Ira Glass’s Advice to Help You Fight Your Way to Master Any Skill

When what you’re making tastes bitter, keep showing up.

It was 2015 and my first day to teach a class of 50 adult students. On this particular day, I was hoping to deliver good public speech. After all, I’ve been practicing in front of a mirror on how to stand in front of people for months. I’ve been studying good public speakers who are eloquent and graceful on any public stage. At the end of the day, I was hoping my students would stand up and clap for my public speaking ability.

What that day ended up with was far more interesting.

My first public speaking failed spectacularly. I knew a great speaker when I saw one. But when I stood in front of people and started speaking, it was hard to pull it off, even for a minute or two. I had the taste of what good speaking tastes like but not the skill.

That day, I almost gave up. Even though public speaking is a skill I wanted to master, my wavering voice disappointed me. As I walked out of my first failed class, shoulders slumped, I convinced myself I will never be as good as those expert speakers I watched meticulously.

If you’ve ever felt like your skill will never match those experts you aspire to be, you understand what I’m talking about. If, for example, you’ve ever felt like you can never write a good sentence like good writers, you’re with me. You start writing consistently and you’ll begin to notice when you read great work. But when you try to do great writing yourself, you fail to produce something great.

It’s easier to recognize a masterpiece than it is to create it.

You want to write good sentences, but your sentences are not good enough. They are trying to be good enough, but they are not there yet. Your terrible sentences feel like they are crawling — not even walking — towards a masterpiece.

Maybe developing writing skills is not your thing. Conjure up in your mind any skill you are trying to master. Painting. Drawing. Content creation. Video making. Customer handling. Leadership.

What do you do when what you’re making disappoints you? What do you do when your skills are not good enough?

Most people can’t get past this terrible feeling of disappointment. They quit at this stage. They stop working on their skill.

In my case, I learned something unforgettable at the end of my horrible day. While I was crying in my bedroom replaying my failed speaking attempt, a friend gave me a printout that changed my life. This printout was an insightful paragraph from the host of a popular national public radio show.

“Nobody tells this to people who are beginners and I really wish somebody had told this to me.”

Ira Glass is the host and executive producer of the popular National Public Radio show, This American Life. The show had led to a wide range of opportunities (book deals, feature films, and appearances on popular TV shows).

Such a huge success did not happen overnight.

When Ira Glass was a 19-year-old intern, he had a taste for journalism and storytelling. He knew what good journalism looked like when it was done well. But it took him 17 years of hard work before he could start to do it well himself. 17 years to master journalism skills.

Most of what we hear or read about mastering a skill misses something.

Most people forget this crucial part of mastering any skill. The brave part where a person shows up every day to practice a particular skill despite his heart cracking in its entirety — because his work is disappointing him.

What makes this person show up when his skill level is so low?

Many articles and books tell us to show up for our work. But I’ve never read an article that helps me to deal with my feelings of utter disappointment when what I’m making is not good enough. How do I keep working on my skill when disapproval for my own work barges in my door and glares at me? How do I silence the insidious voice that whispers to me, your skill will never be good enough?

I’ve never read any good insight on how to deal with disappointment until my savior friend gave me the printout of this paragraph on that horrible day,

“Nobody tells this to people who are beginners and I really wish somebody had told this to me. All of us who do creative work, we get into it because we have good taste. But it’s like there is still this gap. For the first couple of years that you’re making stuff, what you’re making isn’t so good. It’s not that great. It’s trying to be good, it has the ambition to be good, but it’s not that good. But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell what you’re making is kind of a disappointment to you. A lot of people never get past that phase. They quit.” — Ira Glass

When I read Ira’s insight, I was lying on my bed mourning the loss of my public speaking dreams. When a particular paragraph reminds you of your own life, you stop and think. That moment felt like Ira was talking to me. I probably read the paragraph 50 times.

When the message sank in, I got up from my bed and dried my tears. Ira’s words gave me the courage and determination to never give up on my public speaking skills.

I told myself, my public speaking skill is not good enough now. But one day, it will be.

This is true for any skill you’re trying to master.

The gap between being an apprentice and being a craftsman is the enemy that stands in our way of becoming an expert on any skill.

The apprentice has the taste but not the skill. The craftsman has taste and skill.

Think about it. Let us say you want to master painting. You’ve been studying the works of a famous painter you admire. The paintings your idol produces is mouth-watering. You can’t take your eyes off his pieces. You recognize a good painting when you see his work. You want your paintings to be as good as him. So you start painting.


Your work disappoints you. You can’t even look at your paintings. In your mind’s eye, you saw people lining up to buy your paintings because they were that good.

You want your skill to taste as delicious as your ambitions.

Except the reality is so far from your imaginations.

You have a long road ahead of you. A wider gap exists between the skill you have now and where you want your skill to reach.

This gap becomes the enemy.

When you find your current skill tastes bitter, misery and discouragement creep in. Your skill level at this stage is so low that you start thinking you will never match your taste with the skill you need. You start retreating from working on your skill development. You end up abandoning your skill in the middle of a road.

Instead of giving up, think of the thing that got you into the game.

What got you in your skill development in the first place? We need to think about the love and strong reason that urged us to walk in the direction of developing a particular skill.

We need to remind ourselves of why we are in the game when we are at our lowest. Never forget what got you there in the 1st place. You still belong, even if you don’t feel like it right now. Even if your talent is questionable.

Think about your love, passion, purpose, and taste when you fail to produce something good.

When producers failed to notice him, Ira Glass reminded himself of why he wanted to be a good journalist. Nothing boosted his self-esteem like his compelling reason to pursue journalism. “I love storytelling. That’s why I need to keep working on my skills.” This reminder gave his thirsty skill much-needed water when his skill was walking all alone in a desert. Reminding myself of why I wanted to be a public speaker gave me the courage to stand in front of people the next day after my failure.

Do yourself a favor. When what you’re making disappoints you, remind yourself of why you’re pursuing a particular skill. You love making videos. You love cooking. You love creating sentences. You love talking to clients. You love architecture. You love designing clothes.

Oh yes. You’re working on something because you love doing it and want to produce something good.

Remind yourself of your compelling reason when what you’re producing is not good enough.

This is the strategy I apply to my writing as well. When I feel the sentences I’m creating are not as good as Ryan Holiday’s (he’s my favorite writer). When doubt creeps in with its insidious voice, “Will I ever write such delicious sentences like Ryan Holiday?” I remind myself of why I’m writing in the first place. I’m writing because I love creating words and want to produce good sentences one day.

When you feel your skills will never be as good as your ambitions, think of the thing that got you into the game.

And one more thing…

You’ll never score a goal if you hold a beloved ball and dream about scoring a great goal.

To score a goal, you need to dribble the ball. One dribble at a time. And if you have never dribbled a ball in your life, you have to learn how to. And practice what you’ve learned.

The same is true for mastering any skill.

You need to commit to the process. Reminding yourself of why you’re pursuing a particular skill is not enough. Just like holding a beloved ball and dreaming about scoring a magnificent goal is not enough. You need to dribble the ball. Do the same for any skill you love pursuing. Even when the level of your skill disappoints you, show up. Put in the work. Be consistent. The small improvements you make day after day are sharpening your skill. In time, your skill will be good enough.

In “All You Need Are a Few Small Wins,” Ryan Holiday writes,

“Creating anything of consequence or magnitude requires deliberate, incremental and consistent work. In the beginning, these efforts might not look like they are amounting to much. But with time, they accumulate and then compound on each other. Whether it’s a book or a business or an anthill or a stalagmite, from humble beginnings come impressive outcomes.”

Never stop dribbling your ball.

No one could stop me from continuing to dribble my ball (my public speaking and writing skills). Ira worked on his journalism skills for 17 years before he became a popular host for a successful Radio show. I worked on my public speaking skills for 5 years. Today, I’m a sought-after public speaker in Ethiopia. I still have the printout of Glass’s insight on mastering any skill. It helps me to fight my way to master any skill.

What about you? What skill do you want to master? Writing? Painting? Taking photos? Video making? Giving online classes? Content marketing?

Will you keep showing up even if it takes years to master a particular skill?

Join my readers for similar content: Banchi Inspirations

A passionate Writer. An irreverent personal development trainer. Blogger at I am on a mission to write sparkling blog posts.

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