The four horsemen of a dying career (and the shields that protect you)

| In Productivity
| 9 minute read |by Constantin Gonzalez
Four hooded figures in dark robes riding horses through a destroyed modern city street at night. The scene is illuminated by vibrant neon lighting in pink, purple, and orange hues from damaged storefronts and buildings. Debris and rubble are scattered across the wet pavement, creating an apocalyptic cyberpunk atmosphere.

Working for my then employer’s Munich office in 2011, I felt it—that hollow sensation when your career becomes a treadmill. The acquisition of the company I originally joined had stripped away the technological beauty and purpose I’d thrived on for more than a decade. The rigid culture, the pure commercial focus, the loss of autonomy.

I wasn’t incompetent, broke, or irrelevant… I was just bored.

And boredom, I realized, was the first horseman of a dying career.

The four horsemen of career death

In my 27 years in tech, I’ve watched these four horsemen claim countless careers:

Boredom: Subtle but persistent, the spark dies. Monday mornings become something to survive rather than embrace. You go through the motions, but the passion that once drove you to stay late reading documentation for fun? Gone.

Incompetence: Not because you suddenly forget everything, but because boredom kills learning. While you coast, the field evolves. Your skills atrophy. The imposter syndrome that once kept you on your toes? It starts winning.

Irrelevance: The market moves on. Your expertise, once critical, becomes a footnote. Once industry-leading, Solaris, UltraSPAC, and Sun Workstations are nostalgic tech fossils now.

Going Broke arrives last, the final horseman. When you’re bored, incompetent, and irrelevant, the market notices. Opportunities dry up. Compensation stagnates. The annual layoff cycle becomes just another season to survive.

These horsemen don’t ride alone—they compound. Each one strengthens the others until escape feels impossible.

But what if you had shields to protect against each one?

The four filters: your shields to keep your job safe

A hooded figure stands in a futuristic corridor with their back to the viewer, surrounded by streaks of neon light in blue, red, yellow, and green colors. Text reading 'PASSION,' 'ABILITY,' 'NEED,' and 'VALUE' appears to float in the illuminated space around them, creating a dynamic, cyberpunk-style scene with motion blur effects.
The four filters that protect your job.

Standing in that office, I knew I needed a change. But to what? Startups like Amplidata, Nexenta, and Joyent felt exciting but also risky. Most of my then colleagues simply joined competitors, but I kept thinking: “isn’t this just the same?”

Through trial, error, and eventually success, I discovered four filters that act as shields against the four horsemen of the job apocalypse. They work for big changes, like finding a new job, and small, like figuring out what skill to dive into next. Each one is a question you can ask to evaluate any career opportunity:

Passion defeats boredom

“Is this something you’re passionate about?”

When AWS appeared on my radar, something sparked that I hadn’t felt since Sun’s glory days. Cloud computing wasn’t just virtualization—it was a whole new paradigm. Infrastructure as code. Infinite scale. Pay-per-use economics. 100% self-service. My pulse quickened just thinking about the possibilities.

Make a list of things that genuinely excite you. Go broad—new technologies, emerging industries, even adjacent fields. What makes you lose track of time? What do you read about for fun?

But passion alone isn’t enough. I knew plenty of passionate experts who became irrelevant.

Ability defeats incompetence

“Is this something you can become really good at?”

My decade of enterprise infrastructure experience wasn’t obsolete—it was foundational. Cloud computing was just distributed systems at scale. My Solaris expertise translated directly to Linux. My understanding of storage architecture from ZFS mapped straight into cloud storage patterns. Even my graphics chips and SPARC microprocessor knowledge would later prove valuable for understanding AWS’s Graviton-powered instances and GPU computing in AI/ML.

List your transferable skills. What foundational knowledge do you have that transcends specific tools? What do colleagues ask you about that seems easy to you but hard to them? Again, go wide and include “off topic” skills like public speaking, community management or YouTube video production.

Need defeats irrelevance

“Is it needed?”

In 2010, I filled our largest conference room with people eager to learn more about cloud computing. Soon, executives were reading about cloud in airline magazines. Not much later, business departments were secretly experimenting with AWS behind IT’s back. This wasn’t just another technology trend—it was a fundamental shift in how companies would build and run systems.

Pay attention to signals. What are decision-makers talking about? What problems keep appearing across different contexts? What’s moving from “interesting experiment” to “strategic initiative”?

Value defeats going broke

“Are people willing to pay for it?”

AWS wasn’t just another startup—it was backed by Amazon’s resources and determination. Customers were already spending millions. VCs were pouring money into cloud-native startups. The economic engine was clear and powerful.

Look at the money flows. What are companies budgeting for? Where are investors placing bets? What skills command premium compensation?

The Expert Generalist flywheel

After my move to AWS, I discovered the following: Expert Generalists don’t use these filters once. We spin them like a flywheel, each iteration building momentum.

Every year at AWS has been different for me. IoT one year, AI/ML the next, then digital transformation and innovation management. Each “mini-career” added another leg to my expertise, another connection point, another bridge I could build between domains.

This is how Expert Generalists thrive—not by choosing one path forever, but by continuously iterating through these filters, building a portfolio of interconnected expertise.

The filters work differently for us than for specialists:

  • We develop sustainable curiosity across domains, not just deep passion for one
  • We nurture transferable fundamentals, not just tool-specific skills
  • We see connections between needs, not just one market requirement
  • We create value at intersections, not just in one value stream

Making It Real: When and How to Apply

When do you deploy these filters?

Sometimes the moment chooses you. A reorg, an acquisition, a sudden shift in strategy. But you can also be proactive.

At an early point in my career, during my first big reorganization at Sun, my new leader placed me in the “Desktop” group—my brand at the time. But I knew I needed something more relevant, with more business potential and exciting technical challenges. It took all my courage to walk up to him (two hierarchy levels above me felt enormous then) and ask to join the new core technology team instead.

“Sure,” he said. That was it. One question, one answer, and my entire career trajectory changed.

Look for these signals:

  • The “Hell Yeah!” moment—when an opportunity makes your whole body say yes
  • The plateau signal—when learning stops and days blur together
  • The market shift—when three people ask about the same thing in a week

How do you navigate ambiguity?

Passion can be developed. When I moved into “non-sexy” topics like digital transformation at AWS, I initially felt skeptical. Who’s passionate about organizational change? But then I realized: companies are just systems, like computers and cloud architectures. Once I saw the patterns, the passion followed.

Trust your gut, but give it good data first. Create your four lists. Sleep on them. Then listen to what your instincts tell you.

Most importantly: experiment before committing. When I discovered cloud computing in 2008, I didn’t immediately change jobs. I played with the very early PaaS providers I can’t even remember now. I set up my AWS account in February 2009. I organized Munich’s first CloudCamp in 2010. Over time, my view on cloud solidified into a clear conviction. Only in 2012 did I make the leap. I was confident in my choice, even as my previous colleagues remained skeptical. Yes, it took me four years to make the full leap, but good choices tend to marinate.

Your AI-Powered Career Coach

Unlike 2011, you don’t have to figure this out alone. In 2025, you have an advantage I didn’t have back then: AI can act as your career exploration partner. Here’s a prompt that turns Claude (or any other LLM) into your Four Filters coach:

You are a career exploration coach helping me apply the following Four Filters framework.

Ask me questions about:
1. Passion - What excites me, gives me energy, makes me lose track of time
2. Ability - My existing skills, transferable knowledge, and quick wins
3. Need - Market signals, emerging trends, and what decision-makers discuss
4. Value - What people/companies pay for, where investment flows

Help me find the intersections and identify potential next moves.
Start by asking about my current situation and what’s triggering this exploration.
Then guide me through each filter with specific, probing questions.

AI can also act as a coach and accelerate your learning once you’ve chosen a direction. Use it to create learning paths, explain complex concepts, and simulate scenarios in your new domain.

The choice is yours

Back then in 2011, I faced the four horsemen. Boredom had already arrived. The others were saddling up.

The four filters led me to AWS, where every year brought new challenges, new expertise, new connections. They kept my flywheel spinning: cloud architecture, IoT, AI/ML, digital transformation. Each iteration made me more valuable, not despite the variety but because of it.

You might be facing your own horsemen right now. Maybe boredom has been whispering in your ear. Maybe irrelevance is knocking at your door.

Tonight, create your four lists. Look for the intersections—those rare spaces where passion, ability, need, and value converge. Tomorrow, pick one intersection and run a small experiment. Write a blog post. Build a prototype. Organize a meetup. Take a course.

The flywheel starts with a single push.

Because here’s another lesson I learned: The opposite of a dying career isn’t a “safe” career. It’s a living one—constantly evolving, perpetually learning, always building new bridges. Antifragile.

The four horsemen are always out there, waiting. But now you have shields to protect you.

Use them. Now.

For deeper exploration of these concepts, check out: Derek Sivers’ Hell Yeah or No (1-minute video summary), Cal Newport’s Deep Work on developing passion through mastery, and the Fish! Philosophy on choosing your attitude. The four filters framework draws inspiration from the Japanese concept of Ikigai, which is also featured in the article What should you work on?, by James Gurney, and Paul Graham’s much more elaborate essay on How to Do Great Work, adapted specifically for the iterative journey of Expert Generalists.