You can ask for anything

There’s a catch, though.

Sep 05, 2024

“Your friend shouldn’t have asked you for that, it’s so inappropriate.” Dad’s voice is laced with concern: my daughter has surrounded herself with people who take advantage of her.

I smile, “Why not?”

Dad’s insistent. “It’s just not something they should ask for.”

“That’s where we differ,” I explain. “I think my friends have the right to ask me for anything—there’s no ‘should’ or ‘shouldn’t.’”

I can tell from dad’s silence that my line of thinking has never crossed his mind. He appears deep in thought, slightly uncomfortable. I continue, “I don’t mind my friend asking me for that. In fact I applaud them for having the courage to ask.”

“Did you agree to it?”

I laugh, “Of course not! It’s not something I’m willing to do.”

Dad looks worried again, “How did they react?”

“They didn’t. We moved on. It’s forgotten.”

“Easy as that?” Dad’s surprised.

“Yes. Easy as that.”

Asking is a superpower

Ask me for my biggest lesson in three and a half decades of living and learning, and with complete conviction I’ll say: Asking is a superpower.

Every single dream I can’t believe I’m living began as an “ask”:

I wouldn’t be on top of this beast of a newsletter at work if, six months ago, I hadn’t asked our Head of Operations to extract me from irrelevant tasks that prevented me from allocating the hours required to understand all the intricate newsletter processes that, back then, were as transparent to me as an undiscovered life form.
I wouldn’t have 250 subscribers to my own newsletter if, when I started, I hadn’t asked my friends and family to subscribe and if, later on, I hadn’t routinely asked writers I barely knew to recommend Val Thinks to their readers.
I wouldn’t have a #1 New York Times bestselling author for a writing mentor if I hadn’t asked him to do me this favour.
I wouldn’t have my best friend in HCMC if I hadn’t first asked for her number, then invited her for coffee one day.
I wouldn’t have a solid community beyond HCMC if I didn’t regularly reach out to each and every friend, ask how they’re doing and, if I was in town, whether they wanted to meet.

I asked for all these things, by the way, not because asking came easy, but because I realised, somewhere in my 30s, that if I never asked, I’d never receive.

It’s not anyone’s job—your partner, your parents, your child, your friend, your boss, your colleague, your doorman—to divine what you want and give it to you.

It’s your job to ask.

Which is why, time and again, I steeled myself for rejection and bit the bullet. Everything I wanted, I asked for. I 100% would not be where I am if I hadn’t, year after year, trained myself to be the kind of person who always asked for what I wanted.

But there’s a catch.

The catch

Asking isn’t free.

“You’ve got nothing to lose” is bullshit—there is a cost to asking.

Depending on who and what you’re asking, your ask could use up what social capital you have, damage your standing with that person, even provoke them into cutting the cord.

Which is why I suggest approaching asking very, very thoughtfully.

The next time you want to ask someone for something, first ask yourself: What is the price and am I willing to pay?

Is it worth being perceived as an unhelpful team member for a shot at being an amazing newsletter manager?
Is it worth annoying my friends, my family, writers I respect for one or a handful more newsletter subscribers?
Is it worth changing my relationship with my boss to get world-class mentoring for my writing?
Is it worth the embarrassment of a rejection to gain my first friend in this city I’ve just moved to, and to keep my friendships elsewhere alive?

Once you’ve decided the price is worth paying, there’s one more question to come to terms with before making your ask: Am I OK with a “no”?

For every successful request I’ve made, there’s three more that got turned down or ignored. And I wouldn’t be surprised if a few bold asks have alienated a friend, a family member, an acquaintance.

Every time you ask for something, you’re not only setting yourself up for success, you’re also setting yourself up to fail, sometimes spectacularly.

And it’s on you to live with the consequences, whatever they may be.

What do you think?

No class of individual dismays me more than someone who asks me for a favour, then gets indignant when I say “no.” You can ask anyone for anything, but no one is liege-bound to grant your request, however small.

Two questions for you this week:

What’s the last thing you asked for? And were you OK with a “no”?

If you got what you asked for, congratulations on exercising your superpower! If you didn’t, how did rejection make you feel? Did you react with understanding or indignation? Please hit “reply” or leave a comment—I read every response and I’d love to hear from you. If you’re still reading, I ask you to share this post with whoever you think might get something out of it.