99 Problems: I’m going to stop planning for the future like it’s some distant horizon. Here’s how

You know how it goes. You’ve got a grand plan. A five-year strategy that sounds impressive when you say it out loud. “This is where we’ll be in 2029,” you declare confidently. But in the back of your mind, there’s that quiet voice saying, “How many of those plans have ever actually worked out?” And that voice? It’s usually right. 

Planning for the future is a bit like building a sandcastle on the beach while ignoring the tide coming in. You can see it; it’s not far off, and yet we still think we’ve got all the time in the world before it sweeps in and undoes all our hard work. We plan in the abstract—strategic, detailed, beautifully optimistic plans—and then the real-world hits us with its messy, unpredictable chaos. Well, it does for me! 

I see this all the time. Businesses lay out meticulous roadmaps, then realise halfway through that the world around them has changed. Suddenly, they’re scrambling, caught between sticking to the plan or throwing it all away and starting again.

The thing is, planning for the future isn’t about guessing what’s next. It’s about being ready for whatever comes. It’s about clarity, flexibility and adaptability, not rigid blueprints. And that’s where my approach to visual thinking comes in. 

1. Inform: Most organisations think they’ve got the right information, but it’s often cluttered with unnecessary details or outdated ideas. Make sure you are dealing with the right information—not just an info dump that no one will ever read. Strip away the noise and highlight the insights that matter, visually. Imagine walking into a strategy meeting and being presented with a clear, visual roadmap instead of a 50-slide PowerPoint. Which one would you trust to guide you and your team.

2. Develop: There’s no point in having all the information if you don’t know what to do with it. Develop new skills through visual storytelling. It’s not just about what you know; it’s about how you communicate that knowledge. I’ve seen businesses transform just by learning how to express their goals more clearly. It’s like handing someone a compass when they’ve been wandering in circles for hours.

3. Enable: Now, let’s talk action. How many times have you sat in a meeting and heard someone say, “We should really do something about this,” only for the conversation to fade into oblivion? We’re all guilty of it. But when you see your plan laid out visually, with clear steps, there’s no hiding. Make sure you are able to move from discussion to action, cutting through the paralysis that comes with too much information and not enough direction.

4. Animate: Finally, planning for the future isn’t just a task for the brain; it’s one for the heart. If your strategy doesn’t inspire people, it’s doomed to fail. I believe the best plans are the ones that animate the people behind them—bringing ideas to life and connecting them emotionally to the future they’re building. That’s what keeps the momentum going when the tide inevitably comes in. 

The harsh reality? Most businesses don’t fail because they lack a plan; they fail because their plan can’t adapt. A study by McKinsey found that only 30% of strategic initiatives succeed, and more often than not, it’s because those plans were too rigid, too complex, and too slow to evolve. Another study by PwC revealed that businesses with flexible, adaptive strategies saw a 33% increase in long-term success rates.

So, what’s the lesson? Planning for the future isn’t about predicting it—it’s about preparing for it. Stop seeing the future as a distant target and start engaging with it as a dynamic, evolving landscape. Make sure your plans aren’t just theoretical—they’re actionable, adaptable, and designed to succeed, no matter what comes next. 

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Let’s be clear: Planning is a lot easier if you have a decent map. Maps are visual and you can use them to see into the future. So, pick up your pens, stop worrying about planning for the future and start shaping it. Ready to think differently? Let’s roll!