The American View: The Useless Secret of their Success

It’s not that rich people’s advice isn’t effective; it can be. It just isn’t realistic for anyone who isn’t already well off. Business Reporter's resident U.S. 'blogger responds to reader feedback on his ‘incompatible perspectives’ trilogy

Right after the second column in my ‘incompatible perspectives’ series posted, a former client messaged me to argue (quite politely) that wealthy people surely have good advice to offer those less fortunate than themselves. I understood the fellow’s argument since he’s a telling example of someone who studied those more fortunate than himself and leveraged their lessons to join their ranks. I knew the fellow back when he was a penniless squaddie and have been pleased to watch him skip over the middle class and join the country club set. That said, I think my old client is both right and wrong, which tells me that I need to clarify my point.

I didn’t argue that wealthy people can’t give good advice to people poorer than them. What I argued was that wealthy people can’t give good career advice to people poorer than them. There’s a significant distinction there.

To be clear, I know from personal experience that well-off folks can and sometimes do share valuable tips about living rich and staying rich. Those are important topics when you’re wealthy – especially when you’ve just made it into the ranks of the nouveau riche where one ignorant mistake could send you plummeting back down into the despised plonk-swilling underlings. Heaven forbid! [1]

Case in point: many years ago, an acquaintance of mine (let’s call him Bruce) made a small fortune when he sold his start-up. Bruce vaulted from lower middle class to lower upper class [2] overnight. As expected, he did exactly what a diligent, working-class fellow traditionally does when coming into money: he traded in his and his wife’s utilitarian Honda people-haulers for a pair of top-of-the-line German luxury cars. Why?

Aside from the obvious factors, like how gorgeous they are, how well they handle, how fast they can scream down the Dallas Tollway at 3 a.m. …

First, because working-class Americans are utterly dependent on their car in most cities. [3] Your car is almost always the second-most expensive thing you’ll ever buy (after your home). Second, your car is often the only thing you own that truly conveys your success (or lack thereof) to your co-workers and friends. Consider how ‘making it’ in American culture used to be symbolized by buying an ostentatious Cadillac. So, Bruce upgraded both of his family’s cars to ‘reward’ himself for his achievements and to show off a bit to his mates. There was no harm in that, right?

Well … yes there was. Without realizing it, Bruce’s stylish new cars put his wife and children in danger. They still lived in the same working-class house in the same working-class neighbourhood after their windfall, and kept on parking their cars in front of their house. Bruce’s wife still did the daily school run, only now she did it in a $90k Cayenne. Bruce’s average lifestyle and dinged-up Hondas had never attracted unwanted criminal attention before. Then, overnight, Bruce started broadcasting to the entire community that he was now loaded … and thereby made his family a target for a quick snatch-and-ransom job.

It took a stern warning from one of Bruce’s wealthier business colleagues to convince him that he needed to change his lifestyle to accommodate his new-found wealth. He sold his cosy little ranch house, moved into a new neighbourhood in a more prestigious zip code, and found a school system where his high-end cars wouldn’t stand out. It was a smart move. I hope it worked out for him; we completely lost touch after his move.

So, yeah. Rich people can and do have good advice to share … when speaking to their areas of expertise. That’s not the exclusive province of the rich; successful people at all levels learn how to optimize their situations and manage risk based on their environment and the totality of their circumstances. Back when Bruce was still a struggling small business owner, he’d figured out how to balance his commute time, neighbourhood location, car selection, access to decent schools, and cost-of-living so as to maximize his ability to grow his business while still supporting his family. Once he jumped ‘up’ three levels on the socioeconomic ladder, those optimization skills no longer applied. Bruce needed a seasoned lower-upper-class native to show him what elements were most important and what elements no longer mattered in his new tier.

Ever hear the phrase ‘good fences make good neighbours'?

That being said, I’m arguing that someone who exists on a completely different socioeconomic tier from you usually can’t offer practical or useful advice on how to solve a problem that’s specific to the tier you’re in. Mostly, because they’ve never experienced the circumstances that dominate your situation. Put another way, the well-meaning career advice that a rich bloke offers to a poor bloke may make perfect sense in the context of the rich bloke’s world; that advice is either useless or actively counter-productive for those of us who don’t (and likely never will) live in that world.

One compelling example of this is that wealthy folks have – whether they recognize it or not – a crucial strategic advantage over everyone else. That is, the freedom of manoeuvre. I recognize the cognitive whiplash potential here. What does that have to do with career choices? Think of it like this:

In military science, one of the crucial strategic advantages that commanders seek to secure and retain in field operations is called ‘freedom of manoeuvre’ (also called ‘freedom of movement’ depending on the Army). Depending on who’s teaching the principle, ‘freedom of movement’ includes the subordinate concepts of ‘situational awareness,’ ‘freedom to engage,’ and ‘freedom to disengage.’ It’s that last one that most important for this discussion.

In simple terms, the friendly force wants to be able to choose when and where they’ll fight, while limiting the enemy’s ability to make that decision for them. A shrewd commander commits to a fight only when she can bring her strengths to bear against the enemy’s weaknesses, while denying the enemy the use of their own strengths.

This is why the U.S. Air Force spends obscene amounts of money to guarantee that no enemy will be able to field combat aircraft after the first day of a major conflict. 

If a commander can catch the enemy in a vulnerable moment, she can strike and win … but only if she has the freedom to engage. That is, the commander can quickly deploy her forces into range to attack while the enemy is at a disadvantage. Similarly, if a commander can spot a potentially disadvantageous battle coming and avoid it before being committed to fight, the commander can increase her chances of winning later on when the odds are more to its favour. That’s freedom to disengage.

The exact same principle applies in career planning and management. I know it seems odd; military strategy seems like it exists on an entirely different plane. We’re only treating this conceptually, not literally.

As an individual worker, you have a limited number of ‘tools’ to bring to bear when managing your career. This includes your education, relevant experience, technical skills, geographic location, past job titles, and financial reserves. For discussion’s sake, let’s assume a truly professional environment where sexism, racism, ageism, and other -isms aren’t affecting your competitiveness. [4] To paraphrase SecDef Donald Rumsfeld, you ‘go to war with the [you] that you have, not the [you] that you might want.’

You can’t compete for a developer job, for example, if you don’t know how to write code (education). You can’t compete for a Java developer role if you only know COBOL (technical skill). You won’t be considered for many jobs if you don’t have a minimum number of years in the role already (experience). You can’t take an on-site-only job in Chicago when you live in Miami (location). You can’t compete for a Senior Manager role if you’ve never been at least a Manager (titles). You compete what’s on your CV.

Your sunny disposition, rapier wit, and captivating charisma don’t come into play until after you secure an interview. 

For most working-class people, you go into battle (so to speak) with finite resources. Your education, experience, skills, and past titles only allow you to compete for a very narrow range of gigs within a reasonable commuting distance. Sure, there might be better-paying gigs, better titles, and/or better work environments near you, but if you’re missing any required attribute, you can’t compete for them. You’re stuck.

So, what do you do? Re-skill, relocate, or reinvent yourself. Logically, in order to become competitive for the available roles, you’d need to ‘fill in’ the shortfalls on your CV. The problem is, you can’t correct any of your competitive disadvantages (e.g., go back to school to pick up a new programming language) if you don’t have enough cash-on-hand to cover your household expenses while you stop working in order to re-tool. Likewise, you can’t relocate to an area with better opportunities unless you have cash-on-hand to burn covering your expenses while moving (which is to say, ‘not working’).

This right here is why so much well-meaning advice falls flat. My favourite is ‘Just move to San Francisco! [5] They have tons of high-paying tech jobs!’ Other great flops include ‘Just go back to school and get a completely different undergraduate degree!’ and ‘Stop working for others and start your own business!’

A well-off person usually doesn’t comprehend why their perfectly-logical advice provokes outrage rather than gratitude. That’s because they wealthy advisor actually can follow their own advice and almost certainly will achieve the desired benefit. All of those suggestions will, if followed enthusiastically, increase a person’s odds of achieving career success. The problem is, only a person who is already financially successful can attempt those techniques. A working-class person almost always can’t.

As the American middle class disappears, we’ll soon achieve President Reagan’s vision of ’shining city upon a hill.’ Only it’ll be an exclusive gate community where those inside can be and do whatever amuses them, while everyone outside can only be and do what their ‘betters' allow. That’s the America that our Founding Fathers wanted, right? 

Wealth is the ultimate ‘trump card.’ If you have enough cash, any mundane obstacle can be bypassed. You can go back to school. You can secure new certifications or licenses. You can learn new skills. You can create your own business and grant yourself the title that you need to compete for the job that you really want. Money grants its possessor the freedom to engage whenever and wherever opportunities present themselves, and the freedom to disengage from disadvantageous or unsatisfying situations.

I know that this is stating the obvious. The thing is, it’s not obvious to someone who has always possessed that advantage. Their world-view assumes it. Thus, when they advise someone else on how to solve a thorny career problem, they can’t help but assume that the other person also possesses the same metaphorical freedom to manoeuvre.

Look at Bruce’s case and you’ll see it plainly. The person who helped Bruce escape the mess that he’d inadvertently gotten himself into in my opening example assumed that Bruce could afford to relocate because of course he could. Everyone can! I’d bet a tenner that it never crossed the speaker’s mind to inquire whether or not Bruce had blown all of his newly-acquired dosh on the new cars or was mired down in personal debt. He pitched his solution based on a tier-specific assumption and everything worked out. Good for Bruce.

As for the rest of us, we don’t have that ultimate trump card. It’s not that we’re bad people; we just don’t have the freedom to manoeuvre that folks like Bruce do. Odds are, we never will. Therefore, the kind of career advice we can use needs to focus on making the best of our circumstances while taking pragmatic risks. That’s not as exciting as the universal daydream of quitting your job and relocating to a glamourous city to have some whirlwind romance, earn stacks of dosh, and follow your *#&$ passion … But daydreams don’t get you to an interview, secure an offer, or pay off your student loans.

[1] He typed, pausing to swill his plonk.

[2] I’m using the U.S. standard 3X3 model here; lower, middle and upper class as the core levels, with each level having three sub-levels.

[3] Remember: American cities tend to hate mass-transit, since cheap and efficient transportation networks allow ‘undesirables’ (that is, everyone considered poor and/or any type of minority) to venture out of ‘their’ areas and into ‘proper’ people’s neighbourhoods (meaning ‘rich white people’ country). See Corinne Ramey’s Slate.com article for a longer and more depressing explanation.

[4] Even though they sure as hell are.

[5] Or New York City or London or Orange County or Seattle …

Title Allusions: Herbert Ross, The Secret of My Success (1987 film)


POC is Keil Hubert, keil.hubert@gmail.com

Follow him on Twitter at @keilhubert.

You can buy his books on IT leadershipIT interviewinghorrible bosses and understanding workplace culture at the Amazon Kindle Store.

Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant.

Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

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