Going Rogue With Your Career Before You Even Start

Almost the exact opposite of what my career counselor said.

Photo: Jasmine Coro/Unsplash

Not too long ago I watched a YouTube video of an author named Neil Gaiman. Neil’s a force of a writer who claims someday he’ll “grow up and get a real job.”

When he was asked why he only writes novels and doesn’t sync his books into a series, he said that he’s far more interested in finding new shiny objects than getting bored with just one idea.

In other words, he’s not putting all of his eggs into one creative basket. His Starz deal for American Gods and 9 million Twitter followers suggest this is a decent idea.

Neil went rogue. My career counselor probably would have vomited if Neil had said such heresy in her presence.

According to Forbes, though, it’s not heresy. This craving for something different actually cuts deep into our attitude about work and culture.

The workforce in the United States has been subjected to swift radical changes over the last decades, including automation, globalization and go-nowhere jobs… Sadly, only less than 50% of U.S. workers feel that they are in good jobs.

It’s weird that we need to make decisions at 18 — like college majors — that are supposed to ripple forth into the rest of our existence so heavily.

Because if I were to weigh my masters degree with my life experiences, like a few weeks in a third world country, I’d gladly take the latter. Hell if I were to were to stack up my degrees with a few weeks of YouTube and some good books, I’d take the latter.

A college major is an important decision, not a permanent set of ankle weights. If you’ve got a creative itch — or side-hustle itch — that needs scratching, going rogue is a legitimate option.

This article is about how to avoid the common pitfalls of this unchartered territory.

I started a few months ago by keeping my mouth shut, and I’ve yet to open it except for 4:00 AM coffee.

So don’t tell anyone…

No, your rogue ambitions don’t need to be cult-y or secretive, but the widespread notion of tell everyone isn’t the right advice for everyone, either.

Some shudder at the idea of being “caught” going against the grain.

Some even have workplace repercussions. It might sound silly, but social consequences keeps swaths of people from taking action.

My wife just finished reading a book titled Educated by Tara Westover. By the way she described it, it’s a hellish true story about a young girl overcoming the psychological and emotional prison of her family.

My life was narrated for me by others. Their voices were forceful, emphatic, absolute. It had never occurred to me that my voice might be as strong as theirs.

Tara Westover

Maybe it’s not that heavy for you, but here’s the point…

Rather than getting unanimous support, it’s just as likely that we’re surrounded by people who superficially wish us well but passively hope our unconventional ambitions trip over a rock. Maybe it even comes from a place of love.

Whatever it is, it’s a ceiling on whatever you’re trying to explore.

American writer, programmer and entrepreneur Derek Sivers gave a 3 minute Ted Talk that racked up 1.3 million views on this exact topic.

The message was simple: those who stay quiet feel a healthy pressure to keep moving forward; those who share their goals ahead of time feel a negative pressure to keep up with undeveloped promises.

This common “accountability buddy” myth spreads like wildfire on popular sites like CNBC, which touts it as a motivational push in the right direction. But there’s a problem, and you’ve probably felt it before I even say it.

If we tell someone who’s more successful than us, as the article suggests, our anxiety shoots through the roof. That can be a performance killer.

Tucked further into that same CNBC article, here’s the bottom-line context from Ohio State University lead researcher, Howard Klein:

We didn’t find it in this study, but it is possible that you may create so much anxiety in trying to impress someone that it could interfere with your performance.

Idea sharing works in small, tight teams. This was the case when I worked with small military units and certain people who I worked with at a juvenile detention facility. (Hell, even some of the kids who were locked up were more receptive to creative ideas than straight-edged adults.)

Who you tell matters.

Anti-cubical thinking

Our culture is obsessed with conventional thinking — boxes, cubicle farms, standardized testing. We love us some squares…they’re predictable.

We’ve all got a schema in our mind, a story of who we are.

Your schema might tell you you’re a blue collar person, a tech-junkie, a numbers guy, a creative “type.” Don’t let your square assumption of who you are limit what you can do or be.

This type of thinking is called a cognitive distortion, a warped kind of thinking that leads to an overly rigid and boxy kind of life.

A Boston College study found that 80% of young adults were willing to go above and beyond to see their organization be successful. Young people work their asses off…the question is where that work is placed.

Or better yet, who’s vision is that work bringing to life?

Travis Hubbard wrote a story on Medium about the time he found out he was making his employer $24,000 a month but he was only taking home a fraction of that at his hourly rate.

His hard work was going into the conventional box.

Where’s your going?

Immediate feedback

Of the few phrases I should have learned at a younger age, this is one: immediate feedback.

If you’re trying to get something done, it’d make sense to have a dozen redirections a day rather than over the course of a year, right?

For example when learning to use rifles in the military we used the term immediate action to unjam a misfire. Essentially, fix the problem as fast as possible and get back to work.

Deviating from a 9–5 has similar though less rifle-like qualities. The faster you identify what needs to get done, the faster you can be on your way.

Citing research from Frontiers in Human Neuroscience, one article states the following:

In one study that looked at delayed versus immediate feedback, the researchers found that participants who were given immediate feedback showed a significantly larger increase in performance than those who received delayed feedback.

Some of the feedback will be good, some not so good.

You’ll experience the “pain, enormous rejection, bullies and gatekeepers” that Tim Denning referred to in his article on being a generous writer.

So if you laid out your options for going your-kind-of-rogue, what would they look like? Side hustle? Make money online? Quiet the voices that tell you who you should be for a second. You can be free in your head, if only for a minute.

What do you hear?

Whatever your flavor of rogue, find a lane where you can assess how well or sh*tty you’re doing in a relatively quick amount of time.

All information is good information if you know what to do with it.

Make a choice

A buddy of mine is working on the side with an organization called the Flow Research Collective. In a nutshell, it’s the science of high performance based on the idea of flow, our ability to lose ourself in a task.

One of the guys who runs it is named Steven Kotler (who happened to write one of my favorite books The Rise of Superman: Decoding the Science of Ultimate Human Performance).

Here’s his take on convention:

“If we are hunting the highest version of ourselves, then we need to turn work into play and not the other way round. Unless we invert this equation, much of our capacity for intrinsic motivation starts to shut down. We lose touch with our passion and become less than what we could be and that feeling never really goes away.”

Settling into a job you don’t enjoy is like pouring concrete. Let it rest a little too long and it becomes a lot harder to break.

If you’re already there, start chipping away at your rogue ambitions and see what takes shape. Worst case scenario, you fail — which is actually best case scenario, because that’s your roadmap.

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Dad & husband, former Marine and a couple degrees in psychology. Writer for a few publications that care about giving people a hand.

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