And How to Escape the Cycle of "Getting Ready"

Have you ever spent hours, days, or even weeks crafting the “perfect” plan? I’m talking about the full, glorious production. You’re there, armed with a fresh coffee, a clear desk, and a head full of dreams. You open a new spreadsheet, and it’s a blank canvas of pure potential. You start building your masterpiece: color-coded timelines that would make a rainbow jealous, intricate task dependencies linked with elegant arrows, and mile-long checklists that promise the sweet, sweet dopamine hit of a hundred future check-offs.

You research, you strategize, you optimize. You move virtual sticky notes around a digital whiteboard, finding the perfect workflow. You label your folders, you set up your project management tool, you bookmark the articles you’ll need for “phase two.” The sense of productivity is intoxicating. It feels like work—serious, important, adult work. You lean back, looking at your creation. This is it! The blueprint is flawless. Success isn’t just possible; it’s assured. You have charted the course, and now all you have to do is follow it.

Then, life happens. A day goes by. A week. You open the document again, and that beautiful, intricate plan stares back at you. It’s… quiet. The vibrant colors seem a little less bright. The first task on that impeccable list, the one that seemed so logical during the planning high, now feels like a sheer cliff face. A strange inertia sets in. You notice a typo in heading three and fix it. You adjust a color that’s not quite right. You tell yourself you’re “refining.”

But deep down, you know the truth. You haven’t actually started the real work. The grand, exciting project you were so passionate about now feels heavy, burdened by the weight of your own perfect expectations. That gorgeous roadmap you built? It doesn’t feel like a guide anymore. It feels like a set of instructions for a machine you don’t know how to operate. The plan, your beautiful, detailed plan, has quietly become a prison of your own making. You’re frozen, and you can’t quite explain why.

We’ve all been there. I know I have, more times than I care to admit. We fall into this trap because we confuse the feeling of planning with the action of progress. We believe, with a strange and stubborn faith, that the more detailed our map, the less chance we’ll get lost on the journey. We think if we can just anticipate every bump, every detour, then the path itself will be smooth. It’s a seductive illusion.

But here’s the painful, liberating truth: often, the opposite happens. That meticulous planning becomes the very thing that holds us hostage. Over-planning is the quicksand of productivity—it looks solid and promising from the shore, but the moment we step onto it with all our weight, we sink. The more we struggle to create the perfect next step within the plan, the deeper we get stuck. We’re busy, we’re moving our arms, but we’re going nowhere. The real world is messy, unpredictable, and gloriously imperfect, and our pristine plans are hilariously fragile against it.

This is what I call the Planning Pitfall. It’s the trap of getting so profoundly, utterly caught up in preparing for the journey that you never actually pack your bag, lace up your shoes, and walk out the door. The preparation becomes the hobby, and the dream stays a dream.

Today, I want to walk right beside you through this all-too-common experience. Let’s unpack not just why we do this to ourselves—why our brains sometimes prefer the safe simulation of planning to the scary, rewarding act of doing—but, more importantly, how we can break free. How can we plan effectively, with clarity and purpose, without letting that plan become a wall? How do we build a scaffold that supports action instead of a cage that prevents it?

The Illusion of Control

Why do we make these big, detailed plans that end up stopping us? I think it comes down to one basic feeling: we want to feel in control.

Life is full of surprises. We can't know what will happen tomorrow. That's scary. So we try to make the future feel safe and certain. We try to plan away the surprises. I do this all the time. When I feel nervous about starting something big, I don't start. Instead, I make another list. I organize my notes again. I tell myself I'm getting ready. But really, I'm just trying to calm my nerves.

You probably know this feeling. You have a big goal. Maybe it's a new project at work, or learning a skill, or even just cleaning out the garage. Thinking about it makes you feel a little unsure. So you focus on the plan. You research. You make schedules. It feels like you are moving forward. It feels safe. You think, "If I have the perfect plan, nothing can go wrong."

But here is what we need to understand together: that feeling is an illusion. It's a trick we play on ourselves. A plan is just a guess about the future. It is not a magic spell that controls what will happen.

Why? Because real life doesn’t follow a plan. A plan happens in your head. Life happens in the world. You can plan your entire morning, and then your car won’t start. You can plan a talk, and then the projector breaks. You can plan a diet, and then a friend shows up with cake.

We hold onto our perfect plans because they protect us. They protect us from the hard part: starting. They protect us from looking silly, or failing, or finding out something is harder than we thought. A plan lets us feel ready without ever being vulnerable.

So we get stuck. We think, "My plan has to be perfect, or I will fail." We wait. We add more details. We fix tiny things. We think we are building a solid bridge, but we are just drawing a bridge on paper. You cannot cross a river on a drawing.

The way out is to see the plan for what it really is. It is not a rulebook. It is not a contract. It is just a first idea. A starting point. Your real power doesn't come from controlling every step. Your power comes from knowing you can handle whatever the steps bring. You can adjust. You can learn. You can change your mind.

Action Beats Perfection

So, how do we get out of that trap? How do we stop fixing the plan and start doing the work? The answer is simple: choose action over perfection. Choose to move, even if it's messy.

I want you to understand this: doing something is better than doing nothing perfect. Think about it. You want to learn to cook. You could read every cookbook. You could buy the best pots. You could plan a huge dinner. But if you never actually turn on the stove, you will never be a cook. The learning is in the doing. In the chopped vegetables and the sometimes-burnt rice. The plan is just words. The real skill comes from your hands.

We have to remember this: A simple plan you start today is better than a perfect plan you start next year. "Next year" often never comes. The excitement you feel right now? It fades while you wait for everything to be just right.

You might worry, "What if I do it wrong? What if I waste my time?" I have that fear, too. We all do. But here is the big secret: An imperfect action is never a waste. It is a lesson. When you do something, you stop guessing. You start learning what works and what doesn't. You get real information from the real world.

Let me tell you a story about me. I wanted to write. I planned the perfect website. I planned all my topics for the year. I had everything ready, except the writing. I was stuck because I wanted my first post to be amazing. Finally, I just wrote something short. It wasn't great. But I published it. A few people read it. And I learned how it felt to share my work. That small, imperfect action did more for me than all my planning. It got me moving.

We get stuck because we think the first step has to be a huge, perfect jump. That is scary. It freezes us. Instead, think of your first step as a small test. Just see what happens. You are not signing a contract for the whole journey. You are just trying one thing.

This is where we use the idea of "Good Enough." For any task, ask yourself: what does "good enough to move on" look like? It is not perfect. It is not the best thing ever made. It is just done enough. It is the simple meal that feeds you, not the fancy one for a photo. "Good enough" is not your final stop. It is how you get started.

Your confidence comes from finishing things. Each time you finish a small task, even an imperfect one, you prove to yourself that you can do it. You build trust in yourself. One "good enough" action makes the next action easier.

So, here is my question for you, and for me: What is one small thing you can do today? Not the perfect thing. The "good enough" thing. Can you write one rough page? Can you make one simple phone call? Can you do ten minutes of the project?

Information Overload

Now, let's look at another trap. This one is very easy to fall into today. It's called Information Overload. This is when planning turns into endless research. When you tell yourself, "I just need to watch one more video," or "I just need to read one more article." You keep looking for more information, but you never feel ready to start. You are collecting facts instead of taking steps.

I do this all the time. I get an idea, and instead of trying it, I start searching. I open ten tabs on my computer. I read what other people say. I watch tutorials. I feel busy. I feel like I'm learning. But really, I'm just putting off the moment where I have to do my own work. The research becomes a way to hide.

You know this feeling. Maybe you want to start a project. First, you search for the best way to do it. You find one article, then another. You see a video that suggests a different method. You fall down a rabbit hole of information. The goal was to start your project. But the activity became reading about other people's projects. You end up confused by all the different advice. You feel like you need to know everything before you begin. So you never begin.

We do this because research feels safe. It feels like we are moving forward, but we are standing still. We think, "If I have all the information, I can't fail." But it's another trick. There is always more information. You can never know everything. The search for perfect knowledge can stop you forever.

This creates a funny problem. Your brain gets full of ideas, tips, and warnings. It gets noisy in your head. With so many "right ways" to do something, you can't pick one. You freeze. The simple joy of your idea gets lost under a pile of opinions.

So how do you and I fix this? We have to set a limit. We have to be strict with ourselves.

Here is a simple rule that helps me: Give yourself a short time to research, then stop and act. Decide you will search for one hour. When the time is up, you close everything. You look at what you found. You ask, "What is the one small thing I can try right now?" Then you go try it. Not the perfect thing. Just the first thing.

We also need to know the difference between what you need to know and what is just nice to know. What you need to know is the basic idea to start safely. If you want to plant herbs, you need to know: put seeds in dirt, add water, give them sun. That's it. The nice-to-know stuff is the perfect soil mix or the best time of day to water. You can learn that later. First, just plant the seeds.

Remember, you learn best by doing. You don't learn to swim by only reading books about swimming. You have to get in the water. Information makes more sense when you have a real problem to solve. Right now, your problem is too much information. You need to trade that problem for a simpler one—the problem of starting.

The Flexibility Factor

Now, let's talk about something that can make or break your plan. Let's talk about flexibility. This is what keeps a plan alive. A plan that can't bend will break. A plan that can bend will help you keep going, no matter what happens.

I used to make very strict plans. I would write down what to do at every hour. If something interrupted me, I felt like I had failed. My whole plan was ruined. I would just give up for the day. Maybe you have felt this way too. Life happens. Your kid gets sick. Your boss calls an unexpected meeting. You feel tired. Your perfect plan crashes into a very imperfect day.

But here is what we need to understand together: The plan is not the boss. You are the boss. The plan is a tool to help you. If the tool isn't working, you can change it. The problem is not that life interrupted your plan. The problem is that your plan did not expect life to happen.

So, how do you and I build a plan that can handle real life? We build in space for the unexpected. We make it flexible.

First, we add extra time. I call this a "buffer." If you think a task will take 30 minutes, plan for 45. If you have three meetings, don't plan important work right after. Give yourself breathing room. This extra time soaks up small problems—the phone call that runs long, the traffic jam, the quick help a coworker needs. Without this buffer, one small delay makes you feel rushed and stressed for the rest of the day. With it, you can handle surprises calmly.

Second, plan your week, not just your day. This changed everything for me. Planning every single hour is too tight. It will always break. Instead, think about your whole week. On Monday, ask: "What are the two or three most important things I need to finish this week?" Write those down. Then, each morning, look at your list. Ask: "What can I do today to move toward those big goals?" This way, if Monday is a mess, Tuesday is a new chance. You haven't lost the week. You just adjust your steps.

Third, know when to change the plan itself. Sometimes, the plan is just wrong. Maybe you started a project and learned something new that changes everything. That's okay! Build checkpoints into your plan. Every Friday, or after a big step, stop and ask: "Is this plan still working? Is this still the best path?" If the answer is no, change the path. This isn't quitting. This is being smart. You are using what you learned by doing to make a better plan.

Think of it this way. A rigid plan is like a train on a track. If the track is blocked, the train stops. A flexible plan is like a car with a map. If the road is closed, you find another route. You still get where you want to go. You just take a different street.

Your plan should be your helper, not your master. It should work for you, in your real life.

So this week, I want you to try something. Look at your plan. Where can you add a little extra time? Can you focus on your big goals for the week instead of every hour of today?

The Momentum Mindset

Now, let's talk about the most important part of all. This is the secret that turns starting into finishing. Let's talk about momentum. Momentum is not a big, loud push. It is a quiet, steady feeling. It is the feeling that once you start moving, it becomes easier to keep moving.

Think about a heavy ball. It is hard to push at first. You have to use a lot of strength to get it moving. But once it is rolling, it is much easier to keep it going. That first push is the hardest. Your plans and goals are like that heavy ball. Starting is the hardest push. The momentum mindset is about making that first push so small and easy that you can't say no.

I want you to understand why we get stuck. We look at our big goal. It seems very far away. The first step feels too big. "Write a book" is a huge mountain. "Get organized" is a giant mess. Our brains see that big thing and they freeze. It's too much.

But what if we changed the first step? What if the first step was too small to fail?

This is the idea of a Quick Win. A "win" is not finishing the whole race. A win is taking one step past the starting line. It is a tiny, complete success. You need to plan for these wins right at the beginning.

Let me give you an example from my life. My goal was to get better at drawing. The old me would think, "I need to draw a perfect portrait." I would never start. The new me thought, "I will draw one simple circle." Just one circle. I did it. It took ten seconds. I finished it. That was my quick win. It felt silly, but I did it. Then I thought, "Maybe I'll draw a square next to it." And then a triangle. Without even realizing it, I was drawing for five minutes. I had momentum. The first step was so small it didn't scare me.

You can do this with anything. Your big goal might be "clean the house." That feels overwhelming. Your quick win is: "I will put five things away from this table." Done. Your big goal might be "start running." Your quick win is: "I will put on my running shoes and walk to the mailbox." Done.

We often think these small things don't matter. We think, "What's the point of just five push-ups?" But the point is not the push-ups. The point is the win. The point is teaching your brain that you can start and finish something. It changes how you see yourself. You stop being someone who "plans to do things" and start being someone who "does things."

This is how you and I fight feeling stuck. We stop looking at the faraway finish line. We only look at the next three feet in front of us. We build a chain of tiny finishes. One small win leads to another.

So here is what I am asking you to do with me. Tomorrow, when you look at your big goal, ask yourself this one question:

"What is the smallest, easiest first step I can take?"

Make it so small it seems almost silly. Make it something you can do in two minutes. Then do it. Finish it. Let yourself feel that little win.

We are building a habit of action. We are teaching ourselves that starting is not scary. Momentum comes from small beginnings. Don't try to push the whole heavy ball at once. Just give it a tiny nudge. You will be surprised how quickly it starts to roll on its own.

Your Plan is a Compass, Not a Railroad

After everything we've talked about, there is one last idea you need to know. It is the most important one. It's a simple way of thinking that changes everything: Your plan should be a compass, not a railroad.

I want you to really see the difference between these two things.

A railroad is a fixed track. It is made of steel and it cannot move. Once you get on the train, you can only go where the tracks go. You cannot turn left or right. If something is blocking the tracks ahead, you have to stop. You are stuck. You have no choice. For a long time, I made my plans like railroads. I thought being disciplined meant forcing myself to stay on those exact tracks, no matter what. When life blocked my tracks, I felt like a failure.

You might have felt this way too. We make a perfect, straight-line plan. Then, something happens—a problem, a new idea, a change—and our plan is ruined. We feel lost. But what if the plan was wrong all along? What if we were using the wrong tool?

Now, think about a compass. A compass is different. It does not give you a set path. It does not tell you exactly where to walk. It only shows you one thing: North. Your big goal, your main dream, your important reason for doing this—that is your North.

The compass doesn't care how you get there. It only makes sure you know the direction. You are the explorer. You get to decide the path. If you hit a river, you can look for a bridge. If you find a mountain, you can go around it. You have freedom. You can adapt.

This is the idea that sets you free. We are not train engineers, locked onto one set of rails. We are explorers with a trusty compass.

Here is what a plan-as-a-compass means:

It lets you take action before you're perfect. You don't need to know the whole path. You just need to take a step north.

It stops information overload. You don't need a map of the whole world. You just need to know your direction and look at what's in front of you.

It is flexible by nature. A compass expects you to go around things. That's the whole point.

It builds momentum. Every step you take toward your North is a win, even if it's a little to the east or west to get around a tree.

I am learning to do this. Maybe you are learning with me. The power is not in a perfect plan. The power is in knowing your direction and being brave enough to move, even if the path is not straight.

So, next time you make a plan, ask yourself this: "Am I building a railroad, or am I setting my compass?"

Are you making a rigid track that will break? Or are you finding your True North so you can start your journey?

We are human. Things change. We get new ideas. Problems pop up. A railroad plan breaks when this happens. A compass plan just helps you find a new way forward.

Here is what to do. Look at your big goal. Forget all the complicated steps for a minute. Just ask: What is my true North? What is the main point of all this? Write that down.

That is your compass setting.

Now, just figure out the very first step that moves you in that general direction. It doesn't have to be a perfect step. It just has to point roughly north. Take that step. See what you find. Then check your compass again and take the next step.

This is how we stay out of the planning trap for good. We are not stuck on tracks. We are on an adventure with a trusted guide.