We go to great lengths to deal with risks. We purchase insurance policies, park emergency funds, and have backup plans. We do everything to deal with unplanned negative events that will damage us. But luck is just the other side of the coin. Luck is an unplanned positive event that helps us flourish. Do we have any plans to deal with it? As much as we plan to limit the downside of risks, shouldn’t we plan to extract the most out of lucky events?

In 1854, Louis Pasteur wrote, Chance favors the prepared mind. More than 170 years later, it still remains the best way to extract the most out of chance events. Being prepared.

I have spent 30 years watching people I admire get “lucky.” They meet the right co-founder at a conference. They land a dream role because someone read their blog. They raise funding because an investor saw their open-source project. From the outside, it looks random. From the inside, it is not.

The luckiest CTOs I know do not wait for luck. They engineer it, much like they engineer the software they build. They put themselves in motion, prepare before opportunities arrive, and make themselves findable long before they need to be found. Luck is not a single event. It has layers, it rewards motion, and it favors the prepared. Here are five things I have learned about engineering it.

1. The Luckiest Engineers Are Not Lucky. They Are Prepared.

I learned early that luck works in layers. The Indian economic liberalization of the 1990s happened while I was studying software engineering. I had no role in it. That was blind luck, and I benefited from it. But most of what people call luck in a career is not blind. It is active, discerned, or personality-driven.

James Austin classified luck into four types in Chase, Chance, and Creativity. Only the first is accidental. The other three can be cultivated. The distinction matters because it shifts the locus of control. If luck is random, there is nothing to do. If luck is cultivated, there is everything to do. I have written about the four types of luck in detail here.

2. Motion Creates More Luck Than Talent Does.

In 1998, I was on the bench between projects. I could have spent these days sleeping in the library like everyone else. Instead, I started experimenting with sending emails programmatically using Visual Basic. That small experiment led me to a mentor who changed my career trajectory. The people who seem luckiest usually try more things than others. They launch more projects, meet more people, test more ideas. Most experiments fail. Nobody notices them. People only pay attention to the one that succeeded. And call them lucky.

3. The Best Career Moves Feel Like Wrong Turns at the Time.

When I was 10, I wanted to be a writer. I even joined a journalism course with all the pocket money I got. I went to college and studied engineering. When I graduated as an Electronics engineer, I wanted to be in computer graphics. I ended up in healthcare informatics. I went to the US expecting a green card, got transferred to Belgium, was forced back to India, and found myself advising the Government of India in Delhi. Each move felt like a detour. Each detour opened a door I could not have planned for.

I wrote about this in Life is a series of lost, found, and lucky breaks. Getting lost is not failure. A person cannot find a path without wandering first. The leaders who seem to have all the breaks are the ones who kept moving through the wrong turns instead of stopping in disappointment.

4. Luck Favors the Engineer Who Ships, Not the One Who Plans.

I have watched intelligent people stall because they never shipped anything. Meanwhile, the engineers who experiment in public, launch small projects, and share what they learn create more surface area for luck to find them. One of the main reasons people do not get lucky is surprisingly simple. Nobody knows they exist. Push code to GitHub. Write about what was built on LinkedIn. Create a portfolio that speaks louder than a CV. The experiments compound invisibly. What appears to be luck is often the result of countless small bets that nobody saw.

5. The Paranoid Prepare. And They Become Lucky.

I borrow this from value investing. When I buy a stock, I ask what’s the worst thing that can happen to the price of the stock. Will I still hold if that happens? If I can hold without panic, then I buy. This rule has helped me build a growing value based stock portfolio.

I apply the same thinking to career decisions. Before I commit to anything significant, I ask what could go wrong. I prepare for the worst outcome so that if it arrives, I am not shaken. Charlie Munger said, Tell me where I am going to die, so I will not go there. The paranoid do not freeze. They prepare. And when the storm arrives (they always arrive), the prepared are the only ones standing. I have written about this in Luck Loves the Paranoid. The thesis is simple. The paranoid prepare, hence prosper. Others perish. Margin of safety is not just for portfolios. It is for careers, for relationships, for every decision that carries real consequences.

Becoming Lucky In GenAI Era

Everyone is asking whether AI will take their job. I think the better question is whether I am positioning myself for the luck that AI is creating. I am already experimenting. I use ChatGPT and Claude regularly. I code with AI agents. I installed Hermes, an AI assistant that manages my workflows, reads my wiki, and drafts blog posts. I post my learnings on LinkedIn so others can see what works and what does not. I do not know if luck will find me. But if it knocks on my door, I will be ready. I will not be found wanting. If the past is any indicator, it will.

The tech leaders who thrive in the next decade will be the ones who experiment with agents now, publish what they learn, study trends before they are obvious, and make themselves findable to opportunities that do not exist yet. A career’s future luck depends on what a person does today.

Every career framework I have seen focuses on risk mitigation. Nobody teaches to prepare for luck. But luck is the higher-leverage variable. Prepare not only for storms, also for the day the wind is at your back.

Field Notes

Observation Luck is not a random event. It is the compound interest of motion, preparation, and visibility applied over years.

Question What are you doing this week that creates surface area for luck to find you?

Experiment Ship one small thing publicly this week. A blog post, a tool, a talk. One new pathway for luck.

CTO Field Notes

Engineer Your Luck