got into the press conference, I knew that this was an important opportunity for me.  I had to ask questions and make myself heard.  I couldn’t be nervous.  I couldn’t be shy.  I had to bet on myself.

I raised my hand.  They brought the mic to me.  I introduced myself as Alicia Jessop from, and asked Pujols how changing leagues might impact his game.  In the minutes that followed, my phone would begin buzzing with people who heard me on ESPN.

A couple weeks ago I was in Arizona covering my second Super Bowl for a major media outlet.  If you had asked the 27-year-old sitting at the Pujols press conference if she ever thought that’d happen, I’m not sure what she’d tell you.  When I was in Arizona, I had a chance to speak to several groups of law students about breaking into the sports industry.  My advice to them was simple:  Bet on yourself.

Betting on yourself means believing in your knowledge and abilities.  Betting on yourself looks like letting your passions soar and going where they direct you.  Betting on yourself means going after any dream you might have, no matter how big it is or what the naysayers might say.

When I tell students to bet on themselves, I tell them to never take “no” as an answer when it comes to achieving their dreams.  Betting on yourself means hustling, going the extra mile and taking risks that others wouldn’t.  On the other hand, though, betting on yourself doesn’t mean stepping on people, acting unethically or taking actions that hurt others.  Rather, betting on yourself is about having the utmost belief that you are capable of fulfilling your dreams and living out the passions you were put on this Earth to engage in.

One thing I’ve noticed in life, is the people who are doing exactly what they want to do are the people who bet on themselves.  I know people who have quit lucrative careers and started all over as unpaid interns to get the job they wanted.  As their family members and friends looked on at them confused, they knew that they were betting on themselves.  All along, they knew where their path would take them and that they were capable of getting there.

When you bet on yourself, you must be ready to remove fear from the equation.  Failure cannot be an option when the currency you’re rolling the dice with is yourself.  Kobe Bryant may have said it the best when he said, “If you’re afraid to fail, then you’re probably going to fail.”

What, though, if you told yourself there is no possibility of fear?  What if you told yourself that regardless of what happens in the venture you’re pursuing, you will succeed?  What if you tell yourself that success is giving it a go and believing deeply enough in yourself to bet on yourself and give your dreams a chance?

I’m not much of a gambler.  I don’t take many risks.  I generally like to play it safe.

However, I always have and will continue to bet on myself, because I haven’t lost yet.

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