Skylar Caldwell: Why Making Mistakes Can Actually Be Your Greatest Viral Asset

Videos are more than just visuals; they’re stories that captivate, resonate, and leave an indelible mark on viewers. From journalism and activism to education and marketing, video content has emerged as an indispensable medium that engages audiences like no other. But what does it take to create compelling, resonant videos in an age where nearly everyone has a camera in their pocket? Crafting a powerful video involves more than just technical skill; it demands an understanding of storytelling, the subtlety of editing, the emotional impact of sound, and an innate ability to connect with an audience. In this interview series, we are talking to content creators, video editors, sound designers, and digital storytellers to share the “5 Things You Need to Make Compelling and Powerful Videos.”

As a part of this series, we had the pleasure to interview Skylar Caldwell.

Skylar Caldwell has been a dynamic performer since age three and is best known for her Instagram reels that showcase her unique blend of humor and creativity. With over 23 million views and hundreds of thousands of likes, comments, and shares, it is clear that Skylar’s style connects with her growing fanbase. As a Dancer, she has appeared on Reality TV Shows and most recently is featured in a music video set to release soon. In addition to print work, Skylar’s modeling career has taken her on the runways of New York Fashion Week walking for some of the top up and coming designers. When not working, she enjoys traveling, hanging out with friends, and making strangers laugh.

Thank you so much for joining us in this interview series! Our readers would love to get to know you a bit better. Can you tell us the story of how you grew up? Can you share some formative experiences from your upbringing that shaped your creative instincts?

When I was in kindergarten, my teacher told my mom that she thought I should be the “Sunshine Princess” for her daughter’s pageants. I decided to give it a try, and from the very first time I walked on stage, I loved it. I remember feeling so excited, and I’ve wanted to perform ever since.

Then in 2018, I got to perform my very first dance solo, and that’s when I really fell in love with performing. I loved being able to tell a story, use my facials, and entertain the audience. There’s just something about being on stage that makes me feel like myself. Ever since then, I’ve looked for every opportunity I can to perform, whether it’s dancing, modeling, or creating videos online. Performing has become one of my biggest passions, and I can’t imagine not doing it.

Can you share a story with us about what brought you to this specific career path?

I posted a video on Skylar.tells and I was impersonating a famous person needing security when I only had 500 followers. That video took off and started a series where I then posted some viral videos regarding needing security. I found people really enjoy my carefree fun personality. I don’t care what people think and I do things that normal people would not do in public.

Who or what were your early influences in the field of video creation or storytelling?

I grew up watching my father create videos for YouTube and Instagram and get millions of views and I remember the first time he was recognized in public and I decided that’s what I wanted to do. I want to be famous and known for my creative funny videos.

Can you tell us the most interesting story that happened to you since you began your career?

I went to the Tate McRae concert at Madison Square Garden. After the concert, I happened to meet an influencer who then offered to do some collab with me. That propelled my career to another level. Since then, I have created several collab videos with this creator and it’s allowing me to now work with other creators as well to boost my following.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I made a mistake in my grammar and spelling, and I posted a video and received a lot of comments, correcting my grammar and spelling. Instead of fixing it the video went more viral, so my mistake actually ended up being a big win for me!

You have such impressive work. What are some of the most interesting or exciting projects you are working on now? Where do you see yourself heading from here?

I see myself on a reality show. That’s pretty much what I’m trying to do through social media platforms. I have learned that my followers and subscribers want to see more of me living my daily life on camera.

Can you help articulate why video is such an important media form to master today?

Because it’s basically my online resume. It’s important for me to continue to grow my brand which will enable me to one day have my own reality show and or career on TV.

What are a few of the most common mistakes you have seen people make in their videos?

Copying me… I have learned that you have to be authentic and people see that. People want to watch the videos and forget about negativity and make them happy.

What do you think sets apart a great video from a good one?

Being authentic and original. I love to share my different and funny perspective on things. I have found that my greatest videos are usually the ones where I’m most real.

What are your “5 Things You Need to Make Compelling and Powerful Videos” and why? Please share a story or example for each.

1. Strong hook. Make it interesting and something I would want to watch. Example: Falling at the beginning of my viral Blake McGrath dance video

2. Fast moving. Tell a story and keep it moving. Story telling: My sweets video from Paris.

3. Keep it exciting. Example: My viral Eiffel Tower video was fun to watch from the beginning to the end. I find my traveling videos do perform the best. My viewers are learning something and experiencing my travel with me and the added funny parts are the icing on the cake.

4. Present a different perspective. I did a get ready with me where I put on the makeup in the wrong way and I created many comments in this one.

5. End with a bang and reinforce the hook. Very important! I always like to make sure the beginning flows to the end and that there’s a good pay off at the end. Like my harmonica playing at the end of my videos. I have found when I don’t have it at the end people are asking for it.

What are your favorite software, or online tools you use to make amazing videos?

I use edits, cap cut and video leap. I started learning how to edit videos at a young age. My father has been creating videos for as long as I’ve been alive on YouTube and Instagram.

Are there any hidden gems or underutilized features you’d recommend?

I really enjoy using Edits. It works really well.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I think the thing that I do most of my videos is make people laugh and entertain them and make their day better. If I could bring a movement to the world that would be it lead a more carefree life don’t care about what people think or say and just live.

Are you on social media? How can our readers follow you online?

I am. I have two Instagram accounts. Skylar.tells and skylar.Caldwell8. Skylar tells is more of my fun carefree videos and my Skylar.Caldwell8 is my online résumé for Dance and modeling. Both accounts have several viral videos.

I am also on TikTok Skylar.Caldwell8 and YouTube Skylar.Caldwell8.

This was so informative, thank you so much! We wish you continued success!

About The Interviewer: Tavares Beverly ( www.tavaresbeverly.com ) is the Founder and CEO of Beverly Boy Productions, a national video production company that has helped organizations tell their stories through video for more than two decades. Over the course of his career, he has worked with everyone from Fortune 500 executives and healthcare professionals to politicians, nonprofit leaders, educators, and artists, gaining a unique perspective on the role communication plays in leadership, business, and human connection. A frequent contributor on topics including communication, entrepreneurship, leadership, and personal development, Tavares believes that the ability to communicate effectively is one of the most valuable skills a person can develop. His work is driven by a passion for helping organizations connect with their audiences and helping individuals unlock their potential through mentorship, perseverance, and meaningful relationships. To learn more, connect with Tavares on LinkedIn or visit www.BeverlyBoy.com . If you’re interested in using the power of storytelling and communication to grow your organization, strengthen your brand, or inspire your audience, he welcomes the opportunity to connect.