The Skill I Stink At: Learning to Ask for What You Want

Confession time. I stink at asking for what I want. I’ve also been guilty of expecting others to be mind readers, although I didn’t recognize it as such at the time.

“Can’t he see I’m upset? He should ask me what’s wrong.”

“They’ll notice how busy I am and offer to help.”

“I could really use a listening ear right now—surely someone will be inspired to call me.”

Sound familiar? If you often feel disappointed or frustrated because others didn’t meet your needs, it might be time to ask yourself: Am I expecting people to read my mind?

I’ve talked about this before when I mentioned the “manuals” we write for other people—those unspoken rules about how we think they should behave. But here’s the truth: People are terrible at reading minds and following rules they don’t know about.

Why Asking Feels So Hard

Let’s be real: asking can feel super uncomfortable. Somewhere along the line, many of us equated asking with being selfish—think again. Asking isn’t selfish—it’s just honest, clear communication.

In fact, asking can make other people’s lives easier at times. When I was caring for my mom, it would have been so much simpler if she’d told me what she needed instead of leaving me to play the guessing game.

But when we don’t ask, we set ourselves up for disappointment, discouragement, and yes, even resentment.

Start Small

If this skill doesn’t come naturally to you, don’t panic. Start small. Ask for help with minor things and work your way up to bigger asks. This has been an awkward but worthwhile practice for me.

Instead of trying to do it all, I’ve started leaning on others. My daughter helps me with the techy backend of my website (she’s a whiz at that stuff). My husband? He’s my go-to for graphics—several of my blog visuals now sport a little “Ron flair.” As president of a children’s organization at church, I’ve learned to delegate responsibilities to my assistants instead of shouldering the bulk of the work out of fear of burdening others—a big win for me. And recently, I got brave and reached out on social media, asking for conversations. The result? Some truly meaningful connections.

Here’s the thing: every time I ask, I feel a little braver and a lot lighter.

The Birthday Test

Birthdays are like the Olympics of mind-reading expectations, aren’t they? We think, “Surely they’ll know exactly what I want and make it happen!” No one knows your birthday wishes better than you.

Want a party? Ask someone to throw it—or throw one yourself, exactly how you envision. Craving your favorite treat? Request it—or make it. Eyeing a specific gift? Drop hints—or treat yourself!

In fact, I’ll practice right now. For my birthday this week, I’d love a gift from you. Could you share one small way I’ve made your life a little better in the comments below? I’ll keep your kind words handy for those days when I’m feeling discouraged or stuck.

Practice Asking

Here’s your challenge: go practice asking. Start small, but don’t stop there. And remember, the goal isn’t to always get what you want—it’s to get comfortable asking.

The discomfort of asking is far more empowering than the disappointment of unmet expectations. Trust me.

Now go ask for something.

High five ✋

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