It Never Hurts to Ask a Question — Why Silence Is a Real Risk for Entrepreneurs
Most missed opportunities are not the result of rejection. They die long before that. They die from never being asked.
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Key Takeaways
- Don’t be afraid to ask questions.
- It might just be the practice that leads to your next opportunity.
“It never hurts to ask.”
People nod when they hear that. They agree. Then they ignore it.
Because asking feels risky. Asking puts your ego on the table. Asking opens the door to rejection. Asking forces you to admit you want something.
Most adults hate that feeling.
So they stay quiet.
They convince themselves that the timing is off. The ask is too big. The other person is too busy. The answer is probably no anyway. That logic sounds responsible. But, it is actually expensive.
Related: How Crisis Taught Me to Ask for Help
The opportunities that die quietly
The most common answer you will ever receive is not ‘no.’
It is silence.
Not because the other person would have said no, but because you never asked in the first place.
I see this constantly. People want the deal, but never send the email. They want the raise, but never start the conversation. They want the partnership, but wait for the perfect intro. They want the house, but never make the offer.
They assume rejection will hurt more than regret. They are wrong. Regret compounds. You remember the chances you did not take far longer than the nos you received and moved past.
Why asking feels hard as an adult
Kids ask for everything. Can I have dessert? Can I stay up later? Can I try again?
Adults lose that instinct.
Somewhere along the way, asking got wrapped up in pride. We started believing self-reliance meant silence. We confused confidence with not needing anything from anyone.
That mindset kills momentum. Entrepreneurship does not work without asking. Neither does leadership. Neither does growth. Every meaningful step forward involves a request.
Capital.
Advice.
Forgiveness.
Help.
A chance.
No one builds anything alone, even if they pretend they did.
Real estate taught me to ask before anything else
My entire career started because I asked questions. I did not grow up knowing how to invest. I did not wake up one day magically understanding deals, capital stacks or risk tolerance.