How to Be an Expert at Failing (and Survive to Tell the Story)

27 Jan 2026 #misc

“I’m not an expert at anything. Only at failing.”

A friend and ex-coworker told me that when we caught up over coffee after many years. Well, I was giving him a paperback copy of my latest book. Shameless plug.

I don’t know why, but our conversation shifted after that line. I had to ask him why he said that.

You have to start from scratch

At college, everybody told him he had a talent for coding. But he was fired from his first job for his performance.

After losing his job, he broke his wedding engagement. He disappointed his parents. He thought he had nothing else to do. Failure wasn’t a stranger. It had become his shadow.

He started as a teacher. He thought he had found “his thing.” But he got fired from that too. Another disappointment.

Then, to try something new, he went back to college. He had to find something. He had to find his calling.

One day on campus, ready to quit, he sat at a table with his head in his hands. The pose of a disappointed, frustrated man.

That’s when he heard something unexpected.

“Which plant grows faster? A tomato plant or a mango tree?”

“A tomato plant,” other students who had joined the table said.

“Which plant gives fruit for longer?” the mysterious voice said. He kept his head down all that time.

“The mango tree,” the students said.

“Exactly! You have to be mango trees. The tomato plant dies after harvest. A mango tree gives mangoes for a lifetime.”

After many failures, that was his wake-up call. At first, he thought it was a wise student. But when my friend raised his head to find out where that voice came from, he found a teacher.

“It was God,” he told me.

That day, he decided to get up and work for himself. If his parents or family were disappointed because he didn’t meet their expectations, that was their problem. Not his.

Lesson 1: Live up to your own expectations.

Lesson 2: You have to start over and over. That’s a skill no class teaches you, only failure and life do.

Lesson 3: Be a mango tree.

That was a moment to start from scratch again, after failing at his first job, his first relationship, and first everything.

Be good at making an extra effort

Being fired from his first job was a sign he wasn’t as smart as he had thought.

Maybe it was impostor syndrome. Trust me, he’s smart.

But after months, he was interviewing at the same place where I was working.

“I know I’m not the smartest, but I’m going to be the most charismatic,” that’s what he thought before the first interview.

That strategy worked. He got the job. But failing at so many things, he was ready to get fired after the first month.

Later, at my workplace, he carried a notebook and wrote down everything. When I asked him about it, he told me, “I had to take away something, at least some notes.”

“After many failures, I learned to read who was really someone who knew and who was just a charlatan. I learned from everyone and I wrote it down.”

He was at the office before clock-in and still there after clock-out. “I had to make an extra effort. It took me 5 hours to finish what others did in 1.” Effort was his secret weapon.

Lesson 4: Take a notebook with you everywhere. (Thank goodness I had a napkin to write down the lessons my friend taught me as soon as our conversation was over.)

Lesson 5: Persistence beats intelligence. If you aren’t the smartest, you have to be the one who puts the most effort.

“A coding problem? Nah! That’s not a problem. I’m used to failure.” Sure, a compilation error was nothing after many disappointments and setbacks.

“That’s why I say I’m an expert at failing.” Wow! We shook hands and went our separate ways. That day, I met a true expert and a wise man—and realized failing isn’t the end.