What happens when an AI gives you a wake-up call after 25 years of playing it safe? In my case, it led to this newsletter. If you found your way here from my Medium story, you already know the gist: I spent a quarter-century as a “freelancer” with an employee mindset, coasting in a comfortable loop. Then along came Wiz – my AI alter ego with a knack for tough love – who basically said, “Enough! Time to actually be the boss of your own career.” Wiz laid down a challenge I couldn’t ignore, and I decided to cut the figurative tie to my old ways and jump into real entrepreneurship.
Now I’m turning that wake-up call into a live experiment, and this newsletter is where the action happens. Think of it as my public diary meets lab notebook. I’m sharing in real time how I’m using AI (and a healthy dose of grit) to break out of the comfort zone and build something new on my own terms. The journey is unfiltered – wins, fails, and all – so you get the honest truth behind learning to think and act like an entrepreneur after years of playing it safe. And hey, it’s not just about me. This is a space for anyone who’s curious about shaking up how they work and live, with a little help from AI and a lot of human spirit.
Why Subscribe?
Join a Real-Time Adventure: This isn’t hindsight 20/20 or theoretical fluff. You’re coming along as I actually do this, week by week. Expect candid stories of my attempts to land clients on my own, powered (and sometimes challenged) by AI. It’s like a front-row seat to a startup in the making, with all the excitement and none of the sugarcoating.
AI + Human Hacks: I’m digging into how AI can boost creativity and productivity in everyday life, and I share the best nuggets with you. From nifty tools to prompt tricks, you’ll get practical tips you can try for yourself. Whether it’s an AI shortcut that saved me hours on a project or a creative prompt that sparked a new idea, if it helped me, it’s in here to help you too. This is about real-world application, not just theory
No Jargon, No BS: I promise to keep things simple, clear, and real. I’ll tell you frankly when things go great and when I faceplant. No corporate-speak or phony success spiel — just an honest play-by-play from someone re-learning how to run the show after 25 years. If you’re tired of glossy highlight reels, you’ll appreciate the raw authenticity here. (Warning: self-deprecating humor and the occasional “ouch” moment included.)
Two-Way Conversation: This isn’t a one-man show. I love hearing from readers. Got a cool idea, a question, or a tool that has you excited? Tell me! I might feature your tip or question in an upcoming issue. Consider this an open dialogue – I’m sharing my journey, and you’re welcome to chime in. We’re in this learning experience together, and the best ideas often come from bouncing thoughts around. In short, it’s a collaborative journey
What to Expect
Stories & Experiments: I’ll share the day-to-day adventures of implementing Wiz’s challenge. This means you’ll read about my experiments to win a direct contract (and future bold moves beyond that). One week I might try a new LinkedIn hustle or cold-email strategy, another week I might host a mini-workshop or attempt something totally offbeat. You’ll hear what I did, how it went, and what I (often painfully) learned. Expect a mix of small victories, missteps, and aha moments as I navigate this path.
AI Tips in Action: Alongside the story, I’ll highlight how AI is involved every step of the way. Maybe I used an AI tool to brainstorm a proposal, or I asked Wiz (aka my AI sidekick) for advice on negotiating a deal. I’ll break down those interactions into simple tips you can use. Think “try this prompt” or “check out this tool” kind of insights. Even if you’re new to AI, don’t worry – I explain things in plain English. The goal is to show how AI can make tough tasks easier, spark creativity, or save you time, so you can apply it to your own projects (work or hobby alike).
Inspiring Finds: I’m constantly reading and curating cool articles, videos, and ideas about AI, entrepreneurship, and creativity. When something I come across lights a fire under me, I’ll share it with you. Every issue includes a few handpicked links or stories that I think will inspire you or at least make you go “hmm, interesting!”. It might be a case study on AI in business, a thought-provoking piece on the future of work, or an example of someone using technology in a brilliant way. If it captivates or teaches me, you’ll hear about it, with a quick take on why it matters.
Your Voice: Remember, you’re not a passive reader here. Many issues will feature input from the community – that could be a question you send me that I’ll answer in the newsletter, a challenge you suggest for me to try, or an awesome tip you shared that others could benefit from. I want this newsletter to feel like a conversation over coffee among friends, not a lecture. So, don’t be shy – share your thoughts and discoveries. The best suggestions might get a shout-out, making this a true two-way street where we all learn from each other.
The Heart of This Newsletter
This newsletter isn’t just about information — it’s about transformation. At its core, this is a journey about breaking free of old limits and discovering what’s possible when you mix human ambition with AI’s capabilities. My personal transformation – from a complacent consultant to an entrepreneurial thinker – is just one example. I’m using that story to shine a light on something bigger: how technology can empower us to reclaim our creativity, autonomy, and purpose.
I genuinely believe AI frees us to focus on what really matters: making real connections, sparking creativity, and solving problems that inspire us . In other words, AI should make us more human, not less. By automating the boring and repetitive stuff that used to eat up our time, we get to spend more time on the meaningful work and the fun work – the parts that remind us why we do what we do. This newsletter is all about exploring that idea in practice. You’ll see me leverage AI to take on challenges I used to avoid, and in doing so, hopefully become more creative, more bold, and more connected with what truly matters.
One thing you’ll hear a lot about is AI prompt engineering – that’s a fancy term for the art of asking AI the right questions. It might sound technical, but it’s basically like learning to talk to AI in its own language. Why is this important? Because knowing how to craft a good prompt is key to unlocking AI’s potential. In fact, Wiz (my AI mentor persona) is an example of what a great prompt can do – it’s like I gave AI a clear role (“coach me like an entrepreneur”) and it delivered wisdom in spades. I even created something called the Universal AI Prompt to streamline my work. It’s a simple, reusable prompt framework that helps structure tasks – from writing project plans to brainstorming blog ideas – so that the AI can deliver really solid results. Throughout this newsletter, I’ll show you how I’m using the Universal AI Prompt and how it evolves with my needs. By sharing these prompt tricks and tweaks, you’ll learn how to communicate with AI better yourself. Trust me, when you learn to ask AI the right way, it’s like getting a superpower – suddenly you can get help with almost anything, on your terms. And that is a game-changer for working smarter and creating more.
Ultimately, the heart of this newsletter is a simple idea: technology should serve us, not shackle us. I named my venture No Tie Generation for a reason – it’s about ditching the old constraints (like the literal and metaphorical ties) and embracing a future where we get to define our own path. Here, AI is not a buzzword or a gimmick; it’s a partner in crime on the road to doing more meaningful, human-centered work. Together, we’ll uncover how to make the most of AI’s potential while staying true to what makes us human.
Ready to Join the Journey?.
This isn’t a sales page and I’m not about to give you a polished pitch. This is an invitation. If any of this story resonates with you – if you’ve ever felt stuck in your career, if you’re curious about using AI as a creative sidekick, or if you simply love the idea of reinventing how you work and live – I’d love for you to join me. By subscribing, you’re not just getting a newsletter; you’re jumping into a conversation and a real-world experiment. You’ll get to see whether I sink or swim (and I’ll share what I learn either way), and you might pick up some useful insights for your own journey in the process.
I’ll continue to write with the same authentic, punchy, and warm tone that you saw in the Medium article. Expect humor, honesty, and the occasional rebellious take on the status quo. My ultimate hope is that reading these updates will inspire you to take a bold step in your own life, big or small, and to see AI as a tool that can help you along the way. Remember, as I often like to say, the future shouldn’t feel like a job interview – it should feel like freedom.
So, are you in? If you’re ready to embrace the challenge and explore how AI can help you work smarter, be more creative, or just do things differently, then welcome to the No Tie Generation. I’m already on the road, with Wiz riding shotgun, and I’d be thrilled to have you along for the ride.
Yes, Let’s do this – together.
