Christian Oh had written approval from Singapore’s Ministry of Education to sell property while it paid for his degree. Three and a half years later the ministry made him choose anyway, and walking away cost him close to US$93,000 (S$120,000). If you are building something on the side of a job that pays you, the same call can come for you, and by his account the leap is the easy part.

He was reading Chemistry at the National University of Singapore on an MOE teaching scholarship. That kind of scholarship comes with a bond, a contract to teach for a set number of years or repay a large sum to leave early.

He was going to teach secondary school chemistry. “It was a good plan,” he says.

He wrote to MOE before he sold a single property, and it approved him. “I wasn’t hiding,” he says.

The first year paid him nothing at all. Two hundred doors a day and a hundred calls, mostly answered with no, by a self-described introvert who used to look at the floor instead of people’s eyes.

“The first year I made zero dollars. Not a little. Zero.”

At eighteen months an investor who saw how much he cared about his clients opened her network to him, and the deals began to compound. By year three he had more than 100 clients, six people training under him, and real estate was taking about 80 percent of his week.

Then the stipend, the monthly allowance the scholarship paid him, stopped.

One month, then two, then close to six, with no explanation. Then he was called in. Somebody had complained that an MOE scholar selling property was not right.

The ministry gave him two options. Drop real estate and keep the scholarship, or break the bond and pay back six figures.

“I didn’t walk away from the safe path,” he says. “I was made to choose between two.”

Hesitation at the plant doesn’t protect you.

It took months of mentors, counsel and prayer.

What settled it was a picture of himself as “salt and light” in the industry, the Bible’s phrase for people who make the world around them better. It was so real he broke down and cried, because he knew exactly what it would cost him in no fixed salary, and sometimes a year before a closed deal paid him anything.

“I could have run. Like Jonah,” he says, meaning the prophet who fled the job God handed him. He paid the bond from his savings.

You already know to count the cost before a jump like this. That instinct is right, and Oh had counted his. What he had not done, he says now, was decide what he was jumping for.

The rule he would hand you comes from his own pole vaulting, and he is the first to say he broke it.

“Set the bar before you run.”

A pole vaulter fixes the height of the bar before the run-up starts, never halfway down the runway. “Decide while you’re already moving and you’ll always talk yourself into something lower.”

Before you ask anyone whether to quit, write one line that says what winning looks like for you, with a number and a date in it.

Oh walked into the biggest decision of his life without that line.

He had never defined what winning looked like, so “every person I asked gave me a different answer and I had no way to weigh any of them against each other.” That is why it took months, and why your line goes to every mentor you ask, so their advice gets weighed against your bar instead of theirs.

The second half of his rule is about the moment of commitment. In pole vaulting that is the plant, when the pole drives into the box, the slot at the foot of the jump, and the vaulter throws his whole weight forward. Hesitate there and you get no jump, and usually an injury.

Hesitation at the plant doesn’t protect you.

People do the same with a decision like his, he says. They keep one foot in each life and call it being careful. “Halfway in is the only position where you carry all of the cost and none of the upside.”

If that describes you right now, his arithmetic says you are paying for both lives and collecting from neither.

He is thirty now. The property site Stacked Homes reported that he held thirteen properties, sold four, and that the rest bring in about US$80,000 (S$103,000) a month. In May he bought the Food Haus coffeeshop at Block 421 Ang Mo Kio Avenue 10, facing the block he grew up in.

This time he set the bar before the run-up. He went six or seven times before he bought, mornings for the breakfast crowd, evenings to see whether the estate was alive after dark, weekends because it is a different place again.

“A seller will show you the best hour,” he says. “The other hours are the actual information.”

The same goes for a job you are about to quit or a business you are about to join. Look at it in the hours it is not performing for you.

He set two more bars when he took over. He promised the stallholders he inherited no rent increase for two years. And he is proving the model on one coffeeshop, with his own money at risk, before he asks anyone to put theirs into the fund he is building.

The line he keeps for founders standing at the edge is about what comes after it.

The leap is one afternoon.

“The leap is one afternoon.”

“What costs you is the three years afterwards, when nobody’s watching, nobody’s impressed anymore, and you still have to show up and knock on the door.” So before you jump, count how many months your savings carry you at zero. His first year was all zero.

His last test is harder than the question of whether to jump. “Ask yourself whether you’d still do it if it took five years and nobody ever wrote an article about you.”

Someone did write one, in the end. He had done the years first.