KK

Getting Comfortable With Failing

September 03, 20251 min read

One of the things that helped me early on in my business journey was when someone told me, “The business works on you just as much as you work on it.”

One of the main things business has revealed in me is my fear of failure. Business didn’t create this fear—it just put a spotlight on it. The reality is you are faced with yourself in your business. You can’t hide behind anything. You’re forced to deal with more uncertainty and risk than the average person is used to. You will be confronted with whatever is on the inside.

I can’t tell you where this fear of failure started, but I can tell you how it manifested. My thoughts often play out worst-case scenarios. Thoughts of hope are short-lived because I don’t want to be disappointed if things don’t turn out that way.

A book I’m reading that has helped me develop a biblical understanding of business is Business Secrets from the Bible: Spiritual Success Strategies for Financial Abundance by Daniel Lapin. He talks about how missteps and setbacks are not only impossible to avoid but should also be expected. The only people who don’t make mistakes or experience setbacks are the ones who don’t do anything.

I carried so much shame from the mistakes I’ve made in business and life that it actually trapped me. The perspective that missing it doesn’t ruin your story or derail where you’ll end up in life has been the most life-giving truth for me.

So try more. Fail more. Experience setbacks. And get right back up again.

Keep building—it’ll be worth it.

—KK

Kaitlyn Webb

In 2020 the Lord led me to quit my job and start a business. In 2023 I moved to Charleston, SC to help plant a church, where I now serve as worship leader—sharing the daily journey of life in business and ministry.

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