Bold leaps don't work

📸 Photo by Nick Page on Unsplash

She’d had a proper week away.

Lake District, properly disconnected, the kind of break that actually works.

Day one back, back at her desk and with some BIG ideas about changes she wanted to make about how she managed her day. She’d planned to start with a nice long walk before work, a genuine lunch break, then boundaries around the blurring of the work day into the evening. Then a one hour gym session…

The alarm goes off. She hits snooze… a sneaky part of her tells her it’s ok, it’s the first day back. Take it easy…

And bang - she’s back in her old patterns, working through her lunch break and into the evening, fighting fires, not getting a little fresh air or giving herself time to move her body, not doing anything that she needs to recharge and stay sustainable.

Judging herself as failing. Losing a lot of energy just to that - the inner mind monkeys throwing their insults. The sense that because she failed at the very first hurdle - a rather idealistic one hour walk goal - then that’s it. It’s all too much and not worth trying at all.

When we looked at what had happened, she said: jumping to the top of the ladder hasn’t worked. Not once. She reaches for the biggest, most perfect version of the change every time, and every time she ends up back at the bottom, trying again, more discouraged than before.

Most of us don’t reach for a top rung and miss the grip dramatically. We just decide, every time, that the big version is the only version worth trying - and when it doesn’t stick, we call it a failure of willpower instead of a failure of sizing.

The myth of the leap

We’re sold progress as a leap. The breakthrough. The overnight transformation. The moment everything clicks and you’re simply, permanently, at the next level.

It’s a nice story. It’s also not how change works for anyone I’ve ever coached.

Progress happens in rungs. And the whole art - the actual skill, the thing worth getting good at - is sizing the rung correctly. Too small and nothing shifts. Too large and you don’t reach it, and falling short teaches you to distrust the ladder altogether. Her first rung, once she stopped aiming for the top one, wasn’t ‘transform my mornings.’ It was: go for a short 10 minute walk around the block.

Naming the rungs

A client of mine is a CEO working with governments and some of the most significant organisations in the world. You’d assume someone making moves that size doesn’t need to break them down. He does exactly that - and it’s not the deals he splits into rungs.

The sticky stuff, the stuff he actually brings to me to think through properly, is never how to close a deal. It’s his team. Motivating them. Getting the best out of them. So that’s what gets named, out loud, rung by rung: being intentional about his WhatsApp responses. Small team issues. Then - only then - the bigger conversation he’d been avoiding.

Not ‘sort out the team’. Granular actions, and ranked by difficulty. Named precisely, each rung stops being an overwhelming abstraction and starts being something you can actually put your foot on.

The stretch that doesn’t break

Another client is coming back from a long period of ill health - the kind that punishes overreach immediately and without negotiation. A good day feels like proof she’s back. She can do the full day, clear the backlog, cook a proper meal instead of ordering in. Seven hours of feeling almost normal.

Then the crash.

She’s a problem solver by instinct, motivated by progress and movement - which is exactly what makes the good day so dangerous. It doesn’t feel like overreaching. It feels like finally being herself again. What she’s learning, slowly, is to pace against her actual baseline, not the version of herself a good day makes her believe she’s already back to. The stretch is pushing slightly past yesterday. Not past what’s possible on the best day she’s had in months.

That distinction - a stretch that builds versus a leap that breaks - is doing more work than it looks like it’s doing. A stretch respects what you’re actually able to hold today. A leap is a bet against a version of yourself that isn’t reliably there yet, and mostly you lose those bets quietly, then wonder why you feel worse than before you tried.

What the stretch actually asks of you

Getting the stretch right takes more attention than just deciding to be bold. Boldness is easy - it’s one decision, made once, from the comfort of not yet having to live with the consequences. Sizing a rung correctly means checking in with where you actually are, not where you’d like to already be. It means choosing the smaller, less impressive version of progress, over and over, when the bigger version would feel so much better to announce.

None of the three people in this piece are short on ambition. They’re all building things that matter enormously to them. What they have in common isn’t caution. It’s the discipline to ask, before every step: is this a stretch, or is this a leap I’m about to fall short of?

Progress doesn’t need you to be braver. It needs you to be more precise.