Learning to think in experiments over equations.
giving yourself permission to go astray
If you just…
Most of us were raised to believe that life works like an equation. It’s one of those things that might never have been stated directly and explicitly, but it was baked into the narrative.
Do the right things, in the right order, for long enough — and the outcome will predictably make sense.
If you just…..
Work hard.
Be sensible.
Accumulate credentials, experience, savings, status.
You should arrive somewhere solid.
“If you just” logic shaped how we approached careers, relationships, success, even identity. It’s the “just” that gets you, right? Because it implies a simplicity, an obviousness to issues and choices that are rarely simple or obvious. But that was its promise - to turn pretty weighty and personal decisions into simple “just do this” equations.
And for a long time, “if you just” worked well enough - it delivered on stability if not satisfaction, predictability if not meaning.
But it’s not working so well anymore, and we all know it, we’re living with and through it. Because the world no longer behaves like an equation…geez, a lot of us feel nostalgic for when it did. We’d give anything for even a hint of “if you just” in our life choices.
This world is behaving like an experiment- the smoke coming out of the lab kind, the what-happens-if-I-add-this-to-this variety. The kind where you’re afraid something might blow up.
And nothing in your life has prepared you for that.
Why experimenting feels so hard
Would you describe yourself as an experimental person? Most wouldn’t. Literally nothing in most adult lives has incentivised experimentation - trying new things, placing small bets, taking smart risks, acting without knowing the outcome.
We think of experiments as something scientists do in labs, teenagers do in the dark, not something serious adults do with their lives.
You might even take pride in being the opposite of experimental — steady, sensible, risk-aware, responsible. You fancy yourself more of an accountant than a scientist.
Someone who plans, calculates, optimises.
Someone who likes to know where things are heading before they begin.
That’s what we were told to be, it's what we were admired and rewarded for being.
That approach made sense in a world that rewarded predictability. But in a world that is changing this fast, that attachment to steadfast calculation is quickly becoming a liability. Because here’s the truth whether we like it or not: you cannot calculate your way through uncertainty. You can only move through it by trying things.
What it really means to think in experiments
Firstly, let’s rehabilitate the concept of experimentation for today’s grown up use. Thinking in experiments doesn’t mean being reckless or blowing your life up. In the broadest terms it means giving yourself permission to operate differently.
Permission to:
Value questions as much as answers.
Work in shorter timeframes
Act without knowing the outcome
Take small steps over big, irreversible leaps.
Appreciate lives with curves over straight lines.
It means loosening your grip on the idea that your progress must be gradual, sequential, and accumulative. That it must always look neat, move upwards, and make sense from the outside.
That was probably always an ideal that not everyone attained, but now it’s a fantasy that we all need to let go of. Let go of in favour of a version of progress that’s not only more realistic but more relevant. You might recognise that version as
Messier.
Stop–start/up-down
Harder to explain at a dinner party
Often invisible while it’s happening.
And that’s the part we don’t prepare people for.
The uncomfortable truth about this kind of progress
Here’s the part I want to name clearly, because I think we need to be particularly explicit about this now. As AI reshapes how work is done and value is created, more people will find themselves pushed off linear trajectories — sometimes abruptly, sometimes quietly, sometimes without a clear explanation. In this context, the ability to think experimentally is no longer optional.
Which means accepting this: when you work experimentally, there will be stretches — sometimes long ones — where it won’t look like you’re winning. Not by old metrics or familiar measures or by the standards you were raised with or taught to aspire to.
In real terms that means there may be less money, not more. Less status, not more.
Less certainty, not more. (Is your blood pressure rising as I list those?!)
During those periods, the hardest voice to deal with won’t be anyone else’s. It will be your own.
The shouting/whispering voice that at 3am and 4pm says:
You’re falling behind.
You’re too slow.
You should be further along.
This doesn’t count.
This doesn’t look impressive.
You’re failing.
Please accept this now: that voice is not some Truth. It’s like a voice of Boomer past. It’s the echo of an old scoring system being applied to a new game. It’s trying to keep you safe, but its effect will mostly be to keep you small and scared.
The real work is internal
Which is why I keep coming back to my theme of permission. Because the real challenge of experimental living is not just external risk, it’s internal management.
Developing your capability for things like:
Staying with uncertainty.
Tolerating not knowing.
Resisting self-judgement.
Soothing yourself when progress isn’t legible yet.
These might sound soft and intangible, but they’re the actual work of navigating the fluid world. They’re what real life self-direction looks like now: not having a perfect plan, but being able to keep moving without one. Not constant confidence, but enough steadiness to keep experimenting anyway.
Going astray, on purpose
This is what Permission #2 — Go Astray — is really about.
Not losing your way, but letting go of the idea that there is a single, correct path you’re supposed to be on. It’s about allowing yourself to test, explore, wander, adjust.
Try things that don’t add up yet. Move before the maths works. Trust that learning happens in motion.
Because in a world that no longer follows neat equations, the people who thrive will be the ones willing to live experimentally. Even when it doesn’t look like winning. Especially then.
Let’s Go Astray Together!
If this idea of going astray is landing for you, I’d love to continue the conversation.
On Thursday April 19 at 2pm GMT, I’m hosting a Substack Live with Iwana Johannsen, where we’ll be exploring what it really takes to navigate periods of uncertainty — personally, professionally, and collectively — when the old paths no longer hold.
We’ll talk about experimentation, permission, identity shifts, and what it means to keep finding your way when progress no longer looks linear.
You’re very welcome to join us live.
And if you want the broader framework behind this way of thinking — the permissions that support you to navigate change without a map — you’ll find it in The Ten Permissions.
This is the work.
And you don’t have to do it alone.