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PROJECT OF THE WEEK

I love the quote by James Clear: "What is something you would be proud to fail on, if you had the courage to attempt it?"

As a perfectionist, I hate failure. Too often, the fear of failing overshadows the dream of success.

When I tell the story of how I left the corporate world to start my own business nine years ago, the most common response I hear is, "Wow, you were so brave."

But the funny thing is, those words don’t really resonate with me.

Looking back on that decision, I had money saved—originally intended for buying a house. I had spent countless hours researching how to start a professional organizing business and had a detailed business plan. As a professional catastrophizer, I had already mapped out my worst-case scenarios. And if everything fell apart? I could always return to the corporate world.

Logistically, I had a plan. But I also knew the odds weren’t in my favor—more new businesses fail than succeed.

Yet, in taking the biggest risk of my life, I wasn’t afraid to fail. I believed that, given the amount of time we spend working, it was worth the risk to build a career I loved. The potential upside of success far outweighed the downside of failure.

I didn’t know who James Clear was in 2016 when I launched Happy Spaces, but his quote perfectly captures why that decision felt right—it wasn’t necessarily about bravery; it was about the pursuit of something worth failing for.

Now, whenever I face big decisions, I ask myself: "Would I be proud to fail on this?"

That question guided me when I started this blog, when I moved upstate, and when I became a foster parent.

There have been failures, and there will be more. But I am proud that I tried.

Getting Started

This week, I want to leave you with another favorite quote:

"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat." — Theodore Roosevelt

So, the next time you're faced with a risky decision, ask yourself:

"Would I be proud to fail on this?"

If the answer is yes, make a plan—and go for it!

Ready to Get Started?

If you're feeling excited about putting this strategy into action and could use a little extra accountability and support, the It’s All in the Planning Starter Pak is here to help! Designed to set you up for success, it’s the perfect tool to keep you on track and moving forward.

Let’s make progress together—because great results start with great planning!

get started

A Note from Happy Spaces

Our goal is simple: to add value to your life. If you think this project will be helpful, here are some steps to set yourself up for success:

Estimate how long it will take—then double it. Giving yourself extra time helps reduce stress.
Schedule it on your calendar for the week ahead. Setting a specific date increases follow-through.
Break it up if it will take more than an hour. Tackling it in smaller steps makes it more manageable.
Make a list of every action needed before you start. A clear plan helps keep you on track.
Do what works for you—you don’t have to complete every part, just what adds value to your life.
Find an Accountability Partner—having support makes it easier to stay committed.

We understand that building new habits and systems can be challenging, but you don’t have to do it alone. For additional support, visit HappySpacesBySarah.com and let’s make organizing and planning easier together.

Creating a life you don't need a vacation from! ®

Sincerely,

Sarah Weingarten

Meet Sarah

As the oldest of nine kids with two working parents, I grew up juggling many responsibilities at home. Organization and time management became my lifeline amidst the chaos.

I attended the Cornell Hotel School and pursued my childhood dream of working in the hospitality industry. In 2016, I launched Happy Spaces, combining my passion for structure and efficiency with helping others.

I love working with students to develop essential organizational, time management, and study skills. These skills empower them to reach their full potential, build confidence, and create a future they feel good about.

Would I Be Proud to Fail on This?