The Tomorrow School is built on a simple but deeply held belief: so much of what it takes to be a good entrepreneur is also what it takes to build a content, resilient, and fulfilling life.

Entrepreneurship doesn’t just teach you how to build companies. It teaches you how to live with uncertainty, how to detach effort from outcome, and how to keep moving forward when things don’t go your way.

And nowhere is that more evident than in how it teaches you to fail.

Because if there is one guarantee in entrepreneurship, it is this: failure will happen. Repeatedly. Publicly. Sometimes painfully. What people see as successes on the outside are often just the highlights. What they don’t see are the dozens of attempts that didn’t work before one finally did.

Why we start with failure

On the very first day of every Tomorrow School cohort, we set intentions together. We talk about the skills students want to build and the milestones they hope to reach. But the single most important intention I ask every student to set is this: Embrace failure as an inevitable, necessary, step in this journey.

Ideas might succeed sometimes. Business models might work sometimes. But the one thing I can guarantee will happen during the course of the program is failure. Something won’t land. An assumption will be wrong. A solution won’t resonate. A pitch will fall flat.

In entrepreneurship, much like in life, there are inputs and outcomes. Some inputs are within your control: how hard you work, how thoughtfully you approach a problem, how open you are to feedback. But outcomes, while correlated, are never fully determined by your effort alone. Timing, context, incentives, and sheer randomness all play a role.

Doing your very best does not guarantee success. That realization can be terrifying, or it can be liberating.

Failing well is an important founder skill

Adi and I have failed so many times in so many decisions - it's how we learnt how to be good entrepreneurs. Over the lifespan of rePurpose Global, for example, I can guarantee that there were ten ideas that didn't work as expected for every one idea that did work well. Today, the company has catalyzed over $100M in impact toward solving the plastic crisis, providing waste management as a dignified human right to over 2 million people across 3 continents. But none of that erased the reality of the failures it took to get here, and the failures that I absolutely expect will still come in the future.

As I tell every student - failure is simply something that happens to you. It is not a reflection of your worth, your intelligence, or your potential. Obsessing over the failure itself is rarely a good use of emotional bandwidth.

What matters is what you do next.

Do you shut down?
Do you externalize blame?
Or do you pause, take accountability for the outcome, extract the learning, and move forward - slightly wiser than before?

The ability to process failure without being consumed by it is a skill, there's nothing intrinsic about it. And like any skill, it can be practiced.

Why this matters so much for students

Framing failure as a guarantee, rather than an exception, is especially important for our children, for three reasons:

1. It shifts their focus from outcomes to inputs.
Fear of outcomes can be paralyzing, especially when you haven’t experienced meaningful failure yet. Worrying about what might go wrong takes up enormous mental space. When you accept that failure will happen eventually, you stop fixating on avoiding it and start investing in what you can control: effort, curiosity, and craft.

2. It teaches how to act after failure.
Many students we work with have been high achievers their entire lives. School is a controlled environment where effort and results are tightly linked. Life is not. University, careers, and relationships will inevitably at some point have a disappointing outcome - and when that happens, many students don’t know how to move forward, leading to adverse mental health conditions.

Learning to take accountability, process disappointment efficiently, and try again is not optional for founders, and practicing it can make our children generally more resilient across all facets of their lives.

3. The absence of failure is often a warning sign.
If you’re taking enough shots, some will miss. The only way to guarantee no failure is to stop trying altogether - which also in turn guarantees stagnation. Movement matters. Our brains evolved to pursue, adapt, and respond to challenges. Staying in one place for too long is often far worse for our mental health than failing while moving forward.

I want our children to excel.
I want them to have disproportionate success.
I want them to build things that meaningfully change the world.

But that level of impact requires the ability to face disproportionate failure—and to do so without losing momentum, or self-confidence.

So we don’t just teach students how to win. We teach them how to lose well.

Because the people who learn to practice failure early are the ones who keep going long enough to do something extraordinary.