Whose game are you playing?
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Tom Parson
Sometimes, you already know what you need to do to work better, and even how to go about it, but you are still held back by your idea of what your business "should be."
Recently, I wrote about the three reasons why you never finish any of the big ideas you have for your business.
But sometimes, even when everything is set up for success, you find your ideas still don't happen. Even when you know what you need to do, and you have all the resources to do it.
The typical model
When I ran my digital agency, our revenue came from a combination of monthly retainers and one-off projects.
The retainers provided valuable predictable income, essential when we had to meet payroll each month - like web hosting. The one-off projects often provided much more income, but across a period of a few months, and with less predictability - like website builds.

If you ask most business how they might expect to pay an agency for a website build project, they'd assume several invoices, dependant on deliverables, probably with a 30-40% deposit required to book the project in. This is exactly how we used to work at Huddle.
Our projects often lasted several months, and, being honest, most were subject to delays of some kind.
"We've always done it this way"
Of course, sometimes our team just took longer than expected on things, and life got in the way.
But sometimes, we would be working towards invoice milestones which were contingent on our clients being able to prioritise the project, something that can be difficult for them to do. Signing off app design mockups, providing data for a migration, commissioning photography for a website, etc.

In these situations, we were itching to send the next invoice, but had to wait for the client to play their part. This not only lead to cashflow issues, but also demotivated the team and lead to momentum on the project stalling.
It took us a long time before we really challenged why we even invoiced projects in this way. The best answer we could come up with? "That's just how it's done."
Otherwise known as "That's how it's always worked."
Or "That's how everyone else does it."
Which isn't really a reason at all.
How do we want to work?
Once we realised this, we started to wonder, if we were to shoot for the moon, what perfect invoicing scenario would we really want?
Well, we already had the perfect model with our monthly retainers - repeatable, predictable income. That's the kind of revenue we can build a business on.
So, on new projects we started using the same model.
Invoices spread evenly across the projected project timeline. Total project budget divided by projected months, with the first month payable in advance as a deposit. If projects were delayed, we would draw up a new timeline, and divide the remaining amount payable across the remaining months.

To our surprise, every client that was offered this accepted it. After all, there was no big up front payment, the invoices were predictable for them too, lined up with their monthly spending, and were often easier to get through finance since they were for smaller amounts.
And, of course, we preferred it as well. Predictable monthly income, yes, but also it kept up momentum on the project - providing an incentive to keep the project on time, lest we have to extend and reduce our monthly invoices.
Our cash flow improved, our on-time delivery improved, client satisfaction on projects improved. It truly felt like we were working to our strengths - not how everyone else worked - but how we worked best.

What game are you playing?
This taught me to never underestimate the assumptions I am making at any given time about how I "should" be working, and how they could be holding me back from a way of working that is more aligned to me and those around me.
When I hear other business owners feeling constricted by industry norms, I'm always reminded of this quote by philosopher Kwame Anthony Appiah:
The challenge is not to figure out how best to play the game; the challenge is to figure out what game you're playing.
Whose game are you playing right now?
What are you doing because you "should", not because it's what's best for you?