Making the ask

Lately I’ve been trying to get better at something simple and surprisingly difficult: making the ask. Not just in work, but everywhere. Asking for help. Asking for the meeting. Asking someone to be a mentor. Asking for the funding. Most people don’t struggle because they ask for too much. They struggle because they ask for too little, or not at all. I noticed this recently when I spent an unreasonable amount of time debating whether I should reach out to someone I deeply respect and ask them to be an advisor. They were busy, accomplished, and well outside my immediate circle. I told myself I should wait until the company was further along, until I had more traction, until the timing felt “right.” Eventually it became clear that the thinking itself was the problem. Asking the question would take 1 minute. If they said no, I’d have an answer and could move on. If they said yes, incredible. Either way, the ambiguity would disappear. The only bad outcome was not asking. The same pattern shows up with investors. You can research endlessly, refine the pitch, and wait until everything feels perfectly aligned. Or you can get on the phone, be clear about what you’re building, say what you need, and ask. Most of the time the answer will be no. That’s normal. You learn something, improve the product, and keep going. What feels like fear of rejection is often fear of clarity. Possibility is comfortable because it hasn’t collapsed into reality yet. But possibility is also a kind of inertia. It lets you delay action while convincing yourself you’re being thoughtful. Not asking has a hidden cost. It creates imaginary narratives. It turns uncertainty into background noise that quietly drains attention. You end up spending more energy avoiding an answer than you would getting one. People I admire tend to be unusually direct—not aggressive, just clear. They’re willing to ask plainly and accept whatever comes back. It’s just information. There’s also something respectful about making the ask. It signals that you value your own time and the other person’s. It replaces ambiguity with honesty. In that sense, asking is a form of kindness. I’m learning that confidence doesn’t precede action. It follows it. Each time you ask and discover that you’re fine either way, the fear loses a bit of its grip. So I’m trying to ask more often. Not impulsively. Not without preparation. But without waiting for certainty or perfect timing. Because the cost of asking is brief discomfort. The cost of not asking is remaining stuck. And progress, in startups and in life, seems to favor the people who are willing to find out.