Hey, Hey, Hey Reader,

“I don’t want to bother them.”

Have you ever said that to yourself about following up on a proposal?

Or about checking in with a former client you haven’t talked to in two years? Or asking a colleague to introduce you to someone they know?

So you wait.

You tell yourself they’ll reach out if they’re interested. You reread the email you drafted, tweak the first line, and leave it sitting in your drafts.

In October, inside The Expert Up Club, we set out to bug people during 🍂 Asktoberfest.

We failed spectacularly.

592 asks went out the door, and not one came back “you’re bothering me.”

Twenty-two experts spent the month pitching podcasts, emailing people they’d never met, and sending 80 direct “want to work together?” invitations.

By the end of the month, 174 of those asks had turned into a yes and 130 into a no.

The no’s sounded like “not right now,” “not in the budget,” and “we’re all set.” That’s information about someone’s calendar and budget, and it’s useful.

Former clients told one member it meant a lot that she’d checked in, even though they weren’t in a position to hire her again.

And then someone swung big.

This member made three of the biggest asks you can make, all to the same organization, on the same day.

One was a no. Then the CEO wrote her back and wanted to hear her ideas. She’s now sending a proposal to her dream organization. (See what happens when you ask?)

What a month of trying to bug people taught us:

Silence means they’re busy.
Nearly half the asks still haven’t gotten an answer. Your email landed in the middle of someone’s week, and they meant to get back to you (and didn't)

The follow-up is the favor.
183 of the asks were follow-ups. In one week alone, 18 follow-ups turned into 5 yeses. As Heidi Taylor (our guest expert in residence) likes to say, a follow-up is often a gift to the person getting it.

Sometimes the fear is the yes.
A few members realized the thing they were dreading was what happens if the ask works. If you’ve been circling an ask for months, check which outcome scares you more.

Asking is a muscle.
The first ask is the hardest one you’ll make. You rewrite it, read it out loud, and hover over send for a while. The fifth ask is easier. By the twentieth, it’s something you knock out on a Wednesday morning between other things.

One member made 101 asks in her first 12 days. When I asked what got easier, she said she’d proved to herself that nothing bad happens.

Once the small asks feel routine, you’re ready for the money ask. In the first week of November, “want to work together?” became the most common ask in the Club: 20 of 71.

Which brings me back to that email in your drafts.

The members didn’t want to stop when October ended, so we kept going. Asktoberfest is now 🎄Askmas. (Yes, it’s a terrible name. I love it anyway because it sounds like Ass-mas every time I say it.)

The scoreboard reset on November 1, and on December 17 we’ll celebrate the asks we made at our year-end party, holiday prizes included.

If you want to send those drafts (finally) with the accountability of a room full of experts cheering your no’s as loudly as your yeses, come join this asking holiday.

​Check out The Expert Up Club →​

Your first ask might be the one that turns into a proposal for your dream client.

Yours in rebellion,
Michelle