Three Questions To Ask Before You Do Something Scary

This post is by Heather Caliri, regular contributor to The Happiest Home and blogger at A Little Yes. Heather writes about saying “yes” to little things that scare us. You can read all her posts here.

Ever since I started a website about saying ‘yes’ to things, I’ve been trying to take intentional risks.

But as I practice being brave in the everyday, I’ve realized something important.

Fears are not equal-opportunity.

Years ago, I pushed past fears about writing, and felt like I’d put myself through a meat-grinder. Honestly, the fallout hamstrung my creativity for years.

But facing almost entirely the same daunting tasks recently, I’ve felt empowered and excited.

What gives?

I’ve learned that I need to ask some hard questions before I face fears. Pushing past stuff that scares me can open doors and empower me—or it can be too much too fast.

How to tell the difference? I ask some hard questions.

Is this a good fit for me?

Almost ten years ago now, my husband bought me a book about freelance writing. At the time, my job as a tech writer was on life support, and I was trying to figure out what to do about my “career”.

“What about this?” he asked.

I looked through the book, my heart in my mouth. I smiled at my husband, because it was a thoughtful gift, but inside, I felt terrified. The author seemed so carefree about sending out work to strangers. Seemed at ease writing on dozens of different subjects.

But I wanted to write. So I decided to set aside my fears and try.

I lasted about two months. Every time I sat down at my computer, I felt like crying. Calling potential sources made me want to curl up in the fetal position.

I finally quit, ashamed I’d failed.

Looking back, I see that freelancing wasn’t a good fit for me back then. I didn’t have a strong enough sense of my own creative voice. I didn’t yet have enough confidence to put my creative work out there.

The writer said that confidence would follow on the heels of submitting. But his advice didn’t work for me. Instead, submitting work I didn’t feel sure about made me feel naked and ashamed.

His advice was great for other people, but not for me.

You know what? That’s okay.

It didn’t make me a failure. It just made me me.

Now, when I’m tempted to try something new, I think about my temperament, and try to gauge whether the new thing will be a good fit.

Do I care?

I spent a lot of time as a kid feeling embarrassed about all of my phobias. Bees, swimming, diving, scary movies, downhill drops, heights.

When I started saying intentional yeses to scary stuff, I assumed that those old fears would be the first ones to go.

But as I set goals for myself, I found the ones that changed my life were closer to my heart. They built off of strengths I already had, and were centered right in the middle of my passions and burning needs.

Writing. Reading. Faith. Family. Self-care.

Honestly, I don’t have a lot of extra time or energy to reshape my life. Unless the fear was holding me back from something I loved, spending the energy to defeat it felt exhausting.

But facing fears close to my heart was like nuclear fusion. I still remember the afternoon I spent buying my first domain name for my blog. Yes, my hands were shaking as I filled out the forms and pressed BUY NOW, but I also felt like this tiny step, this little bit of intention, was wrapping my spine with steel.

That tiny effort had enormous impact on everything. Not just with my confidence as a writer, but my self-image, my joy, my excitement about life.

I’m still afraid of roller-coasters, but at Disneyland, I walk by them with a spring in my step. I’ve faced fears that are much more important to me.

What does success look like?

I usually expect way too much of myself.

If I start a website, it has to look professionally designed without me spending any money or very much effort. If I invite friends over for dinner, I need to have everything cooked on time, but not too early, have the kitchen clean, and be relaxed when everyone arrives.

Part of focusing on little yeses has been all about defining what success means, and making sure that “success” has a lower-case S.

I focus on writing a certain number of words each day, rather than whether they’re coherent.

I pray through a set liturgy at night for two or three minutes, instead of feel like I should do something longer and more “spiritual.”

Different seasons require different measures of success. When I had a one-year-old, I defined success as writing for fifteen minutes a week. Even sleepless, and overwhelmed, that bar was low enough for me to hurdle.

When I define success in such small, achievable chunks, I actually do something instead of yearning for something unrealistic.


I used to try new things, and then feel disappointed when I couldn’t keep up with them. I was on a constant quest for self-improvement, but felt ashamed that I didn’t really ‘improve’.

Now I see that unless my yeses integrate into my passions, temperament, and life, I shouldn’t bother.

It’s funny—deciding to say yes intentionally has made me say it less often. Evaluating whether a facing a fear will actually bring me more joy means I can save my energy for stuff that matters.

But even as I do less, I feel more brave. I trust that when I have more time, I’ll use it courageously–for yeses that matters to me.

Image credit: Ishikawa Ken

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