#13 Fall down, get up, repeat

How to thrive when the world keeps rewriting the rules

29 August 2025

I’ve fallen off a bit lately, haven’t I? Been meaning to send this letter for weeks, but between projects and travel, it just didn’t happen. Now summer’s over and I’m back in Madrid.

Maybe it’s fitting that it took me so long to get this one out, because today’s issue is about what happens when things don’t go to plan, and how you should keep going anyway.

Since starting WIWILAS earlier this year, I keep coming back to the same themes: how to connect with people, build stronger communities, protect our attention and sanity, and use tools in a way that serves us instead of hijacks us. Ultimately, I think this project is about defining our own missions rather than defaulting to what the system hands us.

And the more I read about the coming AI apocalypse – all the talk of how it’s going to transform, disrupt, or obliterate society – the more I think that the real skill missing from school is resilience.

Seth Godin has a lot to say on resilience, and here’s how he defines it:

The ability to survive and thrive in the face of change.

Change used to move in centuries. Then decades. Now it’s annual. Sometimes it feels like it’s weekly! Just think how different the world looks from when you were born.

So the faster things shift, the more deliberate we have to be about building resilience. If we don’t move with the times, we’re doomed to fail.

School, on the other hand, teaches us to avoid failure at all costs – smash every test, hand in perfect work, get the right answer the first time. Then when failure eventually shows up (as it always does), you don’t know what to do.

That was me: As a naturally “gifted” child, I managed to coast through primary school well into secondary school. I found everything easy, until suddenly I didn’t. When I had to start applying myself, I got stuck.

That’s why I think we should be proactive about teaching what to do when things don’t work out. Sooner or later, we’re going to face some sort of seemingly impossible challenge. Why don’t we prepare for it now?

What if school stopped trying to keep kids from failing, and instead showed them how to recover quickly?

That shift could run through every part of the classroom:

• Exams: These don’t have to be one-shot affairs. Make them cumulative so one bad day doesn’t destroy your grade. Mistakes could be openly discussed in class instead of hidden away in shame. Students could set “bounce-back goals” after each test, turning results into fuel for the next attempt.
• Coursework: Here resilience could mean building “failure milestones” into the process – moments where students show what hasn’t worked yet, rather than just the polished final product. Every project proposal could have a “Plan B” baked in from the start. Grading could factor in iteration as much as the outcome, and points could be given for creative recoveries when things go sideways.
• Day-to-Day Lessons: The classroom could reward more risk-taking. Run quick-fire challenges where wrong answers carry no penalty. Celebrate retries just as much as getting it right the first time.
• Group Work: Groups could be given structured failure scenarios to solve, forcing them to adapt under pressure. Ask for a “what we fixed” section with their final work, highlighting the bumps along the way. Recognise the fast adapters, not just flawless finishers.
• Feedback: This might mean starting with self-assessment before receiving external critique, to give students a chance to practise being responsible for their progress. Feedback could be a two-way street, not just a verdict. And any criticism could come paired with a question to promote resilience: “What’s your next move?”

And of course, this applies just as much to adults as it does kids. But that’s enough for one day.

What do you think we can do to survive & thrive in the 21st century?

PS. What I’ve been reading: This week I began Oliver Burkeman’s Meditation for Mortals and I’m hooked. I’d love to binge it all, but he limits you to one chapter per day to give the ideas a chance to sink in. In a nutshell, the book’s about making peace with the fact you’ll never be able to do everything. The minute you stop pretending you can, you create the space to focus on what matters with the little time you’ve got.

One part that’s particularly stuck with me so far is his analogy of the superyacht vs. kayak. We fantasise about gliding through life with the perfect routine, everything smooth and under control, like being at the wheel of a big impressive superyacht. But real life is more like white-water kayaking: messy, reactive, unpredictable. Instead of waiting for the perfect conditions to arrive, preparing for a day that will never come, you just get stuck in and do your imperfect best.

I know I’ll bring this book up again, but if you want to dig in now, this video goes over some of the top ideas: Oliver Burkeman: Why you’ll never “get on top of everything”