Why I am raising rule breakers

Unexpected link between rule breaking and success in life

During a recent family holiday, my mother-in-law—an impeccably polite woman who steers clear of conflict—said, “You should probably instil more discipline in your children”.

For her to say that, she must have hit her breaking point. And yes, my kids are loud. They argue, they push back, they don’t take “no” for an answer.

My mother-in-law isn’t wrong. It would be easier if my kids just did as they were told. But growing up in Luxembourg, they’ll absorb plenty of rule-following from the structured, German-influenced system.

I think I should go a bit more against the grain.

Why? Well, rule-following only takes you so far. To earn outsized rewards, you have to question the rules and break the ones that don’t make sense.

Breaking the rules means taking a calculated risk—one others see as controversial—and succeeding. Both parts matter. If you take a risk and fail, you pay the price. If you follow the script and succeed, you’ve executed a playbook. You get an A and a pat on the back. But no real breakthrough.

Taking a risk and succeeding requires both guts and good judgment, hallmarks of a strong leader. I want my kids to develop both and get plenty of practice.

I have seen this at work. Early in their careers, people advance by doing what their manager wants — faster and better than their peers. They volunteer, take on extra responsibilities and get promoted. Once, twice - and then it stops working. To reach the next level, you have to take risks—and win.

I’ve seen this story repeat in Amazon promotion documents. Someone goes against the grain, challenges conventional wisdom, sticks with it, and wins.

• “Anna took a small business no one valued, made a few bold moves, and grew it 10x into a key growth pillar”.

• “Tom proposed an idea that got little support. He stuck with it, proved the naysayers wrong, and created huge value for the business”.

The first time I noticed this pattern, I questioned myself. At Amazon, you can only read promo docs if you’re on a promo panel or a promo bar raiser, and you see the docs for levels below you. I had been promoted—but I hadn’t cracked the “secret sauce”. Was this it? Why did no one tell me before? Had I done something like this?

Then I remembered that butterflies-in-the-stomach moment.

At the time, I ran operations for one of Amazon’s smaller businesses—direct import. For those unfamiliar, direct import means buying goods straight from a supplier’s factory overseas and handling the logistics yourself. Many retailers build their whole businesses on it.

Back then, this business was just getting off the ground at Amazon. Everything was manual. My team gathered sales forecasts from dozens of category planners by email, compared domestic vs import costs in Excel, negotiated, and sent desired quantities to suppliers so that they could plan how to fit these goods into the containers. Then we placed purchase orders based on supplier plans and shared what we ordered with category planners.

We were growing fast and adding new suppliers all the time. My team spent their days buried in forecasting and ordering. The process was well-documented and we had a strong team executing it, but the business was growing too fast for us to keep up. People were reaching their breaking point. And besides, it wasn’t anyone’s idea of a dream job. A new employee told me in their third week,“I didn’t join Amazon to do *this*”.

Automation was the only way to scale—but experts warned me it was nearly impossible.

How could we predict what customers would want nine months ahead? Suppliers discussed marketing budgets and “hot” products with category planners, who used their experience and knowledge to forecast sales. A system couldn’t replicate that intuition —human judgment was key.

And besides, only seasoned packers on supplier side knew how to Tetris-pack containers for maximum utilization. We didn’t have that know-how, so we couldn’t create a program to automate it, so we will not be able to raise purchase orders correctly.

But we weren’t starting from scratch. We already had a system placing automated orders for domestic vendors. The US team had modified it to handle direct import. Skeptics pointed out key differences: The transit time to US was twice as short, making forecasts more reliable. US was a bigger marketplace and they only bought bestsellers in full containers. If we did that, we would only order a handful of products. We had to do mixed containers with multiple products. And US container utilisation? Terrible. Truly terrible. They must be losing money, they said.

So I made a plan: first, crack long-term forecasting. Then, solve container packing.

Forecasting reminded me of an old story: Two people spot a tiger. One starts putting on running shoes.

"You think you can outrun the tiger?" asks the other.

"I don’t need to outrun the tiger," the runner replies. "I just need to outrun you."

Short-term forecasting was the tiger — always more accurate. But I only needed to outrun human experience.

I got manual forecast data from the past 12 months and system long-lead forecast. I measured the accuracy of both against the actual sales. The system outperformed humans every time.

When I dug into the data I discovered two main reasons:

1. Planners were conservative. When they saw large order numbers, they revised them down—leading to stockouts of bestsellers.

2. Manual errors. A simple mistake—misplaced cells, deleted lines, or the wrong spreadsheet version—could throw off an entire order.

The mistakes were frequent enough that automation was clearly the better option. I showed my boss the analysis. He was convinced.

Next, we tackled container packing. We started with a single supplier—two factories, a limited product range. We ran the system and issued a test purchase order.

The supplier’s response? “This is all wrong”.

We asked them to correct it. Then we worked with the tech team to tweak the inputs. After a few iterations, we got it right.

We repeated the process with a second supplier. Once we knew which inputs to fix, we emailed all suppliers to get the correct data.

Category planners were nervous. “You’re letting the system place orders without our oversight?”

To reassure them, we built reporting so they could audit the system and override parameters. But they were busy people and direct import was only small part of their responsibilities. They told us, “We can’t forecast manually and review automated orders at the same time”.

It was decision time.

My boss wanted to run both processes in parallel and have a safety net in case automation failed. But I knew that we could invest people’s bandwidth either in doing manual planning or in cleaning up inputs and auditing results of the automation. We couldn’t do both well. If we wanted automation, we had to take a leap of faith. If it failed, we would have no products to sell to customers on time.

We ran a pilot with one category. It worked.

But my boss was still uneasy. “Will this scale? Are you sure?” His job was on the line.

“Yes", I answered—more confidently than I felt.

Then I went back to my desk: Oh shit. What have I done?

I double-checked everything—inputs, reports, contingencies.

Yes. It will work.

I felt butterflies in my stomach.

As you might guess, it worked. I didn’t know it at the time, but this story made it into my promo doc. My boss retold it afterwards multiple time over beers—how I convinced him to take a huge risk, how we took that leap of faith together, and how we landed safely on the other side.

The business scaled faster. We freed up bandwidth, improved long-lead forecasting, and onboarded more categories and suppliers.

***

What does this have to do with rule-breaking?

I had to question authority. Experts — with years of experience in import business —told me this would not work. I had to push back. I had to convince my boss to take the risk.

It plays a bit differently at home. I am the one being pushed back on.

When my eldest was three, he refused to wear long pants in winter. I had grown up with the rule: Dress warmly, or you’ll catch a cold. But we were not in -30°C/-22°F — we were in -3°C/27°F. My husband, who grew up in South Australia, didn’t see the problem. So we tested the rule.

My son went to kindergarten in shorts in February. (I left long pants in his locker, just in case). He never got sick. Instead, he became The Kid Who Wore Shorts Year-Round. This kindergarten legend outlived him—other parents told me the story later, not realising this was my son.

He’s eleven now and dresses normally, but still runs hotter than I do.

Every rule deserves scrutiny. Why does it exist? Does it still hold? If yes, follow it. If not, break it. I want my kids to practice. To challenge authority—including me. This does make my life harder now.

But I hope that one day, this will make them better leaders.

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