Find 'Trouble' and 'Shoot' It, for Fun and Profit

It's a long read -- with a nice, short review here -- but I highly recommend Paul Graham's engrossing contribution to my collection of troubleshooting stories.

Troubleshooting? you might ask. The essay, by writer/investor/entrepreneur/Reannaissance man Paul Graham, is titled simply, "What I worked on."

Painting, and successfully getting rich in order to be able to paint are among those "things."

I regard the story as troubleshooting of the highest order because it helped me make a connection about why I like troubleshooting stories, particularly those about reformed criminals and others who manage to recover from grave mistakes in life.

The common thread to such stories is that the protagonist reaches a point that he cannot evade the fact that he must act constructively to improve his own lot. Quite often, something or someone that person cares about provides motivation.

Paul Graham makes mistakes like anyone else, but he he never messes up enough to reach such a point, because he finds strong motivations around him all the the time. I think he does explicitly mention that an important problem is picking the right thing to pursue.

The reviewer I point to above states of the essay:

To my mind, the most compelling [lesson] was to work on whatever you want. He doesn't put it that way; he says to not be afraid to work on non-prestigious projects. He says that, mostly by happenstance, that's what he's done and that it's worked out well for him.

I think this is on the right track, but it doesn't completely capture what I think you'll see: I would go so far as to characterize this essay as something like reading a microcosm, across the span of an individual life, of Steven Johnson's Wonderland. That book is about the role of delight in the evolution of the modern world. Here, we're seeing a near-perfect marriage of value -- of being in touch with what one wants to do -- and effort. The fact that Graham has a formidable intellect is beside the point: There is a lesson here for us all.

My best first stab at this lesson is in my title, Find trouble you like, and shoot it for fun and profit.

Enough of my still-forming thoughts for now: Let's look at a few gems...

Here is Graham on the importance of having the right motivation:

Image by Rifqi Ali Ridho, via Unsplash, license.

It's not that unprestigious types of work are good per se. But when you find yourself drawn to some kind of work despite its current lack of prestige, it's a sign both that there's something real to be discovered there, and that you have the right kind of motives. Impure motives are a big danger for the ambitious. If anything is going to lead you astray, it will be the desire to impress people. So while working on things that aren't prestigious doesn't guarantee you're on the right track, it at least guarantees you're not on the most common type of wrong one. [bold added]

From prior experience, Graham knows that scaling a new business can be tricky. Undeterred, he started his angel investment firm in a way that could teach him how to do it well as he went along. Just as his values continually helped him discover opportunities (trouble other people would pay him to shoot), they help him realize solutions when they appear:

Fairly quickly I realized that we had stumbled upon the way to scale startup funding. Funding startups in batches was more convenient for us, because it meant we could do things for a lot of startups at once, but being part of a batch was better for the startups too. It solved one of the biggest problems faced by founders: the isolation. Now you not only had colleagues, but colleagues who understood the problems you were facing and could tell you how they were solving them.

And, just to stress that the essay is as entertaining as it is valuable, here's some comic relief:

So I said no more essays till Bel [his new computer language] was done. But I told few people about Bel while I was working on it. So for years it must have seemed that I was doing nothing, when in fact I was working harder than I'd ever worked on anything. Occasionally after wrestling for hours with some gruesome bug I'd check Twitter or HN and see someone asking "Does Paul Graham still code?"

I, too, have caught myself wondering the same thing about his writing at times. Now I know why, and am glad to see that this master practitioner-teacher (as Alex Epstein might call him) is still going strong.

-- CAV