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Congratulations, You're Really Good at Waiting (And It's Killing Your Dreams)

By Art Harrison • July 13, 2025

Perfectionist waiting is a skill that's sabotaging your entrepreneurial success. Learn why your preparation addiction is costing you opportunities and how to break free.

You've been planning this business for eight months. Maybe longer.

You've researched your market thoroughly. You understand your competition better than they understand themselves. You've refined your business model until it's theoretically perfect. You've created detailed financial projections, marketing strategies, and operational plans.

You're incredibly good at preparing. You might be the best preparer I've ever encountered.

But you still haven't started.

Congratulations—you've mastered the skill that destroys more entrepreneurial dreams than lack of money, lack of connections, or lack of ideas combined. You've become an expert at sophisticated procrastination.

The Perfectionist's Paradox

Smart, capable people often get trapped in what I call the Perfectionist's Paradox: the better you are at planning and analysis, the harder it becomes to actually start anything.

Your intelligence becomes a liability because you can see all the potential problems. Your thoroughness becomes paralysis because there's always one more thing to research. Your high standards become excuses because nothing ever feels quite ready yet.

Meanwhile, people with "worse" plans but better execution are building the businesses you're still planning.

Why Waiting Feels Productive (But Isn't)

Waiting feels like progress because preparation requires effort and produces tangible outputs. You have documents, spreadsheets, research notes, and plans. You can point to hundreds of hours of work.

But preparation isn't progress toward your actual goal—it's progress toward feeling ready to pursue your actual goal.

And here's the brutal truth: you'll never feel ready. No amount of preparation creates the confidence that only comes from taking action despite uncertainty.

The Preparation Addiction Cycle

Step 1: You identify something you want to pursue
Step 2: You start researching and planning
Step 3: Your research reveals complexity you hadn't considered
Step 4: You decide you need more preparation before starting
Step 5: Repeat Step 2-4 indefinitely

This cycle feels responsible and intelligent, but it's actually a sophisticated form of self-sabotage. You're using your intelligence to create reasons not to act.

The Hidden Cost of Perfectionist Waiting

While you're perfecting your plan, three expensive things are happening:

Opportunity Cost Accumulation

Every month you spend preparing is a month someone else is building market share, developing customer relationships, and learning what actually works. They're gaining advantages that your better plan can't overcome.

Confidence Erosion

The longer you wait, the more evidence you collect that you're not ready. This creates a negative feedback loop where waiting makes you feel less prepared, which makes you want to wait longer.

Market Evolution

The market you're researching is changing while you're researching it. Customer needs evolve, new competitors enter, technology shifts, and economic conditions change. Your perfect plan for last year's market might be completely wrong for this year's reality.

The Action-Before-Readiness Principle

The most successful entrepreneurs I know share one trait: they act before they feel ready. Not because they're reckless, but because they understand that readiness comes from experience, not from preparation.

You don't become ready to start a business by thinking about starting a business. You become ready by starting a business and figuring it out as you go.

This doesn't mean acting without any plan—it means acting with an imperfect plan that you'll improve through real-world testing.

The Minimum Viable Plan

Instead of creating the perfect plan, create the minimum viable plan—just enough preparation to take the first meaningful action.

For most businesses, this includes:

  • One clear problem you're solving
  • One specific group of people who have this problem
  • One simple way to solve it that you can implement immediately
  • One method for reaching these people and testing their interest

Everything else can be figured out after you've started.

How to Break the Waiting Habit

If you recognize yourself as a perfectionist waiter, here's how to break the cycle:

Set Artificial Deadlines

Give yourself two weeks to take one real action toward your business goal. Not to finish your research—to do something that puts you in contact with actual customers or starts building actual value.

This deadline will feel arbitrary and uncomfortable. That's the point. Entrepreneurship is full of arbitrary deadlines and uncomfortable action. Practice starts now.

Embrace the Messy Start

Your first attempt at anything will be imperfect. Your first website will look amateur. Your first sales pitch will be awkward. Your first product will have flaws.

This isn't failure—it's the natural process of becoming competent through practice. You can't think your way to competence; you have to act your way there.

Use Preparation as Procrastination Detection

If you find yourself doing more research on a topic you've already researched, that's procrastination disguised as productivity. If you're refining plans instead of testing them, that's fear disguised as thoroughness.

The cure for over-preparation is under-action. The cure for perfectionist paralysis is imperfect action.

The Waiting vs. Building Mindset Shift

Waiting mindset: "I'll start when I have enough information to ensure success."

Building mindset: "I'll start with enough information to survive the first attempt, then improve based on what I learn."

Waiting mindset: "I need to understand all the risks before proceeding."

Building mindset: "I need to understand the biggest risks, then take action to test my assumptions about them."

Waiting mindset: "My plan needs to be complete before I begin."

Building mindset: "My plan needs to be good enough to get started, then I'll iterate based on reality."

What Happens When Perfectionists Finally Act

When perfectionist planners finally start taking action, they often discover something surprising: their thoroughness becomes a competitive advantage, but only after they're actually building something.

The research skills that kept them stuck in planning become powerful business intelligence capabilities once they're applying them to real market feedback.

The attention to detail that prevented them from starting becomes quality differentiation once they're delivering actual products or services.

The careful analysis that created paralysis becomes strategic thinking once they're using it to optimize real business results instead of theoretical plans.

Your perfectionist traits aren't the problem—using them as excuses to avoid action is the problem.

Your Anti-Waiting Action Plan

Today: Identify one action you could take right now with your current level of preparation. Don't take it yet—just identify it.

This week: Take that action, regardless of whether your plan feels complete. Set a deadline that forces action before you feel fully ready.

This month: Build a habit of taking action with incomplete information, then using results to improve your approach rather than waiting for perfect information before acting.

If you're struggling to move from planning to action, you're not alone. Most high achievers get trapped in preparation mode because it feels safer than risking imperfect execution. The free challenge is specifically designed to help perfectionists practice taking action despite uncertainty.

Remember, the goal isn't to eliminate planning—it's to prevent planning from becoming a substitute for action. Your plan doesn't need to be perfect; it needs to be good enough to start testing.

Stop being good at waiting and start being good at building. The market will teach you what your planning couldn't.

For more insights on moving from analysis to action, read about overcoming analysis paralysis and learn about taking imperfect action.

Your thoroughness is an asset, but only after you start using it on real business challenges instead of theoretical planning exercises. The world needs what you're preparing to build—but only if you actually build it.

Ready to Take Action?

Stop planning and start building. Take the first step toward turning your ideas into reality.

Video Transcript

Well, congratulations. No, seriously, congratulations are in order because you have been doing something that takes real effort. You've been waiting. You've been waiting for the stars to align. You're waiting for someone to hand you that golden ticket that says "Okay, it's your turn now." And let's be honest. You've gotten really really good at this whole waiting thing. And you're not just waiting for a red light to change. You're not just waiting for your coffee to be ready, no: You're waiting for permission to live your own life. And to go after the things you want, to take a risk, and to make a move that's actually going to matter to you. It's impressive. It's impressive just how much you've convinced yourself that you can't do the things you want until somebody else says it's okay. Maybe it's your boss. Maybe it's your parents. Maybe it's just that weird voice in your head that sounds suspiciously like Susan from accounting. That's telling you to hold off just a little bit longer because, you know, maybe that'll be the right time. Let me let you in on a little secret. That moment that you're waiting for, that person you're waiting to hear from, it is never going to come. Nobody's going to show up and tell you that now is the time you're allowed to go for it because that's not how the world works. And I do get it. We've all been there. At some point we've all convinced ourselves that staying put is the smart move or the safe move. But let's call it what it really is. It's fear. And worse than that, it's fear that's dressed up in the cozy clothes of responsibility and caution. Waiting feels safe, but all is really doing is giving you a place to hide. It's giving you an excuse not to try things, not to fail, not to risk looking like an idiot in front of the people who are probably too busy worrying about their own lives, even notice what you're doing. Waiting isn't just costing you time, it's costing you everything. Every single opportunity that drifts by while you're just sitting there and hesitating is a moment of your life that you'll never get back. You want to speak up, but you wait because you're not sure if it's your place. You want to try something new, but you hold yourself back because what if it doesn't work? You've convinced yourself that waiting will make life easier. Make it less risky, but it doesn't do that. All it does is make you more comfortable with doing nothing. And guess what happens when you get really good at doing nothing, absolutely nothing. Do you think the people that are out there living their lives, making changes, making noise, are somehow more qualified than you, they're not? Most of them are clueless, they're just as scared as you, and some of them are absolutely terrible at whatever it is they're doing. They're out there making things happen, not because they know anymore than you or because they're any better, but because they decided that the waiting game just wasn't worth it. Every big city has some guy who started some multi-million-dollar chain of sub-par fast food restaurants, and I guarantee you not a single one of those guys waited around for their mum to give them a call and say, "Guess what honey, now's the time for you to go for it. It's finally time for you to start selling guacamole to teenagers." That's just not a thing that has ever happened. So let's not pretend that the people that you're waiting on know any better than you do, because they don't. Your boss, your boss is probably at home right now Googling how to make tomorrow spreadsheet look a little bit more impressive. Your parents sure they love you, God bless them, but they don't know. They grew up in a world that was completely different. Where a stable job and a pension were the standard of success, so they don't know what it's like to chase a dream in today's world. And people like Susan, well, Susan's just waiting for her own chance to step up, but she's too busy side-eyeing everybody else's ambition to realize that she's already ready. Just imagine if every great thinker sat around twiddling their thumbs and waiting for somebody else to come up and say, "Hey, you're smart, you're good enough. Why don't you start something?" If that were the case, we wouldn't have half of the things that we take for granted today. Obviously not everybody is trying to make the world the better place. There's some people out there right now that are just making terrible choices. There's screwing things up left and right and the worst part is not a single one of them is waiting for permission to do it. They're just out there. They're just living their lives, they're taking dumb risks, but you know what at least they're moving forward. Meanwhile here you are sitting, doing nothing, you're perfectly capable, you're perfectly good, but you're waiting for someone else to tell you that it's okay to even try. The reality is nobody cares as much as you think they do. No one is sitting around right now with a clipboard evaluating whether or not you should be allowed to do the things you want. People are busy. People are so consumed with their own doubts and fears, but they just aren't paying attention so why are you giving them so much power over your life? Why are you letting them and the imagined opinions you think they have be the thing that decides your future? The world doesn't need another person who spends their life hiding behind maybe later and not yet. It needs people that are willing to be uncomfortable to be awkward, to be messy, and to take imperfect action. It needs people that are willing to show up even when they're scared, even when they're not ready, even when they might fail spectacularly and that could be you, but it's not. So congratulations. You've waited, you've spent hours, days, maybe even years perfecting your art of staying put. But what you have to ask yourself is what is that actually given you? Has it made you a happier? Has it made you more fulfilled? Has it made your dreams any closer to a reality? Or has it just made you a master of sitting still while the world moves forward without you? The only person who gets to decide when you go, where you go, how high you leap, when you live your life is you, and you're not getting any younger. Those dreams, those ambitions, the fire that you feel, it doesn't last forever. If you just keep pouring cold water on it, it does go away. So just go, mess it up, take the leap, make the mistake, try the thing, not because I told you, not because anybody said you could, but because you decided that you wanted to, because waiting is just another word from letting life pass you by, and you know what, you deserve more than that. You deserve to live a life that is messy. That's unpredictable. That's full of mistakes, full of moments that actually make you feel alive. So do it. And the next time that's Susan or anybody else, like Susan gives you the side eye or tells you to wait just a little bit longer, just smile. Smile because while they're sitting there, waiting for someone to grant them permission, you'll have already granted it to yourself. You'll be out there taking risks, living your life and actually doing something.