The Hypocrisy of Career Hipsters
In: Newsletter

Hello everyone!

It’s been another busy week for me, but despite the hectic schedule, I wanted to share an idea I’ve been working through. Over the years, I’ve observed a particular demonization of figureheads within professional spheres. In design, people like Mike Monteiro both lead the charge and take the heat for their controversial opinions, often stated loudly.

For me, I’ve come to recognize and identify this phenomenon as what I call career hipsters: a navel-gazing group that claims to be above traditional management and public-facing career paths while maintaining a single-minded focus on improving their "craft."

We all know these people. But, what happens when we become what we once despised?

Whoever fights monsters should see to it that in the process he does not become a monster. — Nietzsche

As the hipster qualities begin to fade, our path and connection to the craft changes. Becoming what we once despised is nearly inevitable. Meanwhile, I believe it’s possible to maintain a meaningful relationship to our work while we ascend in our career.

I’d love to hear your thoughts on the subject. Have you experienced the wrath of design-Twitter or another elite-tribal force?

Either way, I hope this serves as a great reminder of how our ideals intersect with reality. Have a great week!

- Kevin K.

Two-Faced: The Hypocrisy of Career Hipsters

Hipsters are everywhere. It used to be that we'd only see them in expensive coffee shops or record stores. But now, thanks in part to the magic of the internet, we see them online as well. They've birthed a new breed of hipster—what I refer to as a "career hipster." These new hipsters are the prominent personalities in our professional circles that exist solely to ride—or create—the latest contrarian trends and say whatever garners the most attention or likes/faves within their bubble. They pride themselves on being both digital contrarians and arbiters of authenticity.

While cultural hipsters still rule the physical environment, career hipsters rule now dominate the professional online environment. Cultural hipsters are relatively harmless—don't let the beards and mountain range tattoos scare you. Career hipsters are far more dangerous.

Career Hipsters: Who They Are and How to Spot Them

I’ve come to recognize, identify, and name the people who embody this phenomenon as “career hipsters.” For me, they’re defined as a navel-gazing group that claims to be above traditional management opportunities and public career paths while maintaining a single-minded focus on honing their "craft." These people will often arrogantly tout their role in “doing the work,” as-if those who speak at conferences or manage teams are incapable of getting their hands dirty.

Cultural Hipsters and Career Hipsters share similar qualities. It's not hard to draw parallels between the two groups.

They travel in small but passionate groups. They tend to inhabit similar locations both physically and digitally; physical locations like Seattle, Portland, Brooklyn, and Austin; digital locations like Twitter or an obscure blogging platform that is clearly superior. Once something goes mainstream, they lose interest. They pride themselves on being interested in things before they were popular—the modern cultural and career Lewis and Clark. Like Lewis and Clark, Cultural Hipsters love wool, plaid, beards, and fur. Fashion choices aside, hipsters are best known for a nearly universal navel-gazing penchant. Career hipsters love new frameworks, tools, black shirts, and the latest #FutureOfWork trends.

They define themselves as much by what they don't like as by what they like. The career hipsters say things like "I'm not in it for the fame like they are, I just want to focus on my craft." They see themselves as the purest, most honest form of their profession—defining and refining from their community from the inside out.

Creating A Common Enemy

Antagonists are a galvanizing force. The mere presence of a central enemy motivates us to act, to change, to improve, and to focus. Military units are particularly good at bringing people from different backgrounds together to rise up and defend against the enemy at hand. Sports teams, political tribes, and startups use the same psychological principles to motivate and embolden their teams. No matter the circumstances, common enemies are a powerful unifying force.

In the early days of a career, it's valuable to have a personal and professional north star. And to some extent, it's equally valuable to know the areas to avoid. The presence of a north star keeps us focused on the art and craft that led us to a particular profession. When we lose sight of that, we're destined to lose the emotional connection to our work. The irony is, what makes us great at our “craft,” might just be what drives us away from it.

But if we love our craft so much, how could we possibly let it go? As we grow and develop, new opportunities present themselves. This might come in the form of a promotion to management, an opportunity to start a new venture, or simply to change direction. This is when the qualities that we held so tightly early in our career start to conflict with the new paths and opportunities in front of us. This is where the hipster faces a critical idealogical crossroads.

Whether we're designers, engineers, strategists, or sales teams, we're accustomed to interacting with people that embody qualities that don't match our idealistic views of our profession. Our instincts tell us they're insincere and vapid. In most cases, they're either figureheads within a profession or rapidly ascending the ranks. We know that most of these people start off with pure intentions—do great work, make an impact, or change the world. But as time passes, the idealistic trappings fade. Those who once proudly bore the hipster badge have become everything they once despised.

But what happens when the force for good turns on the negativity switch? More importantly, what happens when we become what we despise?

Mainstream Hypocrisy: Must We Become What We Despise?

We spend so much of our time thinking. To most of us, our thoughts seem harmless. But armed with a target, our feelings become habits, our habits become actions, and our actions influence our perceptions.

For example, many professionals see someone in their field and say “I’d never want to be that person.” You know these people; the career types, the professional blowhards, the talking face without clear substance. To you, they represent everything that's wrong with your profession. This is the antagonist that once compelled you to grow professionally while avoiding the traditional management path.

As a young professional, I knew that feeling all too well. After years of comparing myself to others, I finally realized that, for me, these feelings came directly from my own insecurities. The thoughts were an emotional response to someone receiving fame, attention, or notoriety that felt unwarranted. It was a winner-take-all mentality; their success could only mean my failure, and therefore, I must despise them. But, in time, I came to realize that their success was simply that—their success.

The more time I spent thinking about someone else’s success or my failure, the harder it was to actually move the needle on my own work.

“You Either Die A Hero, Or You Live Long Enough To See Yourself Become The Villain”

Our personalities are influenced by what we spend our time thinking about. If you let it, an enemy can absorb your mind and control your thoughts. The more we despise our enemies, the more likely we are to be affected by them. So if we spend too much time thinking about these people, they’ll become a fixture in how we behave, think, and feel. It’s easy to lose sight of ourselves when we’re lost in the dark.

Guarding Your Craft While Building Your Career

Let's be pragmatic for a minute. Being a career hipster is a fine quality in the early stages of your career. If the leaders at the top of your profession help motivate you, either positively or negatively, then great. But guess what—being a career hipster only works for a short period of time, and if everyone buys into your hipster mindset.

The reality is that the career-types—the ones at the top of the chain—were probably just like you one day. In fact, many of them built their careers without realizing they'd ended up as figureheads. It’s easy to lose ourselves in judging others’ success and building a negative narrative to support our own goals and boost our ego.

But the bottom line is the hipster mentality can eventually lead to hypocrisy. If you want to advance in your profession, you’ll likely become exactly what you once despised. Even worse, you’ll look that much more ridiculous because you spent so much time railing against someone else's career, only to eventually find yourself in the same position. But here’s the good news: you can be both a talented craftsperson and a talking-head-style leader.

Though it might seem cool to tear other people down, it’s only going to hurt down the road. Do you know what's cool? Doing great work with great people. It’s that simple.

“Whoever fights monsters should see to it that in the process he does not become a monster”


People want to work with people who don’t attack or tear down colleagues So put down your weapons, stop the backhanded tweets, and realize that you can be great at your craft without sacrificing your soul. The people you despise might be fighting the same internal battle, so be kind — and avoid being a hipster.

Internet Reading

1. AI Is Coming for Your Favorite Menial Tasks

When it comes to AI, there’s no shortage of opinions for a utopian or dystopian future. What is clear is that it threatens our pre-existing notions of work and creativity, forcing us to clutch to ways of the past. I want to believe that AI will free us from remedial work and expand our capacity to take on more meaningful, challenging, and engaging problems.

2. The Problem With Believing What We’re Told

This WSJ article rings loud the increasing value of mental models and heuristics (flashback to last weeks’ newsletter, anyone?). In an increasingly complex world, it’s essential to have a toolset to help defend against falsehoods and misjudgment.

3. VIDEO: How Craving Attention Makes You Less Creative

The title of this video speaks for itself. I don’t want to give away the ending, so I’ll leave it to you to watch this particular—cough, well known—speaker explore how attention erodes creativity.

Apps & Tools

Descript — Record. Transcribe. Edit. Mix. As easy as typing. Take control of your podcast with Descript.

As the producer of a podcast (season 2 coming soon!), I couldn’t be thankful for a product like this. At its core, Descript is an AI-based audio editing app. But the product offers a suite of features like overdubbing, text-to-audio editing, auto-transcription, and more. It is, without a doubt, a game-changer for the podcast industry.

Weekly Challenge #19

Carry a book to read when you have a break.

Enjoying Path Nine?

If you liked this post, I’d really appreciate it if you share the post!

Thanks for reading, and see you next week,

— Kevin K.

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