The Hidden Costs of Executive Glory

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Strange things are afoot at the Circle K. I have seen a notable uptick in my clients wishing their commitment to executive leadership goes away. Or they are actively working toward independent contributor roles. Questioning whether executive leadership is really right for them.

I’m wrestling with why that is. 

I most often work with the hard-charging type. The up-and-to-the-right type A high performers. You know the sort. And if you haven’t unsubscribed from my rather arrogant and elitist perspectives, you probably are the sort too.

Why would anyone want less? We’re talking about money and power here. Executive control is the epitome of success, status, and glory. Anything on the contrary appears blasphemous.

After all, living the big bad top-dog chieftain lifestyle is alluring. 

The American Express is Centurion black, the shoes are red bottoms, the flights come with champagne, and the vehicles are Italian (or electric, if I’m frank). 

Executive leadership is akin to societal supremacy for city slickers and suburbanites alike. That’s right, Joneses; suck it! I’m the boss now.  

Am I grossly mistaken? 

Executive Leadership Glorified

Too often, executive leadership is lauded as the pinnacle of career success. Like you will achieve a pseudo-celebrity status when you win. Or something.

Executive positions pay well and carry an air of exclusivity. They are not easy to come by, and once you get one, they may be even harder to keep. Earning an executive role recognizes a track record of organizational excellence and ambition. But not necessarily true leadership.

Leadership positions are highly desirable, even for those who need more time to be ready for the challenge—or those entirely incapable of steering a team at the helm but think they can. So the rose-colored glasses glisten while ambitious appetites grumble for more.

I expect that it’s the status many desire, not the realities of the work.

My hunch is that, in many’s urge to climb the ladder, they force a promotion or career transition prematurely when presented with any opportunity. I’ve been guilty of this too. I accepted my first VP role eons before I was ready. I reckon others have too. 

It got me thinking about how those who seek power rarely deserve it, and those who deserve it rarely seek it. But then again, that line of thinking may have more to do with this week’s midterm elections. 

Suppose executive roles only appear to be all sunshine and rainbows. What ugly and unattractive truth causes many to pause, reassess their career ambitions, and look for the nearest exit? 

I’ll reveal in the final point below.

The 3 Fundamental Factors for Executive Leadership

There are many paths to becoming an exceptional executive leader; however, these three high-level areas must be true at a minimum. 


Professionals who lack determination will never find themselves with meaningful executive opportunities. Most don’t climb the ladder by accident. I’m highly suspect if you disagree.

In your career, you’ve found clarity around your ambitions, set a goal, made a decision, and got to work climbing the ladder. The effort alone requires steadfast determination to make any meaningful progress.  


Without direction, aspiring professionals will spin their wheels. In most cases, you must commit to a path and stay in your lane. You’ve likely had to avoid digressive paths for the sake of “putting in the time” or “paying your dues.”

While this is only sometimes the case, executives must tell a story that others perceive as planned progression (even if it’s not) to articulate that they’ve had intentional direction in their career.  


Discipline is the battle between what you want now and what you want most. Every executive I’ve worked with meets the determination criteria. Most have a strong sense of direction. Unfortunately, it’s often the discipline where the results get hazy, and some need help to hack it. 

I don’t mean that discipline is the issue in getting to the executive role in the first place. Most executive-bound professionals illustrate discipline while on the rise. More often, discipline breaks down once the executive begins facing the realities of actual executive work. 

Beyond the table stakes of making decisions that influence the business’s success, the number of families supported on payroll, or the complexities of board pressures, executives face immense real-world pressures that are often unknown to others. Or at least not shared with them openly.

Many executives shoulder these burdens without breaking character. However, when these challenges escalate even further, I’ve noticed that their discipline frequently breaks down. 

I’m talking about layoffs. Pandemics. Recessions. Failing business models. Unfavorable financing environments. The “hard things” that were previously camouflaged by the rose-tinted glasses of naivety. 

The reality is that executives are thrust into “a rock and a hard place” scenarios—whether it was their fault or not. They are forced to decide between terribly unpopular or catastrophic business-failing choices. Some of which affect the greater public, stock prices, and politics. 

The stressors and repercussions of executive decisions are often magnitudes above what everyday people experience (at work). And often do not adequately align with their compensation. (They get paid 2x – 3x on average, but the responsibility is 10-15x at least)

Many executives can weather the storm once. But the stains associated with their negative experiences have them considering new opportunities.

Is the juice really worth the squeeze? 

Sometimes this means they are open to relinquishing the wheel and looking for a ride in the passenger seat.

And here’s the hard truth. 

If you lack the discipline to lead through unpopular decisions more than once. Or you lack the courage to inspire contentious conversations with other leaders and shareholders when appropriate. Or you struggle to take ownership of failures and the responsibility to protect and respect your team. Or if you thought the celebrity of being the big boss in charge isn’t all it’s cracked up to be—then you must reevaluate your career.

If you lack determination, direction, or discipline, you’re disqualified.

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