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Home Entrepreneurship

The Questions Entrepreneurs Are Too Embarrassed to Ask

g6pm6 by g6pm6
July 16, 2026
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Should you suppose you’re the one one with questions on your corporation, I’ve information for you.

A fast search brings up questions entrepreneurs identical to you and me have rolling round in our heads and are too afraid to ask. Questions like:

So why are you embarrassed to ask questions?

Entrepreneurship sells you a lie: that confidence and competence are the identical factor. They’re not. You generally is a phenomenal operator and nonetheless really feel a flicker of dread each time you open your accounting software program. Competence was by no means about certainty. It’s about being keen to study.

The entrepreneurs I love most ask questions continually, and it’s not as a result of they’re inexperienced, however as a result of they by no means stopped studying previous the purpose the place everybody assumes they need to already know all of it. I’ve sat throughout from founders operating companies price greater than I’ll ever construct who nonetheless ask, “Are you able to clarify this to me like I’m new right here?” 

That’s why they’re nonetheless constructing twenty years later.

Embarrassment has a price ticket most individuals by no means add up. Each month you keep away from a tough query is one other month you delay the repair. The hole between “I don’t perceive my numbers” and understanding them could be a single ten-minute dialog. Let disgrace block that dialog for a yr, and also you haven’t averted a tough second; you’ve spent twelve months making selections on unhealthy data.

What you are promoting doesn’t want you to guard your ego. It wants you to guard its future. Confuse the 2, and also you’ll stall out quietly, with out ever understanding why.

So this week, I’d ask you to do one thing uncomfortable however genuinely helpful. Sit down with these:

  1. Title the factor you’re pretending to know. Each entrepreneur has one. It’s normally one thing you nod alongside to in conferences whereas doing math in your head to maintain up. Say it out loud, even simply to your self. Naming it is step one to closing it.
  2. Put a quantity on revenue. Not income, however what you retain, after every little thing, that’s genuinely yours. Most homeowners can let you know final month’s gross sales immediately and don’t know what they personally banked. If that’s you, open your account and look. Discomfort right here is data, not failure.
  3. Discover who already is aware of what you’re making an attempt to determine. Someone in your circle, or one connection away, has already solved the precise downside you’re sitting on. Discover them earlier than you reinvent one thing they’d hand you for the value of a espresso.
  4. Ask one query you’ve been avoiding — this week, out loud, to an actual individual. Not a search engine. An individual. The precise act of claiming it to a different human strips it of most of its energy. And I’m keen to wager that they let you know aboue a query they’ve in some unspecified time in the future, too.
  5. Decide one small ability to shut the hole. Not a course, not a certification, however  one ability, practiced as soon as, this month. Understanding a revenue and loss assertion. Operating a single crew assembly with out over-explaining. Development compounds, however provided that you begin.

One of many biggest presents you can provide your self is permission to confess you don’t know every little thing. That’s the form of management that holds up beneath strain, as a result of it’s constructed on honesty as an alternative of efficiency.

Normalize asking for assist, beginning with your self. Your crew, your mentors, and your friends don’t anticipate your perfection. They anticipate your honesty. Give them that as an alternative, and watch how a lot lighter the entire thing will get.

You’ve received this.

-Mike

PS – Have a query you wish to ask me? E mail help@mikemichalowicz.com and I’ll reply you!

Tags: EmbarrassedEntrepreneursQuestions
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