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Not especially non-conformists - non-conformity is merely a symptom.

As you say, risk seeking behavior, resulting from the actual cause: "poor risk assessment" - ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).

I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports - clearly the accuracy or the precision of my risk assessment model is significantly outside the norm!

People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.

Now, I personally think those people are rather safe and uninteresting - but then we've already established I'm probably not the person to base your decisions on!

If people are interested, there are good psychological tests for risk assessment skills - https://en.wikipedia.org/wiki/Impulsivity#Assessment_of_impu...

In my experience, most successful entrepreneurs are usually quite good at accurately assessing risks. They are simply more capable and willing to embrace certain risks in pursuit of greater rewards in the future.

Agreed. I think the dominant entrepreneurial trait isn’t risk taking, it’s optimism.

Optimism is basically the same as poor risk assessment. Risk assessment, aka spending time analyzing everything that could go wrong ahead of time. Show me an optimist who does that and I will show you a pessimist.

But the dominant trait at least for serial entrepreneurs might still be pessimism at the core, because it requires willingness to fail. You need to be pessimistic enough to expect to fail many times as a normal course of action until you luck out. If you don't expect to fail then the first large failure becomes the final blow.

This is the same kind of error people make when they assume an introvert must have poor social skills, even though that's often not the case.

There's a meme/comic that goes like this:

Panel 1, "Nothing really matters": a little creature in a void, sad. "What people think nihilism is."

Panel 2, "Nothing really matters": the same creature surrounded by rainbows and puppies, happy. "What nihilism really is."

In the same way that recognizing nothing really matters in our march toward entropy means we can get on with choosing our own path in life, recognizing the pitfalls of a potential path means we can walk it in confidence.

I know there be dragons, and I'm going to date them all.

> I know there be dragons, and I'm going to date them all

I want to steal that quote. (Pessimistically I know I will forget it, so optimistically I'll try to have it printed on a T-shirt!)

Arguably, in part, optimism could be considered a derivative of poor risk assessment.

In my experience people are inaccurately pessimistic, in part due to a lack of imagination. So risk assessment that's more accurate will present as more optimistic.

>As you say, risk seeking behavior, resulting from the actual cause: "poor risk assessment" -

You project value judgement into places where there need not be any. Most of these people who are doing "entrepreneurial things" come out somewhat ahead over their careers. It's not like they're dying destitute. Do they (in aggregate) come out as far ahead in terms of dollars as someone who grinds leet code and job hops between BigcCo? Probably not. But that's not what they're optimizing for.

> ties right in to difficult childhood, mental health issues, and the market misjudging you (all causes or signs of trauma and being outside the norm).

Ah, yes, the ol' anyone who doesn't agree with you must have something "wrong with them" or "be damaged" line of reasoning.

>I say this as someone with an appetite for trying new things, being non-conformist, and adventure sports -

Having a hobby that might put you in a cast isn't the kind of risk being discussed here. It's misleading (to be charitable) to portray that kind of risk exposure as analogous to doing things that will have large impact on your earning potential in the short, medium and long term.

>People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.

You are conflating loss avoidance with risk assessment.

And I say this as someone who is living the exact career you are trying to stereotype in a positive light.

Risk aversion is not an immutable trait.

At age 6, I was tested for my tendency towards risk aversion. I scored as high as possible in risk aversion; in other words, I was extremely risk-averse, as my parents worried. That tendency marked a better part of my life, and it brought forth/was comorbid with GAD and generalized depression. All of those things make you think that if you just had more control you would feel better, but the grasping for it only exacerbates the symptoms.

Now I'm 41, and am really interested in bootstrapping (I have made one small app, working on the next). In particular, I love the risk/reward calculus especially. I've gradually awoken to the amount of value I bring via programming and strategy versus the salary structure in place at a lot of companies. This year I'm focusing on amassing leverage in several forms, be that a more public voice, a more fit body, additional income streams (however small), etc. (Typical midlife stuff, yes.)

> People with excellent and accurate risk estimation and assessment work as actuaries, or accountants, certain kinds of insurance brokers, something nice and safe where you can do good work for 35 years and retire. The quintessential "brown volvo" driver.

To work as an actuary, it is better if you are rather on the risk-averse side (i.e. err into this direction instead of having a tendency for excellent and accurate risk estimation) because insurance companies and regulatory authorities are very biased into this direction.

> This is why I can’t play any games which require grinding (looking at you Eve) because I know it’s more fun IRL. ¯\_(ツ)_/¯

This realization almost permanently put me off most online video games. Most team-based games are made such that one individual can't swing the game too much, because that's seen as bad. Thus only about 20-30% of games you can directly impact, thus you're mainly just burning time with limited agency for player skill. MMORPGs are timesinks first and foremost, rather than skill-based games.

I replaced them (mostly) with music. Music has an infinite skill ceiling that is apparent, it is cooperative, creative, and tends to have people that want to be there, versus people who are there because they don't have anything better to do.

Have to throw a good mention of Dark Souls here. The vibes, the story, and the themes resonate deeply with me and connect naturally with the highs and lows of entrepreneurship.

Had to chime in here RE: music. When I encounter people that wish they could play guitar/piano/etc and say "they have no time", but then I find out they play games for hours per day. Well... priorities right? (I hardly play games anymore)

"including turning down a job at Microsoft in the nineties I can still see my dad shaking his head about turning down Microsoft…"

That was quite a while ago... Probably should forgive and forget that one. Forgiving the disappointment makes mental space for new opportunities.

I agree non-conformists start the really visible flashy companies. A new aircraft maintenance company can make bank, but it doesn't really grab headlines.

>This is why I can’t play any games which require grinding (looking at you Eve)

Eve actually broke my desire to play a lot of games for this exact reason.

That's why I can't play almost any game, because I'll grind everything, even useless achievements.

At least I have idle games and I'm also working on one which will probably end up in nothing.