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faith & finance · Jul 20, 2026

When I’m too scared to ask the “dumb” question

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Nicholas Garofalo · faith & finance

My friend has some lofty career aspirations. And they’re stalling. He’s been in one lane for over a decade and he’s trying to switch. If you’ve been there before, you know how hard it is. There’s so much momentum pushing you toward the lane you’ve always been in, and yet there’s a subtle whisper calling to go elsewhere, to venture with God into the unknown.

Sounds exciting! …Until the plans stall. Then it feels embarrassing. And that’s exactly what he said:

“I’m embarrassed.”

Not embarrassed because he’d made some wild, scandalous mistake. More like embarrassed because he felt behind. Behind his peers. Behind where he thought he’d be. Behind where he “should” be.

This kind of embarrassment stings. And it shapes behavior because we make heart-level agreements like, “I never should have…” or “I’ll never try that again.”

It shuts you down.

It makes you think twice before reaching out again.

It stops you from asking the next question.

It makes you delay the awkward conversation.

There’s a weird current at work here:

Sometimes we feel embarrassed for something that didn’t happen to us.

You weren’t taught. You didn’t have the framework. You didn’t have a parent who pulled you aside and said, “Here’s how this works.” You didn’t grow up in a home where money was talked about clearly and calmly. So now you’re 40 or 50 or 60 and you feel like everyone else got a memo you missed.

That embarrassment is a sneaky form of shame, because it acts like you did something wrong… when the truth is, you’re really upset because you didn’t do something — because something was missing or not given to you when you wished it had been. It’s embarrassment by omission — and not your own, that of those you looked up to to lead the way.

And when you feel behind, you start managing perception instead of engaging with reality.

Money is just the obvious place it shows up.

You don’t know the financial jargon. You feel kinda stupid for not knowing. You aren’t sure how to invest your 401(k). Or whether you should have life insurance. Or maybe you’ve read enough smarasset.com articles to feel dangerous, but still lost your hat last year in your attempts at investing. Your personal cash flow is “a bit messy” and you’re honestly not sure if you’re doing well or not.

But if you notice, the pattern isn’t merely financial.

It’s fear of being exposed.

So it bleeds into other parts of life:

  • career moves

  • obedience decisions

  • ministry transitions

  • hard conversations in marriage or parenting or friendships

  • anything that requires action without perfect clarity

And that’s where we’ll pick it up next week, and talk about the difference between actually waiting on the Lord and using “waiting” as a nicer-sounding word for fear.

Read the original on faithandfinance.substack.com

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