I Think I Should Be Braver

I haven’t told many people this, but about 12 years ago, I lost a lot of money. I mean, a LOT of money. Basically everything I’d made from Jennifer Government, plus my inheritance from my father, which was half of everything he’d spent his life scraping together while refusing to spend anything on himself.

The problem was I didn’t understand financial planners: I thought they were like doctors, i.e. experts with your best interest at heart. But it turns out they are actually salespeople operating on commission. So I thought I was prudently deferring to the advice of professionals, but actually I was taking out loans to leverage investments in schemes that instantly turned to smoke when the Global Financial Crisis hit.

Luckily, I also bought a house. But for 18 months or so, I experienced a regular gut-churning fear that I was about to lose it, and my family and I would be turfed out. In practical terms, this wouldn’t have been the end of the world—no-one would have starved. But I had failed hard, really hard, in a way I hadn’t experienced before, that hurt people I cared about. It was terrifying every day.

Since then I have dug myself out. Everything is fine now, thanks. But I was thinking about it this week in the context of my career, and I’m not sure that feeling ever completely went away. I think touching the hot stove and realizing how badly it could burn left me more cautious. And not in a good way, like, hey Max, don’t give your money to salespeople. Although also that. But in a fearful way, like, don’t do anything that might let people down.

For example, I don’t blog as much any more, and part of the reason why is that I wonder whether someone will get my email in their inbox and be like, ughhh, why is Max bothering me about that. And every new book I start—like I’m starting one now—I think about whether it’s the best book I can possibly write. Which sounds noble, but is also maybe a little cowardly.

When I look back at some of my earlier work, I most like its crazy, oblivious energy. It’s not always great from a technical perspective. Some of Jennifer Government is barely readable, to be honest. But it has a wild abandon that works because it doesn’t much care about its missteps.

I used to collect rejection letters and stick them on my study wall. This was before I was published. I would sit down at my PC to write, surrounded by letters telling me my stories weren’t good enough. This sounds pretty masochistic, in retrospect. But I found it inspiring: The letters were evidence that I was a real writer, doing real writer things, getting correspondence from real people in the industry. Not great correspondence, obviously. Correspondence that said no. But I knew every great writer got rejected a bunch of times, so therefore each of mine was a step along the path to eventual success.

I think I should embrace failure a little more. Not a ton. I don’t want to, you know, be bad. But a little more trying things for the hell of it would be good. A little less thinking about how worthy something is.

So anyway, I just wanted to say, get ready for some really stupid blogs.