Getting Comfortable with Failure

A few months ago, I was giving a presentation at a…

By Jesse Flores

A few months ago, I was giving a presentation at a StartupWeekend on building MVPs and learning to fail fast. At the end of the presentation, someone asked me how I became comfortable with failure. I don’t remember exactly what my answer was, but I remember not feeling fully satisfied with it.

I do have, I think, a higher risk tolerance than many. But I don’t think that’s the reason I’m comfortable with failure. The truth is, I’m not 100% comfortable with it, depending on the topic at hand. 

As I’ve thought about it, a few things occur to me:

The Frame Matters

I think, when talking about failure, the frame matters considerably. If I’m emotionally or personally invested in the thing I’m doing, I’m more likely to be afraid of failing. When I take a minute to think, there’s usually a concrete outcome I’m really afraid of. So, when I experience anxiety that something I’m doing might fail, I try to take a minute and think about what concrete outcome I’m afraid of. Once I envision it, I almost always realize pretty quickly that the worst possible scenario is not that bad. Or, at least not insurmountable.

The other thing I’ll do is try and frame the project as a learning experiment. For instance, if I have a startup idea I want to validate, I might decide on the front end that I’m willing to invest x resources (time, effort, money) to learn something concrete. And I’ll try to devise an objective test: if I speak to z people about, I’d expect b results. If the return is greater than b, move forward. If not, move on to something different. By the way, I’ve found this is a really useful tool for cold calling and customer discovery. Because that s**t can be scary.

Practice Iterating

For some reason, we are programmed to want to get things right the first time. It’s probably a function of school where you do an assignment, turn it in and get a grade. There are no do-overs and, at the end of the term, the grade is the sum of your individual outputs. Then we rank each other based on this number. The results are cumulative, penalties for failure are steep, messy learning isn’t permitted, and we tie the output to our identities. That’s a recipe for disaster.

And it’s not how my experience in life seems to go, especially in entrepreneurship. There is so much less certainty than school would have you believe. But we spend so much time in school that those habits get formed.

One of the tactics I’ve embraced to overcome this is to practice doing things without giving myself the opportunity to edit. I separate out doing, from evaluating, from learning. For example, when writing posts like this, I give myself a 15-20 minute timebox to “free-write”, where I’m not allowed to go in and edit. I just have to write.

Then, when the timer goes off, I can begin the editing phase. Again, I set a time box to prevent myself from feeling too perfectionist about the whole thing. After about half an hour, I’ve completed the exercise.

The important thing about this exercise (most of my free writing doesn’t really turn into posts or shared content) is to get comfortable separating creation from redaction. Even now, I find myself tempted to go back and edit while I’m writing. It’s a conscious process not to do that.

For “more important things”, the size of the timebox may vary, the duration of the effort may vary, and the resources required to move forward may vary, but the process stays roughly the same: create, edit, share and learn.

Anxiety about failure is natural. In some ways, it can be good. It can prevent us from doing some really stupid things. But, fear can also prevent us from doing some really amazing things. By reframing failure and practicing the art of separating creating from critique, I think it becomes easier to know when the fear is justified and when it’s not. And hopefully that leads to some wonderful outcomes.

What do you think? What scares you about failure? How do you overcome it?

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