I had two clients in the same week hit me with the same thing. Not a tech problem. Not a strategy problem. But massive overwhelm. One person has taken over a new role at an existing client, and the other is a founder we’re working with.
Both were sitting in front of something big. A build, a pivot, a decision that mattered and both had gone a bit rabbit-in-headlights. Our founder was dealing with something that looked so large they couldn’t see where to put their hands. And the newly minted COO was grappling with inheriting the project we were helping them with, and getting to know the new organisation. Fun, right!
So I did what I always do. “How do you eat an elephant? One bite at a time.”
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Define the goal, break it into actual tasks, put your attention on the one bite in front of you, and stop staring at the whole animal. With our founder, he got the ball rolling. With our COO, it’s only just happened, so the jury’s out. But I’m confident betting she’ll get there.
When the size of the obstacle stops being the thing stopping you from starting - but you have to start, this is the way to do it!
In these scenarios, I sometimes feel like a therapist. There’s absolutely psychology at play in any business and personality that you’re dealing with. And don’t be fooled: Successful business people and high-flying execs get caught out in this too.
Different people experience this at different levels - which is fine. But it’s important to realise that if you’re biting off more than you can chew (to borrow a ‘relephant’ phrase) - and doing so with the intention of creating something bold and new and incredible - well, you’re going to have to learn this skill.
Because nothing extraordinary is simple. Or easily explainable at the start. Or a clear line to success.
I use something I call the MAD Rules of Reinvestment. Whenever you put time, money or energy back into your business, you’re making one of three moves.

More - Doing what already works, harder.
Adjacent - Extending into neighbouring territory.
Different - Building a genuinely new engine that loops back and changes what the business is.
Two of those feel like building. Only Different compounds. And the catch is that Different, by definition, is the thing nobody’s done yet.
That’s the whole point of it.
Which means it always arrives looking like an eleven-headed dragon, breathing fireballs and nail pellets aimed at your manky head. And you’ve got to slay the beast. Or, for the calmer-headed foodies among us, an elephant - and you’ve got to eat it one bite at a time.
There’s no version of a Different that shows up small and tidy and already solved. If it were small and solved, it’d be More.
So if you’ve chosen a Different and it feels overwhelming - good.
That’s the correct emotional response to the only kind of move that actually transforms anything. That’s all part of the D in MAD Rules
Or, the “Yahoo Serious of Business.” Get it? MAD? Ok, moving on.
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I’ve eaten a few elephants in my time. In another life, I owned a video game developer, and we landed the Stargate SG-1 game licence from MGM, beating bigger players to do it, and then taking it to publishers, flipping the way it was normally done.
A few years on I set myself another Different: solving piracy for the film industry. Not stopping it. Monetising it - legally, and signing Disney in the process. Now, if you think getting Disney onboard for a distribution system - torrents if you’re old enough 😉 - that had previously been robbing them blind for a decade was not elephant eating, I don’t know what to tell you…
To make that work we had to convince the studios to license content for distribution via a method they were terrified of, build an advertising model that didn’t exist, win over media buyers who’d never seen anything like it, and crack security problems nobody had solved on torrent-based content.
Bold D projects like that are a hydra - you cut apart one firehose-mouthed monster and another steps right up. Solve the legal question, a technical one appears. Solve that, the commercial model breaks. Any single head, looked at in isolation, was a reason to back away slowly. Stacked together they were paralysing. If we’d let the size of the whole thing intimidate us, we’d never have taken the first bite. We broke it into pieces and ate them in sequence. That’s the only reason it happened. And if it’s D - truly revolutionary - there’s no guarantee that with any success you have with Problem A, it means you can definitely solve Problem B (and I’ve certainly had my set of failures). It’s relentless - but that’s the cost of D.
When a Different scares you, and it will - 11-headed fire breathing hydras that survive having their heads cut off are scary - there’s a very seductive escape hatch:
You retreat into More and tell yourself it’s ok, it’s progress.
You break the big scary thing “down,” except the bites you actually pick are the safe, familiar, More-shaped ones.
You tidy the CRM (lovely). You reorganise the folders (oooh, how satisfying). You spend an afternoon choosing a project tool (abso-smurfly delightful). It feels like work. You’re taking bites. But you’re eating the ears and the tail and leaving the part of the elephant that actually feeds you.
That’s the smaller-tasks trap, and it’s sneakier than doing nothing, because it looks productive. You end the day busy, tired, and no closer to the Different you set out to build. You’ve converted a transformation back into iteration and called it a good day’s work.
The fix is the half of the trick people forget. One eye stays on the goal (the one with the moley-moley under it above). Every bite should be a bite of the actual elephant - the Different - not a comfortable More you’ve convinced yourself is a good - safe- move.
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Before you start a task, ask the honest question: is this moving me toward the Different, or is it just easier than the thing that would? If it’s the second one, you haven’t broken the problem down, you’re simply procrastinating.
So break it down. Both my clients needed exactly that this week. Just make sure the bites are the ones that count. And when the hydra grows two new heads, understand that’s part of doing something Different. It’s not failure. Read it as confirmation you’re finally eating the right elephant.

Look at where your time and energy actually went last week. Sort it honestly into More, Adjacent, and Different. Do you have a Different? Is there a Different you’ve been toying with?
This resource The Five Whys Exercise from Challenge The Frame can help you get started if you have problems breaking big tasks down into smaller chunks.
The resource above is from a module in Challenge The Frame called Bold Thinking for Transformative Results. This covers the MAD Rules of Reinvestment in a different way. The first 3 chapters of Module 1 are free to review.
Annnd, go!
Ben Lenzo
#BeAVillager