I Didn't Even Ask

"You gotta remember," my cousin said, "I'm Sri Lankan."

I was in my attic office, laptop open, cousin on speakerphone. He'd been telling me about the coach he didn't hire five years ago.

A friend recommended an established coach as he stepped into his first CEO role. The coach quoted twenty thousand for six months. A second quoted twenty-four thousand for a year, as-needed. His first thought was that it was too much. His second was that he didn't have the time. The company had raised ten million. Looking back, he told me he had the authority to write the check himself.

I'd been scribbling on post-its as he talked.

"I didn't even ask the board."

The pen stopped.

I knew that sentence. I had said a version of it eight years into my own career, looking at an executive MBA application. I'd been at my new job for six months. The class met on campus every other Friday and Saturday, and I'd have to ask my manager for the Friday, for two years, before I'd earned any standing to ask her for anything.

I almost didn't apply. A friend enrolled in a similar program asked me, "What do you lose by asking?"

I asked. I got the Friday. I got in. The two years that followed changed everything.

"What would you have said yes to?" I asked my cousin.

"Well, you gotta remember, I'm Sri Lankan."

We laughed, because it was funny, and because it wasn't.

A few years before that MBA, I had signed for a mortgage far bigger than that program without flinching. I had taken a car loan the same way. Debt for a thing was normal. Debt for myself was different. It meant betting on me. And I wasn't sure I was worth the bet.

After we hung up, the rest caught up.

A woman I'd coached. When I checked in three months later, she was steady. Grounded. In one of the hardest stretches of her life, she was thriving. The work had held.

I'd been meaning to ask if I could share her story for two weeks. Added it to my list twice. Hadn't done it.

It was the same bet. Me and that application. Me, now, with a message I keep not sending. This time, my livelihood. The same old fear, now with a price. And it still wins.

Here is the part I'd rather leave out. I'll finish this, then text her.

The caution was not all wrong. The same instinct that made the bet feel impossible got my cousin to the CEO chair, and me to that application. Our family couldn't gamble on themselves. The discipline they handed down kept us safe. It got us into rooms they were never invited into. It worked until it started costing us the next thing.

The next thing is rarely a house or a degree. It's a coach. A pause. A message sent. The quiet bet you're worth backing, the one nobody taught us to place on ourselves.

The woman I keep meaning to text already made hers. She did the work. It held. I've watched it hold for others. I'm only slower to bet on myself.

"You gotta remember," my cousin said. "I'm Sri Lankan."

I remember. I am too.

And I'm still learning to bet on myself anyway.