Winging It Only Works If You Have Wings

Photo by Alexander Sinn on Unsplash

Recently at work, I have always felt like I've been winging it. I couldn't seem to hold on to having a full team because the work is tough, and people no longer want to play the long game to whatever success they have in mind. So most of the time I have to do the work of 3-4 people, yet I also want my own work-life balance.

So I deliberately cut out overtimes and weekend work for myself. Made everything fit within the work week. At most I would add in an extra 3-4 hours in the early morning, starting as early as 5AM to get ahead of the day.

Most importantly, I experimented on how to make my work smarter rather than longer. And it paid off.

At first I felt like I was just winging it, what with the overwhelm and the fatigue and the deadlines frequently locking horns and yet somehow I end up delivering pretty well much to my own surprise. Surely I must be cutting some important corners, but the work output is good. So I am doing good work even while I am supposedly just winging it - by this I mean I would often be able to get started on a task a day or two before the deadline, skipping a lot of my usual steps to get things done, diving into shortcuts and smartcuts, experimenting on the go, making snap choices on whether to pursue a point or not. Before, I would plot out a week, or four days at a minimum, three if pushed and that would already mean pulling in an allnighter or two.

There was a short period when I felt I was working "dishonestly" because I felt like I was just winging through every task and no longer able to do things with diligence.

But something has changed with the way I think and process things. I suddenly find myself finding stuff in my head and my brain doing its own magic. I am recognizing things I didn't realize I knew, Yes I have been winging it, but I am able to to do well because I actually have wings.

What do I mean?

Wings, in this metaphor, are not just about luck or innate talent—they are the unseen foundation of experience, knowledge, preparation, and adaptability that make flight possible. Imagine a bird launching itself off a branch. To the casual observer, it may seem effortless, even reckless. But beneath the surface is a creature with feathers evolved for aerodynamics, muscles honed for power, and instincts sharpened by countless flights.

When someone "wings it" successfully, like I do (which seriously amazes me), it can look like magic—an ability to think on my feet, find the right words, or make decisions without hesitation. But that magic is often the result of years of preparation. It’s the seasoned professional who walks into a last-minute presentation and nails it—not because they were unprepared, but because they’ve spent years mastering the subject. It’s the artist who improvises beautifully because they’ve practiced their craft to the point of muscle memory.

Winging it works because I've built my wings through:

• Experience: The countless hours spent honing my craft, learning from successes and failures.

• Knowledge: A deep well of understanding that gives me confidence to navigate uncharted territory.

• Preparation: Even minimal prep work can give me the edge—reading a lot (books and people and situations), paying attention to contexts.

• Adaptability: The ability to pivot, respond, and adjust when things don’t go as planned. Which includes staying calm enough to think things through as the moment needs

Winging it without wings is like trying to fly with no structure or safety net—it’s risky, and it rarely works. Confidence alone isn’t enough; without the foundation of preparation and practice, it can quickly tip into arrogance.

The good news is that wings can be grown (whether you are aware of it or not). Whether you’re starting from scratch or looking to refine what you already have, here are a few ways to prepare for life’s leaps:

1. Invest in Learning: Read, watch, listen, and stay curious. Knowledge builds the confidence to improvise.

2. Practice, Practice, Practice: Repetition is what turns effort into ease.

3. Embrace Failure: Each stumble teaches you what doesn’t work, sharpening your instincts for what does.

4. Know Your Strengths: When you’re aware of what you bring to the table, you can lean into it when flying blind.

5. Prepare Just Enough: Even when time is short, take a moment to anchor yourself—review key points, center your thoughts, and trust in your ability to adapt.

   
   

When you’ve built your wings, winging it becomes less about throwing caution to the wind and more about trusting in your ability to soar. It’s not about having all the answers but knowing that you have the tools to find them. It’s not about perfection but about embracing the moment with confidence and creativity.

So the next time you wonder if you can “just wing it,” pause and ask yourself: Do I have wings for this? If the answer is yes, then leap boldly, knowing that your preparation, experience, and adaptability will carry you. And if the answer is no, don’t be afraid to build those wings first.

Because when you’ve got wings, winging it isn’t reckless—it’s freedom. And it opens up new skies.