Scary good and scary bad

Jenni Gritters
5 min readSep 6, 2024

When you start working for yourself, you’re going to feel a little bit shaky. Entrepreneurship can be scary, and I talk a lot about how to manage that fear when I’m coaching creatives.

But recently, I’ve been having a lot of conversations about the difference between the “scary good” kind of fear that says you’re moving towards your dreams, and the “scary bad” kind of fear, which warns you that this situation isn’t aligned for you.

As always, I’m going to tell you a story to kick us off. (These stories are always anonymized and based on a composite of my client conversations.)

Today, we’re meeting Nia.

Nia is a graphic designer who wanted to add a new service to her offer line up. She set up a landing page on her website with a new offer (fixing up resumes and CVs) and did some quick math: She could make about $2,000 extra per month on this offer if she could sell it to six new clients per month. She invited her clients to test out the new program and had a lot of interest to start. But six weeks in, no one had actually made a purchase.

Nia kept waking up at 3 am with panic. She’d kept her schedule open to make space for this new offer and now she didn’t have enough money in her bank account to easily pay her bills. She was terrified.

This is where we get to scary-good and scary-bad.

When Nia first launched the new offer, she reached out to her current and former clients via email. She posted on LinkedIn. She asked…

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Jenni Gritters

I’m a writer and business coach for freelance creatives based in Central Oregon. I write about the psychology of small business ownership.