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The Power of Planning
Lessons from Over 10 Years in Software Startups: Why Planning Is Key to Success
After more than a decade in the software startup world, I’ve learned a thing or two (or twenty) about what it takes to survive—and thrive. The most important thing? Planning. Yes, that thing we love to put off until the last minute, hoping the stars will align and make everything magically fall into place. Spoiler alert: they don’t.
Before I get into the deep end, let me give you a little background on how far we’ve come (and how far we still need to go). When I started in the software space—back before AI could spit out a half-decent block of code with a friendly, knowing wink—we had to do everything manually. No shortcuts. Want to find a bug in your code? Good luck, buddy. Hours of your life, gone. While the tools today are faster and smarter, the reality is that planning is still as essential as ever, if not more.
The Pre-AI Software Landscape: A Glimpse of the Past
Picture it: 2010-something. You’re in a dimly lit room, staring at lines of code that feel like hieroglyphs. It wasn’t just about writing code back then—it was a battle of endurance. No Stack Overflow wizardry or GitHub shortcuts. You learned through trial, error, and a lot of late nights.
Back then, software development required patience, problem-solving, and above all, planning. Each step had to be carefully considered because there was no “undo” button when things went wrong. If you didn’t plan, you paid for it—often with sleepless nights or endless hours debugging. And while it was frustrating, it was also an invaluable lesson: planning ahead is the best way to avoid trouble later on.
AI Explosion: How the Landscape Has Changed
Fast forward to today, and we’re in a totally different ballgame. AI tools are everywhere, automating tasks that used to take hours. Developers now rely on machine learning to help them write, test, and optimize code. The speed and efficiency have skyrocketed, but here’s the kicker: even with AI, the core principles remain the same. No amount of machine learning can replace a solid plan.
In fact, AI can make it easier to procrastinate on planning. Because the tools are “so smart,” it’s easy to think they can do the heavy lifting for us. (Spoiler: they can’t.) No matter how sophisticated AI becomes, you still need a strategy, a blueprint, and a direction. In the end, AI is just a tool—it’s how you use it that matters. And that’s where planning comes in.
Think Twice, Code Once: The Golden Rule of Software Development
Over the years, I’ve realized something: planning isn’t just helpful; it’s life-saving. I’ve messed up enough times to know that. There were moments when I thought, “I’ll wing it, how hard can it be?” And then I ended up buried under bugs and spaghetti code. Planning saves you from that.
Every successful project I’ve worked on—whether it was pre-AI or post-AI—started with a solid plan. You can have the best idea in the world, but if you don’t take the time to map it out, you’re setting yourself up for failure. In coding, we say, “Think twice, code once.” It’s the same with building a startup. You have to think through every step before you dive in, or you’ll end up redoing the work (and possibly rethinking your entire approach).
My Worst Planning Disasters: And How I Survived Them
Okay, time for a confession. There were projects I tackled without a plan—because, hey, I knew what I was doing, right? Wrong. So wrong. In one particularly chaotic project, I dove headfirst into coding without laying out a clear roadmap. Halfway through, I realized I had overlooked a crucial function. The fix? I had to rewrite 80% of the code. Ouch.
That experience taught me two things: first, always take the time to plan, no matter how eager you are to start building. And second, it’s okay to make mistakes as long as you learn from them. If I had planned that project properly from the start, I would’ve saved myself—and my team—a lot of pain. But sometimes, failure is the best teacher.
Planning Before and After AI: What’s Changed (And What Hasn’t)
If you’re curious to dive deeper into how planning has evolved in the software world—from the pre-AI days to now—I’m currently working on a small book that covers just that. It’s packed with insights, lessons, and strategies for startups and entrepreneurs on how to plan new ideas and execute them effectively in today’s landscape.
Whether you’re navigating the waters of a new startup or fine-tuning your product development, the book will break down how to make planning work for you—using my own experiences and hard-learned lessons, both from the early, manual days of software development and the AI-assisted world we now find ourselves in.
Stay tuned for its release, and I promise it’ll be worth the wait. From idea conception to execution, from manual coding to AI-powered tools, I’ve got you covered. Whether you’re just starting out or looking to improve your existing process, this book will help you learn the art of planning to avoid the traps I fell into and give you a smoother path to success.