When Plans Don’t Work Out
Career Planning in the Cage: Why Posture Matters More Than the Plan
In Florida in 1987, professional wrestlers Bruiser Brody and Lex Luger tied up at the beginning of what was supposed to be a standard cage match. And that’s the last time anything went according to plan. After several strange minutes, it turned into a total shoot – any unplanned, unscripted, or real-life occurrence in a wrestling event. Brody simply stopped reacting to anything Luger did to him. Not in a “your best shot can’t hurt me” way, but in a “your punches aren’t real and I don’t have to play along” way. Eventually, the referee called for a disqualification, and Luger climbed out of the cage.
Professional wrestling might be the most planned performance in all of sports—ask someone on the street and they’ll probably call it “fake.” We all know it’s scripted, choreographed, practiced, and rehearsed—planned to within an inch of its life. But even the most orchestrated scenarios can go sideways. And yet, we still plan. Especially when it comes to our careers.
Uncertainty > The Plan
Most people crave certainty—particularly when it feels like the world is spinning faster than we can track. Career planning, job searches, promotions, pivots, and even professional identities can feel like unstable terrain. In response, we plan. We map out five-year goals, make checklists, draft résumés and cover letters, create Notion dashboards and color-coded calendars.
But in all that planning, we can forget that a plan is not a guarantee. In fact, plans can easily become illusions of control—masks for uncertainty rather than antidotes to it.
The Lin Wells memo is a famous example of this trap. In 1930, the U.S. military’s guiding assumption was “no wars for 10 years.” Nine years later, WWII began. Conviction in the face of unpredictability is dangerous—whether it’s predicting global conflict or banking on a job offer, promotion, or startup exit.
Careers, like plans, break for a long list of reasons, but many trace back to one principle: Goodhart’s Law, which tells us that any measure or pattern we observe tends to break down the moment we try to control it. In short: the more pressure we place on outcomes, the less reliable they become.
For a plan to go “perfectly,” you’d need:
Complete knowledge of your environment
A future that unfolds exactly as expected
No one else influencing the outcome
That’s not how careers—or life—work. Economies shift. Managers leave. Industries change. Algorithms update. Job markets flood. Priorities evolve.
Here are just a few reasons plans don’t hold:
Incomplete information: You can’t wait for perfect information, but failing to account for unknowns—especially when making big moves—can leave you vulnerable. (e.g., Accepting a job without knowing the company’s runway.)
Pride: Overconfidence in your own path can blind you to other options or emerging realities. (e.g., Holding out for a dream role that no longer exists.)
Unreasonable expectations: Ambition is great. Delusional optimism is not. (e.g., Thinking you can pivot industries, relocate, and upskill in six weeks.)
Flawed assumptions: Cognitive biases lead us astray. Recency bias, confirmation bias, and anchoring can all sabotage sound judgment. (e.g., Overestimating job security based on a good performance review.)
Forgetting that other people exist: Careers happen in ecosystems. You need mentors, collaborators, champions, and sometimes, just people not actively working against you. (e.g., Banking on a promotion that requires stakeholder support you haven’t earned.)
False positives: Did that success happen because of you—or in spite of you? (e.g., Assuming early career acceleration will always continue on the same trajectory.)
Ignoring the plan (or following it blindly): Sticking to a path that no longer fits is just as dangerous as never having a plan. (e.g., Staying in a “safe” role that’s slowly becoming irrelevant.)
The wrong motivation: Planning your next steps based on prestige, fear, or someone else’s expectations often leads you into dead ends. (e.g., Going to grad school just to avoid the job search.)
If we’re honest, most career plans derail because of two main culprits: unknown unknowns and pride—about what we think we know, or what we think we should want. Not to mix sports metaphors, but Mike Tyson said it best: “Everyone has a plan until they get punched in the mouth.” The real test is how you respond to the hit.
Planning > The Plan
The point isn’t that you shouldn’t plan your career. It’s that the process of planning is often more valuable than the plan itself. It sharpens your thinking, highlights trade-offs, and helps you articulate what matters most.
But judging the quality of your career decisions by their immediate outcomes is a mistake. Sometimes the job that didn’t pan out, the rejection you didn’t expect, or the role that burned you out teaches you more than any neat win.
When we use planning to force certainty—“If I take this job, then X will follow”—we end up creating a fragile story. Those stories often snap when tested.
As John Kay and Mervyn King put it in Radical Uncertainty:
“Real households, real businesses, and real governments do not optimize, they cope.”
So do real careers.
You still need plans—for timelines, finances, applications, conversations, development, and decisions. But the best ones leave room for the unexpected, are rooted in your values (not someone else’s playbook), and give you a compass, not a turn-by-turn route.
Planning helps you identify what matters. It gives you a starting point, a set of guideposts, and the ability to recalibrate. In that way, plans create feedback loops—not guarantees.
The Posture > The Plan
The best wrestling isn’t just scripted. But it’s not chaos either. The peak performances happen when wrestlers stay attuned to what’s unfolding in real time—reading the crowd, adapting on the fly, and adjusting the plan without losing the narrative.
That’s the posture you want when navigating a career: high adaptability, high honesty, and a readiness to respond rather than control.
This posture means:
Acknowledging you don’t have perfect information
Considering multiple future paths—not just one
Staying open to change, while retaining your values
Creating options without clinging to them
Focusing your efforts, but not fixating on outcomes
And when your posture falters—as it inevitably will—it’s easier to regroup if you’ve held your plans loosely.
Ultimately, your career isn’t a fixed script. It’s a live match. And while you won’t control every twist, you can develop the awareness, flexibility, and resilience to keep showing up—even when the plan goes out the cage door.
Adapted from “Why Plans Don’t Work Out”
