Preventing Career Failure (Explained with 2nd-Grade Math)
Why we focus on addition/multiplication and ignore subtraction/division • Enormous success ×0 still equals failure • Counterintuitive reasons why avoiding failure > striving for success
You read The 7 Habits of Highly Effective People. You add +7 items to your toolkit of “winning at life.”
You attend a training course about strategic thinking. The instructor teaches you 10 ways to outmaneuver and vanquish the competition. You add +10 ballistic missiles to your mental arsenal.
You graduate from Shartford University’s School of Busy-ness with a Master of Bossing Accreditation (MBA). Add +42 to your elite bossing skills, then multiply ×3 to credibility, hirability, and date-ability.
You complete a difficult assignment, then accept an invitation to visit the peak of Executive Mountain (the active volcano at the heart of Leadership Land) and showcase your success to the top brass. Your name has been whispered in the C-suite before, but this is the first time they’ve witnessed the glory of your golden touch first-hand. Multiply ×2.5 to your year-end bonus and ×10 to reputation.
You’ve read all the success books in the world, taken all the training, gathered all the diplomas, and solved all of your organization’s pain points. You’ve added and multiplied until you have 524,747,482 success points. Soon, you’ll have a corner office at the peak of Executive Mountain. You’ll gaze through the floor-to-ceiling windows and think to yourself:
Everything the light touches is my kingdom.
Then comes the fateful day you multiply all that success by zero.
Your second-grade math teacher probably taught you that any number multiplied by zero is zero. When you multiply 524,747,482 × 0, your result is career failure.
Goodbye, Executive Mountain. Hello, Career Swamp!
How To Avoid Career Failure: An Educational Blind Spot
The Institute of Conventional Wisdom teaches a simple formula for success:
Seek jobs and assignments that add to your knowledge, skills, and abilities in a virtuous spiral of upward mobility.
Network to find mentors and advocates who can multiply your social currency and put you on the fast track.
Figure out how successful people added and multiplied their way onto the cover of Forbes magazine and into the pages of history books, then emulate them.
Read all the success literature and take all the success training conveniently offered by the Institute. Sure, you’ll have to subtract the low, low price of $8,999 (per hour) from your bank account, but it’s a good investment that’ll pay for itself later! You can’t put a price on success!
The overwhelming majority of advice you’ll find on the surface of Leadership Land is about achieving success by addition and multiplication. If your job title or income isn’t as lofty as you’d like, the solution is simple: MORE. You just need to keep adding and multiplying until you have more “success points” than the guy or gal above you on the org chart.
Then you wake up one day and wonder why you’re working for someone much younger than you. You’re laid off/denied tenure/reassigned to corporate Siberia, and (adding insult to injury) the notice is delivered with dehumanizing indifference. You wonder why the “MORE” formula that worked for 40 years has abruptly led you to career failure at 40.
You’re not alone, as this comparison of Google search data show:
The Google search data show that very, very few people are interested in how to avoid career failure. For every person asking how to prevent career failure, there are hundreds – possibly thousands – seeking advice on career failure that has already happened.
If you’re here because you feel like you’re trapped in the Career Swamp or you’re failing at your job:
Please accept our condolences. We’ve been there, and it hurts like hell. The fact that you’re reading this shows that you haven’t given up, and you’re still trying to escape. When you’re going through hell…keep going. Don’t stop to fornicate with the burning cacti.
Congratulations! The disillusionment caused by career failure is exactly what you need to break out of the oversimplified “success formula” pounded into your head by the Institute of Conventional Wisdom. This is a golden opportunity for you to detoxify your addiction to adding more, multiplying more MORE MORE.
There are many articles about recovering from career failure by the Harvard Business Review, Forbes, and LinkedIn. We have nothing to add. However, we can teach you a mindset to avoid your next career failure. This mindset is useful to everyone – no matter if you’ve recently suffered a career failure or if you’re a rising star.
Prevention is Boooooriiiiing
Beneath the Institute of Conventional Wisdom, in the subterranean bowels of Leadership Land, you’ll find the Contrarian Caves. The Caves are dark, filthy, and uncomfortable, making them unpopular with leaders…which is precisely why the best secrets are hidden away down here.
Let’s get the uncomfortable stuff out of the way first. Prevention is usually a thankless job, and preventing career failure is no exception. The proactive leader who prevents a fire from ever breaking out at an orphanage will never be worshiped like the hero who rescues the photogenic baby from the other orphanage that did burn down. If you do a good job in risk management, civil engineering, and security, congratulations! You’re invisible. The only time you’re recognized is when something goes wrong, and people start yelling four-letter words at you1.
No wonder the Institute of Conventional Wisdom only teaches you how to strive for success! Avoiding career failure feels like sitting idly in the Contrarian Caves while other people are marching closer to their goals. Adding and multiplying more to success is exciting; subtracting and dividing less from success feels like getting a prostate exam from a thick-fingered proctologist.
This is why the Contrarian Caves suck. You can’t measure success you’ve never lost, you can’t brag about successfully avoiding career failure on your résumé, and the President supreme-in-chief will never place a Medal of Honorific Awe-chievement on your shoulders for all the times you could’ve torpedoed your career but didn’t. Is it any surprise that people chase the big, tangible rewards of fixing problems rather than preventing them?
But wait!
Before you run off to save photogenic orphans from arsonists, there’s a reason the Contrarian Caves are worth it. Keep exploring, and you’ll eventually stumble upon a Secret Grotto full of Cerebrium. These glowing crystals of Cerebrium are secrets in solid form – some counterintuitive, some that make you shout “Eureka!” – that will help you avoid multiplying × 0.
Why Avoiding Failure > Achieving Success
There are obvious benefits to avoiding the “multiplying ×0” events that lead to career failure. However, we’re now deep enough in the Contrarian Caves to find several shards of Cerebrium. Here are some upsides to failure-avoidance that are severely underappreciated.
Why assault the front gate when you could stroll through the unguarded backdoor?
“Achieving career success” invites you to think in the forward direction, while “avoiding career failure” forces you to approach from the opposite direction. As we described in our About page, it’s a lot easier to get to the core of many big, complex issues by thinking in the backwards direction.
In other words: It’s often easier to avoid subtraction and division than it is to strive for addition and multiplication.
Success, “good communication,” and happiness (+ ×) are difficult to define, and are elusive even to the best of us. Failure, bad communication, and unhappiness (– ÷) are much easier to define, and even regular people can learn to evade them.
Taking the road less traveled to avoid a traffic jam on the highway
Sometimes, a problem is equally approachable from the forward and backward directions. However, you can learn a lot about the many different paths to success and still struggle to add + progress. That’s often because you’re trying to apply conventional wisdom in a competitive environment.
Maybe your approach to achieving career success isn’t wrong, but you’re jostling with other people trying to reach the same goal as you. Everyone’s struggling to add + to their share of a limited pie, which means your addition + causes their subtraction -, and vice versa. Your approach could be valid, but you’re competing all your success away.
Contrast that with avoiding career failure, which is usually the road less traveled by. When the highways are crowded, you can travel farther and faster along the empty side streets. Even if the road less traveled is narrow with a lower speed limit, you add + more simply because there’s no one around to subtract – away your progress.
For a thorough analysis into this shard of Cerebrium, check out When “Best Practices” Produce the Worst Results (our most popular post of all time).
An ounce of prevention is worth a metric crapton of cure
Even if avoiding career failure is at least 50% of a successful career, you don’t have to spend 50% of your time on preventing failure. For white-collar office workers, a little career risk management goes a long way. You only need to spend a little time spelunking in the Contrarian Caves, then return to the Institute of Conventional Wisdom and spend the rest of your time browsing the literature on striving for career success.
Note: if you’re not a white-collar office worker, be sure to read this footnote for some game-changing information ↗2.
Few agree on how to win, few disagree on how to lose
There are so many strategies for adding and multiplying your way to success that it’s hard to remember them all, even harder to apply them consistently3. Worse still: many strategies for achieving success are mutually exclusive, and no one agrees on the best one. In contrast, there are comparatively few strategies for avoiding subtractors, divisors, and multiply ×0 wipe-out risks, and just about everyone agrees on their usefulness.
This is why we love Charlie Munger’s “seven ways to be a miserable failure” speech, which we summarized at the beginning of Why Inconsistency is Worse than Snorting Cocaine. His speech zeroed in on a few strategies for avoiding career failure that few people would disagree with. This makes Munger’s singular speech worth many, many speeches on achieving career success.
Only the Paranoid Survive
These glowing shards of Cerebrium are the payoff for braving the dark and dingy Contrarian Caves. However, there’s one more obstacle: even if you agree that it’s worthwhile to spend time on preventing career failure, it’s too easy to take your success for granted.
Safety, health, and indoor plumbing are like oxygen:
When you have them, you don’t think of them.
When you don’t, you think of nothing else.
Just like oxygen, it’s especially easy to take success for granted if you’ve enjoyed an uninterrupted supply of it for years. It’s been so long since you tasted the bitter cruelty of defeat that you no longer remember what it’s like to divide ÷ or subtract – from your success. Ambitious type-A go-getters are especially prone to believe (sometimes correctly, sometimes not) that their actions resulted in continuous upward mobility, and that setbacks only happen to mere mortals. This hubris trap makes them vulnerable to multiplying ×0.
Rising stars are most self-assured immediately before the Sword of Damocles strikes them down. A farm-raised turkey develops the highest trust in its human caretakers on the day before the Thanksgiving slaughter. The orphanage director detects no evidence of fire in his building for 1,000 consecutive days, eventually arriving at the statistically significant conclusion that the orphanage is not flammable4. He reaches maximum statistical confidence in this science-based conclusion right before the building goes up in smoke on day 1,001.
Andy Grove was famous for saying:
Success breeds complacency. Complacency breeds failure. Only the paranoid survive.
If you’re serious about avoiding career failure, we recommend practicing the following to vaccinate yourself against taking your success for granted:
Inoculate yourself with regular doses of healthy paranoia.
Practice gratitude regularly, which we described in our Thanksgiving post last month.
By indulging in 1) the fear of loss and 2) the joy of having, you aren’t merely thinking that preventing career failure is important. You feel it. The absence of feeling makes it easy to take success for granted, while the presence of paranoia and gratitude serves as a buffer against complacency.
What the Experts Say About Achieving Career Success by Preventing Career Failure
We’ve been covering Charlie Munger a lot recently. What did he have to say about all this?
The way complex adaptive systems work, and the way mental constructs work, problems frequently become easier to solve through “inversion.” If you turn problems around in reverse, you often think better. For instance, if you want to help India, the question you should consider asking is not “How can I help India?” Instead, you should ask “How can I hurt India?” You find what will do the worst damage, then try to avoid it. Perhaps the two approaches seem logically the same thing. But those who have mastered algebra know that inversion will often and easily solve problems that otherwise resist solution. And in life, just as in algebra, inversion will help you resolve problems that you can’t otherwise handle.
– Munger’s Commencement Address at the Gould School of Law, University of Southern California, May 13, 2007
Munger touched on yet another reason most people fixate on achieving career success: they assume it’s functionally the same as avoiding career failure! The fact that achieving success and avoiding failure are not the same (they are asymmetric) is one of the best-kept secrets of leadership. We consider it to be one of the finest pieces of Cerebrium in the Secret Grottos.
We credit Nassim Nicholas Taleb with introducing us to the secret asymmetries of leadership. Here’s his take on what Munger called “inversion”:
Charlatans are recognizable in that they will give you positive advice, and only positive advice. Yet in practice it is the negative that’s used by the pros, those selected by evolution: chess grandmasters usually win by not losing; people become rich by not going bust (particularly when others do); religions are mostly about interdicts; the learning of life is about what to avoid. You reduce most of your personal risks of accident thanks to a small number of measures.
– Antifragile: Things that Gain from Disorder, “Where is the Charlatan” pg. 302
What To Expect In the Next Article
The purpose of this article was a mental jailbreak; we wanted to extract you from the Institute of Conventional Wisdom’s comfortable bubble of false certainty, and to acclimate you to the unnerving darkness of the Contrarian Caves. Hopefully, we shifted your mindset from “how to achieve career success by adding/multiplying” to “how to prevent career failure by not subtracting/dividing.”
We’re going to spend the next article in the Secret Grottos, delving deep into the secret asymmetries of leadership. We will explore Nassim Taleb’s fragile—robust—anti-fragile framework and apply the concepts to avoiding career failure, dealing with career failure, failing for the right reasons, and improving from failure.
The secret asymmetries are the closest we’ll get to actionable advice on how to avoid career failure. Even though we mostly use for-profit terminology, our readers come from government, academia, non-profits, and the military. It’s difficult to provide granular advice for such a diverse audience, so we’re trying to be more like Charlie Munger: providing fundamental and timeless information that’s applicable to all industries.
Check back next week for Anti-Fragility and Asymmetry: Leadership's Best-Kept Secret. If you want to learn more about the first secret asymmetry right now, check out Don’t be a Good Boss. Avoid Being a Bad One. We provided a brief introduction to the asymmetry and applied it to leaders starting new roles.
This is post #1 in the Leadership Land Consistency Experiment, Phase I. We’re building better writing habits by publishing weekly between 12/20/24 – 2/28/25, instead of once every someday. Are we compromising quality for increased quantity? Was this post any better or worse than usual? Please share your comments below or reply directly if you’re reading the newsletter!
Ever notice how utility companies always seem to have 1-2 star reviews? When they do their jobs well, people forget they exist. When there’s an outage, or a company employee makes a mistake, customers become irate.
A more complete and accurate statement would be that the importance of risk management is not linearly proportional to the investment needed. Instead, it follows the Pareto Principle, popularly known as the 80/20 rule. All professions follow the Pareto Principle, but whether they’re 80/20 or 20/80 depends on how much risk their practitioners face.
We assume that most readers are white-collar office workers, and their daily work is low-risk. They can get by on something like 20% risk management/80% striving for success.
Astronauts, elite soldiers, and other high-risk professionals spend most of their time preparing for life-threatening catastrophes and all the things that could possibly go wrong. Their distribution is closer to 80% risk management/20% striving for success.
These are not accurate numbers; we’re just using 80/20 and 20/80 to illustrate how an existential risk will skew the distribution from one extreme to the other. The takeaway is that if your job involves extreme risk-taking, your survival depends on your spending much of your time on avoiding failure.
Case in point: the very first chapter of The 7 Habits of Highly Effective People is about being proactive, not reactive. If more people applied this principle, there would be more Google searches for “how to prevent career failure” and fewer searches for “how to deal with career failure”!
Inflammable means flammable? English r hard