Aug 8, 2018–When I owned my first flock of sheep, I learned something about people.

One day my wife called me at work to tell me the sheep had escaped from the pasture. This was no surprise, since my fences include sections of uptilted pallets and repurposed fire grates.

So I rushed out of the office to undertake what in my mind had grown to become a wild west roundup.

Veteran ranchers know what happened next. I arrived home only to find the sheep back in their pens, contentedly chewing their cuds and waiting for me to refill their feed buckets.

And that’s what we are like, as our least ambitious selves. Here, the sheep had broken free of their bondage of boredom, and entered a wide open world teeming with fresh grass, sparkling streams, secret corners to explore, and rocky outcrops to scale. They took one longing look, then decided inside their little sheep brains, nah, we’re good. They turned and went back to their pen, to patiently await feeding time.

Tellingly, I did the same, turning around and going back to the office. Who is really the sheep?

For much of my life, I was bewildered by those who need to do things in groups. For example, why are there 5K races? What drives us to sign up in advance, get a number, gather in one place, buy a T-shirt, and hopefully end up in the same place as 150 other individuals? If we want to run, why don’t we just lace up our sneakers, head out the door, and start running?

A veteran 5K-er explained it to me: running with others holds him accountable. He likes the incentive of running against people in the same age group. Not as a challenge of whether he can beat them, but as a way to measure his own progress and standing in the group.

I realized I do the same. I can always shoot baskets in the driveway. But I also like to join a group for a game–as long as they are over a certain age, over a certain weight, and under a certain shooting percentage. You still get a workout, but it’s more fun to run with the herd.

But are we trading our freedom, time, and energy for the security and safety of a regular feeding time, a workplace surrounded by a boundaries we don’t even notice?

It’s a calculation we all make, and it works most of the time, or at least for short stretches. Trading freedom for security makes sense when you are raising a family, caring for a damaged loved one, or dealing with a range of unexpected contingencies. The danger is that complacent contentment becomes the default position. We need to feel secure, with a regular paycheck, insurance, and coworkers who pretend they are family at the company white elephant gift exchange.

I’m not judging or preaching, just pondering. I’ve been all of the above. A free-spirited, free-range entrepreneur. The loyal tenured employee. A self-employed scribbler that starved and self-employed scribbler whose legions of fans breathlessly await his next scribble (not mutually exclusive, come to think of it).

Each has its vices and virtues. But we need to be aware of the position we prefer, and our reasons for being there.

Are you the sheep? Are you the lone wolf.

And why?