The Second Time Around

On unrealistic deadlines and keeping your sanity before launch

May 2, 2015

There's a lot of things that are difficult about starting a company. Staring down a blank sheet of paper with nothing more than an idea is hard. Deciding on which technologies to bet on is hard. Choosing to pull the trigger and leave your job is hard.

The hardest thing, though, is staying motivated and believing in yourself and your vision without having any real evidence that you will succeed.

TaskTorch is the second company that my wife Niki and I have started. Six years ago, when we launched AgileZen, we did it in a blitz. I'd built a proof-of-concept of the product on nights and weekends before leaving my job, but after I left we launched in six weeks. We really had no choice but to run a dead sprint — we were basically betting our entire savings (a modest $20,000) on the company. It was enough runway, but it was a terrifying prospect to consider that we could actually go broke.

After we sold AgileZen to Rally, and after Rally's IPO last year, we're fortunate to have enough money in the bank to take our time with TaskTorch. This is both an enviable position and a dangerous one. I left my job at Adzerk in September of last year, and Niki left shortly thereafter. Originally, I expected we'd be able to ship an initial version of the product at the end of January. It's now May, and while we're getting close, we still haven't shipped a real beta.

This has been surprisingly difficult for me. The lack of feedback and validation is harder than I expected. Ever seen a cartoon where they illustrate the passage of time by showing pages flying off of a calendar? That's kind of how life feels right now.

In retrospect, the January deadline was completely unrealistic. Difficult and specific deadlines can help ensure a sense of urgency and keep you on target, but missing made-up, dartboard-picked deadlines isn't a big deal.

Even knowing that, it can be difficult not to feel a sense of failure, which can interfere with your motivation and creativity. It's really fucking weird.

Anyway, there are some very good reasons why it's taking longer this time.

First, the minimally-viable version of TaskTorch is substantially more complex than Zen's. This is mostly intentional — the entire purpose of Zen was to create a very simple tool, because at the time we felt that the main problem with the dominant project management systems was their complexity. While we're obviously trying to make TaskTorch simple, it's a significantly more powerful system, but a bit more complex than jamming some cards on a board and hoping for the best.

Second, when we originally launched Zen, the user interface code could be best described as a horrendous shit show, and I had to basically rewrite the whole fucking thing. Having the product on the market was great, because we were able to validate it while I built the go-forward version, but when you have customers betting on your MVP, and you want to show momentum, stopping to rebuild everything sucks. The weakness of the design of the Zen UI also contributed significantly to the failure of the product after we were acquired, but that's another story.

Third, after six weeks of grinding out the Zen launch, I was exhausted at exactly the time I needed to be ready to start sprinting. A couple of months after we launched, I got a bad cold, followed immediately by the flu. I was sick for a month. I wanted to avoid repeating that mistake, and so I've forced myself to work at a sustainable pace. Striking the right balance between working hard without burning out has always been hard for me, and I vacillate between working too hard and feeling like I'm not working hard enough. :)

I guess the lesson I've learned is that the only thing worse than having no deadline is having an unrealistic deadline. I'm very proud of what we've built so far. I think it will be a real solution to a very real problem. I think it's also very well-engineered software, built on some great technologies like React and RethinkDB.

When we ship it, I know it's going to be great. Now we just need to ship it. :)