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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.


January 24, 2015

I wish I had a cameraman walking behind me last night as I walked home.

Yesterday, I covered the Heat game for The Huffington Post.  In terms of games, it’s probably not one that I’m going to remember.  The walk home, though?  Yea, I’ll remember that for awhile.

To get home, I have to cross a bridge.  There’s always a decent number of people passing over the bridge, so when I approached it last night and saw a sizable crowd, I didn’t think much.

There’s always something happening in Miami, too, so I didn’t think much when I saw flashing police lights.  I also didn’t think too much when I saw a lot of police officers roaming about the area.  I guess my perception could be better, but I’ll tackle my perceptiveness on another blog.

It only hit me that something was wrong when I got to the point of the bridge’s beginning and saw “DO NOT CROSS” tape blocking my entry.

I then became a little bit more perceptive and noticed the bomb squad car and multiple Homeland Security vehicles and officers.

Even as all of this came into my view, I still stood there.  My feet as close as they could come to the bridge, without crossing the “DO NOT CROSS” tape.  I didn’t immediately look for a detour.  I didn’t start walking another way.  I just stood there.

And I just stood there with a growing group of people.

For some reason in my life, people come to me.  With their problems.  Their stories.  Their issues.  My family.  My friends.  They come to me.

People I don’t know come to me, too.  For my whole life, people I’ve so much as blinked at have walked across rooms or stood up to talk to me and tell me their problem.  Their story.  Their issue.

And last night was no different.  Except it was in Miami.

As I stood by that “DO NOT CROSS” tape trying to figure out my own path home, a beautiful, blonde model approached me.  Her first words to me?  “WHY DID HE DO THAT TO ME!?  WHY?!?!  WHY ARE PEOPLE HERE SO WEIRD?”

“Um, what are you talking about?” I said.

“The taxi driver! Why did he do that to me?!”

“I have no idea what you’re talking about.”

“I paid him $75 and he dropped me off here and this isn’t where I’m even supposed to be and now I can’t get over the bridge!”

“Oh, wow.  Yea, I’m sorry,” was about as good of response as I could muster.

Because I now appeared to be helping solve this woman’s issue, I suddenly became a mayor of sorts of a scene precipitated by a bomb squad and some “DO NOT CROSS” tape.  A couple from Bulgaria approached me to ask what was going on. “I have no idea,” I said.  A group out on a double date asked me where the closest bar was,  “Behind you,” I said.  The model returned.  “WHY DID HE DO THAT TO ME?!”  Girl, I don’t know why people do what they do.

As this scene unfolded, and as I grew more tired, my thoughts finally went to the right place:  Home.  I needed to get home.  Right then.  Officers said the bridge wasn’t going to open for at least a couple of hours, and there was no way I was standing on the other side of it, blocked off by some “DO NOT CROSS” tape and fielding this circus.

I needed a detour.

Life is funny sometimes, because it gives you moments like the one I faced last night.  I’m not saying bomb threats are funny, because clearly they aren’t.  I wouldn’t be writing any of this if a bomb went off, but one didn’t and I can’t even find a news story about what caused the closure of the bridge.

I only say the preceding, because sometimes in life you are given great, big, crazy happenings that mirror exactly what is going on in your own life.

Last night, I stood in front of “DO NOT CROSS” tape for longer than I should have.  I fielded crazy questions and pacified upset people.  And in the midst of all of that, it took a really, really long time before something in me finally kicked in and said, “Alicia, you do not need to be here right now.  Go another way.”

Why are we sometimes afraid to go off of the path we’re on?  Why are we afraid to go another way?  Why won’t we give up a set direction that may not get us where we need to be?  Why won’t we take a chance on something that may be a little bit further out of our way, but will definitely get us where we need to go?

Why don’t we take the detour more often?

I hit a detour this week.  Forbes let me go.  Truth be told, I wanted to quit Forbes in November 2013.  I told my family, my close friends and even the guy I was seeing at the time that I was quitting.  Everyone thought I quit.  I didn’t write anything for Forbes for a month.

But then I got scared.  I thought quitting would derail my writing career.  I thought everything would be over if I didn’t keep going down that path.  Metaphorically, I thought it was the only way for me to get “home.”

For a long time, I’ve wanted to write a book.  I’ve started and stopped.  I’ve put it off and started other things.  I know the story in my head that needs to go on paper.  When I see it getting there, I imagine it as a film.  A story coming to life.

I’ve been afraid of taking the detour to write it, though.  And so, I just stopped.  I stopped in my tracks, where I was and didn’t move any other direction.

When commonsense hit me last night and I realized I could go another route to get home, I felt a calmness overcome me.  Suddenly, in the midst of a crazy scene, I knew that everything was going to be ok.  And so, I started walking the other way.  And along the way, I met the most hilarious couple and followed them to the Metromover.  As I took literally one step onto the Metromover, a complete stranger looked at me and said, “Hey!  I’m lost.  Can you tell me how to get to where I’m going?”

Having just escaped the melee surrounding the “DO NOT CROSS” zone, I initially thought to myself, “Oh, COME ON!  Can’t I just enjoy this Metromover ride in PEACE?!”  My words, though, said, “Where are you going?”  She told me where she was going and as fate or luck or the universe would have it, she was going to the building next to mine.  “I’m headed that way, if you want to just walk with me, I can show you where it is.”

We talked first about the scene on the bridge and how crazy Miami is.  We talked about how she lives in New York.  And since I didn’t really know her, I didn’t ask what she did.  She said it, though, out of nowhere.  “I’m a writer.”  “Oh, that’s cool!  I write, too,” I said.  “I write books and screenplays,” she said.


Sometimes, people, life hits you over the head and tells you where you need to go.

There are some of us, who move through life smoothly, naturally and without much resistance.

And then there’s me.

It took me 14-months, being let go from my first paid writing gig, a bomb threat on a bridge, and meeting a complete stranger on a train to get me where I need to be going.

Sometimes, though, a detour is the best way.

On The Road

January 19, 2015

There’s a line in Jack Kerouac’s “On The Road” that I particularly love.  It goes, “But why think of all that when all the golden lands ahead of you and all kinds of unforeseen events wait lurking to surprise you and make you glad you’re alive to see?”

I love that line, because in a sense, it’s been the mantra of my life for the last four years.

I’ve definitely been on the road for the last four years.  Perhaps the person who knows this the most, other than me, is my mother.  She frequently reminds me how much I’ve been on the road.  Too much, perhaps.  Yet, not enough, perhaps also.

The desire to pack up my suitcase and go wherever I can as often as I can bit me four years ago on this day.

At the time, I was a national officer for my sorority, Sigma Kappa.  I wasn’t writing for Forbes yet, and in fact, I hadn’t even started  So, at that moment of my life, my travel for the sorority was the only travel I did outside of trips with friends.

On Martin Luther King Day weekend in 2011, I flew to Iowa to visit one of my best friends and her family.  On the way back to California, I had a layover in Memphis.  My connecting flight was delayed, so as it turned out, my layover ended up being around five hours long.  When my flight from Iowa touched down in Memphis, I rushed straight to the rental car counter.  I paid $100 to rent a car for a few hours.  I had somewhere to go, though.  Somewhere I was willing to pay any price to see.  Especially on this day.

As a child, my hero was Martin Luther King, Jr.  Every year on his birthday, I would wake up and read his “I Have A Dream” speech, and cry that we as a society still hadn’t gotten it all right.  I’d smile, though, at the hope that the dream persists.

After leaving the rental car counter, I made my way to the Avis shuttle.  The driver, an older African-American male, shot the breeze with me, a young, light-skinned Caucasian.  We talked about music and food and life.  We laughed and both muttered “mmmhmm” to the more serious things that arose in our conversation.  Our conversation seemed to have lasted days, because we covered so many topics.  Our conversation seemed to have lasted days, because it flowed so naturally.

When he dropped me off to pick up my car, I said, “Thank you, sir!”  And he said, “Now, don’t forget the directions I told you!  They’ll take you right there!”  “Of course I won’t forget.  Thank you, again,” I said.

And from there, I drove.  And I felt freedom unlike anything I had ever experienced in my life.  I was alone, on the road, doing what I wanted to do and seeing what I wanted to see.

I followed his directions.  A few turns here and few turns there.  And then finally, I turned the corner and there it was.  A page from a history book ripped out and laid right before me and my rental car.  I scrunched my face up the way I do when I don’t want my emotions to pour out.  And then I cried.

In front of my car was the balcony where the man who was my hero was shot to death.  In front of me was the spot, where for a brief period in history, hatred overcame love.  In front of me was a place where the dream could’ve died.


I’ll never forget that winter day in January 2011 when I parked my car and under a grey sky, walked alone towards the Lorraine Motel.  For once in my life, I was grateful for solitude.  As someone who is usually surrounded by many, I was glad it was just me and my thoughts together on that day.

In the last four years, I’ve traveled alone more than I can count.  And even though sometimes the road is a lonely place, it also provides a release for me.  For me, there’s something cathartic about being behind the wheel, unsure of where I’m really going, with just me, my thoughts and the road.

The road is also fun.  I’ve met some characters in the last four years.  That Avis rental car shuttle driver being the first of many.  There have been chefs, professional athletes, maids, businessmen, doormen, and even the occasional rock-and-roll band that have come into my life while I’m on the road.  These people have all made it a little less lonely.

Overall, though, the road will always be a second home to me, because of the opportunity it gives me to step outside of my comfort zone.  Don’t get me wrong:  I love home.  And some day, I hope to have a husband and babies to keep me home more often.  Yet, there’s something that being on the road does to drive you out of your comfort zone and into finding yourself.

As a 30-year-old, these days when I listen to Dr. King’s “I Have A Dream” speech, I think what he is really trying to say, is that in order to experience life to its fullest, in order to love to the greatest boundaries of our hearts, we must step out of our comfort zones.  We must do that which we may fear.  We must do that which maybe doesn’t feel natural.  And we must risk that which has never done before in order to live out our greatest potential and love to the best of our abilities.


Because, if we do all of these things, we’ll see the “golden lands” in Kerouac’s words, or the “Promised Land,” Dr. King preached about.  And then, life will finally feel complete.

Make No Assumptions

January 6, 2015

I’ve spent the last two weeks in Denver celebrating the holidays with family and friends, and well, being cold.  Colorado got a lot of snow this holiday season and the half-Samoan in me doesn’t really dig that.

On Sunday, ahead of another snow storm, I went to the grocery store to pick up a few things for my mom.  I also wanted to pick up a couple of magazines for myself so I’d have something to do in case I got cooped up inside because of the snow storm.

With 2015 upon us, I first grabbed Vogue so I could be up on all of the new year’s fashion trends that I cannot afford.  Word on the street is platforms are the shoe of 2015 and felt hats are here to stay.  Excellent.

As I worked my way to the cashier, I saw all of the celebrity gossip magazines with their incredibly pressing questions spewed haphazardly across shelves.  Are Kim and Kanye getting divorced or not?  Is Kate Middleton pregnant with a girl or boy?  Is Kendall Jenner done with Harry Styles or are they getting hot and heavy?

When I see these publications, I generally have two initial thoughts:  1.  Who cares? and 2.  These poor people.

One of my initial responses is “Who Cares?” because seriously, who cares that deeply about some of the most intimate happenings of complete strangers‘ lives?  Seriously.  What is it to me whether Kim K. and Kanye stay together or not?  How will my world be changed if Kate Middleton gives birth to a boy or girl?  Why do I care whom someone 10-plus years younger than me is or isn’t dating?

Given the number of issues these magazines sell and the money these publications bring in, my gut tells me that my “who cares?” attitude is a minority opinion.

So, that leads me to my second initial reaction, “These poor people.”  Sure, they bring the attention on themselves, but still.  Can you imagine having every, single, mundane action of your life scrutinized and even more so, oftentimes inaccurately scrutinized?  As someone who occasionally enjoys running errands in yoga pants without makeup on and has mad a misstep (or fifty) in dating, I can’t imagine living under a microscope.  For what it’s worth, it’d probably be entertaining for you all to watch unfold, though.

I raise the above to make the following point:  I rarely, if ever, buy celebrity gossip magazines.

On Sunday, though, I bought one.

The cover of People Magazine featured a sprawling picture of Kate Middleton with captions about her pregnancy.  While she’s beautiful and an elegant leader, that’s not what caught my eye.  Rather, tucked high in the upper right corner was a photo of a man with four children and a caption about how a People Magazine writer had adopted four Haitian orphans.  That grabbed my heart, and so, I grabbed a copy and threw it onto the conveyor belt.

As I ruffled through my purse, which these days looks like a bomb zone, the cashier began scanning my items.  My food items moved along the belt first.  At the end of my order were my magazines.  First up, Vogue.  He held the issue featuring Sienna Miller’s porcelain face, shot me a look of irritation and rolled his eyes.  Next up, People.  This time, he gave me the same look, but added some commentary.

“Oh!  You’re one of those.”

I’ve been working hard the last few years on holding my tongue.  Yes, my tongue was sharp enough that it’s been an exercise a few years in length for me to keep it in check.  If I was in some sort of rehabilitation facility for healing sharp tongues, I would’ve graduated on this day.  Because I bit my tongue.

Ok, I bit it for the most part.  Let’s be realistic.  I always have something to say.

“What kind of person would that be?” I asked.

“A person who cares about celebrities and gossip and superficiality.”

Yea, Bro.  That’s me.  To a tee.

Instead of saying, “No, buddy” or what I wanted to really say, which was, “Get over yourself,” I just giggled and said, “Gotta have some good reading material for this blizzard” and picked up my bags and headed on my way.

Earning flying colors in Sharp Tongue Rehab, folks! 2015 is off to a shining start for one, Alicia Jessop.

I may or may not have rolled my eyes as I marched away.  I’m working on one problem at a time, ok?

In the grand scheme of things, it was an uneventful interaction, but the more I thought about it, the more anger stirred in me.  Who was this guy to make an assumption about me?  How could he take a look at a cover of a magazine, see one story on it and thrust upon me assumptions about who I am, what I stand for and what’s important to me?  How did he not know that I care about orphans in Haiti and am so not superficial?

As the day went on, with the snow continuing to fall down out of the Denver sky, I had a lot of time to think about things.  And the one thing I kept thinking, is how damaging assumptions can be.  I thought about times in my own life where instead of seeking clarity, I took the lazy road and just made assumptions.

As I ran through every time I’d made an assumption about something big in my life, I realized that the same outcome happened:  Failure, hurt or destruction. The more I thought about it, the more I was able to point to specific instances in my life that I made a big assumption in a relationship, friendship, class or job opportunity, rather than going directly to the source to seek out a conclusive answer.  With every example that rolled through my mind, the more apparent it became that making assumptions has been one of the most harmful practices in my life.

I think we make assumptions because sometimes, in some matters, we are afraid to face the truth.  With that fear in our hearts, we hide behind assumptions.  “He didn’t call because he was busy.”  “She isn’t being as good of a friend lately, because they’re having financial issues.”  “I didn’t get the job because I’m not smart enough.”  “I didn’t get a good grade in the class because the teacher didn’t like me.”  We tell ourselves things to make sense of happenings that fit our own needs rather than seeking out an answer for why things really are the way they are.

The grocery store cashier, who I had known for all of 90-seconds, made an assumption about me based upon my purchases.  He made an assumption that celebrity gossip and news is important enough to me for me to purchase a magazine about it.  Knowing why I purchased that magazine on that particular day, his assumption was not only unfair, but more importantly, it was wrong.*

And that right there is the problem with assumptions:  Most of the time, they’re false.*

This all got me to thinking about this:  What if instead of making assumptions, we started asking questions?  If we didn’t know the answer to something, what if we simply took the time to ask? “Why did you purchase this magazine?”  “Why did you stop calling me?”  “Why didn’t I get in an A in this class?”  “Why did I get passed over for this job?”  What if getting the actual answer or real reason for something became our mission in interacting with others?

Asking questions is worth it, because I know this much:  Answers are always better than assumptions.

*I do occasionally enjoy a good celebrity gossip magazine sometimes for the sole purpose of reading celebrity gossip.  I am human and I am woman.  Hear me roar.

What I Found In 2014

December 31, 2014

I know that no matter what age you are, we all get 365 turns around the sun every year.  For some reason, though, the older I get, the faster this world seems to turn.

2014, where did you go?  I feel like we were just getting started, like I was finally beginning to understand you.  And now, before I know it, you’re gone.  Like a ghost.

This year was something else.  I traveled the world.  To Greece for my 30th birthday.  To Haiti for serve others.  Across the country for work, friends and family.  I achieved “status” on American Airlines.  I saw new places.  I met new people.  I held new hands.

And in the midst of all of these journeys, what I really found was myself.

Reading that last sentence seems kind of crazy.  Sure, I’ve known for a long time what I stand for.  I’ve known for even longer what’s important to me.  For some reason, though, lost in the shuffle of things was me.  Who I am.  What I want.  What I need.  In the miles traveled, people seen and places visited, though, I came alive in 2014.  For the first time in a life lived for 30 years, I finally found me.

This year was the most adventurous of my life.  I truly lived without fear, and for that, I am proud.

I rode a motor bike around Mykonos–up hills and to dinners on the coast, down hills and to drinks on the beach and realized that adventure doesn’t fade even as time goes on.

I said what I needed to say–face-to-face, eye-to-eye, heart-to-heart, and in those words uttered, opened up a world of new possibilities with the belief that what will be, will be.

I got off of a plane in a foreign country I’ve never been to all by myself–and met new friends, held hands, soothed babies and reached depths of my heart and faith that I never knew existed.

I’m not big on New Year’s resolutions.  Truth be told, we all could probably stand to be more fit, further along in our careers or better with our finances.  When I think of resolutions, I think of the word “resolve.”  What things do I need to figure out before the clock strikes Midnight and a new year–and new chance to get it all right–begins?

For me, 2015 is about resolving to be authentic.  I want to be true myself, honest with my heart and loyal to those around me.

Happy New Year, everyone!  May this year bring you the peace and happiness that we all deserve and may tonight bring you the fun and excitement that we all want.  Cheers!

Why I’m Scrapping The Five-Year Plan

December 17, 2014

“Where do you see yourself in five years?” was a questioned I heard a lot five years ago.

Back then, I envisioned myself working at an entertainment firm or in a large law firm.  As I made my way through the interview rounds, this prophetic question was the one constant I faced in life.

Upon hearing this question, as I sat in front of the interviewer in a freshly pressed suit, I oftentimes would think, “Well, ideally, in five years I’ll be married with a child or two.  We’ll live in a nice house and be surrounded by good friends.  My babies will go to church on Sunday.  I’ll live within 30 minutes of my parents.  I’ll be active in my community and life overall, will be good.”

In law school, they teach you not to answer the question that way.  As it turns out, generally speaking, most law firms don’t care about your personal life, at least when you’re a new associate.

So, time after time after time again, I’d say, “Five years from now, I envision myself being someone who attracts top-notch clients to the firm.  I imagine that I will be close to becoming a partner at that point in my career.  I want to be someone who has my own book of business and someone with whom clients trust, respect and want to work with.  I see myself as a leader in the entertainment industry, completing research into emerging trends and writing law review articles that are valued by my peers.”

Oh, how life has changed in the last five years.

Thank God.

In the corner of my condo sits a 5-foot tall tinsel Christmas tree.  I’m getting ready to leave Miami for the holidays, meaning I won’t be home to enjoy a fresh, pine-sceneted, real Christmas tree.  So, I settled for the next best thing:  An obnoxiously silver Christmas tree from my personal shopping mecca, Target.  The thing is gaudy and tacky and I love everything about it.

The presents sitting underneath my obnoxious tinsel Christmas tree speak loudly to how the last five years–or more accurately, year–have unfolded for me.  When I look underneath the tree, the bulk of the names scrolled on stickers attached to packages are those of people I didn’t know five years ago.  They are the names of new friends.  They are the names of new business acquaintances.  They are the names of ten children living in Haiti.

When I peak underneath my Christmas tree, what I see is the truest testament to what, unbeknownst to me, has been the mantra for my life:  Go with the flow.

If my best friends are reading this (hey, guys!), they probably just spit out their coffee upon reading that.  I know that if my mom is reading this, she also is probably on the floor laughing.  My dad is a little bit more gentle with my feelings, so he’s probably just sitting in front of the computer looking confused.  Each of them is probably saying out loud, “You think ‘Go with the flow’ is a phrase by which to describe your life?”  Fine, I’ll admit it:  In the grand scheme of things, “Go with the flow” and Alicia Jessop have never been synonymous.

I’ve been a planner my entire life.  In fact, I take planning to new levels and to places even the biggest of planners probably doesn’t even know exist.  You can ask any of my best friends about the email they get from me EVERY summer where I lay out about 50 activities we are going to engage in before Labor Day.  “On June 1, we’ll go boating.  On June 8, we’ll have a park day at Wash Park.  June 15 is a brewery bar crawl and let’s climb a 14er on June 22.  Oh, and we need to cross off every happy hour spot we’ve been wanting to try, so Thursdays are happy hour night and on Tuesday, well on Tuesdays, we’re joining a kickball league.  On Wednesday, I’ll have a bar-b-que at my house and we’ll play lawn games.  See you all there.  This is going to be the best summer ever.

Being a planner for most of my life, I generally know the types of responses I will get when I fire off this email to my close circle of friends.  There’s my fellow planner friend, Megan, who says, “Awesome!  Looks good.  Let’s add X, Y and Z.”  There are my friends who have just come to accept that I’m neurotic and respond with, “Sounds fun!  I’ll come out as much as I can.”  And then there is my one friend, Brit, who’s honest.  Without fail, she zings me back an email saying, “Come on.  I’m exasperated just reading that.”  I laugh when I read her response and for a brief moment think, “She’s right,” but instead write back, “Brit, if we don’t have a plan, how are we going to get ANYTHING done this summer?!”

And therein lies my obsession with planning.  If there ever was a spokeswoman for the line, “Proper planning prevents poor performance,” it should be me.  (If you’re my agent and reading this, if we could get to work on that endorsement deal, that’d be legit).  For most of my life, I’ve lived under the belief that if I didn’t have a plan, everything would fall apart.  I wouldn’t have a job.  I wouldn’t have a roof over my head.  And arguably most importantly, my friends and I wouldn’t have fun.  To me, not having a plan–and not just a plan, but a well-crafted and immensely detailed plan–led only one place:  To destruction.

I operated under this belief until relatively recently.  I can’t pinpoint exactly what changed in me, other than to say that everything changed.  For some reason though, planning just stopped being important to me.  Instead, I decided to just start going with the flow.  And guess what?  The world didn’t end!  I have a roof over my head.  I eat every day.  And my friends and I are still having a really, really good time.

In going with the flow, my plans changed.  Clearly.

I’m not practicing law anymore.  I traded entertainment for sports. I’m a professor!  I’m living a life built up by three things I didn’t ever really see happening.

I don’t live within 30 minutes of my family, but I have a job that lets me see them for a good chunk of time each year.  I don’t rock my own babies at night, but my heart is full with love for a nation’s worth of babies.  I still haven’t found “the one,” but I’ve found love and hope to find it again.

All of these things happened without one thing:  A plan.  The life I’m living right now looks nothing even remotely close to what I envisioned for myself five years ago.  Yes, what I’m doing currently involves things that at some point in my life I obviously envisioned.  The difference, though, is that nothing I’m doing now is part of a hard and fast plan that I had.

The best part of all of this, is that I’m happier than I’ve ever been.  Ever.  And that’s what they don’t tell you about failing to plan.  Sometimes, failing to plan leads you to true happiness.

What I mean by that is this:  When you relax your plans, you ease up on your expectations.  When you ease up on your expectations, you give way for life to unfold for you in the way that it should.  When you hold onto your standards but give up on deadlines, perfection and specificity, a world of excitement and surprise has an opportunity to design a life for you filled with joy.

If anyone told 25-year-old Alicia that the thing gripping her heart the most right now was a group of orphaned children in Haiti, she would have said, “Yea, ok.  Right,” and moved on.  She wouldn’t have listened, not because she was a jerk, but because it would’ve seemed so far-fetched.

If anyone told 25-year-old Alicia that she’d write for Forbes and The Huffington Post and gain access to some of the greatest sports leaders in the world and dawn credentials for events like the Super Bowl, she would’ve said, “Yea, ok.  Right,” and moved on.  She obviously would’ve liked the sounds of this, but it would’ve seemed so far-fetched.

If anyone told 25-year-old Alicia that the most joy she would find in her career would be at the front of a classroom in Miami, she would’ve said, “Yea, ok.  Right,” and moved on.  She would’ve remembered the first time she was in Miami–when the city seemed so big and intense–and not have been able to see a path that would lead her to becoming a professor out of law school that didn’t seem so far-fetched.

When I look at life these days–whether it’s Christmas presents under my tinsel tree for new friends and babies in Haiti, the opportunities I’ve been given to cover sports stories or the chance I have to impact future sports leaders at the University of Miami–one thing becomes very clear.  And that thing is this:  My life began when I laid down my plans.

It did.

These days, I don’t stress about what’s next.  And for someone who lived the way I did for most of her life, some days, that’s hard.  Really, really, really hard.  Then I remember this:  The best laid plans can be destroyed, but some of the best gifts in life are surprises.

As 2015 approaches, I’m working, like many others, on resolutions.  And as it inches closer, what I’ve settled on is this:  I’m scrapping the five-year plan.  Actually, I’m scrapping the plan entirely.  I am done pretending like I’m a prophet for my life who knows what tomorrow holds.  Rather, what I am going to focus on is the person I can become.  Instead of making plans for my life, I’m going to work on being the person I want my life to be defined by.

Am I joyful?  Am I giving?  Am I kind?  Am I honest?

Am I happy?

If any of the answers to those questions are “No,” I know it’s time to change.  I know it’s time to shift what I’m doing and move forward.  I know it’s time to get on with things and to take myself and my life down a new path.  I know it’s time to perhaps go somewhere and do something that I never planned.

Sometimes I wish I had a time machine.  Sure, I wish I had a time machine so that I could go back in time and take back some of those decisions I’d later come to regret.  Sure, I wish I had a time machine so that I could go back in time and see historical events and walk alongside history’s greatest leaders.  Today, though, I wish I had a time machine to zap me back to a place that I really didn’t want to be in the first place: Those stuffy law firm board rooms.  If I had a time machine, I’d want to get back there, because five years later, I finally have the best answer to that age-old question.

“Ms. Jessop, where do you see yourself in five years?”

“It’s funny you should ask that, sir.  It’s funny, because I see myself somewhere you probably don’t expect me to be.”

“Oh, really?  Indulge me.”

“Certainly.  Well, after giving it some thought, I know where I see myself in five years.  And when I look forward and when I look at my life and the person I want to be holistically, what I see is this:  I see myself scrapping the five-year plan entirely.  And in doing so, I plan on doing something different, something that maybe isn’t the most rewarded or even respected in this industry.”

“And what would that be, Ms. Jessop?”

“I see myself living.”

Dear Prosper

November 12, 2014

Dear Prosper,

Today is your birthday!  Today, we celebrate you and the fact that you are here on this Earth.  We celebrate your mischief, your funny little personality and most of all, your potential.  Happy birthday to you, dear Prosper!

Last Saturday, I held you on my lap as an interpreter sat next to us so I could have him tell you in Creole that you no longer have to worry and just how much you are loved.  You will be taken care of.

I asked you how old you are, and you said, “8.”  I asked you if you knew what day your birthday is, and you said, “No.”  The date that your life began got lost somewhere in the years you spent living in orphanages.


I pray every night before I go to bed, Prosper.  I pray that God keeps my parents safe and healthy.  I pray that he shows me the path I am supposed to follow for my life.  I pray for world peace and the impoverished.  And these days, Prosper, I pray for you.

I pray for something else every night, Prosper.  Every single night, I pray that God brings me a good husband and that he lets me have a child.

I had a dream in July, Prosper.

I have dreams every, single night.  Vivid, vivid dreams that a lot of times when I wake up, come true. I’ll never forget this dream, though, Prosper.  Like every night, I prayed for that good husband and I prayed for that baby.  And in my dreams that night, the message was sent to me that, “there is a boy.”

When I woke up, I knew in my heart that it wasn’t a baby of my own or that good man I’ve been looking for.  I knew in my heart, rather, that “there is a boy” meant something else.  Every day, I would ask God that He would show me what He meant.  And luckily, Prosper, He didn’t keep me waiting long.

Just one week after that dream, Prosper, you came into my life.


Along with being prayerful and having many of my dreams come true, the other thing you need to know about me, is that I don’t believe in coincidences.

I live my life with intention and purpose and faith.  And when you live your life with those three things, Prosper, there is no room for coincidences.  My path was meant to collide with yours.

I’ll never forget the first time I saw you in Haiti.  They told you I was coming.  I don’t know what they said or who you understood me to be, but when I turned the corner, we both just looked each other in the eyes, raised our foreheads a bit and smiled a closed-mouth grin.

When I see you, Prosper, I see a little boy who is afraid to let people fully in.  I see a little boy who is afraid to let people fully in, because he’s been hurt before.  And in that, I see myself.  I get it.

When I see you, Prosper, I see a little boy who is afraid to let himself go, to live freely, because he’s been hurt before.  And in that, too, I see myself.  I get it.

I will promise you this, though, Prosper.  From July 2014 until the time I leave this Earth, I will walk alongside your life.  I will never quit on you.  I will never give up on you.  I will always believe in you.  I will always support you.  My path was meant to collide with yours.


I spent last Sunday morning playing with you.  We hit baseballs and I chased you on your scooter.  You and that dang scooter go everywhere together!  We worked on sharing with the other children, and well, you have some work to do in that area.  I brought you a basketball and I taught you some dribbling tricks.  I also watched as you played tricks on other kids.  Namely, the kid who got a hold of your scooter.  You hid around a corner, waiting for him to scoot by, with the baseball bat I also brought for you in your hand.  Luckily, it was a soft bat.  When that kid came around the corner on your scooter, you jumped out and WHACKED him with the bat.  I shot you a mean look and said, “Prosper! No,” and you shrugged it off.

You’re too smart and cunning for your own good.  And trust me, I get that.  Well, at least the cunning part.  There are no boundaries between you and what you want.  And trust me, Prosper, I get that, too.


That afternoon, I left you and went with the adults to the beach.  When I came back that night, you and I sat down to talk.  You only speak Creole and I only speak English, so T-john interpreted for us.  As I held you in my lap, and before I could say anything, you uttered something under your breath.  I asked T-john what you said.  “I was sad today,” he said.

I asked T-john to ask you why you were sad.

“Because you left,” he told me.

And in that moment, my heart fell to pieces.  I knew I was leaving the next day.  And this time, I was leaving for much longer than an afternoon.

I had T-john explain to you that I live in Miami and that I’ll be back to see you soon.  As I pointed to my heart, I had T-john tell you that’s where I always carry you with me.  You looked down at the floor and mumbled something else.  T-john shot me a look of, “I don’t want to tell you what he said.”  I waited a couple of seconds, grew impatient and then said, “What’d he say, T-john?”

“Take me with you.”

My heart shattered.


I told David later about our conversation and I think he saw the tears coming.  He said what you said to me was a good thing.  I looked at him and said, “How?!”  He said it was good, because it shows that you are bonding with people.

You are finally free, Prosper.

Free to love, free to feel, free to give of yourself.  The hurt is over.  You will be taken care of.

I came to say goodbye to you last Monday afternoon.  And when I got to the house, your parents were there.  Your parents!  There are no coincidences, Prosper.

From what I know, you haven’t seen your parents in years, when they left you at an orphanage.  When I walked in, you were sitting on your dad’s lap and your mom was sitting to the side of you both.  Your mother beamed.  She looked so proud of you.  You have your mother’s face.  Your father was solemn and serious.  You carry your father’s emotion.  As you sat there, you showed none.  Just as he showed none.  I will never forget the look on all of your faces as I peered into that room.

As I looked at all of you, I thought to myself, “There are no coincidences.”  There is no coincidence, Prosper, that on the day I left Haiti, your parents arrived to see you for the first time in a long, long time.  There is no coincidence, Prosper, because the message to you should be this:  You are beloved.

Like you, I needed to see your mother, too, Prosper.  There are no coincidences.  The thing I want most in this life and the thing that has eluded me the greatest, Prosper, is a child.  Heaven help me–and it–if I have one.  That baby will have to be pried from my fingertips before I hand it over to anyone.  I can’t imagine the pain a mother must feel when she has to give up her son.  You were woven in her womb, Prosper.  She carried you and took care of you while you were growing inside of her to the best of her ability.  I can’t imagine how badly your mother’s heart hurts, Prosper, that she doesn’t get to take care of you and watch you grow outside of her womb.  No mother should have to make the decision your mama did, Prosper, to be forced to have strangers raise her baby.  No mama should have to go years without seeing her boy, the creation that she made inside of her.

I wish your mama had more opportunities, Prosper.  I wish she was educated.  I wish Haiti’s economy was better.  I wish there were valuable jobs and resources for her.  I wish someone was there to empower her to find a way to keep you.  I wish she could hold you and tell you how loved you are every night.

You are beloved.

Seeing your mother lit a fire in my heart, Prosper.  A fire that made me realize that I will fight for your and Haiti’s well-being until the day I die.  I want you to have your own babies, Prosper, and I want you to support them and give them good lives and watch them grow.  I want you to share life with them.

David was talking to your parents and I could tell that the conversation had shifted from chit-chat to something more serious by the looks on their faces.  I knew it wasn’t my place to be in the room, so I turned around and went downstairs to play with the other children.  You were still on your dad’s lap when I walked away and I didn’t know if I’d be able to say goodbye to you before I had to head to the airport some 15 minutes later.  Shortly thereafter, though, you came down the stairs.  You grabbed your scooter, then came straight to me and buried your head in my side.

You kept uttering something.  This time, though, T-john wasn’t there to interpret for us, so I had no idea what you were saying.  You kept saying it though, as you looked at the ground and shuffled your feet around.  I knew I had to find out what you were saying.  I finally found someone who spoke Creole and she sat down and asked you in Creole what you were saying.  You wouldn’t repeat it.  Finally, she coaxed it out of you.

“Take me with you,” you said.

I got on an airplane last Monday, Prosper, and my heart hurt and was happy at the same time.  It hurt, because I can’t take you here with me.  It was happy, though, because we’re building a future for you in Haiti, your home.  We’re building a future where hopefully, someday, your mama will find you again and see how well you’re doing.  We’re building a future where hopefully, someday, you’ll see and understand your mama’s pride and love for you.  We’re building a future where hopefully, Prosper, you will be able to give life to your mama.

David hasn’t told me yet the full extent of his conversation with your parents, but he will soon.  When I landed on American soil last Monday night, though, there was an email waiting for me from him, and it said this:

“We did find out though, that his birthday is November 17, 2006–which means he turns 8 on Monday!!  We’ll make sure to celebrate his life on that day!”

What a difference a day makes, Prosper.  First, contrary to how old you thought you were, you actually gained a year!  An extra year of life!  I don’t know what better thing there might be to celebrate, my friend.  An extra year of life is something many people would fight tooth and nail for and something women in Hollywood spend big bucks on!

More importantly, though, less than 24-hours after I asked you when your birthday was and my heart sunk when you didn’t know, you learned it.  And for your little soul’s sake, Mr. I Get What I Want, you have no idea how excited I am that you don’t have to wait longer than a week to have your first birthday party.  You have a way of managing to get it all, Prosper!  There are no coincidences.


Today you will have one of those great, Haitian birthday parties.  There will be loud singing and music and dancing and cake.  You told me that Bensley is your best friend, and my hunch is he’ll wear his tuxedo t-shirt, which someday you’ll realize is pretty hilarious.  As all of this celebration for YOU goes on, I imagine you’ll be riding your scooter throughout everyone at the party, carefree but still not letting the partygoers get too far into your space.  Regardless, though, it’ll be a celebration.  A celebration of the 8 years you lived that brought you to where you are today.  More importantly, though, it will be a celebration of all that awaits you in this beautiful life that is yours.  And so help me God, Prosper, I promise you this:  Only goodness awaits you.  You can let go, Prosper, because you are taken care of now.

Your life is valuable, Prosper.

And I would give everything in the world to be there today to watch you blow out the EIGHT candles on that cake.

Happy, happy birthday, precious, mischievous and smart boy.  You are beloved.


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