I am not awesome at asking for what I want.

Sometimes, this shows up in little ways, like not asking a server to have a messed up order fixed or not asking the person in front of me in the theater to sit up a bit so their chair isn’t resting on my knees.

Sometimes, this shows up in big ways; not asking for what I wanted no doubt contributed to the demise of my marriage.

I could probably write a whole post on why I think I find this so difficult – why I think so many of us find asking for what we want difficult to the point of being paralyzing. The vulnerability, the social norms, the fear of displeasing others…

But I’d rather share an awesome experience I’ve been having of practicing asking for what I want.

You probably know by now that I joined a fundraiser for Big Brothers Big Sisters. I joined because it’s a fantastic organization (I dig on anyone who’s working to inspire and uplift kids) and because I’m afraid of heights (the 11-story rappel for raising enough made me nervous in that way that often motivates me to march forth).

And, you guessed it, I saw asking for donations as a way of practicing asking for what I want.

It’s a bit of a hack, right? It’s easier to ask for donations for an incredible not-for-profit than to ask for, say, someone to become a client or for a restaurant to remake my omelet without the cheese. (I know, cheese is delicious. Stick with me here.)

So, I signed up and one Friday when I thought I’d be traveling but instead found myself with a wide open day, I sent out just shy of 150 emails asking for donations. Around $1,300 in donations came in over the next two days.

I followed up by publicly thanking each person who donated and again, in those posts, asking for donations. More people donated.

This past Friday, I took a screenshot of my fundraising site showing $2,426 in donations and I asked the wide world of social media to help me round it out to $2,500. Within two hours of posting, a wholehearted friend who was kind enough to love me even when I was an ornery 18-year-old posted: “Done. With love.”

$2,501 for Big Brothers Big Sisters donated by 44 donors.

Now that I recall, it was actually more than 44 donors because I asked my friend Mike Angelillo to ask his crew for donations and he collected $325 of that total – in addition to his own donation – and added it in a lump sum.

I just asked, friends. And when people said no for whatever reason, I said, “Hey, no problem, thanks for letting me know,” because it wasn’t a rejection of me or even of Big Brothers Big Sisters. It was just a decision.

Now my muscles for asking are a little more practiced. Just as I’d add heavier weights to the barbell if I were practicing deadlifting, I’m now prepped to ask for somewhat scarier things – for those clients, or those things I want, or even forgiveness.

Now my gut is a little more steeled for those inevitable Nos, and my mind is a little more prepared to see them not as rejections of me but rather as simple decisions.

What do you want that you haven’t yet asked for? What would it take to prepare yourself?

Oh, and since you’re here, would you be interested in donating a few bucks to Big Brothers Big Sisters? I’d really love to get to $3,000 and as of writing this, we’re only $449 away!

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