Keeping your edge as you grow

A funny thing happens as you climb the success ladder at any level.

You get better at keeping things working. And that can make you worse at trying things that might break them. 

Whether it’s climbing the corporate ladder, gaining years of experience in an industry, or becoming more financially free, you inevitably seem to become more conservative. 

You slowly become more closed to new ideas and leverage old ones, and more terrified of upsetting the stability you’ve built.

It’s totally natural. You have more to lose. More people watching. More systems that “couldn’t possibly change”.

The result is predictable. Your curiosity shrinks, your excitement over potential upsides shrinks with it, and hungrier competitor starts to eat your lunch.

I’ve witnessed this with people inside my own company, leaders of other businesses and in myself too.

The compounding cost of not exploring, not testing new things, and not expanding your mind as you climb through life lands people in a curiosity debt.

It puts them at a disadvantage to others who are hungrier.

Here’s the hard truth I’ve started to realise: you don’t have to personally chase every new or complex thing anymore, but you are accountable for making sure someone does. 

Your job is to own the culture, set the guardrails, and fund the sandbox.

Just because you don’t want to do something scary anymore, doesn’t mean someone inside your business shouldn’t in order to keep you ahead of the game.

So find people with the enthusiasm you had a decade ago to unpack complexity and drive new ideas.

Why success makes you slow 

If this doesn’t land immediately, let’s look at how it happens…

Loss aversion: bigger downside, so you say “later”. And later = never in my opinion.

Reputation risk: the more credible you are, the more you fear visible misses. 

Attention tax: operational firefighting extinguishes your exploration mindset.

Switching costs: switching legacy systems and habits makes change more difficult.

If this is happening to you, it doesn’t mean you’re failing… 

They’re all just conditions to design around.

Here’s one way to look at it:

Build a Two-Speed Org 

Run the core at Speed A (reliability, margin, SOPs). All the repeatable things that sustain your business and keep core customers happy.

Then run exploration projects at Speed B (fast, cheap, reversible). This allows you to unburden yourself and run nimble tests that could yield massive results.

You as the seasoned operator or leader must support both, but you don’t need to execute Speed B if that’s not your thing. 

But you do need to find someone who wants to do this. That person with your enthusiasm from decades ago.

Alternatively, if you’re like me and you prefer Speed B but recognise that it’s f**king chaotic at times, you need a team dedicated to maintaining the consistent Speed A for your core business. 

The main point I wanted to make is:

Good businesses start to fail over time because they lose their edge. 

The original hustle is replaced with the boring (but incredibly valuable) BAU. 

Founders retract. Senior execs fight fires. The core team get spread thin.

That electric culture gets extinguished instead of kept alive, nurtured and controlled. 

But it doesn't have to be that way if we structure it correctly, value innovation and run loads of micro tests alongside the core business. 

I hope this helps!