A couple of years ago, when I was finding myself in a bit of a productivity rut at work, I did something that struck me as a little strange and unusual – I decided to make a daily $50 bet with a colleague that I would complete a certain set of tasks, every day. I would have to email him at the end of each day, or pay him $50. Sometimes I didn’t entirely complete every single thing I wanted to get done, but the bet was tied to the sending of the email. I then went on to be substantially more productive than I normally was. I did fail to send the email maybe once or twice – I think it was on a day when I had something on in the evening, and got home late and sleep-deprived, and typed out the email but didn’t send it. Eventually we stopped with the bet – it sort of informally just tapered off, I don’t remember now precisely how or why we stopped. And then I just sort of didn’t really think about it.

I think I stopped thinking about it because the experiment revealed an uncomfortable truth about myself – that my behavior can be modified with a mere $50 hanging over my head. At the time, the actual sum of money wasn’t a particularly big deal to me. But it wasn’t entirely insignificant, either. The idea of losing $50 for failing to perform a pretty simple task was pretty troubling. More importantly, I think, it loomed over me. It stayed at the forefront of my mind, and it kept me relatively focused.

I’m thinking about this now in the context of incentives in general. For a few months now, I’ve been living quite a feral homebody life – sleeping at odd hours, playing video games, spending hours on the Internet doing absolutely fuck all. At some level, it has been deeply relaxing and “cleansing”. But at another level, it’s been slowly stressing me out. Why stress? Well, it’s late october. I have two months left in the year to really get things done. And… I’ve not been getting very much done each day. Already I think I’ve taken a little too long of a break, and that I’m starting to get a little too sloppy and slovenly for my taste. I’ve been a little too disconnected.

There have been some good things. I’ve been tweeting a lot and building relationships with people. I’ve met a bunch of interesting people for coffee and dinner. I’ve been going through some old pictures and feeling a sense of clarity and growth, I think. I’ve noticed my mind relaxing from letting go of all of the work-related information I was holding on to. But all of this is so hilariously vague! If I want to get things done I need to be very specific about exactly what I want to get done. And one of the things I’d really like to do is to complete this word vomit project. It’s another thing that’s been weighing on my mind for a long time. I also want to clean out all my notes apps and todo lists – which is something I say so often that it feels like something that I’ve gotten comfortable saying. Every person who says that they’re procrastinating would probably also be comfortable saying that they’re tired of procrastinating, and then not do very much about it. Come on, Visa. We’ve written about this for years now. What are we missing? What do we need to be doing?

It feels a bit clunky and hacky to decide to implement the $50 bet system again, but I think I’m going to do it. I have some old friends that I trust to do this with me without laughing at me for it. It’s just a tactic, it’s just a way of focusing attention, it doesn’t need to be anything much more profound than that. Does it imply weakness? So be it, I’m okay with being seen as weak if it means I become more productive and effective as a consequence.

So… what do I bet $50 on next? It’s 1110am. I have a meeting at 3pm. Which means I should leave the house by 2pm. So I have about 2 hours to get as much writing done as I possibly can. It’s not perfect – I did wake up at 6am, and I did spend pretty much 4 hours just dicking around on Twitter. That really is not a good use of my time.

I don’t want to beat myself up about this stuff, I don’t have the energy for it, and I know from experience that it doesn’t change anything. I’m just curious now. I’m curious about how we’re going to change this. I’m curious about how I’m going to switch gears and start putting in the work that I know in my heart I’m capable of. What am I going to say? What am I going to write? This is turning out to be another “JFDI” type vomit. I’m fine with that. Whatever needs to be written to get the motor running.

Let’s close with thinking more about incentives. Maybe the entire next vomit will be about that. What are the incentives that shape me? What am I incentivized to do? What do I want to be incentivized to do? How do I redesign my life so that I can better achieve the things that I want to do? Let’s keep it simple. I want to write, I want to work out, I want to sleep early so that I have a clear head to work with. Why am I not writing more every day? Is it simply a matter of failing to start? I wrote the entire draft of a novel last November because I had #NaNoWriMo as a container to work with. Well. After I publish this, I will have 281 containers to fill. If I have 60 writing days left, I need to fill 4 containers a day. That seems all very abstract. I need to make it concrete. This is today’s first.