I think you should think about it in terms of how much “naive optimism” you want to foster in your friends.

In truth, there’s good reasons do doubt every project, even the ones that end up being highly succesfull.

Unfortunately, it seems like human beings are highly pulled towards either working on something with unrealistic confidence, or sitting on the the couch and watching netflix.

Working on something with unrealistic confidence, even if that project itself is completely doomed to failure, is probably better for you than watching Netflix.

The one exception is, there is a higher than average probability that startup people with naive optimism end up getting into a position where they decide to end their life.

> Working on something with unrealistic confidence, even if that project itself is completely doomed to failure, is probably better for you than watching Netflix.

As someone who’s heavily biased towards just sitting on the couch (but reading a book, not watching Netflix :)), but married to an unrealistically confident wife, I have to agree.

I tend to panic whenever my wife comes up with her way-too-frequent ideas and goes ahead with them with minimal risk analysis, but at the end of the day she’s a much more accomplished and satisfied person than I am. I tend to look at every project from the most pessimistic angle possible and the end result is that I almost never actually do anything. I have a lot of book knowledge about a number of things but little to no experience, whereas she’s the exact opposite, and that tends to be more beneficial in real life.

Can you speak more on how you balance your persoanlities? How do you balance speaking from a pessimistic perfpective while also being encouraging and supportive?

> The one exception is, there is a higher than average probability that startup people with naive optimism end up getting into a position where they decide to end their life.

I wonder if this is true. It's certainly the case that plenty of people who do nothing with their lives end up being suicidal.

It's not your job to keep their spirit up.

But it's not necessary your job either to bring them down.

Just tell them honestly if they take a big risk that you see a risk and why.

Ask questions!

I’ve got a bunch of friends in the same boat…Poorly thought out plans become pretty evident with simple questions like “what’s your plan?” Or “do you know how to build that product?”

But idk the other day I had a conversation like this:

Friend: “In a couple years I’ll be making over $1M/yr!”

Me: “How are you gonna do that?”

Friend: “I’ll just make more sales. Why can’t I?”

Some people are just delusional and I change the topic.

This is the exact conversation I had with my friend, just not the same numbers haha. To be fair to your friend and mine, I don't think its impossible for them for their outcome to come true. Whether its delusions or not, there is a belief they have that its possible what they're thinking can come true. So what kind of "support" is best here? We can be dismissive, and I don't think they'd feel good about that. We can be rational and debative, but that doesn't feel good to be "attacked" in some ways. But at the same time agreeing and staying silent also doesn't feel genuine to myself.

I hope I make $1M/yr of sales (not profit) in a year. But even if I don't, in 5 years may be I can overtake your revenue by a large margin?

If the question is about a start ups, then no job can make the same money as a decent business isn't it?

Therefore instead of asking such questions I think one can discuss about the safety net. The question in that direction would be "How bad might it get if everything about this venture fails? Do you have a plan to recover from that?"

This is exactly like the book "the mom test" but for once we are the mom.

If it is obvious that your friends want support, give them that. Unless they are betting their life savings or doing something extremely risky why bring them down.

If you know them, they know you too, and they are sharing with you for a reason. But if you’re unsure how best to support them - ask this:

“Would you like me you think through potential risks and pitfalls, or are you looking for emotional support?”

If they answer the former, go right ahead and challenge them. If the latter then share your hopes for their success. Sometimes they know they have blind spots and they need your help before investing too much effort in the idea, sometimes they just want to share their enthusiasm.

You have the right mindset. Being supportive of someone doesn't mean you have to be a sycophant and start doing all the song and dance. In fact, these people are the exact antithesis of being supportive, they usually become the catalyst for toxic narcissism and impending doom at some point in life of the people they support. In fact, the most supportive person is someone who speaks their mind out and gives genuine advice they need to hear, not the one they want to hear!

Just remind yourself that these people have probably thought harder about their problem domains than you have.

Just make sure they are risking their own skins, not others, and then provide encouraging words if you don't believe it.

Try a "both sides" approach.

Here's the cool thing, here's the drawback.