Why Asking for Help Feels So Hard (Especially for High Achievers)
I coach others to do it. I'm still learning to do it myself.
Recently I’ve been watching the students I mentor ask for letters of recommendation for college programs and scholarships.
The email sits drafted longer than it should. They reread it three times before hitting send.
Would you be willing to write me a letter of recommendation?
They know it’s reasonable. They’ve worked hard. They’ve built the relationship. The teacher or mentor would likely say yes without hesitation.
And still.
Will they say yes? Do they feel I’m worthy? Is this an inconvenience? Am I asking for too much?
I coach them through it easily. Of course they’ll say yes. You’ve done the work. This is part of their role. People want to support students who show initiative.
And yet I know exactly how they feel.
A few years ago, I was going through a director-level promotion process and was told the approval wasn’t likely. Not because of my performance, but because I didn’t have enough visibility or support for the work I was leading. I had to go back to my manager and ask: What would need to be true for this to be approved? Then I had to reach out to senior leaders and ask for their advocacy. Ask for the opportunity to present my work to a broader audience. Ask people, directly, to go to bat for me.
I knew it was reasonable. I’d done the work. And still, the same questions creep in. The ones I so easily help others dismiss.
Am I imposing? Will this make me look less capable? Should I just figure this out myself?
It’s funny how clearly we can see courage in someone else… and how complicated it feels when it’s our turn.
The Pattern: Independence Gets Rewarded Early
Many of us were rewarded early for being independent. Engineering and tech cultures are built around problem-solving. You were hired for your ability to figure things out. The harder the problem, the more capable you looked when you solved it alone.
So competence becomes part of our identity. Being reliable, low-maintenance, the one who doesn’t need much — that’s the brand that gets you noticed, promoted, trusted with more.
And for many high-achieving women in these environments, there is an extra layer: belonging often means being capable without appearing to need much. Asking for help may confirm a doubt someone might already have.
The trap is subtle. The very traits that carried you forward — self-sufficiency, grit, the ability to figure it out — quietly become the things that make asking feel dangerous. Like exposing a gap. Like admitting the problem-solver can’t solve this one alone.
If I were truly good enough, shouldn’t I be able to figure this out myself?
Asking for Help Is a Leadership Skill
Here’s what I’ve come to see:
Independence builds competence.
Asking for help builds capacity.
Early in your career, the question is: Can I do this myself?
As you grow, the question shifts to: Who should I involve?
And at the leadership level: How do we do this better together?
Independence → Collaboration → Leverage.
Leaders don’t get ahead because they know everything.
They get ahead because they know who to involve.
Asking for help accelerates learning, increases visibility, invites sponsorship, and builds advocates.
Senior leaders ask for help constantly. They just call it collaboration.
High performers don’t wait until they’re overwhelmed to ask.
They ask early.
They ask clearly.
And they ask in a way that makes the other person feel valued — not burdened.
That’s not weakness.
That’s strategic maturity.
The Career-Changing Asks
We often think of asking for help as something small: “Can you sanity check this?”
But some of the most career-changing moments begin with a clear ask:
“Would you be willing to advocate for me for this role?”
“Is there an opportunity for me to present this work to the broader team?”
“What would need to be true for me to be considered ready for X?”
“I’d like to expand my scope. Where do you see opportunity?”
Those aren’t dramatic confessions of inadequacy.
They’re signals of ambition.
They’re invitations.
Those were my asks.
My promotion was approved.
Not because I suddenly became more capable, but because I became more visible and more supported.
The students asking for letters of recommendation are learning something powerful early:
You don’t get opportunities just because you’re capable. You get opportunities because you’re capable and you ask.
That’s true at every stage of your career.
Small asks build visibility. Visibility builds advocacy. Advocacy builds trust. And trust opens doors that capability alone never could.
The ask you make today (even a small one) is rarely just about what you need right now. It’s laying the groundwork for what comes next.
You Don’t Carve Alone
We talk a lot about carving our own path.
But no one carves alone.
Every meaningful step in your career has likely been shaped by someone who opened a door, gave perspective, offered feedback, or advocated on your behalf.
The next version of your path might not require more effort. It might require one clear, courageous ask.
So I’ll leave you with this: Where might asking for help make this easier right now?
Not because you can’t do it alone.
But because you don’t have to.
Keep carving your path, Tracy
I like all of your essays, Tracy, but this one particularly resonates with me! During my career, I never thought of asking for help as a leadership skill… instead, I looked at it as a weakness. I love this perspective and wish I had had it years ago!