Why Career Planning Has Become Career Suicide
What artists know about career success that business schools don't
I'm writing this from Paris, where I just saw an extraordinary David Hockney exhibition at the Fondation Louis Vuitton. At 87 years old, Hockney has been making art for seven decades, and this show spans his entire career from 1955 to 2025.
Looking at his early work next to his recent pieces, it's almost impossible to believe they were created by the same person. His style, his medium, and his entire approach have evolved dramatically over the decades.
The same thing happens when you look at Pablo Picasso's work. His Blue Period looks nothing like his Rose Period, which looks nothing like his Cubist work. If you saw Picasso's earliest paintings without name tags, you'd never guess who made them.
Picasso couldn't have planned his Blue Period. Hockney couldn't have planned that he'd end up making art on iPads in his 80s. Their best work came from allowing themselves to evolve, to go through different seasons of exploration without knowing where those explorations would lead.
Most of us have been raised to believe the opposite. We're taught to be planners. What do you plan to do when you grow up? How do you plan to earn money? When do you plan to buy a house? What do you plan to do in five years?
Planning feels responsible. It feels like the mature, adult thing to do. We write business plans before starting companies. We do financial planning and retirement planning. Planning gives us a sense of control in an unpredictable world.
What I've realized, though, is that planning your life is actually the most irresponsible thing you can do.
Artists understand something fundamental about how human potential actually works, something the rest of us have forgotten. You can't plan your way to your best work. You can't predict what you'll be capable of in ten years because the person you'll be then doesn't yet exist. Our most fulfilling work emerges from periods of uncertainty, from following curiosity even when you can't see the endpoint.
In art, this kind of evolution is celebrated. We expect artists to grow and change. We understand that their early work was necessary, but it wasn't their peak. Many artists create their most important work decades into their careers, after years of experimentation and development.
The corporate world still operates on 20th-century career models. We expect people to know what they want to do at 18 and stick with it. We treat career changes as instability rather than growth. We value specialists who go deep in one area over people who move across different fields. We've created systems that reward predictability over exploration.
This made sense when the world changed slowly. When industries were stable for decades, it was smart to pick a lane and stay in it. When companies had 30-year lifecycles, long-term planning worked, but that world is gone.
Now, entire job categories disappear in a few years. The skills that got you hired five years ago might be irrelevant today. The company you planned to retire from might not exist in ten years. Yet, we're still operating under the old rules. We still tell people to make five-year plans. We still reward linear career progression. We still treat exploration and pivoting as character flaws rather than survival skills.
What we call responsible behavior has become a trap. Someone who spends years becoming deeply specialized in one field looks productive and focused. When that field shifts or gets automated away, all that expertise becomes a liability. They've built their entire identity around skills the market no longer values.
Meanwhile, the person who spends time exploring different areas, building what researchers call “connected knowledge” across multiple domains, looks unfocused to traditional employers. In reality, they're developing the ability to see patterns and opportunities that specialists miss.
Take Reid Hoffman, LinkedIn's founder. He studied philosophy in college, became a Rhodes Scholar, then worked at Apple and PayPal, before starting LinkedIn. His philosophy background taught him how to think about human networks and relationships. His Apple experience showed him consumer technology. PayPal gave him expertise in digital transactions and viral growth. When social networking emerged, he could see the intersection of professional relationships and digital platforms, something others missed.
No career counselor would have recommended this path. It looked scattered and unfocused. What Hoffman was actually doing was accumulating connected knowledge that would eventually create billions of dollars of value.
This doesn't mean all planning is worthless. Tactical planning for immediate goals still makes sense. You should plan your next project, your next quarter, and your next learning goal. What's become counterproductive is strategic life planning that assumes you can predict who you'll be and what the world will need in a decade.
This isn't just career advice. It's how people who study uncertainty for a living actually operate. Professional futurists don't try to predict the future. They create multiple scenarios for how things might unfold, and then prepare for several possibilities instead of betting everything on one outcome.
This makes us ask, “How do you apply this thinking to your own career? How do you build connected knowledge strategically?”
The key is identifying emerging intersections before they become obvious. Look for fields that are starting to influence each other. Find people who are already operating at these intersections and understand how they think. Notice which of your existing skills could transfer to adjacent domains.
More importantly, pay attention to problems that require knowledge from multiple fields to solve. Climate change needs technologists, policy experts, and economists. Artificial intelligence needs computer scientists, ethicists, and psychologists. The future of work needs people who understand both technology and human behavior.
The most valuable opportunities exist at these intersections, but only for people who've invested time understanding multiple domains. You don't need to master everything or jump randomly between careers. Following your curiosity strategically means experimenting with new areas while building on what you already know. The seasons of exploration that feel unproductive are actually where growth happens.
At another Paris museum, I found a piece that perfectly captures this moment. Mircea Cantor created a photograph called "Unpredictable Future" where he traced his finger on a steamed-up window, deliberately keeping a spelling mistake in the title. The image captures that feeling of facing uncertainty, which is somewhere between hope and anxiety.
Cantor says we seek transparency and predictability in everything now. We want to prove, to know, to be certain. There's an inflation in the value of certainty, he argues, and we need the opposite.
The most responsible thing you can do for your future is to give yourself permission to not have it all figured out. Follow interesting opportunities even when you can't see exactly where they lead. Understand that being temporarily uncertain is better than being permanently stuck.
Change is the one certainty in life and planning your career based on yesterday's playbook certainly isn't going to work.
This article is a breath of fresh air! My "connected knowledge" is my superpower, but you’d never know it from my resume. And in interviews, or an ATS? 😬
The irony is that once someone does see it, you become irreplaceable. But most hiring managers don’t recognize it. That’s why networking is so crucial for people like us.
We’re stuck in this gap between how things work and how they should work. Hopefully, one day, this kind of value will not only be understood but celebrated and sought after. That's what excites me today.