Your bold ask is the key to open closed doors
Anyone can ask politely for a meeting. But audacity—asking big and offering value first—is what turns a chilly no into an enthusiastic yes. Consider Emily, a young engineer who dreamed of working at a top-tier robotics firm. Most applicants emailed HR. Emily wrote directly to the head of engineering at 7 A.M., offering to run an unpaid weekend build workshop teaching her team her specialty microcontroller hack. She closed, “I’d be delighted to share this at your convenience.”
She followed up three days later with a friendly voicemail and a link to a video of her hack in action. Within a week, she was on site, leading a working session for ten engineers. Her audacity got her in the door, but her expertise kept her there. Later, she was hired for a full-time role.
Audacity isn’t recklessness—it’s strategy. By pairing a bold ask with a clear benefit for the other person, you flip the dynamic. You’re no longer just a supplicant—you’re a potential partner. That confidence will set you apart every time you step up and say, “I’d like fifteen minutes with you. Here’s what I can bring to the table.”
Tonight, grab a blank sheet of paper and treat it as your audacity incubator. Jot down one big ask you’re afraid to make, then list how it’ll help the other person. Commit to sending that email or making that call first thing tomorrow morning, embracing any refusal as a lesson in refining your proposal.
What You'll Achieve
You’ll build self-efficacy by confronting fear, making bold asks part of your comfort zone. Externally, you’ll gain direct access to high-value connections who might otherwise be unreachable.
Practice making audacious requests
Draft a fearless pitch
Write one bold request—working with a celebrity, a meeting with a CEO, an interview for mentorship—on a sticky note.
Add a generosity hook
Include something you’ll offer first, like pro bono time, a free consultation, or a unique idea they can use immediately.
Time your ask strategically
Call or email at a low-stress time—early morning or evening—so your request stands out amidst fewer distractions.
Embrace rejection as data
If you hear “no,” ask for brief feedback on the best way to approach them next time. Each refusal refines strategy.
Reflection Questions
- What’s the most audacious ask you’ve ever made—and what stopped you?
- How can you pair your next big ask with an irresistible benefit for them?
- What feedback would you seek if your request is declined?
- How will you celebrate once you land that first audacious meeting?
Personalization Tips
- You want coffee with a famous author—offer helpful feedback on their latest essay in the email you send.
- Ask a startup founder for fifteen minutes—offer an honest user review of their beta app.
- Request mentorship from an executive—volunteer to research industry data for their next board presentation.
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