How to Get Better at Anything, Without Feeling Like an Imposter
THE SCENE: STORY TIME
In 7th grade, I sat at my desk, staring at a blank page, feeling completely defeated.
My English teacher, Sister Anne, a no-nonsense nun with an obsession for perfect grammar had assigned us a 15-page research paper, fully cited in MLA format.
We were 12 years old.
It felt impossible. Why was she doing this to us?
I remember crying, overwhelmed by how much I didn’t know, convinced I wasn’t capable. But I pushed through. I finished the paper.
And I got an A.
At the time, I didn’t realize that Sister Anne wasn’t just teaching us how to write. She was teaching us how to push through stretch assignments. The ones that feel completely beyond our reach. The ones that feel like they might break us, but instead, build us.
I didn’t know it then, but that was my first lesson in mastery.
The assignments that make you uncomfortable? The ones that make you doubt yourself? They’re the ones that set you apart later.
And the part no one tells you? High achievers struggle with the emotional weight of learning a new skill more than anyone else. Not because we lack ability. But because we’ve built our identities around being great. And when we’re suddenly not great? It messes with us.
LET’S HAVE FUN: A QUICK POLL
REALITY CHECK: THE IMPACT
Why Learning New Skills Is More Challenging for High-Achievers
You’ve spent years being great at what you do. Your expertise is second nature. You don’t have to think about it anymore—you just know.
Then you step into something new. And suddenly? You don’t know sh*t.
The gap between who you were at your peak and who you are as a beginner is wide. So wide it hurts.
And that gap comes with big feelings.
Inadequacy.
Frustration.
The urge to quit before you embarrass yourself.
We assume that if we don’t pick it up quickly, it must mean we’re not cut out for it. But that’s a lie.
Then doubt creeps in…
You start second-guessing yourself before you speak. You over-explain things that never needed justification. You shrink in meetings where you previously used to own the room. And before you know it, you start wondering if maybe you just aren’t cut out for this after all.
You’ve probably heard of the 10,000-hour rule popularized by Malcolm Gladwell: the idea that world-class mastery requires years of practice. But since then, research has uncovered that you don’t need 10,000 hours to get good at something—you just need 20.
Most people quit because they don’t see immediate results. But repetition comes before results. Always. And if you don’t start putting in the 20 hours it takes to get good at something? You’ll wake up six months from now, still feeling stuck, still hesitating in meetings, still wondering if you belong.
Or.
You could look back and realize you’re already better. More confident. More in control. The only difference? You put in the reps.
20 focused hours of practice is all it takes to move from feeling completely incompetent to being functionally skilled. That could mean 20 executive conversations, making 20 high-pressure decisions, 20 times speaking up in meetings. You could build competence in a matter of weeks.
I saw this firsthand when I launched my coaching practice. I had 25 conversations in my first month. The first ones? Bumbling. Uncertain. Half the time, I wasn’t even sure what I was offering. But by the 20th conversation, something clicked—I had refined my message, my confidence had grown, and I had a few paying clients on my roster.
THE FRAMEWORK: HERE’S WHAT WORKS
Here’s What to Do When You’re Stuck in the Beginner Phase
If you’re in the gap between where you are and where you want to be, here are 3 effective ways to push through your next beginner phase.
1. Achieve The Results You Want by Focusing on Reps
High achievers love results. That’s why learning new skills feel so brutal—because you’re measuring yourself against mastery instead of progress.
Right about now, you’re probably thinking: “I get it, but I don’t have time to just practice—I need to be good now”. Or maybe, “I can’t afford to mess this up at my level”. My clients feel these exact feelings particularly when stepping into new roles. It’s hard because you expect to be great immediately instead of giving yourself time to put in the reps. The shift is uncomfortable because a new role requires you to:
Make decisions with incomplete information
Speak with confidence before you feel ready
Navigate relationships with new peers, leaders, and teams
The only way to get better? Do it over and over until it feels natural. Instead of focusing on results at this stage, my advice is to set reps-based goals.
Examples:
Instead of “I need to be a stronger speaker,” → Try “I am going to speak up in 3 meetings this week”.
Instead of “I need to be a better leader,” → Try “I need to make and communicate 3 decisions this week without over-explaining myself”.
Instead of “I need to be confident in executive meetings,” → Try “I need to contribute one strategic thought in every leadership meeting this month”.
→ The Lesson: The fix for feeling like you’re not good enough? Setting the right reps based goal and then doing it again. And again. And again. Until one day, you realize it’s just who you are.
2. Stop Aiming for Perfection—Start Optimizing for Feedback Loops
High achievers don’t fear failure. We fear looking like we don’t know what we’re doing.
But honestly, no one expects you to get it right the first time. They just expect you to stay in the game long enough to figure it out.
EXAMPLE 1
Here’s an example where I had to challenge myself → one of my clients is brutally honest and for some, his directness is intimidating. Getting feedback from him can feel like you failed, but people who are willing to be direct are incredible growth accelerators. I’ve learned that:
You can workshop things on the spot and get to a better outcome by leveraging people in the room.
If he has feedback, we unpack it. Together. We refine as we go. We get to a great endpoint faster.
Instead of feeling pressure to deliver something perfect upfront, I create intentional feedback loops with him and that makes the work better without the stress.
EXAMPLE 2
Here’s another example → a client was feeling the weight of failure while working on a massive strategy deliverable in a brand new role. He felt like he had to get it perfect the first time—which made the work feel overwhelming.
So I asked: "What if you presented just one or two parts of your strategy—the parts you’re most confident in—to your manager first?"
"What if their feedback helped you shape the rest?"
He did it. And it worked.
Breaking the task into smaller feedback loops made the process less daunting—and the final product stronger. The strategy is locked and as for how he’s feeling in his new role? Settled.
→ The Lesson: Mastery isn’t about getting everything right the first time. It’s about iterating until it clicks.
3. High Achievers Struggle to See Progress—Here’s How to Track It
Honing a new skill doesn’t feel like progress. It feels like a struggle.
And that’s why people quit because they don’t realize they’re getting better.
I watch this happen with my clients all the time—they go from:
Hating public speaking → Volunteering to present at company-wide presentations.
Feeling like they don’t have what it takes to be an executive → Landing an executive role a month later.
Never having negotiated their salary → Pushing past the first “no” and getting a raise.
And you know what happens in almost every case?
They don’t stop to celebrate.
→ The Lesson: High achievers are wired to immediately focus on the next thing. But when we stop and reflect, it puts our progress into perspective. You’re doing better than you think you are. And if you tracked your reps, you’d see how much progress is already happening.
THE WRAP UP
Stop Waiting for Confidence—Becoming Great Comes From Reps, Not Readiness
This week, remember these insights:
Mastery isn’t about feeling ready. It’s about staying long enough to get great.
You don’t need confidence—you need repetition.
You’re not bad at this. You just haven’t done it enough times yet.
And if you still don’t believe that mastery sneaks up on you, try this: when my clients hit a wall when trying something new, I walk them through the following exercise.
Think back to the last time you learned something new.
What was the skill?
What did it feel like in the beginning?
What was hard about learning it?
How did you mess up? What did messing up feel like?
And now—where are you with that skill?
You’ve probably mastered it now. It feels easy. It feels natural. But remember how long it took to get there. If you’re reading this, you’re likely pursuing some sort of greatness—so keep going, like Timothee Chalamet →
Mastery is coming. Stick with it.
Good luck! See you next week.
Ashley
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Love this and deeply resonated with it. The bit about 20 hours is super helpful.