When I started my business, I did it all myself. I didn’t have anyone to ask questions about setting up their business structure, sending pitches to clients, or knowing what to charge. I would have loved to have someone to just riff with—someone who wasn’t my unqualified roommate at the time.
I spent thousands of dollars on a renowned mentorship training program only to be left with a referral to an even scammier virtual assistant.
Everything felt so impersonal. It was too much hustle. It didn’t vibe with how I work. I felt intimidated to speak up in the group Slack channels, no one responded when I did, and I left the community without having made a single connection—just thousands of dollars in payments, some for services never rendered.
I value my happiness more than I value my business. And I’m on a mission to help others do the same. Because when you thrive, your world thrives.
“Working with Alex has been a total game changer for my business. Her advice and encouragement has built up my confidence in my work and allowed me to grow as a writer. Her ability to dial in on the pain points of my business has helped me focus on the next steps I need to take. She is enthusiastic, supportive, and refreshingly honest. I promise working with Alex will be worthwhile.” – Leigh Deweese, freelance writer
This is a focused, one-on-one conversation for freelancers who feel stuck, overextended, or unclear on their next move.
We look beneath surface frustrations to identify the real constraints—structural, strategic, or psychological—that are limiting progress. The goal is not motivation, but clarity: understanding what you want, what no longer fits, and how to move forward in a way that is sustainable and aligned with your strengths.
A clear diagnosis of what is actually blocking progress
A more accurate understanding of their priorities
A defined next step—strategic, not reactive
$200 for a 90-minute session
Intake form
Honesty, transparency, open-mindedness, and willingness to learn
My name is Alex Sheehan and I am a freelance content strategist and writer who currently lives in beautiful Puerto Rico. I was forced into freelancing full-time when I was fired for taking a stand against plagiarism.
My work has earned awards from Content Marketing World and the Custom Content Council, and you’ve probably seen my writing on page 1 of Google and now in ChatGPT—more than once. I have bylines with Four Seasons, Skift, PCMA, Shopify, Wave, and other top luxury, travel, and technology companies. I’ve been an expert panelist for Rutgers University, the American Society of Journalists and Authors, and Peak Freelance. My mom says I’m her favorite oldest daughter, and one time I summited Mount Doom IRL.