Ghosted by Clients, Fueled by Dreams: The Freelance Grind with Annie Woodbury

What if chasing the dream means choosing a different one altogether?

Annie Woodbury thought she’d be cutting movie trailers in L.A.—but instead, she’s editing wedding films in Florida and loving every second of it. In this episode, we meet a woman who redefined success on her own terms, built a thriving freelance career straight out of college, and discovered that contentment isn’t complacency—it’s a quiet kind of power.

We talk creative chaos, algorithm hustle, and what it really costs to be a woman in a creative industry that never stops moving.

You’ll hear:

- Her scrappy start—dog walking, Upwork gigs, and a Facebook post that changed everything

- Building a freelance identity before she even had a diploma

- Why she turned down her literal dream job in Hollywood (and what happened next)

- Releasing the pressure to “make it big” and choosing to love her life now

- The rogue power of picking peace over prestige

Sometimes, the boldest move isn’t chasing the most glamorous path—it’s choosing the one that actually fits. Annie’s story is proof that clarity, not clout, is the dream.

Know a woman who needs to hear this honest, liberating take on success? Share this episode—and if you haven’t yet, hit subscribe so you never miss a truth bomb. This is Fearless and Flawed. Let’s keep rewriting the rules.