Fail in Public

Learning, as I was once told, is a two part process. The first part is experiential. You have to go through a process of doing and making and observing, which allows your brain to absorb the information. The second part is reflective. You have to go back and look at all that you absorb and examine them, connect them, integrate them together.

So in the spirit of working in public, I am going to reflect upon my assignments for Entrepreneurial Design this term. Specifically how I think I have really failed myself by not completing a couple of assignments.


The first failure is giving in to excuses. To be completely honest, I did not even attempt assignment seven, where I was supposed to pitch articles to five different high traffic publications.

  • "I don’t know what to write."
  • "I don’t want to write something I don’t care about."
  • "I have higher priorities, more important assignments to finish first."

All excuses. I didn’t even look at the traffic statistics once to identify who I might want to write for. I threw around some ideas in my head about what I wanted to write about, and basically stopped there. My failure to complete assignment ten was similar, even though I did make one (unpublished) attempt. If I was honest with myself, I ought to have just acknowledged that I didn’t want to do it, and forced myself to do something anyway. Fooling myself into thinking that I was waiting for inspiration was basically giving up through procrastination.


The second failure is more subtle.  It is a failure to focus on learning. For the final project we were supposed to raise a $1000 dollars through a repeatable business model. I chose to teach a Skillshare class. The class was, as some level, a success. I created a class where students felt like they really learned, and I’ve gotten a lot of great feedback on the material. I managed to only make about $750, but I don’t think that’s the important failure.  The important failure was that I didn’t focus on iterating.  A big part of the lesson about building a repeatable business model was experimenting with all parts of the business model. Instead I focused my iterations only on polishing the lesson material.  

I half-heartedly put up several Facebook ads. I didn’t really try much to promote except to tell my friends, make a few posters, and tweeted it a couple times. I submitted it to Charlie O’Donnell’s email list, but didn’t get it listed.  I didn’t change the price to test my pricing strategy. I didn’t make use of the discount options in Skillshare.  Essentially, I focused on what I was already good at, which was teaching a class, and hence did not learn all that I ought to have learned.

So what did I learn?

One of the key things I learned is the huge gulf between theory and practise. I think I understood theoretically all the ideas and methods that Gary and Christina were trying to teach us. Customer development, running experiments, promoting and using analytics all made sense. Those are all systematic, well reasoned methods of getting a business idea off the ground. So what stopped me from getting the assignments done? In practise, the barriers were not at all intellectual.  The two biggest barriers were both emotional.

For ideas that I didn’t care about, I was simply too prideful to put them up. I really ought to have put up a number of silly ideas just to get some experiments up. The point was to get some feedback, and learn from the iterative process. It was the process that was important, but I was too conscious of the results. I wanted everything I do to be “good” and “authentic” but in practise, they really can’t all be good.

For the ideas I do care about, I was afraid to put them in front of people and experiment with them. It was fear, disguised as perfectionism. I ought to have put up a landing page about my thesis ideas as soon as I thought of them. I ought to have submitted them as articles, if for no other reason than to get some feedback. I kept putting it off because I was still embarrassed by how half-baked they are. The truth is, if I wasn’t embarrassed by the first version of my ideas, I’ve waited too long to put them up, and I’ve missed an opportunity to iterate.

Pride and fear. Really awful reasons for failing assignments. The irony is that I know the perfect antidote. The antidote for pride and fear is humility and curiosity. With humility and curiosity, I probably would still have failed some of the assignments. Those failures, however, would have come through more sincere attempts, and I likely would have learned more that way.

I can’t say I’ll never do this again, but this was certainly a visceral lesson learned.