I was sitting in the Barcelona airport after a week-long offsite with Clickbank, the company we partnered with to deliver Clickbank Powered (the equivalent of mixing Squarespace, AWeber and E-Junkie into one).

While sitting in the food court and waiting for our respective flights, Eric (Director of Marketing at Clickbank) and I were chatting about side projects. The convo went along the lines of:
Me – I’d like to write a book on customizing the WordPress admin.
Eric – How much would you sell it for?
Me – Don’t know, probably $5 – $10
Eric – That’s pretty low, what is it actually worth to someone?
Me – I’d say a $100 or so, but I guess that’s not what I’m looking for, I’m in it for the long game.
To my surprise, that was the first time I had used that phrase to describe my activities, and in a reflex-like manner nonetheless. I put the thought aside and we continued chatting.
Their flight left well before mine so I accompanied them to their gate, said our goodbyes and proceeded to hunt down an electricity socket to start trimming down my inbox. Yet, the fact I used the term the long game got me thinking.
The Default
Before continuing, it’s probably important to establish what constitutes “normal game”. That can probably best be described as a career where you’re locked into a monthly salary, getting the occasional raise or bonus along the way. It’s a rat race with few winners. I’d represent it as such:

The only things that remotely resemble the long game, constitute of some additional training and maybe that yearly conference (don’t forget to bring your business cards). Oh but wait… there’s a hiring freeze, so all that shit just got cancelled.
The Long Game
So there I was waiting for my flight, pondering about this label I had just given myself. What did it mean and how did I define it? I came up with a basic definition:
You engage in the long game when you price a product or service at anything less than its worth, in hopes that it will bring you more value down the road (even from completely different buyers).
This begs the next question, where does that difference between the retail price and real value go? If done correctly, right into your personal brand and reputation. For a lack of a better term, this karma is your ticket to larger opportunities. You’re essentially paying it forward. Time for another chart:

Whilst you’re spending a lot of time investing in your brand and yourself, you’re obviously making less cash, duh. But those bursts of income, that’s where the sweet taste of victory comes into play. Said differently, every long game requires an endgame, a moment of “cashing out” (realistically speaking, it’s more likely to be multiple smaller endgames).
So coming back to the initial discussion with Eric, what was my long game with the book?
It certainly wasn’t an immediate monetary gain, the only reason I’d price it is to run another experiment and once again learn something new in the process. Customizing WordPress is also a process, one that Human Made and I are starting to understand and execute extremely well. Thus, the long game here can be described as receiving further opportunities to work on sizable SaaS projects, our brand and reputation adding credibility to our demands.
Applying it
To call it purely a strategy is misleading. I think there are certainly fragments of planning that (should) go into it, but ultimately it comes down to attitude. For myself, I think it’s the overarching desire of owning scalable revenue streams and having the ability to choose what’s next, regardless of the where, what and how. Having done the corporate circuit, it’s tempting to play the same game and apply the same models. I could be a successful freelancer working X hours per day with clients that pay me Y rates, but that’s just the same hustle without a suit. I’m in it for the long game.