Self-Bossers: How to Break Free from Corporate Culture

In the 21st century many of us are living in very privileged societies. And in these societies we have many different choices on what we can do for a living, more so than just about any other time in history. Complex market economies, technology, and especially the internet have given birth to more options and freedoms than we perhaps could have ever imagined a century or two ago.

However, in the midst of these complex economic hierarchies, there is an emerging generation of self-bossers, freelancers, aspiring entrepreneurs, and independent minds who don’t want to work a 9-5 or assimilate to today’s corporate culture. They want to have more control over their labor and what they produce. And today this is more possible than ever before.

Are you a self-bosser?

Are you a part of that growing minority who can’t imagine working for someone else or having a boss loom over their shoulder 24/7? Do you loathe taking orders and only cherish spending time as you see fit?

If not, that’s okay. Plenty of people are more than happy to spend their working lives under the jurisdiction of someone else. As long as you enjoy your job, it doesn’t make you any less of a person; in fact, in many ways it can be smarter, easier, and more financially stable to work as an employee for another company rather than start your own endeavor. However, this article probably isn’t for you. If you prefer working for another person’s business, but perhaps you are experiencing some trouble at your current job, then check out this article: 10 Reasons You’re Losing Your Mind At Work.

On the other hand, this post is intended for a smaller percentage of people who simply can’t imagine having to work for someone else. They value their free time and creativity so much that they are willing to do anything it takes to become self-employed or manage their own business. They desire more productive and creative control over their time, and therefore they are willing to bare the financial and psychological risks it takes to build a career on their own terms.

Self-bossers see the world differently

Self-bossers think about the world in a different way than your average worker. They are filled with ideas and visions about the world they live in and what is possible. Their aim is to act out these ideas, to test them in the real world, and learn more as they continue to mold reality to the best of their abilities.

Their visions however are not without boundaries. A self-bosser must be a practical idealist, always exercising his or her control when possible, and not showing too much concern to the realities that lay outside of his or her control.

However, sometimes the territory outside of our control scares us away from claiming power over our lives. While we often recognize that we have responsibility over our actions, we are often afraid of deviating from the norm, making mistakes, failing, and suffering the consequences of our devious behavior.

But it is precisely this devious behavior that defines a self-bosser. One of my favorite contemporary philosophers Brad Spangler once said,

“All human progress is about abnormality. Innovation necessarily, by definition, violates pre-existing norms.”

But are you willing to exercise your abnormality for the sake of progress and innovation? I presume that not everyone is willing to bare the risks associated with going against the grain of society, and some probably have a great fear of it.

Being a successful freelancer or entrepreneur will require some degree of stepping outside the norm. Anyone who builds their own career must be innovative in their own way, according to their own knowledge, values, skills, and passion. If we only follow blueprints that have been handed down to us from other authorities in society, then we will never maximize our potential, which is partly unique for every individual.

Self-bossing is self-discovery

Because we each can only manage ourselves in our own way, self-bossing is also a process of self-discovery. You need to first identify your strengths, weaknesses, intentions, and goals, just like a good employer should identify these attributes of their employees before assigning them a job. The only difference between you and any other employer is that you must build the self-awareness and self-knowledge to know what you are best at.

Only once you discover your capacities and limitations can you begin to exercise them and start building your empire. This is going to take a bit of introspection and self-inquiry. You need to ask yourself what you are capable of, what you desire to create, and what obstacles you may face in the future.

Self-bossers make tiny changes with long-term leverage

Becoming a self-bosser can seem like a daunting task. You might already be integrated into the corporate world and you have a hard-time imagining how life would be without it. You have to first accept that this is a process that doesn’t take place over night, but over many days, months, and even years. Don’t quit your day job, but start making changes today that will help align you with your goals. Even writing on a blog 10 minutes a night can do wonders to help you organize your thoughts, clarify your values, and face anxieties that many self-bossers face when they begin to make this leap into the unknown.

10 minutes, 20 minutes, 30 minutes a night is all it takes to start making the transition. This is a new way of life that you need to start building brick by brick, and finding just a couple little things to do on a daily basis can build up your momentum fast. Start by asking your friends what you are good at, do some research on the internet or at the library, and contact others who may be able to offer you practical advice.

I guarantee you that the hardest part about this whole process is getting started. The more you invest into your projects, the harder it will be to give up or walk away. Focus on the little things now and you will begin to recognize the bigger things building up over time.

Flexible persistence

Obviously staying committed to your goals is a big factor in accomplishing them. However, there is a point where blind persistence can leave you investing more time and more energy in plans that simply aren’t going to work out (in behavioral economics, they call this the “sunk cost fallacy,” our tendency to throw money at bad investments because we want to fix them, but we just end up losing more). This is when you need to recognize failure and adjust your course of action.

Just because you fail at one endeavor doesn’t mean you are a terrible self-bosser. Self-bossers often pride themselves in the mistakes they’ve made in their past because they realize how important they were in their professional growth. Self-bossers are persistent when trying to achieve their ends, but flexible when it comes to the different means that can be used to achieve them. They can have long-term visions, but they also know how to stay focused in the present and adjust their actions when presented with new information.

Smart risks and failing small

When we first decide to be a self-bosser it can be an enthralling experience. We often have big dreams of the future and we are willing to take big risks to meet those dreams. But while I’ve mentioned that risks are unavoidable, it would be stupid to take out a three hundred thousand dollar business loan and think you are going to be able to build a successful business your first try.

Let’s say you are a musician who wants to record an album. Before you go out to Sam Ash and buy a whole bunch of recording equipment, why not perform your songs live a few times and see how the audience reacts? Although it may hurt temporarily, you want to know if your music is good enough and if people actually enjoy it (and will want to buy it) before you spend all that money for a recording.

By taking smaller risks you find out what areas you need to improve in before you move on to bigger decisions. It’s a process of trial-and-error, but you want to make sure your errors are small enough to be recoverable. This is how you sustain positive growth.

Before I write a whole book and send it off to a hundred publishers, I should probably write a few chapters and get some people’s thoughts on it. You want to get feedback on your work periodically and in moderate doses, so that you can build off of it and not get overwhelmed or discouraged by the bigger failures that often occur when you take bigger risks. Be a smart risk-taker and try to do smaller litmus tests to see if what you are doing is productive or counter-productive.

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