On Expectations and Failure

After a very welcoming response to my first post and tweeting about it yesterday, I found myself cycling into a loop about what to do next.

Immediately thinking about all the pieces I could write, should I start drafting ones for later this week now: how will I come up with interesting enough stuff to say every single day, is it ok to write in the mornings or do I need to wait till the end of the day so its always about what I was thinking about that day, how am I going to talk about X topic while its still secret but it’s the thing I’m thinking about that day, what if I’m too tired, should I be publishing on Twitter directly too or just link to the blog, if I don’t publish there directly it won’t go as far and people won’t read it as much, but also this is an exercise for me not them so should I even care or optimize for that? And a thousand more just like that.

All of these come back to a long held pattern of mine, imposing expectations and creating anxieties where none existed before. Why am I worrying about the distribution mechanisms of blog that I explicitly created as a practice for myself? Why am I imposing a standard of what I need to write before I’ve even started writing on it? More fundamentally, why am I starting by creating a trap for failure instead of just walking into the adventure with an open heart and eyes and seeing what happens.

And underlying it is the complex relationship I have with failure. In the tech world we hold up and celebrate failure and I’m good with it in the abstract or in conditions where I know it’s just a learning experience and not the end of the world. Truly the only way one is ever going to learn things is just by trying, and in doing so, most likely failing the first few times. In fact, succeeding the first time out means you probably learned a lot less since you only have a single data point of experience.

But what about in situations where I don’t feel as secure, especially where I’m doing something in public and others might see? Well there, failure gets a whole lot scarier and so I start creating those expectations and standards, better to impose them on myself before the world does it to me.

Ultimately the only way I really know to handle those fears and discomfort is by doing the thing, and so I’m writing day 2 about them, pushing the questions and expectations out of the way, and I’ll figure out what day 3 is about tomorrow.