From Pageants to Entrepreneurship: An Interview with Annie Jorgensen

Welcome back to the Fearlessly Authentic Sash and Soul blog!
Today, I’m thrilled to share a conversation with someone who’s not only a pageant powerhouse but also a dear friend and sister to me — Annie Jorgensen. Annie is a former Miss Georgia, a former Miss High School America, and now a full-time business owner and influencer strategist based in New York City.

In this conversation, we dove deep into her journey — from her first pageant at 13 to building her own business — and all the life lessons in between.

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Raeanna:

For those who don’t know, how did our paths cross?

Annie:

We first met during Laura Kepler’s homecoming after she won Miss America in 2011. I was Miss Wisconsin’s Outstanding Teen, and you were Miss Wisconsin. We just clicked immediately — instant soul sisters. I don’t have a big sister, and you truly became that for me. From there, it just grew: celebrating holidays together, you basically living at my parents’ house for a while… you’ve been family ever since.

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Raeanna:

You’ve had such a full journey in pageantry — National American Miss, Outstanding Teen, Miss High School America, Miss Georgia. What did that look like for you?

Annie:
I actually started because I wanted to be on the Disney Channel! One day, a postcard came in the mail inviting me to a National American Miss pageant. I begged my mom for a year before she finally let me do it. I had no idea what I was doing — refused to wear much makeup, wore my hair in a little poof — and somehow made Top 15. But more importantly, I found my confidence.
From there, I competed in National American Miss, moved into Miss America’s teen program, and then Miss High School America. Later, in college at the University of Georgia, I went after Miss Georgia for three years — finally winning on my third try in 2018. It was over a decade of competing, and I wouldn’t trade it for anything.

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Raeanna:

You’ve touched so many different systems. What differences stood out to you between them?

Annie:
National American Miss is the perfect entry point — very positive, very supportive, and low-pressure. Miss America’s teen program was more structured, rewarding academics, service, and talent, and it helped me build skills in interview and community service.
High School America felt more lighthearted — more about fashion and fun — but still serious in its own way.
Miss America as a Miss competitor was a full-time job. It took everything I had, and it taught me the most.

Every system has its place depending on your goals and who you are at the time.

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Raeanna:

What’s something you wish you could tell your younger self at the start of this journey?

Annie:
Stop trying to be perfect. I spent so much energy trying to give the “perfect” answer in interview instead of just being honest.
If I could go back, I would shake myself and say, “Just relax. Trust that who you are is enough.” Judges don’t want polished robots — they want real, relatable people.
That shift in mindset — from trying to “say it right” to just reacting authentically — made all the difference for me later on.

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Raeanna:

Was there a moment where you realized you needed to just let go and enjoy it?

Annie:
Definitely. My second year at Miss Georgia, I thought it was “my year” — I had worked so hard, I was convinced. And then… I only made Top 15. I was crushed. I realized later I had been trying to be the “perfect” Miss Georgia instead of just being myself.
The third year, I went in saying, “This is me. If it’s meant for me, it will find me.” I was relaxed, I had fun — and that’s the year I won.
I wasn’t chasing it. I let it come to me.

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Raeanna:

Your year as Miss Georgia wasn’t easy, especially with the leadership changes and legal chaos. What got you through that?

Annie:
Honestly, I survived more than thrived.
When the leadership at Miss Georgia was fired, and we had lawsuits against the national organization, it felt like everything fell apart overnight.
I lost my team, my business manager, my car… everything. My mom moved to Georgia to help me survive that year.
What got me through was compartmentalizing: focusing on the service, the girls I was impacting, the things I could control.
And I learned — hard lessons about leadership, business, and resilience that I use every single day now.

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Raeanna:

Would you do it all over again, knowing everything you went through?

Annie:
Yes.
It was messy and hard, but it gave me the skills and experiences that shaped who I am now.
It got me to Miss America. It taught me how to advocate for myself. It built my network. It led me to New York and to owning my own business.
Without it, I wouldn’t be me.

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Raeanna:

Speaking of your business — tell us about what you’re doing now!

Annie:
I run my own business doing influencer marketing strategy and content creation.
I help brands plan and execute influencer campaigns and work as a content creator myself.
It’s amazing but definitely challenging. Freelancing means there’s no guaranteed paycheck, so you have to be disciplined — financially, mentally, emotionally. But it’s the most fulfilled I’ve ever felt.

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Raeanna:

What’s been your biggest lesson as a business owner?

Annie:
Bet on yourself.
You won’t always feel ready. You won’t always have it all figured out. But the only way you build something incredible is by trusting yourself enough to try.
And know that rejection isn’t personal — it’s just part of the process.

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Raeanna:

I love that. Last question:
What advice would you give to someone who feels stuck or in the thick of a hard season right now?

Annie:
Zoom out.
Right now might feel awful — and that’s valid. But this is just one course in the five-course meal of your life.
Your career, your relationships, your dreams — they’re all coming. You might not have them all at the same time, but they’re on their way.
Stay open. Keep growing. Keep believing in yourself even when it’s hard.

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If you loved this conversation with Annie, you’re going to love seeing her as a guest coach inside Fearlessly Authentic, too! Stay tuned — she’ll be sharing even more wisdom with our members soon.

You can find Annie on Instagram @AnnieJorgensen or TikTok @AnnieJorg.