Wishful Thinking & Becoming Formidable, Telling Your Boss You're Miserable, Cunningham's Law, and More

Bring Ambition Newsletter - February 11, 2021

Hi folks and welcome aboard new subscribers!

In the Bring Ambition Newsletter, I share 5+ things that are fascinating me lately in the world of professional and personal development, peak performance psychology, meta-learning, side hustles, and more. You'll receive unconventional resources, cool gadgets, practical advice, and other inspiring content.

As always, if you enjoy the newsletter please share with a friend!

1.) Wishful thinking and becoming formidable

A fundamental step in the process of becoming your most formidable self is avoiding wishful thinking.

Elon Musk described it best:

"One of the biggest mistakes people generally make - and I’m guilty of it too - is wishful thinking... You want something to be true, even if it isn’t true. You ignore the real truth, because of what you want to be true. This is a very difficult trap to avoid."

Wishful thinking is mistaking what you want to be true for reality. A desirable illusion biases and skews all information and evidence. The problem is wishful thinking not only influences perception but drives irrational behavior and suboptimal decision making.

Catfishing Yourself

Remember the show Catfish? People want to believe they've found some perfect, out-of-their-league partner on the internet, and ignore all the warning signs that it's too good to be true. You can catfish yourself, too.

It's ultra-common in the startup world. People come up with a business idea in isolation. They never actually talk to potential customers. They're enchanted by a romantic flash of inspiration and convince themselves it's the next big thing. They sink endless resources into the venture and are shocked when they fail to gain traction. In the end they discover they've simply built a product nobody wants.

In the investment world, the “contagion” of wishful thinking leads to wishful betting, destabilizing portfolios and markets alike.

It happens at work, too.

I've seen countless careers derailed because of wishful thinking. An employee is utterly convinced they're a stellar performer and when they're provided feedback to the contrary, it simply doesn't register.

They’ve become the “product nobody wants.” The manager is often partially at fault for being a poor feedback provider, or for putting off difficult conversations. But these people would land in my office after a hail-mary nomination for training or an executive coach and say "I don't know why I'm here." These employees are only snapped out of their wishful thinking when a written warning (or worse) lands on their desk.

That’s if it works at all. The terrifying thing about wishful thinking is that even when you do fail, you often fail to recognize it.

Combatting the Catfish

The hard and anxiety-provoking thing is you don't know what you don't know, so how can you fix it?

The ultimate counter to wishful thinking is to inoculate yourself with appropriate and frequent doses of reality. It's forcing yourself to ask “What's the worst thing about ____ that needs to be fixed as soon as possible?" (Fill in the blank with something personal you really care about, like a pet project, your "genius" business idea, or... yourself).

As Musk explains:

"Take that approach of: You're always, to some degree, wrong. And your goal is to be less wrong. Solicit critical feedback, particularly from friends."

Take a more scientific approach: rather than starting with a fairytale and looking for reasons why it's true, start with a hypothesis and work to disprove it. Always be on the lookout for what you don't know, or don't realize, or haven't thought about yet. Challenge your assumptions. Solicit a diversity of outside perspectives. Beg people you trust for constructive feedback.

Criticism is not failure. Failure is failure, and it often hatches from harboring illusions about reality.

No illusions, my friends.

2.) On transparency with your boss:

I commented on an article where the OP sought a technically downward, but more fulfilling career transition. They dropped a last-minute bomb on their manager, sharing that they wanted to quit. They were shocked when their manager responded "What if you could do that here?" The organization helped upskill OP and facilitate a smooth transition into the new "dream" role. The "point" was that you shouldn't be afraid to take a "demotion" if it means more fulfilling work. But everyone missed the more practical takeaway — including below my take / comment:

I can't stress enough the value of having career conversations early and often with your manager. It's not just HR mumbo-jumbo. OP's story is just one example of a potential benefit.

Most organizations actively try to support internal mobility (admittedly with varied success). Companies invest resources in hiring, training, and keeping you. Your manager, as a representative of the company, is wise to amicably transfer an unsatisfied employee to another part of the organization. And as a human being, they probably want to see you engaged and happy at work, even if it means losing you to another team. Plus in this example, OP was a high performer and had already shown initiative, putting in legwork to upskill themselves for the new role. Demonstrated value/performance and initiative are always helpful when asking something of your employer.

Don't be dissuaded by cynical examples to the contrary - those who told their manager about other interests and suddenly and inexplicably got fired.

  • Remember there are two sides to every story — for example, maybe they were underperforming and disengaged for a long time, and then randomly raised the question after their manager reached a breaking point? They won't share that in their post.

  • Also remember availability bias — just because we see these people complaining on forums or "know a guy" doesn't mean it happens frequently enough in real life to be seriously concerned.

In the end you'd be surprised what you accomplish by simply talking to your manager early and often, having general conversations about potential aspirations and leaving the door open for them to say "How can I help?"

3.) Cunningham's Law — a stunning psychological trick

TIL about Cunningham's Law which states "the best way to get the right answer is not to ask a question, but to provide the wrong answer." [1]

This is a great little tactic for several situations:

  • Engaging otherwise disengaged people - Ask boring questions and you’ll get one-worded to death. But make an incorrect statement and a group will jump at the chance to correct you, hence building engagement and participation. For example, asking kids "how was school?" vs asking "did you race motorcycles in the hallways today?"

  • Getting more information - By purposefully making an incorrect assumption (e.g. "You work in marketing - so that means you write advertisements, right?"), the other person is likely to cut in to correct the assumption, teaching you and providing useful detail in the process.

  • Building rapport - We like being around people that make us feel smart. Just don't overdo it or they'll genuinely think you're an idiot.

I would highly recommend this article which does an excellent job of explaining and providing more examples.

[1] “Law” meaning one of those semi-serious internet adages that often proves to be true. Definition is also paraphrased.

4.) New puppy alert

In case anyone noticed that last week’s newsletter was a day late, my excuse is that we just got a new puppy [1]. Larry is a Wirehaired Pointing Griffon / German Shorthaired Pointer mix. Temperamentally he skews toward the latter, so if anyone has good dog training recommendations let me know!

5.) The gorilla who was raised a boy

John Daniel (aka “Sultan”) Cunningham was an African lowland gorilla who was raised as a boy in an English village. Talk about not fitting in.


I'd love feedback on this newsletter. What did you enjoy? What's the worst (or most boring) thing about it that needs to be fixed as soon as possible? Reply here, or you can reach me on Twitter or Instagram.

Have a great weekend!

Jon D'Alessandro

Blog | Instagram | Twitter | Contact

P.S. - Tell your friends about this newsletter!

Share The Bring Ambition Newsletter

FORWARDED THIS MESSAGE? CLICK BELOW TO SIGN UP: