On Leaving Startup Life

It was about this time last year that the writing was on the wall that WideAngle wasn’t going to be a sustainable as a company that employed a full team any time soon. Not the best situation by any means, but one that I am proud of nonetheless. Thanks in good part to our investors, we were able to find our teammates (and friends) new homes, we never missed payroll, and we were able to put a plan in place to keep the product going for our customers that are as fond of 1:1’s as we are.

As far as failures go, it was a positive one. When you’ve built a career working in technology startups, you get used to failing. Very few ever reach the heights that seemed attainable in the heady early days. Fewer still maintain their standing. Which is to say that I felt down and out, but it was expected and I figured the fire would come back when I reengaged with the goings on of the startup community.

I didn’t realize it at the time, but this one hurt a lot more and left a big dent in my confidence level. I couldn’t bring myself to jump back on the treadmill and decided to try and hide as an individual contributor as a big company for a bit. I found writing code one of the more enjoyable and least stressful parts of my job. I could focus on that while earning a steady paycheck with solid benefits.

A solid plan, but not without a few obstacles. The first was stress had become the driver for motivation. For me, getting out of bed is easy if the alternative is the company fails. A department goal that might have a marginal effect on the bottom line is not a sufficient alternative. Instead of business concerns, I had to relearn how to get motivated by craftsmanship. In innovative big company gives countless opportunities to learn new languages and techniques. Some of it is new ways of doing old things, but even that can be used to become better. The remaining missing motivation can be flipped back over into work life balance, which is probably a good thing overall.

The second major obstacle is that it’s impossible to unlearn the learnings from operating a ventures backed business for a few years. Even the smallest businesses require understanding how to represent the business to stakeholders, implications of trade offs, and how reality can be distorted but not changed. When you have good coworkers, they recognize how you can help and the push away from IC begins again sooner than expected. It’s also hard to resist, as it might be the area where you are unexpectedly the strongest.

In the end, years of being scrappy and trying to build value don’t correlate well to the concept of hiding. It’s very hard to keep your head down when there is an opportunity to do something positive.

I didn’t think I would find myself re-energized about work until I reentered the startup scene. For a while I had started to worry that my exposure to mostly small companies had started hurting my growth. The scale and impact may be different, but problems are all the same flavor. The nice part of a larger organization is the stakes are lower, the corrective mechanisms better, resulting in a better environment to try things out.

Part of this is no doubt related to where I went to work. Yet, in this time I don’t feel like I’m beginning the transition to soulless corporate drone. I’m unsure what the future holds. The passion for early stage is still there, but working on bigger systems than startups need is kind of fun. What’s different now is that the path is more about what I want, rather than what the company needs. Being in the drivers seat has some advantages over being hitched on for a ride on a rocket ship.

• Disclaimer: All posts, and especially this one, are my own thoughts and do not reflect the opinions and official positions of any employer, past, present, and future.

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