• Jon D'Alessandro

No Illusions

How to crush wishful thinking, gracefully request and receive feedback, and become your most formidable self.

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. Information is biased and skewed by a desirable illusion.


The problem is wishful thinking not only influences perception but manifests itself as irrational behavior and suboptimal decision making.


Desirable illusions

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, without talking to potential customers. They're enchanted by a romantic flash of inspiration. They're convinced 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 careers derailed because of wishful thinking. An employee is utterly convinced they're a stellar performer and when provided feedback to the contrary, it simply doesn't register.


They become “the product nobody wants.” The manager is often partially at fault, sheltering them from reality by putting off difficult conversations or being a poor feedback provider. But these employees would land in my office after a hail-mary nomination for training or an executive coach and say flatly, "I don't know why I'm here." They're 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, 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).

Sort of like this [1]

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.


Gracefully requesting & receiving feedback

It can be distressing to work in a feedback-scarce environment, never knowing where we stand. We waste precious mental energy wondering how we're perceived, how we fit in, how our product is received, etc.


So to help you move from "desperately wondering" to "knowing and fixing," here are some tactics to gracefully request and receive feedback:


Tactics to solicit feedback:

  • Shamelessness - Ask frankly for feedback. Don't wait for it to occur spontaneously. Give others permission to provide it.

  • Specificity - It's hard to respond thoughtfully to a vague, general feedback request. Asking for very specific feedback give the provider less to think about, making it easier to respond and help. For example: following a presentation, ask "Did I go too fast? Was my anecdote about xyz relevant? Were my main points memorable?"

  • Growth-orientation - Be explicit about seeking constructive feedback. Say firmly that it's a matter of personal importance — you want to get better, so you're trying to identify areas for improvement. Last resort, stress that you will not take it personally.

  • Devil's advocates - If you're really struggling to get constructive feedback, seek out the devil's advocates, the overly vocal coworkers, the constant contrarians. Their feedback might be useless, but you can take it to someone you trust and say, "I got this feedback from someone, what do you think?" Then it's a matter of this trusted person supporting or refuting that data, not providing feedback from thin air.

  • Defined roles - Your manager is a default feedback provider, but it helps to have options. Seek out formal mentors through programs at work or via professional groups, or informal mentors through your own network. Consider investing in a coach. Identify trusted, high-performing peers who want to see you improve.

  • Defined touchpoints - Do whatever you can to have more frequent, transparent development conversations with your manager. Put a biweekly placeholder on the calendar. Make feedback an expected agenda item.

Tactics to receive feedback:

  • Gratitude - Treat feedback as a gift. It may sound trite but it helps create a buffer against the natural pain of criticism. Thank the feedback provider — they'll appreciate the fact that you recognize it as feedback and not a passing comment. It will make them more comfortable providing feedback in the future.

  • Active listening - This is a widely used technique to reflect back what the other person said to check out your understanding. It will make them feel heard, which they'll appreciate, which will increase their willingness to provide future feedback. Here's a good, quick article on active listening for reference.

  • Objectivity - It's natural to react to negative feedback like a threat. Hold back any emotional reaction and remember feedback is a data point, not objective reality.

  • Curiosity - Approach feedback from a mindset of curiosity, like a scientist seeking data for or against their hypothesis. This frame of mind will help you depersonalize, ask insightful questions, and listen actively.

  • Excellence - Remember that the short-term pain of criticism is worth the long-term goal of achieving excellence.

  • Realism - Understand that most people stink at giving feedback. You'll also occasionally receive unnecessarily harsh criticism or unhelpful, nonspecific feedback. Again, the important thing is to seek it out, evaluate it, and if necessary, take action. You're not expected to internalize every piece of criticism that comes your way.

  • Positive intent - Always assume positive intent. Feedback is easy to screw up and people might not come across as intended. Especially in the remote environment, you can miss or misinterpret subtle communication cues when receiving a difficult message. Do your best to listen with the notion that they are trying to be helpful, and have your best interests in mind. Depersonalize the content of their message and reframe it in a positive light.

  • Action - Information is only as valuable as what you do with it.


The key to becoming formidable is to crush wishful thinking, adopt a less wrong mentality, and have the willingness to not only tolerate painful constructive feedback, but consistently seek it out.


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


No illusions, my friends.

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Notes:

[1] Could not resist including the Anti-Wishful Thinking Catfish. Thank you to dimensions.com for the vector.

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