Why Starting Over Feels Hard

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DEEP DIVE

Why Starting Over Feels Hard (and How to Push Through)

Starting over can feel like standing in the middle of a storm—everything familiar is stripped away, and all that remains is you, raw and vulnerable. It’s no wonder we cling to what’s safe, even when it no longer serves us.

But let me tell you a secret: you’re not alone in feeling this way. Fear shows up for everyone. It’s just louder when you’re on the edge of something new, whispering lies like:
“You’ll fail.”
“You’re not ready.”
“What if it’s worse than before?”

Fear has a knack for making you doubt yourself. But here’s the truth: fear only shows up when you’re doing something that matters.

What Makes Starting Over So Hard?

It’s not just about what lies ahead—it’s about what you’re leaving behind. Even when the past is painful, it’s familiar. It feels safe, like an old, heavy coat you’ve worn for years. Taking it off feels... exposed. Vulnerable. But that coat? It’s weighing you down.

And the idea of starting fresh? It’s like standing at the base of a mountain, staring at the summit. The climb feels impossible. But here’s the thing: you don’t have to conquer the whole mountain today. All you have to do is take one small step.

How Do You Keep Moving Forward?

First, be kind to yourself. Starting over isn’t about erasing the person you were—it’s about honoring your journey so far while making space for the person you’re becoming.

Let yourself feel it all: the fear, the doubt, the hope. Don’t rush to push those emotions aside. They’re proof that you’re alive, that you’re doing something brave and meaningful. The goal isn’t to get rid of fear—it’s to carry it with you and still take that next step.

Picture this: You’re painting a masterpiece on a blank canvas. At first, it’s messy, chaotic, maybe even ugly. But layer by layer, it transforms. Starting over is your blank canvas. You don’t need to get it perfect right away—just start.

And when you stumble—and you will, because we all do—remember: falling doesn’t mean failure. Falling means you’re trying. Every step, every wobble, every mistake is part of your climb.

Why Starting Over Is Worth It

Starting over is an act of courage. It’s choosing hope over fear. Growth over comfort. It’s telling the world—and yourself—I’m not done yet.

You have everything you need to create something extraordinary, even from the messiest, most uncertain place. Trust your resilience. Trust the process. And most importantly, trust yourself.

You’ve got this.

QUICK HITS

Here are some tools and ideas to keep moving forward:

Explore Practical Tools

• 10 Simple Steps to Overcome Fear: [Discover the full list →]

• How Celebrities Found Success by Starting Over: [Read Their Stories →]

• How to Be Kinder to Yourself: [Explore More →]

Create a Positive Mindset

• Finding The Positive Side: Create A Gratitude Checklist [Learn How →]

• Spend 5 minutes journaling about what excites you about this fresh start.

Build Your Confidence

• A Guide to Beating the Fears That Are Holding You Back [Dive in →]

WEEKLY CHALLENGE

Flip Fear Into Fuel

Taking risks is scary—no sugarcoating it. But running away won’t help you grow. Try these steps to face your fears head-on and flip them into fuel:

1. Acknowledge it: Admit you’re afraid. If you won’t be honest with yourself, no progress is possible.

2. Own it: Once you’ve named it, claim it. Recognize that this fear belongs to you.

3. Feel it: Don’t numb it out. Emotions move through you faster when you let yourself feel them fully.

4. Express it: Speak up, write it down, share it with someone you trust. Letting it out is how you lighten the load.

5. Release it: Choose to let go—not as a knee-jerk reaction, but from a place of real understanding.

Embrace the fear, work through it, and watch what happens. Once you see there’s nothing wrong with feeling terrified before starting over, that fear can become the very fuel that propels you forward.

COMMUNITY CORNER

💬 This week’s feature:
“I used to feel stuck in a career I didn’t love, but starting over felt impossible. Then, I found this community and realized I didn’t have to do it perfectly—I just had to do it. Now, I’m two months into my dream job, and I’ve never felt more alive. Thank you for inspiring me to take the leap!” — Taylor J.

✨ Share Your Story:
What does starting over look like for you? Whether it’s big or small, your journey could inspire someone else. Reply to this email, and we might feature you in an upcoming issue!

FINAL THOUGHTS

You’re human.

Fear, shame, uncertainty—they’re all normal, especially when you’re starting fresh.

Sure, pushing forward can feel impossible at first. But remember, you’ve already accomplished plenty in your life, so I know you’ve got what it takes to break through these emotional barriers.

Take it one day at a time. Stay mindful of each step. When you feel overwhelmed, pause and find your footing again.

You’re perfectly imperfect—so if the path feels messy, that’s okay. It’s yours to walk, stumble, and rise up on.

I believe in you, always,

Start Over Kitty & The Permission to Start Over Team

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