Bad Ideas

A few years ago Jami bought me a notebook with Bad IDEAS inscribed on the cover. The notebook goes almost everywhere with me. It has become a stage for expressing thoughts bouncing around in my head. I cherish it.

After a nice New Years with our family, I opened up the book and started reading through it. Our house is stacked with hundreds of notebooks but this one is special. Despite early signs (and confidence) that I might be an artist, the notebooks rarely have drawings of memories or moments. They are filled front to back in schematics, prose, and frameworks. Not long ago I found a notebook from junior high drawing out formula’s for figuring out the surface area of circles.

The notebooks make for a hell of a catalog. Even Dwolla started as a sketch on my dining room table. The date on the photo I found was 7/9/2008 and it’s ridiculously rudimentary like many ideas are at the beginning.

That concept was eventually described as PayPal without the fees a few years after the initial go at it. The UI was what we all thought in and this whole vibe ended up coded in ASP.NET Webforms. We didn’t think in continuous integration. We shipped live and I can assure you there were no commit comments. You rolled hot and and that was that. It was a different and very naive time. Eventually we graduated to SVN and then eventually to GIT. Is any of that old code still running in production? Doubtful.

By all measures and for a long time, Dwolla was a bad idea but with testing, countless iterations, and more than a decade of energy from hundreds of team members and millions of users, it found a home inside of innovative products built by other teams. There, Dwolla’s technology and team have thrived. The future just keeps getting brighter. With each year there is more opportunity and life changing impacts for the people involved and I like to think, for the people building with us.

I’m glad we stuck with it, but I admit it’s hard to know what is a good idea or a bad idea at the onset. Testing it and throwing yourself into the world is the only real way to find out. Framing things as bad ideas creates a little room to be ok with being wrong. As time goes on, I’m not sure my ideas have gotten better but I feel more intellectually honest about how quickly I am able to prove them wrong, or conversely, confirm a hypothesis.

In my bad ideas book were many things I chuckled re-thinking about. V-Sum was one that I apparently thought far more about from a format perspective than I recalled. Whether or not it was in the context of an arc of excitement, boredom, or happiness, I certainly thought about it at one time or another. One of the missing ideas I couldn’t help but laugh about was the original concept for Clay & Milk, which was a program for turning parental leave into a package that an employee could take with them anywhere they went or even hand off to someone like a savings account. I never got that one off the ground but the name found a great home.

Actually having acted on (anecdotally) about half of the ideas, it was fun to go through page by page. Each thing I acted on created some new friendship, joy, or insight in my life. Much of what my life has become since Jami gave it to me is drawn out in odd detail through prose, schematics, and apparently ladder logic that felt more like reading an Apple Basic readout than anything else.

The freedom to have bad ideas is a luxury. The freedom to have them where you individually are the judge and jury of your thoughts might be an even greater luxury. The exercise of challenging your own thinking is exhausting but when something clicks, it clicks.

Going through the notebook was a surprising reminder that almost everything is possible if you just dare to write it down and then go do it.