
How I'm PIVOTING My Strategy to Earn $100K Online // Path of the Creator #1
My goal is to earn $100,000 annually as a content creator through platforms like YouTube, Facebook, and LinkedIn. While I have been a full-time freelancer since 2014—a journey I documented in my book, Path of the Freelancer—this new objective is entirely separate from my client work.
Through my freelancing blueprint, I’ve been able to earn a six-figure income working only part-time. This stability has been a blessing, providing steady, reliable income that pays the bills. However, the purpose of designing my life this way was to create space for content creation, writing books (like The Jump), and hosting my podcast, Share Life. My mission now is to transform these creative pursuits from volunteering my time into a self-sustaining, income-generating business.
Life is Hard. Business is Challenging. The World is Uncertain.
Leaders, freelancers, and entrepreneurs: Get stories & systems, for navigating the challenges, in your inbox.
The Pivot to Path of the Creator
In 2025, I decided to get serious about YouTube. I initially tracked this journey through a series on YouTube called Showrunning, but as my strategy evolved, I decided to pivot. I’m now launching a new series called Path of the Creator.
Unlike my previous work, this won’t be a book; it will be a transparent look at my journey toward that $100,000 goal. In 2024 and 2025, I earned a few thousand dollars through sponsorships, affiliate income, and selling my own products. This year, I am taking those lessons and narrowing my focus to maximize impact.
Choosing the Right Channels: YouTube, Facebook, and LinkedIn
Instead of trying to be everywhere, I am focusing on three primary channels:
- YouTube: This remains a cornerstone, though I’ve learned that growth here takes longer than initially planned. I’m committed to the long game.
- Facebook: In late 2025, I unexpectedly became monetized on Facebook. This opened up new opportunities I hadn't originally anticipated, and I am leaning heavily into this revenue stream.
- LinkedIn: My secret weapon on LinkedIn is the newsletter function. I currently manage four newsletters covering small business, freelancing, marketing, and personal development. These newsletters get significantly more traction than standard posts, making them a priority for my distribution strategy.
Building the Foundation: From Content Creation to Promotion
Over the years, I have built a massive library of bricks—nearly 700 blog posts and over 170 podcast episodes. In the past, I spent most of my energy creating, but very little on promotion.
I am now shifting my focus toward pulling these bricks together to construct a coherent, unified business. This involves moving beyond just working and creating to actively promoting and distributing my insights. My goal is to help people live better and work smarter while ensuring the content itself generates direct income, rather than just acting as a lead generator for my freelancing business.
Leveraging AI and Systems for Growth
As you think about your own path, ask yourself: Are you in exploration mode or discovery mode? It’s okay to be all over the place when you’re starting, but eventually, you have to build systems.
I’ve been taking my analytics and reports from the last several years and feeding them into Google Gemini AI. I’m using AI to assess what works, help me build a structured content calendar, and optimize my posting times for maximum impact. By integrating my creative process into these digital systems, I can publish and distribute stories more effectively.
Join the Journey
This series (Path of the Creator) is about tracking the reality of the creator economy—the wins, the failures, and the continuous optimization. I’ll be diving deeper into the specifics of Facebook monetization and my systematic approach to LinkedIn in future updates.
If you’re navigating your own creative path, I’d love to hear from you. What challenges are you facing? I’ll be sharing everything I learn as I strive for that $100,000 milestone. Subscribe and follow along as we walk the Path of the Creator together.


