I was most productive-when I was unemployed - Cobalt Strike Research and Development
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I was most productive–when I was unemployed

I have a friend, who worked as a penetration tester, and recently he quit his job to take some time to himself. For the past few months, he’s learned new technologies and spent time on a few personal projects. My friend [email protected] isn’t the only person like this. I have another friend, 3edc$RFV, who left a management career to do the same thing. He now works as a security researcher.

From both of my friends, their stories have a common thread: they both felt extremely productive when the burdens of the workplace were temporarily taken away from their lives.

I feel productive too. But, I’m productive and I get paid for the privilege of learning while I work. I run a product company. Why do I feel more productive now, than when I worked for someone else?

Could it be working from home (or the freedom to choose where I work)? I don’t think this is the case. I left the US Air Force in 2008, and I’ve either worked from home or was self-employed for all but 11 months since that time. I don’t think working from home by itself makes a big difference.

I think the difference is lack of accountability to anyone, but myself.

Right now, when I design a feature or decide to pursue an idea, I do it without fear of failure. If an idea fails, I chalk it up and go on to the next thing. When I worked at Automattic (WordPress.com), I had a great degree of autonomy. I worked on the After the Deadline software service. I decided how to spend my time. Ultimately though, I knew what folks saw. No one saw my experiments and failed ideas. My coworkers, community, and boss saw the occasional blog post that would announce something new. I felt, that to keep my job, I needed to regularly release something to the world that showed tangible progress.

I do this now too. I try to write a blog post once each week. This blog post is a ping to the world to let you know that I’m alive, I’m focused on my company, and my head is operating in this space. Some of my blog posts get a lot of reads, some only get a few. I write with reader statistics as a secondary goal. The first goal is to hit Publish once each week.

I also feel pressure to regularly push out Cobalt Strike releases. I don’t worry so much about features. New features are a natural side effect of pushing out releases. I focus primarily on making my product better with each release. If all I did was fix bugs and improve user experience, I would consider that a win.

So, working for myself, or working for someone else, I try to demonstrate my productivity by regularly giving the world something tangible to look at. If I have one ability or personal habit that makes entrepreneurship a viable path for me–this is it. This is my secret to forward progress.

Keeping these factors the same, why is an additional layer of accountability a problem? How does it introduce drag on my productivity? The difference comes when I slip. If I slip, I know that I am accountable only to myself. If something goes wrong, I’ll beat myself up sufficiently (if it’s warranted). If something goes wrong that is out of my control, I shrug my shoulders and move on. I don’t worry about how my supervisor or their supervisor will react.

I tend to put off paperwork. Will my tendency to dismiss paperwork or other manufactured requirements make me look like a flake, despite real accomplishments? Right now, this isn’t a remote a concern–well, not until the city dissolves my corporation for missing a filing deadline. But hey! At least I can peg real consequences to most of the paperwork I do.

Long story short, working for myself I feel the freedom to use my best judgement and execute at maximum speed. I can see something through to completion. I can kill a bad idea when I smell it–even if I thought it was great for awhile. I can evaluate potential customers or work and say no to undesirable situations. Working for others, even in an environment with a great deal of trust an autonomy, I never felt this. Now, I don’t second guess myself.

This ability to execute, with no drag, is probably why my friends were able to become so productive while unemployed. Me? I’m thankful I get to do this for a living.