It’s easy to hate on the boss. The clueless middle-manager. The power-hungry doofus. Bill Lumbergh. Michael Scott, if we’re lucky.

So when we see that more and more people are starting to work for themselves instead of for bosses, we celebrate the fact. We throw up giant flags that say “do what you love.” We romanticize it, and for good reason.

But there’s a flipside to all the newfound liberty. While we may be right to take joy in shedding the oppression of full-time employment, we also must take caution in acknowledging the support and security we lose along with it. Shedding the personified human boss above you on the org chart doesn’t mean that the role of the boss ceases to exist; it means that the role now shifts to elsewhere. In large part, it shifts to inside of you.

You become the boss now. You’re the man. You are, now, perhaps, the clueless middle-manager. Heavy is the head that wears the crown, right?

Do we really want that responsibility? Are we well-equipped for it? Are we going to love it?

In a world whose attention is increasingly being consumed by an ever-improving system designed to stimulate our brains with shocking listicles and engagement-optimized tweets, do we really trust ourselves to manage ourselves well?

When the boss is us, who’s going to tell us to unplug the social media and get back to work? Who’s going to remind us that instead of playing into the development of the 21st century Couch Potato, we should be doing what we love– like we said we would?

Not everyone who is making the shift toward independent work is going willingly. Traditional full-time jobs, like them or not, are going away and not coming back. Some people welcome the change, but some are kicking and screaming. They fear a world in which they’re on their own, and with good reason. We’re not meant to be on our own.

I know how badly I need to not be on my own. I don’t want to be consumed by my own lack of discipline. I really really don’t want to hate my boss now, because he’s not going anywhere. I know I’m not the only one facing these sorts of things.

And therein lies an opportunity to shape how this plays out.

We can scatter, each of us on our own, battling social media and our own shortcomings and ever-increasing costs and who knows what else, and hope that we might eek out a happy life somewhere in between. Or we can find new ways to organize and help each other.

This is why I believe so deeply in the potential of Coworking. By putting us in the same room together, it gives us a fighting chance. But it can’t just be window dressing on an office space rental business, as many believe it is now. We have to think of it as a tool to build better ways for us to support each other.

How we approach that is something I’ve been looking at from a lot of angles. I’ve found some answers, but there are so many more yet to be found.

If you’re around next Saturday, a group of us will be talking about these kinds of things all day. I’d love for you to join. I’d also love to hear your voice in the comments below if you have a moment.

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