Ask for what you want.

A few years ago, a company asked me to come speak at their annual conference.

I wanted to quote $25K plus travel expenses, which felt like great money, and I was pretty sure they'd say yes at that price. Plus, we’d been wanting to visit the city where the event was happening anyway. Jennifer looked at the email over my shoulder and said, “Ask for $75K. You're worth it. They'll say yes.”

Then she just walked away. She was so nonchalant about it, and I thought she was out of her mind.

When she came back into the room, I was still baffled by her suggestion. “That…That…That's just not how I work…I don't feel comfortable with that at all!”

“You'll regret lowballing yourself,” she warned.

It irritated me that Jennifer made the ask seem so easy. She wasn’t the one managing this relationship, after all. And what if I lost the opportunity to make $25K?

But I thought about what she said, and I reviewed the response I was putting together. I changed that 2 to a 7. $75K, plus travel expenses.

I stared at my screen for a while, feeling like this was crazy, and I forced myself to press send. Fifteen minutes later, a simple “Sounds good, send over your invoice” was sitting in my inbox. The speed of their response told me I’d probably still left some money on the table.

This was the first time my eyes were opened to the power of asking for what you want. Not just because of the money, but because it made me think about every opportunity I’d missed by not asking. Every room I wanted to be in that I'd decided I wasn't qualified for. Every person I'd assumed was too important to reach. Every raise I deserved but thought the boss would laugh. It stings when you realize the instincts you’ve relied on for so long can be wrong sometimes. Badly wrong.

The reality is that many things you want in your life have some kind of gatekeeper. And the gatekeepers are usually real people, with real names, who might actually hand you what you want…if you just ask. It could be something as small as an introduction or as big as writing the foreword for your new book. Maybe you can even get that speaking fee that feels absurdly high.

Since my speaking event, I like to practice asking for what I want. I’ve adopted a what the hell, why not? attitude. I reached out to a famous author whose writing dramatically impacted my life, assuming he was wildly untouchable. I imagined a fortress of assistants screening his messages, looking for people significantly more important than me. But I decided to take a chance anyway. I found his email address, crafted a thoughtful note, and sent it off to see what would happen.

Two weeks later, we were having a beer on a Zoom call.

There are a million reasons why people don't ask for what they want. It's uncomfortable, or they don't want to be seen as a burden, or they're afraid of rejection. The list goes on. But I think the biggest reason is that asking means you might find information you don’t like.

Because when you never ask your favorite author for a meeting, you get to keep that version of him that lives in your head. Warm, generous, happy to hear from you. But when you make the ask, you risk learning that your imaginary version isn't real. And most people would rather hold on to a fantasy than test it out to see if it's true.

As long as you never ask for more money, you get to believe you're underpaid. Strangely, that's an easier pill to swallow than asking and hearing no. Because when “no” happens, you have to actually go out and do something about it. So most people will never do the asking, remain underpaid, and complain about it.

Once you're willing to risk a no, the only thing left is the ask itself. Lead with them, not you. What's in it for the person you're reaching out to? And why should they care? A crisp, specific ask lands completely differently than a meandering one that makes the other person do all the work. So get to the point, and make it easy for them to say yes.

You'll probably get more nos than yeses. That's just how it goes when you start asking for things you want. But if you make a hundred uncomfortable asks this year instead of none, and even twenty percent of them land, that’s twenty things you didn't have before. New introductions. More clients. Bigger and better conversations with important people. New opportunities. And twenty more yeses a year compound into an incredibly different life.

I won’t pretend this is easy. That nervous feeling I get before a hard ask has never gone away. I felt it before I typed $75K into that email, and I felt it before I asked for a Zoom with one of my favorite authors. The fear shows up right on time, every time. What changed is that I've stopped letting that fear tell me a story about how the ask is going to go. Because fear doesn't know what the other person is going to feel or do or say. Fear is just noise.

And you don't know what's true until you ask.

So here’s an idea worth thinking about. Somewhere out there is something you want. And there's a person who has the power to give it to you. And there's a conversation you've been avoiding because you already think you know how it ends.

But you don’t really know. Maybe today is a great day to find out.

That’s all for this week.

See you next Saturday.