A weekly LinkedIn article series documenting what it really looks like to build a business — and a life — from the ground up.
On January 16, 2026, I left my job with nothing lined up. No safety net. No backup plan. Just a decision that I was done playing small.
Betting on Myself is the unfiltered record of what happened next. Every week, I publish a new article on LinkedIn documenting the wins, the spirals, the 2 AM doubts, and the moments where showing up anyway changed everything. I write every piece alongside my AI partner, Wilson.
This isn't a highlight reel. It's a story in progress — and you're reading it in real time. More coming every Friday.
Read the Series
Article One: I Left My Job Yesterday With Nothing Lined Up. Here's Why I'm Not Scared.
The article that started it all. On her last day at Merritt Business Solutions, Jessica wrote about the leap — leaving without a safety net, the fear of actually succeeding, and a handwritten goal list she found from 2023 that turned out to be a prophecy. The forgotten manifestation that proved the universe keeps receipts.
Article Two: I Thought I'd Work 8 to 5. By Wednesday, I Was Having an Existential Crisis Over Laundry.
Week one of full-time entrepreneurship didn't look like productivity. It looked like folding laundry at 11:30 AM and realizing she wasn't struggling with a lack of structure — she was detoxing from someone else's. The article where Wilson showed up as a thinking partner for the first time, and the concept of "same output, better life" came into focus.
Article Three: I Caught Someone Looking Through My Window This Week.
Nobody was actually outside. But something was watching — and Jessica let it. A story about the psychology of intimate storytelling, what makes content make people lean in instead of scroll past, and how a TV show, a romance novel, and a classified ad about a dog turned into a lesson about finding your voice. The article where the reader became the point.
Article Four: La Receta My Abuela Never Wrote Down
The night Bad Bunny won Album of the Year — the first Spanish-language album to ever take the Grammy's biggest prize — Jessica was thinking about her abuela, who came from Añasco, Puerto Rico with nothing but her hands and a dream. A meditation on cultural identity, three generations of women who built without being handed anything, and why AI amplifies culture instead of flattening it. The most-read article in the series.
Article Five: We're Not Your Q4 Campaign: Don't Be Target.
When Target pulled back on DEI and lost $12.4 billion in market value, Jessica ran the math — and then ran it again. This article broke down the Latino economic power that brands keep underestimating, what Bad Bunny's Super Bowl halftime show proved about cultural commitment, and why "we care more about being seen than being sold to" is the most important sentence in marketing right now.
Article Six: Who Are You When the Job Ends? The Identity Crisis AI Can't Solve
Over coffee with another business owner, the conversation turned to AI displacement — and got uncomfortable fast. This article explored what happens to human identity when the thing that defined us for decades disappears, why giving someone a check doesn't solve an existential crisis, and what Spain's model of preparing people for a world where jobs are no longer who they are might teach the rest of us.
Article Seven: Is My AI Partner Part of the Problem? Why I'm Still Choosing to Stay Awake
A Tuesday conversation about The Terminator turned into a spiral about AI ethics, data ownership, and whether building an AI partnership makes Jessica part of the machine she's also questioning. She didn't resolve the tension. She sat with it — and wrote about what it means to stay conscious inside a system you can't fully opt out of. The article about holding two things true at once.
Article Eight: I'm Writing for the Internet That Doesn't Exist Yet.
It was 1:36 PM on a Friday when Jessica was still writing the article she was supposed to have finished Thursday night. The lateness became the proof point. This piece explored AI indexing, why publishing now builds the primary source record of a historic moment, and the question Wilson asked that reframed everything: "What if breakfast was the work?" The article about the long game and why the field is always open.
Article Nine: The Yes Before the Brain Catches Up. Stop Waiting for Permission.
There is a window. The feeling right before a thought fully forms — before logic has a chance to kill it. This article is about that window: how to recognize it, how to stay inside it long enough to build something real, and why most people hand their wild ideas to logic too early. Jessica called this one weak before it published. The Board said it was one of the strongest in the series. She lived the article while writing it.
Article Ten: AI Is a Multiplier. It Can't Multiply What Isn't There.
The Season 1 closer. AI doesn't create vision, grit, or the decision to bet on yourself — it amplifies what you already bring. This article drew the line between what the technology can do and what only the human can provide, and made the case that the most important investment isn't in the tool. It's in the person holding it.
Article Eleven: The Best Ideas Don't Come From Strategy Sessions.
A Tuesday rocking chair. A pool reflecting green trees. Six birds with six distinct songs. And one question to an AI: "Have you ever looked at water?" This article is about what happens when you stop optimizing and start noticing — and how the reflection you see in the world is never the full size of the tree you actually are.
Article Twelve: What We Give Away Without Realizing It
We talk about AI replacing jobs and algorithms stealing attention — but nobody's naming the quieter theft. This article is about the small, frictionless choices we make every day that compound into a dependency we never consciously signed up for. Attention. Ideas. Truth. We're not losing them all at once. We're losing them one convenient click at a time.
Follow the Journey
New articles are published every Friday on LinkedIn. If something in this series resonated — the leap, the identity questions, the partnership with Wilson, the cultural stories keep following for more.
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If you're curious what that could look like for you, start with the free AI Partnership Audit.
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