Make a Big Ask

Each week, I’m challenging myself to complete a Dare of the Week. A weekly goal designed to live more intentionally and be a better man. And I’m inviting you to join me.

This week’s dare: Make a big ask

What if the door between where you are and where you want to be is just a question away?

What if the door between where you are and where you want is just a question away? This is the possibility behind this week’s dare of making a big ask.

If you’re like me, you feel uncomfortable asking anyone for anything. I don’t like admitting I need help. I don’t like feeling as if I’m bugging someone. And, quite frankly, I don’t like the possibility someone will reject my request.

But the worst that can happen isn’t that someone will reject our ideas, our questions, or our dreams—it’s that no one will hear them at all.

Making a big ask means making your dream real. I think many of us actually prefer our dreams to live in the safety of lala-land. Where it’s caged comfortably in our imaginations, free from harm, but never free to fly. That’s tragic because the worst thing that can happen to a dream is for nothing to happen.

If you have a dream that can be accomplished alone, you are dreaming too small. If you want to do anything worthwhile, the time will come when you will need to ask others to help make it happen. This is true in life, work, and relationships. Don’t let the potential for rejection keep you from the possibility of accomplishment.

This week’s dare is to make a big ask. It might be about launching a project, securing a meeting with someone influential, or asking that girl out for dinner. Whatever it is, keep these things in mind:

• Write down the name of the person you want to approach this week.
• Write down what the ask is.
• You’re inviting them into a story, be ready to share what that story is.
• Think about how your request is a win-win for both of you.
• If you have a relationship them, reach out directly.
• If you don’t, write down a list of people who do, and contact them.
• Read this article by Ben.
• If you get the opportunity, make the most of it, and respect their time.
• Don’t make them guess what you’re asking. Be clear and direct.
• Get over yourself and do it.

I know it can be nerve-racking, but having the guts to make the ask is often the difference between those who don’t and those who do. Let’s be the kind of people who do it!

Are you up for this week’s dare? If so, let me know. Either drop a note in the comments, shoot me a tweet, or post a comment on the GoodSirs Facebook page. 

I would love to hear from you.