Don’t Confuse Optimism and Delusion

Both optimistic and delusional people see how things could be better

Delusional and optimistic people. Sure, both appear to have a positive attitude. Both talk about changing the world. Both are confident, and often charismatic. But there are big differences, and they are important.

Delusion ruins optimism for everyone. Delusional people mislead people, wasting time, money, and energy along the way. They leave behind chaos, and society responds by telling the optimist to be more cautious, more risk averse, more fearful. Optimists are told we’re “playing a fool’s game,” and optimism gets mislabeled as hubris and elitist arrogance.

A large chunk of my work sourcing deals for WOMENA, investing in startups, and doing due diligence, is parsing out optimism from delusion, and I’ve become good at it. I’ve learned that the key to identifying whether I’m looking at an optimistic person or a delusional person can be broken down to 1) roadmaps or lack thereof, and 2) the pursuit of immediate gratification versus an end goal, and 3) the drive to action versus the drive to feed the ego.

The optimist’s roadmap, how she will see that vision become reality, is always rational. She steps away from the future and into the present, opening her eyes and ears to negative and positive information; the negative in order to stop problems from becoming problems and come up with solutions, and the positive in order to tweak and improve the roadmap. She seeks truth in the data she takes in, separating fact from opinion, and data from fabrication. In dealing with the roadmap, she is a realist. She is constantly learning, and is open to constructive criticism from mentors. She takes what she learns and revises and improves the roadmap, always with the destination in mind.

An optimistic person thinks, “Immigration issues are a large challenge, taking into account Cause A and Effect B, so logically we should pursue Plans C and D, to get measurable Result E, in consultation with Expert F, to solve it.” The optimist believes she can solve it, and creates a roadmap to do it.

There was something amazing invented thousands of years ago that goes over walls. It’s called a ladder.

A delusional person says, “I’m going to solve immigration issues! I’m going to build a wall!” and can’t explain to you how a wall will solve issues surrounding illegal immigration, and has not considered negating, but highly relevant information.

A delusional person is threatened by criticism, only takes in positive information, whether fact or opinion. He makes a lot of noise and produces few results. A delusional person can tell you the vision, but when questioned about the roadmap deflects, gives a thoughtless answer, or gets defensive.

“What’s your go-to-market strategy?”

- “We’ve already signed up 2,000 users for our beta and are on track to sign up 2,000 more by the end of the week.”


“What is your competitive advantage?”

- “Well, we have a really passionate team and we are cheaper than the competitor.”

“Has price proven to be a sticking point for your target market?”

- “Clearly, low prices drive the consumer in general.”


“Your technology isn’t scalable and we’ve identified numerous security issues. How do you plan to solve these?”

- “Of course it is scalable! We have the best security guys on our team.”


The delusional person doesn’t build a coherent roadmap because this doesn’t provide the immediate gratification that delusion provides. A delusional person’s vision is more often than not formed by the ego; being idolized, being better than other people, having more things than others. Visualizing herself in these positions is easy and makes her feel good now, so the delusional person says she has a vision so she can think about it right now, feed the ego, and get that little dopamine rush. Ironically, this leads to drifting dissatisfaction in life, so chasing immediate gratification is actually much less gratifying.

A delusional person says, “We’re the X for Y. We’re on track to IPO in five years,” but has been working on her deck for a year. Thinking about that IPO is enough.

An optimist’s vision may be formed by rational desires (wealth creation, problem solving, etc) or passion (save the children, have my art be appreciated, promote healthy living, etc), but the vision and the roadmap of the optimist are not created to feed the ego. When actually doing something, as any entrepreneur (or anyone who has really stuck their neck out) can tell you, your ego gets slaughtered, so leave it at the door. You’re painfully forced to face your fears and shortcomings, work in a world of anxious unknowns, open yourself up to criticism, risk your money and reputation, sacrifice harmonious relationships, and so on.

As the saying goes, “the road to glory is paved with suffering.” “Suffering” may not have been my choice word, but the principle stands: The optimistic person understands that the road has both positive and negative experiences, but she must keep walking it if she is to end up at the destination. Because her optimistic vision is worth it.

An optimistic person says, “We’re the X for Y. Here’s my deck. Since we last spoke, we have Z traction.”

Optimistic people are more driven by not only the outcome of what they will be and have, but the “do,”, understanding that anything worth having is hard to get (and most things not worth having, for that matter). But they’re optimistic that their actions will become their vision. The delusional person is chasing an outcome, and more immediately a feeling. They may know what they want to “be,” and what they want to “have,” and then forget to fill in the blank of what needs to be done to achieve those things. They’re delusional that doing what feels good will become their vision. Never confuse the entrepreneurship rhetoric of “following your passion” with this.

A delusional person asks “I have an idea. Can I get your advice?” and when you meet with them, wants you to tell them exactly what to do, how to do it, and wants you to say it will be easy. And when you don’t hand her a happy plan on a silver platter, she decides that idea isn’t right for her, and comes back a few months later and says, “Oh no, I’m working on something else now. Can I get your advice?”

An optimistic person says “Hey, I’m actually doing it. Do you want to get onboard?”

I’m not saying that to be an optimist you need to be a negative person, but self and environmental awareness is key. It takes one thousand little steps to walk the road, so be present in each step you take. You don’t need to be fearful, risk averse, or cautious, but you do need to think rationally to make a vision reality.

I am not saying that visualizations and positive reinforcement are bad. They are necessary along that difficult road. Just don’t forget it doesn’t stop there. The visualizations and positive reinforcement are there to keep you in a “do” state of mind in the face of adversity.

What I am saying is don’t confuse delusional people and optimists. History teaches us what happens when deluded people have political power. It tells us what happens when deluded people are in business (*cough* financial crisis). If I invest in delusional entrepreneurs rather than optimistic entrepreneurs, well, I’d be looking at some shitty returns.

Most of us fall somewhere in the middle on the optimism/delusion spectrum at different times in our life, in different circumstances, but overall, the delusional person is doing everything she can not to have to face her fears, and the optimist is doing everything she can to overcome them. I’m sure you’ve already decided, but really ask yourself as you move forward in life, and you deal with problems, am I approaching them with optimism or delusion?

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