At some point we had two spreadsheets open at the same time every day.
One was Shopify. The other was our main POS system. There was no direct integration between them, so whenever something sold online, someone had to manually deduct it from the store inventory. We had allocated a specific pool of stock for the online store to make this manageable – a workaround that worked, as long as you stayed on top of it constantly.
The concessionaire counters added a third layer. Sales from those had to be manually entered as well.None of this was unusual for a small retail business in 2012. It was just how it worked. But looking back, those two spreadsheets were an early signal of something I didn’t fully understand yet: the business had grown into a shape that its original structure wasn’t designed to hold. At the time, it felt like an operational inconvenience.
The move towards omni-channel
Around 2010, we started doing what many retailers were beginning to do – moving towards what would later be called omni-channel.
By 2014 that meant writing blog content for SEO, running Google Ads, sending email campaigns, and posting regularly across Facebook, Instagram and Pinterest. At the same time, the business was operating across three different formats: the physical store, the concessionaire counters, and the online store.
On paper it looked like progress. More channels, more visibility, more ways to reach customers.
In practice it meant trying to make multiple systems work together when they hadn’t been designed to. The POS and Shopify didn’t talk to each other. Each marketing channel came with its own metrics, logic, and demands. The inventory picture was only ever accurate if someone had done the reconciliation that morning.
What better systems revealed
When things started feeling difficult to manage, my instinct – like most people’s – was that we needed to get more organised. Better tracking. Clearer processes. Tighter inventory control.
So we tried. We labelled more carefully, tracked stock more closely, introduced more structured ways of recording what was coming in and going out.
And something unexpected happened.
The more visible everything became, the harder it was to ignore what wasn’t working. Inventory didn’t line up consistently across channels. Sales data told different stories depending on which system you looked at. Decisions made for the online store sometimes created problems for the physical one, and vice versa.
What we thought was an execution problem was something else. The systems hadn’t fixed the problem. They had made the problem impossible to unsee.
Systems don’t remove complexity. They make it visible.
Why this matters
When everything is informal, a business can absorb a surprising amount of inconsistency. People remember things, adjust in the moment, compensate without documenting it. From the outside it can still look like things are functioning.
But once you introduce structure – once you try to make things systematic – that flexibility disappears. A system requires consistency. It requires decisions that hold across contexts, inputs that are reliable, logic that applies the same way in different situations.
If those things aren’t already in place, the system doesn’t fix the problem. It highlights it.
What we were actually running by this point wasn’t one coherent business. It was several models layered on top of each other – a retail store, a concession model, an early-stage ecommerce business, a growing marketing engine – each of which made sense individually, but together created friction at every join.
That friction didn’t show up all at once. But as more systems were added to manage the growing complexity, it became harder to ignore.
→ This is explored in more depth here: Why Everything Started Feeling Heavy (Before I Knew Why)
The question that changes
At a certain point, the internal complexity of the business and the external behaviour of customers stopped aligning. The channels we were managing internally didn’t map cleanly onto the way customers were actually moving between them.
→ Related: What Retail Taught Me About Customer Decision-Making
Once you see that, the question changes.
It’s no longer: how do we manage this better? It becomes: does this still make sense as a single business?
That’s not an operational question. It’s a structural one. And it leads directly to the kind of decision I eventually had to make.
→ Related: Why I Chose to Exit Instead of Scale
This was part of the broader Sole2Sole journey.
If parts of your business feel like they require constant workarounds just to function — that feeling is often a signal of something structural, not operational.