The Art of Gig, Volume 1

Way back in 2009, Hugh Macleod of Gaping Void called this the “Sex and Cash” theory.1 The creative person basically has two kinds of jobs: One is the sexy, creative kind. Second is the kind that pays the bills. Sometimes the assignment covers both bases, but not often.

They are what you might call “20% beef” where the starting point is rejecting some core sacred-cow axiom of a prevailing orthodoxy and then building something new and interesting on that foundation of principled dissent based on additional ideas and novel elements.

Discovering and developing a genuine beef into an artful calling card that lands you gigs is hard work. That’s why it’s a costly signal. You can’t fake it with simple bullshitting. You have to put in the work of: spotting a widespread pattern of disillusionment in the margins identifying the prevailing orthodoxy driving the disillusionment analyzin

Indie consultants naturally fit in where the capability gap is either small enough and oddly-shaped enough to be filled by a few individually contracted people, or where the gap is large, but can be filled by a fairly generic type of labor without the help of a labor-aggregating counterparty. The four response regimes of consulting

The work of the knowledge worker is never done. You can always do an infinite amount of work for a finite piece of output. There are always more plans you could make, more background research you could do, more skills you could develop, more trends you could stay updated on, more refinements you could add to the slide deck, more Q&A you could p

It’s weird how often it ends up working like this. You might talk for hours, but in the end, it’s one casual phrase or thought that ends up unlocking the critical idea. My very first client said as much to me—that after twenty hours of chatting, the value I delivered all down to one phrase I happened to drop casually in thinking through a problem:

the problems external consultants solve always fall into two basic buckets: insufficient systematic confidence and insufficient systematic doubt.

These two loops—both of which are metacognitive OODA loops with the sparring serving as an orientation activity for both parties—are at the heart of sparring. Where this beautiful symmetry breaks down is in the relative value of the two loops. The client’s loop passes through the real world. The sparring partner’s loop passes through the adjacent-p

Create choices, not recommendations.