Welcome to Issue #010 of SoloLIVE! Each week, I’ll share practical tips to streamline your solo business, right from my desk, to help you escape the grind and create a life on your terms.
Not All Hustle Is Freedom
You know the drill, after a long day at work, you sneak in a few hours at night for your own project. You dream in silence, worried about what your boss, your friends, your family might think if they knew you wanted out of the 9-5. It’s easier to call it “just something on the side.” That little phrase carries weight: shame, secrecy, the fear that stepping out is somehow wrong. You’re exhausted, but the hope is alive. There’s a way out. AI isn’t just a productivity tool - it’s the lever for real, unapologetic change.
Why Hiding Your Dreams Hurts More Than Hustling
Let’s be real - the rise of “side hustling” looks glamorous on socials, but most solopreneurs are stuck in a loop: nights and weekends, always waiting to feel ready, always avoiding the spotlight. The price is bigger than lost sleep, it’s lost pride, lost momentum, and sometimes, lost opportunities. You can automate tasks and boost output with AI, but that’s not enough if you’re still stuck hiding. The solo creator journey demands visibility. AI lets you plan, execute, and even see yourself and your path more clearly. But the first step is not about tools - it’s about dropping the shame.
The Pain Point: Shame, Self-Doubt, and the Chronic “Side Hustle” Identity
Here’s where most solo creators get stuck:
You’re grinding after hours, afraid colleagues will “find out.”
Every win feels muted (“It’s just a small thing I do…”).
Deep down, you wonder if you’ll ever have the confidence to go all in—or if you’re waiting forever for “permission.”
You’re proud, but you stay quiet. You downplay the successes and rationalize the effort as “just for fun.”
Maybe you burn out before you ever fully launch, always juggling two lives.
That pain? It’s not just the effort. It’s the emotional tax of living behind a mask.
Dickie Bush’s Turning Point: From Hiding in Finance to Leading a Movement
Dickie Bush didn’t start as a full-time creator. He worked in finance, running his “Ship 30 for 30” writing challenge quietly, squeezing sessions in around office hours and never telling a soul at work. Every day, he wondered what they’d think if they found his side project. Could they respect the ambition, or only see it as a threat or distraction?
That fear kept his project small. Traction was slow. And then, Dickie made a simple but daunting decision: to go public. To announce his writing journey on X. To invite others in, and to admit he wanted something more than just a side hustle. Overnight, everything changed. Accountability fueled his growth, community found him, feedback shaped his course. What took months to build in the shadows exploded with just a little sunlight. Dickie owned his story, his ambitions, and with help from digital tools—like scheduling content and automating feedback, he built a movement. The shame didn’t vanish instantly, but every public post chipped away at it. Now, Ship 30 is a household name in creator circles, not because Dickie worked harder, but because he finally worked out loud.
The AI-Powered Solution: Accountability, Confidence, and Public Action
Here’s the lesson: AI turns shame into confidence, if you use it right.
Start with clarity. Use Notion AI or ChatGPT to map your core values, personal mission, and what your solo business actually offers. Don’t just brainstorm, document.
Script your public story. Draft your announcement post, LinkedIn update, or email in Perplexity. “Why are you doing this? What do you want for yourself, and your clients?” Let AI help you put words to the dreams you hide.
Automate honest feedback. Use AI-driven polls or surveys to get real reactions from a trusted audience. Instead of working secretly, let data and feedback guide your next steps.
Systematize outreach. Build a simple process (using Notion or other AI tools) that keeps you visible, share a post weekly, reply to comments, run short updates on your progress.
Replace shame with visibility. Every public step weakens the fear. AI can’t solve all your doubts, but it makes acting on them easier, faster, and more consistent.
What You Can Do This Week: Go Public with AI on Your Side
Ready to move forward? Here’s exactly what to do:
Use ChatGPT or Perplexity to draft your “Hey, I’m building this” post—a short, honest update about your solo journey.
Plug your solo business plan or current challenge into Notion AI and ask for prioritization: “Help me pick the ONE thing that brings me closer to full-time freedom.”
Create a simple poll (X, LinkedIn, wherever) asking your audience what they want from your content or offer. Use the data—not just your fears—to validate your next step.
Give yourself permission. Public accountability is your best tool to break the side hustle cycle.
Reflection & Call to Action: The Power of Being Seen
Ask yourself, what story could you tell if you stopped hiding? What pride, clarity, and momentum could you unlock by showing your ambition to the world rather than stuffing it in a drawer? You don’t have to be perfect. You just have to be visible. Write, post, or share something honest about your solo journey this week. Freedom requires facing the light, not just hustling in the dark.
That’s all for today. See you next week.