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Cross-posted, as always, from Putanumonit.

It’s a core staple of Putanumonit to apply ideas from math and finance out of context to your everyday life. Finance is about making bets, but so is everything else. And one of the most useful concepts related to making bets is the Kelly criterion.

It states that when facing a series of profitable bets, your wagers should grow proportionally with your bankroll and with your edge on each bet. Specifically, that you should bet a percentage of your bankroll equivalent to your expected edge — if a bet has a 55% chance to go your way your edge is 55%-45%=10% and you should risk 10% of your bankroll on it (assuming equal amounts wagered and won). There could be reasons to avoid betting the full Kelly in practice: you’re not sure what your edge is, your bet size is limited, etc. But it’s a good guide nevertheless.

Friends

When your friendships are few and tenuous, people’s inclination is to play it safe and conform to the crowd. It won’t make you a social star, but it won’t turn people away either. But if you have an edge in popularity and enough close friends to fall back on you can make some bets on your own vision.

When I was younger and struggled to make friends I’d just wait to be invited to parties. When I finally figured it out and acquired a rich social life I started throwing my own events the way I like them: controversial topic parties, naked retreats in the woods, psychedelic rationality workshops. Each one is a gamble — the event could fail or people could just not show up. In either case I’d lose some of the status and goodwill that allowed me to plan those events in the first place. But when it works the payoff is equally great.

Creative Talent

Whatever creative outlet you have, you get better by getting feedback from the audience. Show people your paintings, read them your poems, invite them to your shows, link them to your blog. This is a gamble — if people don’t like what you’re making you won’t get their attention next time.

When I just arrived in NYC I was doing stand-up and would perform at bringer shows where you get stage time if you bring 3 or 4 paying guests. My ability to do that depended on the number of friends willing to humor me (bankroll) and my humor (edge). By the time I got decent enough to get an invite to a non-bringer show I had just about run out of comedy-tolerating friends to call on.

Romance

The most obvious way to bet on yourself in romance is to flirt with people “outside of your league”, your bankroll being in part your ability take rejection in stride and stay single for longer. The same applies the other way, with making the bet on breaking up a relationship that is merely OK in hopes of something better.

But you can also bet on an existing relationship. If the person you’re dating just got into a school or job in a faraway city your ability to go long-distance for a while depends a lot on the bankroll of relationship security you have. Ethical non-monogamy is a similar gamble: if you’re don’t have an edge in making your partner happy they may leave you. If you do, their happiness only doubles for their ability to date other people, and polyamory makes you all the more attractive as a partner.

Polyamory makes bad relationships worse and good ones better; if you only know people who opened up when their relationship started deteriorating you’re liable to miss this fact.

Sanity

Psychedelics can drive you insane. They can also make you saner than you’ve every been. The same applies to meditation, mysticism, esoteric ideologies, and whatever else Bay Area Rationalists are up to. Epistemic Rationality is your bankroll and your edge.

Reputation

A lot of people are seeing the rise in callout and cancel culture purely as a threat, a reason to go anonymous, lock their accounts, hide in the dark forest of private channels. But where there’s threat there’s also opportunity, and where reputations can be lost they can also be made. Chaos is a ladder.

In 2015 Scott Aaronson’s blog comment went viral and threatened to spark an outrage mob. Aaronson didn’t expect that popular feminist writers would dedicate dozens of pages to calling him an entitled privileged asshole for expression his frustrations with dating as a young nerd. But he also didn’t expect that Scott Alexander would write his most-read blog post of all time in defense of Aaronson, and that the entire Rationalist community would mobilize behind him. This wouldn’t have happened if Aaronson hadn’t proven himself a decent and honest person, writing sensitively about important topics under his real name. Aaronson’s reputation both online and in his career only flourished since.

Children

Having children is a bet that you have enough of an edge on life that you can take care of another human and still do well. The payoff is equally life-changing.

Risk Averse Irrationalists

I wrote this post because of my endless frustration with my friends who have the most slack in life also being the most risk averse. They have plenty of savings but stay in soul-sucking jobs for years. They complain about the monotony of social life but refuse to instigate a change. They don’t travel, don’t do drugs, don’t pick fights, don’t flirt, don’t express themselves. They don’t want to think about kids because their lives are just so comfortable and why would you mess with that?

They often credit their modest success to their risk-aversion, when it’s entirely due to them being two standard deviations smarter than everyone they grew up with. By refusing to bet on themselves they’re consigned forever to do 20% better than the most average of their peers. To make 20% more money with a 20% nicer boyfriend and 1.2 Twitter followers.

And partly, I wrote this post for me. I spent my twenties making large bets on myself. I moved to the US nine years ago today, all alone and with a net worth of \$0. I found polyamory and the love of my life. I started a blog under my real name, with my real opinions, on real topics.

Now in my mid-thirties my life is comfortable, my slack is growing, and I’m surrounded by younger friends who know all about discretion and little about valor. This post is a reminder to keep looking for my edge and keep pushing the chips in. There’s plenty more to be won.

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New Comment

I feel like one of the people you're writing this for.  25.  900k NW yet still working a boring programming job for one of the top tech companies that I don't care about.  Last time I seriously tried at Tinder I had 5 dates planned in the first weekend and 112 matches in the first week yet I'm spending my time with a casual partner I'm lukewarm about.  Every time I start a side project I go two days and then think "eh, I bet nobody will care about it" and stop.  Besides the job the only reason to stay where I am is I like the swing dancing scene here but that's closed with covid and I don't like much else about here.  In my hobbies I'll get bored right before I'm impressive. Leaving just before world finals in ICPC. Switching to be more casual about my lifting a few pounds short of a state record.

I don't need to start making Kelly Bets, I just need to start making bets period.  I don't know what it would take for me to start doing that.  I have a friend who makes big bets and I look up to him but I don't copy him.  I think a big part is I just don't really trust there to be payoff.  I don't feel like I'll be much happier.  I don't expect any of my side project ideas will be that useful to people.  Or maybe that's just an excuse.  I mostly feel blankness when I try and think of the tradeoffs so maybe there's some emotional block about my inability to take risks?  I'm not even sure where it would come from.  Most of my problems I have an obvious source of trauma to blame it on but not here.

This might not be for you, but I found http://mindingourway.com/ to be very helpful in terms of finding motivation.

The other main thing I'd target would be to spend time around people who make you feel excited about stuff. Don't try to do it alone.

I think a big part is I just don't really trust there to be payoff.

I'm curious how you/your System I responds to high-risk/high-reward ideas. Startups are what come to my mind first: eg. startup ideas that maybe you think are unlikely to succeed, but would be billion dollar companies if successful.

I just don't feel anything.  I do have a certain logical appreciation that if I made a billion dollar company it would be impressive, I'd probably improve people's lives with it, and I could buy more stuff (mostly donate I guess?  I don't have much else I need...) but I don't feel anything.  Those are the words I feel flowing through my head but I don't feel any of the wordless feelings that make up my system 1.

Hell, I don't even feel anything thinking about the pleasure I'd get from getting a peach from my kitchen and there's a 95% chance the peach is good and ripe today.  I just do it because I know I'll have good feels once I actually have the peach.  Which is enough to make me do something low effort like get a peach but not start a company.

Edit: If anyone was curious, the peach was indeed delicious

I am not an expert, but this sounds to me like depression. Maybe there is a pill for that?

Or maybe peer pressure if you could find the right group of peers which would push you in the direction you want to go anyway. (I wonder if you could rent such group. Maybe this is a business opportunity.)

Ah, I see.

The _vast_ majority of interesting decisions are uncertain and have multidimensional risks and payouts that defy such calculation. Even something as trivial as "how much to pay for a residence" has massive variance in the monetary outcome _and_ unknown impact on quality of life, ease of social experiences, what work options there are, etc.

Sure, if you see a 3:1 chance to get paid even money, you should bet half your resources on it (that's not your current net worth, actually - it's the discounted value of your future cash flows, independent of this bet. For young folks, it's likely a large multiple of your current net worth). But you will _never_ see such an opportunity.

The description of the Kelly’s Criterion here seems like it is for the specific case where the house odds (as it were) are 1:1?

I'm running simulations to get a feel for what "betting Kelly" would mean in specific contexts. See code here: https://jsfiddle.net/se56Luva/ . I observe, that given a uniform distribution of probabilities 0-1, if the maximum odds ratio is less than 40/1, this algo has a high chance of going bankrupt within 50-100 bets. Any thoughts on why that should be?

Nitpick: Kelly betting does not ever go bankrupt, at all. Unless the probability is exactly 1 or 0 (which is bad) the Kelly bet will always be less than the total amount of money you have right now - meaning that you can never lose all of your money on a Kelly bet.

That said, the code you linked is systematically losing money over time (though never actually hitting zero) because this line is backwards:

let betres = (dice < pwin) ? (-frbet) : (frbet * odds);

When dice < pwin, that should be a win (assuming that pwin is supposed to be the probability of winning), so the bet resolution should be positive in that case, not negative. With that fixed, wealth shoots up at a pretty quick exponential clip, eventually passes max double (~10^308) and becomes infinity, and then becomes NaN.

Oh darn, you're right. Thank you!

Nice post. I might try to use this idea to force myself to make more bet socially. I'm risk taking in terms of ideas and creation and jobs, but not enough in terms of talking to new people and flirting. Forcing myself to start a conversation with a stranger everyday is one way I'm trying to solve that; thinking about the rationality of the bet might become another.