A Jumped-Up Pantry Boy

Jesse Mortenson on various

Growing Up Flatlander

One of the main barriers many people face with a flat organization is disorientation. Mostly we’re trained in hierarchy, so we’re used to navigating the bumps and dilemmas of a workplace with conventional management. We’ve developed and honed those instincts. Flat organization requires the exercise of some new instincts and judgments, not to mention shaking off some habits. For many folks there’s a steep initial learning curve.

But not for everyone. I’m lucky to have had years of experience working in flat environments. While many folks are steeped in conventional management and hierarchy, many are not. It’s worth observing that people bring different expectations into a workplace, and that no management style is frictionless for 100% of the people in an enterprise. Here are a few experiences that oriented me with flatness:

  • Starting my own business. I started a tiny web development/consulting company with my best friend when we turned 18. Went right from college to doing it full-time, figuring out taxes, making decisions about clients and contracts and rates. Hiring (and sometimes firing) a small group of employees. Stuck with it and paid the bills for almost ten years.

  • Running for office. I ran for the MN House of Representatives in 2006. That was an amazing experience for a 23-year-old. There is nothing like knocking on doors as a candidate to get the feel for just how precious it is for another person to give you a few minutes to listen.

  • Co-founding a non-profit and serving on various all-volunter committees. Motivation and accountability are huge challenges when working with volunteers. But in some ways, I think the paycheck and regular hours can mask just how much these are challenges with paid employees as well.

I am really thankful for these experiences. A few things that strike me, as I reflect on them:

  • Failure and unpredictability. It strikes me that I’ve failed to achieve my goals at least as often as I’ve succeeded, despite spending equal amounts of time and energy in all cases. I think I’ve learned that you don’t have to be perfect, and you don’t have to be an expert. Nobody can predict the future. Small business and grassroots politics are both risky endeavors in environments where many of the variables are out of your control. Some humility about what I can actually affect, I think, paradoxically makes it easier for me to go out on a limb.

  • Working flat isn’t that different from entrepreneurship. Starting your own business entails a lot of the same challenges as working in a flat organization. Success depends on your initiative and there’s no one else to blame if it doesn’t happen. It’s funny that the entrepreneur is so lionized in this culture, while at the same time strict hierarchy is regarded as a norm for employees.

  • All-volunteer projects are great proving grounds. If anyone can just decide to stop showing up, you’ve got to constantly be persuading and motivating the people around you. And finding the ways to work that motivate yourself!

  • Success is that much sweeter, and even failure means something special. The worst scenario I can imagine working in is where nothing I do matters. For better or for worse. All of these experiences have meant a lot to me. They changed me in important ways. I think having the sense of ownership that comes with initiative, ownership and collaboration is a big reason why I’ve gotten so much of them.

    I think those are some of the things people need in order to be successful and comfortable in a flat org: opportunities to be trusted, the experience of failure under your own terms, and the chance to try again with what you’ve learned.