On the recommendation of my friend and colleague Andrew I recently picked up a leadership book called Extreme Ownership. Here’s his take on it.

There is a lot to talk about in this particular book, but the piece that really stands out to me is the idea that structure and discipline can help an individual to a life of greater freedom. This idea is especially germane to remote workers or folks otherwise enjoying highly flexible schedules and workplaces.

Having travelled in some pretty radical circles, I am familiar with the usual backlash against structure, process, and limitations on behavior – there is definitely a mindset that rejects these things in a wholesale way, and while I don’t agree with it (or find it to be particularly coherent as a political philosophy), there it is.

I can acknowledge that on its face, the idea of adding structure in order to increase personal liberty may sound counterintuitive. Stick with me. We’ll go on this journey together.

When I was studying philosophy one of the works that somehow found its way into all of my other classes was a paper called Two Concepts of Liberty.

If you’re so inclined, and have about sixty pages of time to dedicate, I totally recommend giving it a read in its entirety – it’s dense but brilliant, the kind of work you’ll get through and just nod, because it’s simply intuitively correct, something you understood before you even read it, but put into the very words you never could have.

The TL:DR of Two Concepts is that we can think of liberty as falling into two buckets: Positive Liberty and Negative Liberty. 

Negative liberty is essentially freedom of movement or freedom of choice. If I stop you from eating a donut, I’m infringing on your negative liberty. If I tell you to work on this project and only this project or you’re fired, I’m infringing on your negative liberty.

Positive liberty, Berlin says, is self mastery. Being able to make decisions for yourself in an informed and critical way means you have high levels of positive liberty.

When you answer Berlin’s question, “What, or who, is the source of control or interference that can determine someone to do, or be, this rather than that?” – if the answer is “I am the source of control,” then you’re enjoying positive liberty.

These two ideas are often at odds in ways that will help us to understand my above assertion, that through some structure and some discipline, we can ourselves become more free.

Consider driving. I live in the US, so I’ll be referring to US-based road rules – please substitute whatever is appropriate in your region of the world.

Driving in a car requires following certain rules – you stop at red lights, you drive at an appropriate speed, you stay to the right hand side of the road. These are necessarily restrictions on our behavior and as such, limiting factors of our negative liberty.

However, even as our negative liberty is constrained, we’re able to exercise greater positive liberty, as driving becomes a safe activity, it becomes reasonable to engage in, rather than some sort of Mad Max terror situation. We’re able to effectively self govern.

By creating a more structured environment, we’re all able to thrive more fully and accomplish our personal goals. What is the end goal of liberty if not to accomplish our personal goals?

In Extreme Ownership, they talk about a very serious level of discipline, but they’re also dealing with very serious personal goals; kill or be killed. For somewhat less severe goals (decrease churn, make our customers happier), less serious discipline is probably OK.

One of the things that remote workers gain is an open day. There are pros and cons, and the freedom at hand can be thrilling, to be sure.

When you consider your work, and the way that you approach your work, let me encourage you not to mistake negative liberty for positive liberty. Creating structure around your goals and around your day allows you more freedom, not less.

When you’re your own boss, or when you enjoy the freedom to essentially behave as though you’re your own boss, creating your own schedule, etc, one of the best things you can do is to create some boundaries for yourself, to intentionally limit your own negative liberty.

Maybe that means getting up at 5AM to go to the gym, taking away your own ability to stay in a warm bed. Maybe that means always shutting off the laptop at 5PM, because you know you’ll let work creep into your personal time otherwise.

Self mastery, positive liberty, is best accomplished when you impose your own restrictions on your negative liberty – but you do so intentionally, with an eye to your own broader goals and aspirations. A lack of organization will also surely fill your time, and surely will keep you occupied – but will it move you forward in the right ways?

 

 

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