As we navigate the labyrinth of life's decisions, we are bombarded with advice. Some good, some not. It’s the bad guidance masquerading as good that we have to watch out for.

In Dig Where the Water Is, we discussed the Expertise Fallacy, whereby we conflate experience and knowledge. What we think we know to be true can obfuscate what is true in this situation, thereby making us oblivious to what’s obvious.

This isn’t the only member of the masquerade, though. There’s another group notorious for putting the vice in advice. These are a unique breed of fallacies lurking at the intersection of good intentions and terrible ideas - the Misguidance Monsters.

These enigmatic entities are not evil but epitomize the adage, "The road to hell is paved with good intentions." They're the guardians of misguided counsel, often cloaked in the allure of goodwill, and they invite us to follow them down paths that ultimately lead to confusion and missteps.

We've all encountered these beasts at some point - well-meaning friends, family, or even superiors offering counsel that seems sound but, in the end, leads to more confusion than clarity.

The best way to confront these beasts is to learn to recognize their disguises and arm yourself with the wisdom to unmask them.

The Ego-Boosting Banshee

Appearance

The Ego-Boosting Banshee is a siren tempting you with praise, adoration, and popularity. It encourages you to seek external validation, often at the expense of your authenticity, and encourages you to buy into your own hype.

Example

In preparation for a meeting where I would lay out for our COO how a particular sales team was not only unprofitable now but likely always would be, my CFO told me to lead with the conclusion and jump right into the next steps. The COO trusted me, and it would be a waste of all of our time to elaborate on the assumptions and process to come to such an obvious conclusion. I had never felt so empowered and valued.

Well-played, Banshee.

What I failed to appreciate as I was praised was that this particular sales team was near and dear to the COO’s heart. I forgot the first principle of good storytelling - taking into account how my audience would react to the message - and I was bombarded with questions about how I came to such a counter-intuitive conclusion. I wasn’t prepared, so I stumbled over my answers as I tried to pull up the spreadsheet and dive into the details. These optics further solidified his opinion that my work was subpar, and it took weeks of detailed walkthroughs before we could all get on the same page.

Unmasking Strategy 

The Banshee builds us up such that we cross the thin line separating confidence and arrogance.

The key to conquering this demon is to separate how the advice makes us feel from how it resonates with the situation. How we want to be perceived provides a blueprint of what we should do, regardless of whether we think we’ve achieved that status. In my example, a good finance partner would be prepared to dive into the details even if they weren’t on the agenda. So, having backup slides covering assumptions and data sources would’ve preserved the trust I deeply valued.

The Talent Temptation Tengu

Appearance

The Talent Temptation Tengu is a flashy and seductive figure. It lures you with the promise of riches if only you had the right people on the bus while ignoring the condition of the bus those people would be driving.

Example 

Much of my career has been spent supporting Sales and Support teams. These are the lifeblood of any company and, as such, often get the highest level of scrutiny from executives across the company.

Like clockwork, the team would fall short of its aspirations every year. Hold times would be long, sales would fall short, and the question of “why” would invite the Talent Temptation Tengu to show up. Rather than appreciating the complexities of these challenges - long hold times may be due to product issues, and sales targets may have been overly ambitious to compensate for softness in self-serve motions - the Tengu would tell us the challenges we were facing were a function of poor leadership rather than poor systems. We would hire a new leader for this or that department and spend a year supplying them with the tools and people they needed to win, only to find that the underlying challenges remain. Inevitably, we’d be back to square one, thinking we (once again) hired the wrong person and started the search for a new driver for our poorly maintained bus.

As James Clear said, “You do not rise to the level of your goals. You fall to the level of your systems.”

Unmasking Strategy 

The Tengu’s power lies in its ability to oversimplify. Yes, talent is important - critical, even - but rarely does replacing one leader cause meaningful change without addressing the underlying systemic limitations. When considering talent, remember the investment is threefold: people, systems, and processes. It’s the latter that often gets ignored here, causing this three-legged stool to be imbalanced and, ultimately, topple over.

The Parternalistic Poltergeist

Appearance

The Paternalistic Poltergeist appears as an overbearing authority figure, dictating what's best for you based on their own experiences, inadvertently steering you away from your true desires. It wraps you in a web of safety at the expense of your individuality and potential.

Example 

Late in my career at GoDaddy, I was approached with an opportunity to join an early-stage tech startup headquartered in Scottsdale. I would be running all of finance & accounting, reporting to the CEO, and have a front-row seat to what it takes to build a hypergrowth company. It felt like a no-brainer “yes.”

Then, the Poltergeist showed up.

He arrived in the form of mentors I respected, highlighting risks that gnawed at my insecurities. Startups are risky. I wouldn’t have a finance leader to guide me when times got tough. I was mere months away from becoming a father, and even though this new company said they would help me achieve balance, wouldn’t I have a better chance of work-life integration at a company where I was already established?

I ultimately turned down the job - after initially accepting it (ugh) - because I listened to what others thought was best for me. I’m fortunate to have had other wonderful opportunities to further my career, both inside and outside GoDaddy. However, I’d be lying if I told you I didn’t regret outsourcing the decision by relying on what others thought was best for me.

Unmasking Strategy 

The Poltergeist, haunted by its own experiences, pushes for “safe” choices. As discussed in They’re Only Chasing Safety, safety is a limiter on the downside and upside. When pursuing outsized outcomes, you must accept that some people you trust will advise you to deviate from your path because it makes them uncomfortable. While external advice is valuable, your dreams and choices are valid. Assert your voice and make decisions aligned with your genuine aspirations.

The Comfort-Killer Kraken

Appearance

The Comfort-Killer Kraken lurks in a calm sea, promising the tranquility of a life devoid of risks. But beneath the surface, its tentacles are ready to drag you into the depths of complacency. Its power is convincing you that maintaining the status quo is a safe choice rather than a non-decision that allows good opportunities to pass you by.

Example 

Over the years, I’ve developed a reputation as an Island for Misfit Toys. Teams needing a temporary home (whether due to performance or leadership changes) would find their way into my organization until we could figure out the right landing spot.

Early in that journey, I had executives posit that I keep this random assortment of teams. Why rock the boat if everyone is settled and nobody is upset with where they sit?

Luckily for me and these teams, I saw the Kraken lurking underneath the surface. Thankfully, the teams liked me enough to be satisfied with where they were, but structurally, it made no sense for a Finance leader to run a Project Management org or a subset of an Analytics org. Part of leading a team is doing what’s best for them, and in this case, what was best was finding them a permanent home where they were best positioned for success.

Unmasking Strategy 

To defeat the Comfort-Killer Kraken, dare to venture into uncharted waters. Embrace calculated risks and step beyond your comfort zone. While it may seem daunting, true growth and achievement are found in these turbulent waters.

In other words, growth comes from discomfort. If you’re making decisions that optimize for comfort, you’re giving up on what could be for what was.

The Structure Siren

Appearance

The Structure Siren appears as a master architect with blueprints and building tools. She exudes an aura of order and precision, luring you with promises that meticulously building something will inevitably attract success. She convinces you that if you build it, they will come and watch with glee as you inevitably have to tear it down and try again.

Example 

Hiring hurts. The good news is you can choose how it hurts you - at the beginning or the end.

In my career, I’ve (fortunately) only had two regrettable hires. In both instances, I was desperate to fill a role and bought into the advice of those around me that having somebody was better than having the right body. I succumbed to the Siren’s song, opting to ease my current suffering of dealing with an open role, only to have exponentially more suffering dealing with a poor candidate fit down the road.

Unmasking Strategy 

To conquer the Structure Siren, recognize that structure alone does not guarantee success. As discussed in Tacos vs Burritos, we should carefully consider any advice that resembles “Once we have X, we can deliver Y.” When focusing solely on the missing ingredient, we should remember to question how that piece fits into the broader puzzles we discussed in Subtraction, simply adding something to a system rarely improves it.

Said another way: you could build the most fantastic football stadium the world has ever seen, but if the team doesn’t win any games, it’s unlikely anyone will show up.

Conclusion

In the pursuit of wisdom, it's essential to remember that not all advice, no matter how well-intentioned, is suitable for your unique journey. The Comfort-Killer Kraken, Structure Siren, Paternalistic Poltergeist, Talent Temptation Tengu, and Ego-Boosting Banshee represent just a few of the challenges you might encounter along the way.

With vigilance and discernment, you can see through their disguises and emerge from their influence. Trust in your own voice, values, and aspirations. Recognize that wisdom often requires a blend of structure and adaptability, courage to take risks, and the capacity to chart your own path.

By unmasking the Misguidance Monsters and understanding the nuances of well-meaning but misguided advice, you take a step closer to making decisions that truly align with your authentic self and your unique aspirations.

The journey to wisdom may be fraught with challenges, but it's your unique path, and you're the one who holds the map.

Thanks to Roman Eskue for graciously reviewing this post to help me improve it before publishing!

Suggested reading

• Dig Where the Water Is

• Tacos vs. Burritos

• Subtraction

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