The Living Emoji: The Sporting Gals: Alexa Datt

The Sporting Gals: Lindsey Joy Caldwell

Coming from someone who’s moved across country, it’s no easy feat. Let alone when you don’t know anyone in the new city you’re moving to. The latest Sporting Gals interview features Lindsey Joy Caldwell, a freelance reporter and writer who has moved across country not once, not twice, but three times! All because she trusted her gut enough to make the moves.

From interviewing Cam Newton with Gatorade to chatting up JJ Watt on the red carpet, it seems like Lindsey’s gut definitely knows what its doing. Listen close, folks: this is a gal who can talk chalk as well as she can rock rhinestones. Read on for her killer advice on following your own gut feeling, moving to a new city, and chasing your own crazy dreams.

Thanks for chatting with me, Lindsey!

THE SPORTING GALS: LINDSEY JOY CALDWELL

The Living Emoji: The Sporting Gals: Alexa Datt

First thing’s first: what are you up to currently?

I’m currently a freelance reporter, host, and writer based in Nashville. [Jujubee’s note: a couple weeks after this interview, Lindsey scored her own show on Nashville Insider called “Trending with Lindsey”. Congrats, gal! 🙂 ] To be honest, I took a really big leap of faith and left my job at E! in Los Angeles, because I just had this unshakeable gut feeling I needed to move to Nashville. I knew in taking the risk that I would also have to accept the “consequence” that this could be a wrong move, that it could be a “mistake”. However, one of the biggest things I’ve learned in my life and career is to trust those unshakeable gut feelings, there’s a reason you feel a certain way.

After seeing those gut feelings work out successfully in the past, I made a little promise to myself to never stop listening to them. I think when you stop listening; you’ll stop getting them, or it will be so faint, you’ll not be able to distinguish it with all the “noise” around you. I know it sounds cheesy, but I had a whirlwind week in Nashville when I came for the Country Music Awards in November, and on the last day, it just felt like God was calling me here, and to trust him in making the move, no matter how unplanned, and as scary as it was.

I’m very much still discovering what my career looks like in this new city. Nashville to me represents a unique opportunity to capitalize on a really authentic, growing market, as well as have the capability to report and host in entertainment, music, and sports.

You got your start at Seventeen when you were picked to document your first year of college, which then turned into an internship and then freelance reporting. What was it like to get such a strong start in journalism with such an incredibly well-known magazine?

Honestly, it was crazy! I remember I was flipping through Seventeen one night, and saw a page that had 15 girls that were in college, and they each had a quote about their experience. At the time I had just decided to go to USC in LA and didn’t know anyone. I read one of the girl’s quotes, which was about how she went far away for school, and I thought, “I want to do that.” The next day, I filled out the application, and it was pretty surreal finding out I got chosen.

Twitter was the “new thing” at the time, and I remember we all had a conference call to learn about hash tags, and were encouraged to tweet every day, in addition to submit a quote monthly, and keep up a blog on the Seventeen website. It was always really fun when people from my hometown of Cypress, Texas would reach out saying they had seen my photo in the magazine. I actually chose to go to USC, instead of Texas A&M where I could have studied Business, and it was an extremely tough decision. Most of my friends were at A&M, my whole family had gone to that school, and when I got selected to be in the Seventeen Freshman 15 program it felt like confirmation that as scary as my decision was, it was right for me, and USC in LA was where I was supposed to be.

Your experience as one of the Freshman 15 writers led to an internship in New York City at Seventeen’s headquarters, and then to even more opportunities as a red carpet reporter for the magazine when you moved back to LA for your sophomore year of college. Then, you pulled the same move when you interned for E! News in LA and turned it into a freelance job reporting for them and eventually a full-time position. You’ve clearly cracked the code for turning successful internships into jobs! What would you say were the most important things you did as an intern to make this happen?

Bring a notepad and pen to your first day. Later on in my career, I oversaw our department’s interns, and this is huge! Days get crazy, especially in news, and time is limited. Bring a notepad, and write down what your supervisor is saying, even if you think you’ll remember everything (chances are you won’t). If you don’t understand something, don’t feel stupid, ask then! I actually didn’t bring a notepad my first day at my NY internship with Seventeen, and I remember my boss, Elisa, took me to get one from one of their cabinets. It felt like a supportive older sister move, I never started an internship without having a pen and paper ready after that. Value your supervisor’s time, it shows respect as well as shows that you are dedicated and responsible.

Know your place. I think this is important. I’m someone who always has ideas whether it’s digital, editorial, social, or marketing, my mind runs endlessly. However, it’s important to know your place, you are intern. Make relationships first, then once you’ve established relationships, trust, learn the company culture, and then you should start to share your ideas or be more vocal.

You never know until you ask. My first ever red carpet was with Seventeen, and it all developed over me simply emailing my past supervisor asking if there were any ways to do event or red carpet coverage. Sure enough, a few weeks later they had a very small charity event red carpet, and they decided to send me with a former intern of Seventeen who was older and was also at USC with me. I prepared like crazy for the red carpet and learned a ton. I treated it as if it was my job, and I think that is important as well.

Prepare, prepare, and over prepare.

That experience ultimately led to more red carpets, and eventually I got to do the Grammys at 19, which was crazy, but it didn’t come without a lot of preparation, hard work, and simply “owning” whatever assignment I was given no matter how small or big it was.

You’ve made a name for yourself in social media as an entertainment and sports reporter, talking to everyone from Taylor Lautner to JJ Watt. When were you first interested in journalism, and what steps did you take to learn more?

Honestly, I took it one day at a time. Also, I think it’s because I was young, but I simply dove in head first. I was almost naïve in that sense. My first movie premiere was actually Twilight, and in those days no one had ever seen fan fare like the ways that film produced. As shaky as I was on the way to the premiere, I remember my Mom told me on the way, “Don’t worry Lindsey, they put on their pants the same way you do, one leg at a time.” That quote is kind of odd, but the sentiment is important, everyone is human.

Roll with the punches, and be confident in what you have.

I think Hollywood can also be a place of smoke and mirrors, if you don’t know how, just try it out, don’t make excuses and think of all the ways you can’t do something. I also was like a sponge on the red carpets, always asking fellow reporters about their career journeys, getting their cards, adding them on LinkedIn, etc.. I learned a lot about the industry, and avoided some mistakes, by simply asking and listening to other reporter’s stories.

The Living Emoji: The Sporting Gals: Lindsey Joy Caldwell

While at E! News, you spearheaded a lot of their sports content. How did you make this happen for a network that is known for their celebrity and entertainment news?

Time: I had a meeting set up by a friend before I took my job at E! with the network’s casting director, who isn’t directly associated with the department I worked in, but even then I expressed wanting to do sports in whatever capacity. I bring up that meeting, because from day one I knew I loved sports and thought there could be more ways to cover these athletes who were quickly becoming pop culture celebrities in their own right. I worked on whatever assignments I was given, and worked as hard as possible. When appropriate, in big meetings I expressed interest in taking any sports related content, and really tried to “own” that space, no matter how big or small the story was. Eventually, if there was a sports related topic, I was then thought of to take on the reporting. It wasn’t until about 2 years in, that I really started getting to work on more sports opportunities. Also, by then I had built up a reputation of being a hard worker, and I think that’s important as well. When you’ve paid your dues a bit, and your ideas have shown to be successful, then is a good and appropriate time to be more enterprising. Patience and “paying my dues” were important to the process.

Research: I did a hefty amount of research over the years, which athletes did best with our audience? Which angles worked? Who was not known well, but I felt would grow to be more popular? JJ Watt was one of the first athletes I identified, and had to really pitch to our team why I thought he’d translate, ways to incorporate our interview. It took some convincing, because at the time JJ was well known to football fans, but didn’t resonate much elsewhere. Once I got the approval to interview him, I had no contacts; I just called, called, and worked my way through. If you feel strongly about something, don’t give up on it, no matter how difficult it may seem. At the time, Watt was a hot sports commodity, and I had to sell the idea to his team to trust me. At the time, I didn’t have one sports story example yet that I could send them.

Thinking Outside The Box: I’ll be honest there were certain sports stories that I thought would be homeruns, and they just didn’t resonate with our audience. I learned that I couldn’t cover a sports story in the way other outlets did, or even how I would normally think a sports story would or be covered. When the “deflate-gate” news hit, I knew it’d be a big story, but lots of follow ups on the nitty-gritty details is something that wouldn’t resonate with our audience, so I had to think outside the box on what would still cover this soon to be trending news, but would be fun for our audience. That’s when I looked up Brady’s backup, and realized they had some similarities in height, and found various other similarities. It didn’t hurt that he was cute, and our audience loved good looking athletes, so instead of covering the “deflate-gate” news black and white, I pitched writing a piece on Brady’s replacement. I remember it was a crazy news day in general, so it didn’t take priority, but I stayed late to make the piece come together. The piece ended up doing so well, it became a trending story on our website, got picked up by multiple outlets, even various other outlets were re-wording the facts, and the online numbers were impressive enough they decided to make the piece into an entire segment for the show the next morning. It was a really proud, cool moment!

Speaking of sports — you’ve made clear that you’re a gal who loves both her pink and her football, sports with a side of sass, if you will. Where does your love for sports come from, and what is it like being someone who can rock rhinestones as well as she can talk chalk?

Oh, how I LOVE this question!

My dad didn’t have any sons, and I’m the youngest. I’m really close with my family, and my dad and I have a really close bond. I was always the kid adventuring, pushing the limits, constantly in the mud, and was 100% a tomboy growing up. My dad taught me to throw my first spiral, and I just really valued our time together, which really began at a young age when I was in sports, whether he was coaching my sister and I, or he was staying in the backyard until the sun went down helping me perfect my jump serve for volleyball.

Another reason I love football is my Dad was a walk-on at Texas A&M, and some of the best lessons in life he’s taught me really stemmed from the time he was a walk on, and then later a scholarship athlete at A&M. I think it’s incredible what good leadership, sports, and teamwork teaches you, and how it translates on and off the field. I think it’s also something just innate in me; my heart physically beats faster when I’m at a football game. I also think the power of the underdog in sports is HUGE. It doesn’t matter who you are, if there is a will, if there is discipline, if there is strong leadership, if there is teamwork, there is a way!

Also, TEXAS HIGH SCHOOL FOOTBALL games, are just another way of life. I was a cheerleader, and being right next to the bench was amazing, I sometimes would forget to turn around to do cheer routines, because I was so focused on the plays, or what the coach was telling our players.

I think I surprise a lot of people, who assume I’m one way, and then realize I’m pretty much split down the middle– 50% tomboy, 50% “Hey, let me throw on this sparkly dress and head to the red carpet.”

The Living Emoji: The Sporting Gals: Lindsey Joy Caldwell

You’ve reported everywhere, from the CMT Awards to the ESPYs. What were those experiences like, how did you prepare, and what advice would you give to aspiring reporters?

Those types of events are my favorite, interviewing others, and storytelling in general just makes me feel some kind of joy. I can’t quite explain it, but when someone opens up about his or her story, this robot image of a celebrity cracks, and he or she simply become human, and I get chills. I think it’s different in each industry, but at the end of the day, talking to the media is a big part of athletes, actors, and musician’s careers, and it’s only a matter of time before they get in the routine of their answers, what not to touch on, what to touch on, what to promote, etc. But, when you can crack that, and talk to someone human to human, and see their eyes sparkle, and connect with them, it’s something else. It’s moments like those, where I just think to myself, even with as confusing as this industry can be, as risky as it is, this is what I’m supposed to do. I’m meant to tell stories, and I want to tell ones that inspire others, by simply telling the truth, the truth of the journey.

Advice: Listen, and listen well. Watch and ask to shadow anyone you can in the industry. If your internship has you transcribe, don’t discount the lesson! It’s tedious, but man, I learned A TON while transcribing for hours. Think to yourself what would I ask here, or how did that type of question produce that type of response?

Ways to Prepare: Use Twitter, Instagram, and Snapchat to your advantage, look up everyone you’ll be interviewing, and see if there’s something fun to ask a question on whether it’s for a story, or simply to break the ice, and helps you avoid the typical question, “Who are you most excited to see tonight?” Also, I always check google news, and type whoever it is that I’m interviewing in the search bar, because they might have released exciting news, casting news, etc, and only a local radio station picked up on it. I’ve found a lot of great question ideas, by simply using this tool and discovering new elements I didn’t know about their career or life.

You’ve done two huge moves in your life: from Texas to LA, and from LA to Nashville. What have these moves taught you, and what would you suggest to others that are considering a major move?

So much! My faith grew a lot, because to be honest, it can be lonely when you move to an entirely new place without knowing anyone. I also grew a lot independently, for the first time I didn’t have someone I could just call if my tire got flat, or if I got really sick. I had to figure out how to do things I used to have the luxury of having friends and family there for, and that made me stronger than I thought I was and independent, which in turn has given me confidence in other life decisions and future leaps of faith type moves. I loved what US Women’s Soccer and gold medalist, Abby Wambach once told me about challenges: they carve you, to ultimately create a place for more joy, and I found that to be true in moving. It can be really lonely, as well as tough, but I’ve learned to appreciate and have joy for so much more.

Suggestions: Get out and go make friends! I am extremely extroverted, but even I have to push myself to get out when I move to a new place. You can feel awkward, no one knows you, they don’t know your story, and frankly they don’t need to, unless you put yourself out there. In essence, what I continually learn is that if you want friends, you have to be a friend. Rather than focusing on not getting invited, host a dinner party of your own. Made 3 friends? Great! Organize you three eating out to dinner somewhere. As uncomfortable as it is to be the new girl or guy, it will never get better if you don’t put yourself out there. I moved to Nashville right before my 25th birthday, I’m not in college, and I’m not one or two years out either. I find myself attending a lot of professional networking events I find on Facebook, Google, or through new friends. Try new things, and then try some more. I’ve adopted this new mindset for myself in Nashville, which is essentially “Have I ever regretted a meeting?” No. So, it’s time to not make excuses. Get people’s numbers, get their business cards, email them, and follow up. Don’t let your insecurity of being new outweigh opportunities that could unfold.

The Living Emoji: The Sporting Gals: Lindsey Joy Caldwell

Recently, you’ve been working with different companies, from Gatorade to NASA! That’s so killer. How did you get those gigs, and what has it been like to work with them?

I think what I learn consistently in this business is the power and importance of relationships. When I was at E!, I established a great relationship with the PR team over at Gatorade, and I LOVE them. I love what Gatorade stands for, and how they value athletes for so much more than just their athletic ability. Now that I’m freelance, a huge part of that job is finding interviews, and thinking of which media outlets I could write, report, or host the interview on. My website, If You Can Dream It Do It, is very in line with Gatorade’s principles, and my goal is to highlight more of people’s journey’s, so for the last Gatorade Player Of The Year Awards, I covered the event for my site, and interviewed athletes like Cam Newton, Abby Wambach, and April Ross about their journey and rise towards their dream.

NASA came through a social media camp they offer. A friend from junior high, actually messaged me on Facebook, saying she had seen the opportunity, and thought even though it was outside of what I cover, I should apply if it was of interest. It was very much outside of the realm of what I report on, but I thought it would be a great opportunity to expand my network, as well as learn more about a subject I don’t report on very much. Also, when else would I be able to say I walked on the launchpad right before a rocket launched into the air, and experience the sonic boom, that is so loud you can feel it in your chest? @NASASocial is a great resource for anyone looking to gain more information on the programs they offer.

Social media has played a big role in your career, including how you obtained your E! News internship and a sweet shipment of Skinny Pop. What are your best tips for a strong social media presence?

If you’re interested, engage in the conversation! I remember a friend recently asked me why I was live-tweeting the ESPYs, and I couldn’t explain the “why,” but I just have learned it’s important to engage in the conversations and events you’re interested in. The next day, one of my tweets actually led the Today Show’s segment on the ESPYs, which was crazy!

Don’t get caught up on number of followers, that will come in due time. Be authentic to who you are, and don’t try to just be “relevant.”

The world is changing, and we are SO connected. Be friendly online to others, if you like an article someone wrote, find them on Twitter, look up their email, and tell them! If you loved a play from an athlete, tweet it and tag them. You just never know who will “favorite,” “retweet,” or “follow” you. Build relationships.

The Living Emoji: The Sporting Gals: Lindsey Joy Caldwell

One of the hardest things to do in the on-camera world is simply break into the business. What was the best advice you received, and what advice would you give to hopefuls?

A friend recently told me, “You can either be criticizing, or creating,” which really resonated with me. I’ll be honest: being freelance for the first time can be scary, and if I do stories for my own site, I’m super critical of video, and it not being network quality, or I feel like the angle makes me look fat (you know all the critical things us girls judge ourselves on in our brains). The reality is I simply don’t have the funds or equipment to produce video at an international network quality right now. Another piece of advice came from Pharrell, which was, “Don’t let the veil of perfection come between you and an opportunity.”

Give yourself grace, and know that it takes time. You’re going to have a lot of late nights.

You’re going to have those days where you’re going to longingly look at your friends who are accountants who seem to have a very planned out path, and envy that security, but don’t stay in that mindset long! Heck, you’re honestly going to go through some dark periods, wondering if you really should even do this, because someone will always be prettier, smarter, more connected, but it’s VITAL to not fall down that fatal path of thoughts, and NEVER stop believing in yourself and what you offer.

Originally, you went to USC with a dream of becoming an actress, but along the way, it’s turned into more of a social-media-maven / reporter career. Are you still pursuing acting, and what are the next steps for Lindsey Caldwell?

So, what’s been really fun in this new season in Nashville, is my Southeast agent represents me in acting as well as hosting. At this time and in this market, I’m able to do pursue both. Remember the Titans is hands down my favorite movie, and wanting to be an actress was my dream ever since I could talk. As I’ve gotten older I realized the reason I love acting was because you have the ability to entertain, to bring someone joy, and if doing a proper job you can move someone to really feel something. You can move someone in a way that resonates with them beyond the TV/movie screen or stage, and resonates into their own live, to where they evaluate their own life with what they discovered. I found reporting is very similar. I love revealing new pieces of someone’s journey, dusting off the cobwebs on parts they’ve forgotten after years in the limelight, and taking those nuggets and sharing with others to inspire them.

Career: Well, this is kind of an oddball goal, but before the year is over I want to act in a country music video for a Top 100 Billboard artist. (Hi Sam Hunt and Brett Eldredge).

I want to be on camera digitally either for a brand or syndicated with a network telling inspiring stories. I’m not saying I’m going to be the next Oprah, but I’ll be the first Lindsey Caldwell ;). I think there’s a place out there for more hopeful, redemptive, positive stories whether I’m taking on someone’s story as my own as an actor, or as a host/reporter. If the path unfolds, I think it would be awesome to really take If You Can Dream It Do It to the next level, and it really become a hub for interviews with athletes, actors, and musicians about their journey towards their dream, and the nitty, gritty details that really defined them. Those cornerstones of people’s journey where they thought they couldn’t keep going, key defining periods of their journey towards their dream.

Personal: I’ve put a lot in my career, even though I’m still fairly young. I love the term “girl boss,” and love it when someone compliments me with the term. However, I don’t want to do it alone. I want to eventually team up with a guy who loves Jesus, is ambitious, and look forward to seeing what that will look like and how that journey unfolds as well.

Follow Lindsey’s blog here, If You Can Dream It Do It, where she shares personal advice and interviews athletes that are changing the game.

Follow her on Twitter, Instagram, and Facebook too!

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Julia Jean Kennedy

Julia Jean Kennedy

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