#7 Failing forward: How to keep bouncing back

27 June 2025

Here's the uncomfortable truth about learning Spanish (or any language): you have to mess it up. Repeatedly, out loud, in front of other people.

There’s no shortcut. You can’t just lock yourself away, stockpiling vocab, then emerge one day speaking fluently.

The grammar isn't the hard part…it's the ego hit. The real skill is learning to look stupid, over and over again, until you don’t look stupid anymore. Or less, anyway.

Once I accepted that being bad at it – publicly – was part of the process, everything got simpler. Still frustrating and hard, but with a clear path forward. It wasn’t a mystery why I wasn’t improving: I just wasn’t embarrassing myself enough.

A big reason children pick up languages so fast is because they just try, get it wrong, try again. Their plastic brains help, but the real trick is not caring about looking silly. It’s the same with learning to walk. If toddlers had adult levels of pride, they’d fall down once and decide crawling was more dignified.

So this week’s about that mindset shift: turning failure into progress. How do we build that bounce-back reflex, and how do we encourage it in others?

Stop fixing, start facilitating

Recently I watched The Secret Life of Four-Year-Olds. It’s kind of a cross between Big Brother and a David Attenborough documentary. Kids get chucked into a new environment, and have to figure out how to exist alongside each other.

What really stuck with me was how the adults managed any conflict that came up. Every time two kids started butting heads, no one panicked. No one swooped in to “solve” it. They just let it play out. They saw those little clashes as opportunities, nudging the conversation and giving the kids space to figure it out themselves.

And the kids always did figure it out. Even when it looked hopeless, they somehow moved past it. That shift in approach, from intervention to facilitation, changes everything. Not rescuing kids from conflict or failure, but creating the space for them to wrestle with it and come out stronger.

We could use a lot more of that approach – at home, work, in schools, everywhere. Sure, it’s a TV show, and maybe the edit was designed to give me a tidy little moral arc. But the core idea stands: every conflict is an opportunity to learn, if we let it be.

Here are a handful of mental habits that help me keep going, even on the days I’d rather not.

1- Failure is a feedback loop

One of the most useful mindset shifts is to stop thinking of failure as the opposite of progress, and start seeing it as data.

Courses, books, frameworks – they’re all maps. But the only way to really learn how something works is to walk the terrain itself. When you try something and it goes sideways, that’s the actual learning happening.

James Clear encapsulates this idea perfectly: “The secret to winning is learning how to lose.”

That’s why “failing forward” matters. It’s not about pretending the failure didn’t happen, but about mining it for information.

2- Make it crap on purpose

Here’s something I do all the time in my writing: I deliberately aim to write something bad. Whenever I've got Blank Page Syndrome, I follow one golden rule: make something crap, then criticise it until it's good.

We’re all great at coming up with rubbish, and we’re also quick to spot the flaws in something. So lean into that. Bash out something terrible, then start pointing out where it goes wrong.

This stops me treating the blank page like some sacred ground I need to get “right” on the first try. Suddenly I’ve got a rough sculpture I can chip away at.

This applies beyond writing. Whatever it is – a project, skill, idea – drop the pressure to “succeed” and just make the crap version first. It kills off that fragile, perfectionist mindset that wants to get it right before you even begin.

3- Learn from the crash before you start driving

If you’re feeling stuck in a loop – starting things with good intentions, hitting the same wall, then quietly drifting away – it’s time for a pre-mortem.

Before you start a new project or habit or goal, sit down and imagine it failing. Not vaguely, but spectacularly. It flops. You give up. You get derailed, distracted, drained. What happened?

List everything that went wrong. Psychological stuff, logistical stuff, emotional stuff. Maybe you overcommitted. Maybe you got bored. Maybe you got discouraged by some random overachiever on the internet and decided to burn it all down. Get it out of your head and onto the page.

Now look at that list and ask: Which of these have actually happened to me before? Then write one possible response, workaround, or alternative approach for each.

This is how you stop repeating the same cycle. You learn from the crash before it happens. Once you've done that, throw yourself into it. Take your best shot. You’ve already looked failure in the eye and made peace with it. Now it’s time to act.

Bouncing back, resilience, whatever you want to call it… it really comes down to showing up, even when you can’t be arsed.

My mum’s a great example: since 2021, she’s been doing a drawing or painting every day. Some days are brilliant. Some are less so… But that’s not the point. The point is she kept showing up. She was already a decent artist when she started, but when you look at her progress over the past 4 years it’s really inspiring. Just keep showing up, and the rest takes care of itself!

So… Is it really failure? Or just a terrible name for progress?

Maybe we need a better word. “Failure” feels final, heavy, shameful. What if we just called it something else?

When you zoom out, failure is just part of the process, a stepping stone. The people who win are the ones who kept showing up after the “failures.”

So, instead of failure, I propose we use: Flopportunity.

No? OK, I'll keep working on it…

P.S. After all my doom-and-gloom about AI last week, I thought I’d share some of the upsides. AI is a great partner for thinking out loud, stress-testing ideas, and moving faster through the mess.

When you can draft something in seconds, test an idea in an afternoon, or prototype without burning weeks, you stop being so precious. It can actually help you fail forward, faster! So here are 3 underrated ways I’m using AI every day (that I think you’ll find useful too) → How I’m using AI to move quicker