Planning Won’t Save You. Preparation Will.

When Preparation Beats Planning

Most people believe success comes from having the perfect plan—a step-by-step roadmap that guarantees results.

But here’s the truth: plans rarely survive reality.

No matter how well you map things out, life will throw curveballs: unexpected setbacks, last-minute changes, and opportunities that don’t fit neatly into your blueprint. And when that happens, people who rely solely on planning freeze. They don’t know what to do because their script didn’t account for this.

I know this from first-hand experience. My 20s have been full of “missed plans”.

I had planned to go to a specific grad school.

I had planned to make six figures by 25.

I had planned to be married by 26.

Own a house by 27.

Have a baby by 28.

And the list goes on and on.

But to this day, almost none of my plans have come to realization.

But the one thing I did learn from through this journey?

Preparation always beats planning.

What’s the difference?

• Planning is a theory. Preparation is a skill.

• Planning assumes control. Preparation embraces uncertainty.

• Planning is about predicting. Preparation is about adapting.

Think about it:

• A boxer doesn’t plan for every punch—they train to react to anything.

• A comedian doesn’t plan for every laugh—they prepare to handle any crowd.

• A successful entrepreneur doesn’t have a flawless plan—they’re just prepared to adapt when things don’t go as expected.

This applies to every area of life. The most successful people aren’t necessarily the best planners—they’re the ones who can handle whatever comes their way because they were prepared.

The Problem With Over-Planners

Ever met someone who spends months obsessing over the "perfect" business idea but never launches? Or someone who plans every detail of a fitness journey but never actually hits the gym? I am guilty of this on numerous occasions. Including “over-planning” to start this newsletter!

That’s the danger of over-planning—it tricks you into thinking you’re making progress when, in reality, you’re just delaying action.

Meanwhile, prepared people just start. They build skills. They experiment. They make mistakes, learn, and adjust in real-time. And when the unexpected happens, they aren’t thrown off course—they adapt.

I’ve only recently come to realize the important distinction between preparation and planning, but it’s a skill I’d like to grow in with you all.

How to Focus on Preparation Over Planning

1. Build habits, not just strategies. Instead of planning the perfect morning routine, just start waking up earlier. Instead of outlining a business idea for months, start selling something today. It might look messy now, but you’ll learn through it all and come to refine the process, the idea, the sale over time.

2. Develop a wide skill set. The more skills you have, the more adaptable you become. Learn to communicate, problem-solve, and think on your feet.

3. Train for chaos, not just control. The world is unpredictable. Instead of resisting change, build resilience. Put yourself in uncomfortable situations and practice solving problems in real time. Only rigid trees break in the wind.

The Bottom Line

Instead of asking, “What’s the perfect plan?” start asking, “Am I prepared for the unexpected?”

Because in life, it’s not the best planner who wins—it’s the one who’s most prepared.

With you in the Journey,

Rebecca

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People I Love Learning From

Free Resources

Access my book list-” Books to Transform Your 20s” The books that will change your mindset, career, and life—all in one list.

Click on the link below. Copy the book list to your personal Notion account by clicking the “Duplicate” button in the top right corner.

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