You’re not supposed to get it right the first time

I had a situation last month that completely made me think of our lives as adults and business owners in a new way.


"Do you want my other mechanical pencil?" my daughter asked me.


"No. Thanks for offering, though."


"Why not?"


"Um, I mostly use pens now. I don't need pencils because I don't need to erase as often as I used to. I guess I don't make as many mistakes when writing," I answered truthfully.


It got me thinking…in a metaphorical sense, as we get older, we erase less. And it’s not because we’re perfect, but because we start believing we know it all.

However, this makes us fear failure.

We look at our life as written in pen, instead of written in pencil. One mistake has us spiraling down into, "I'm never doing this again!"

But in business, you have to always be open to changing, pivoting, trying different things. 

Starting and maintaining a business involves a lot of erasing, yet too often, new freelancers treat it like it's written in pen. If something isn't working, we think there is no going back and so, giving up is a lot easier.

Instead, I challenge you to approach your business like a nine-year-old with a pencil. Sometimes it will be going really well, but sometimes you'll have to erase 2/3 of the equation and start over.

The truth is, I have a pile of erased pages behind me. That’s how I learned what actually works. Same thing with every other successful freelancer.

Erase when you have to and rewrite when you’re ready. I promise that no one writes a great business in pen.

If that’s what you’re chasing right now, and especially for 2026, reply here. Tell me where things feel uncertain or unstable in your freelance business. I’d love to hear what you’re navigating and help you spot what might be holding you back.

If you celebrate:

  • Yule: may you find what you need in this time of reflection within celebrating the rebirth of the sun.

  • Hannukah: may it be full of family, connections, and honor the rededication of the Second Temple in Jerusalem.

  • Christmas: may it be filled with warmth and joy as you proclaim Christ’s birth.

If I missed your holiday, let me know what you celebrate, I’m always open to learning more about other cultures and traditions.

***

If your goal is to work fewer than 25 hours a week and still earn the income you had in corporate, I can help you get there. I coach freelancers and service providers to scale their businesses with strategies that actually work. Connect with me here.



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The corporate mindset I had to unlearn