Betting Futures

Jacky Tang
5 min readMay 12, 2019

After sending out dozens of applications a call comes in while you were browsing through some emails. Hi, we wanted to set up an interview for you. Finally! You pick a good time and prepare yourself. Then the day before your interview you get another call. Another interview! This one is more competitive, but it’s the one you were really aiming for. You schedule it in for next week. You head into the first interview. They are very impressed and make you an offer on the spot. Shit… you want to go to the other interview, but you also know you might not get that one.

What would you do?

If you skip out on the first one, and the second one doesn’t go through, then you end up with nothing. Maybe you can push back the offer for a few days, but still you won’t get an answer from the second one before then. One path comes at the expense of another.

My latest reading is called Thinking in Bets, written by a poker champion turned psychologist. She uses some of the lessons that she gained at the table playing high stakes poker to everyday decisions. Some of the main features of thinking in bets is to use the information that you have, and try not to skew it to stay objective. We carry with us a lot of biases and strategies that we’d like to believe are right even when the evidence in front of us might say otherwise. More importantly, don’t forget to include luck.

In poker, obviously there is a luck component from how the cards are dealt each round. It comes down to sheer probability what the chances of a hand is at winning in the end. Yet, poker has also a component of skill. Even with a bad hand they may be able to bluff their way into a win without ever revealing what they had to begin with. Poker has incomplete information unlike games like chess or go, so it’s possible to manipulate the uncertainty to a players advantage. So a big part of thinking in bets is to assess the chances in a given situation that will lead to the outcome that you want based on the information that you have on hand. In this framework, it is possible to make a good decision yet still have a bad outcome. With a 90/10 chance of success there is still a chance of failure.

Part of this ideology is to learn from every decision and not take it so hard when things don’t work out. Even the best poker players in the world will lose some of the time even if they maximize their chances of winning. The trick is not to take that loss as a reflection of a bad decision or a lack of skill. Instead try to tease apart how much of it was due to skill and how much luck came into play. It’s always possible, too, to have made a slip in judgement only to have things work out anyway. A part of our psychology likes to take the wins as a direct effect of our own choices and skill, while the losses were simply because of poor conditions that stacked the odds against you. What this book says is to take the ego out of it and see what really happened. If you happened to get lucky, then it’s just that. If you made a good decision and still lost, then it’s just that. No need to kick yourself while you’re down, but also don’t take too much credit when things go well. The important part is to learn from whatever happened, to examine it closely, and apply it in the next round.

Of course, a hand of poker only lasts a few minutes so it might be easier to repeatedly adjust your strategy. Choosing one job over the chance of another could mean years of your life before that kind of situation ever comes up again. Still the core principles apply. It would be better to assess the strategy you used, than to repeat the same one next time. At the very least you may get many chances to interview and learn from those even if it doesn’t work out.

When it comes to the aspect of luck, I’ve noticed that it can be too easy to think our chances at something are pretty slim before we even give it a shot. It’s sort of the worst kind of catch-22, where if you don’t try your chances are bad, but if you’re chances are bad then you don’t try. Borrowing from the philosophy of Brene Brown, we have to be willing to step into the arena, to be seen. We also have to be willing to be vulnerable in order to be courageous, and to take risks is to fail. So, I’ve learned to try things even if I know I won’t excel at it only to gain some skills and get some insight into how it works. By doing so my luck increase magically as if I added some skill points to my luck attribute. I met new people which increased my chances of getting leads, I got better at talking to and working with strangers making connections easier to find, and I applied my skills in different ways which expands my resume. There was definitely my share of failures and awkward encounters that went nowhere, yet it gave me a better gauge of how to improve and what kinds of people I get along with.

One side of my life I still have yet to take enough risks is dating. If you’ve read my other posts you’ll know I’ve tried the dating apps, but honestly they didn’t really help me with anything except how to send out random (terrible) jokes with no response. It’s like playing poker by yourself. Not all that helpful. I still have a hard time knowing if someone is interested enough without asking. Another catch-22. At the same time, I think I’d rather get to know someone a bit better before asking them out, but maybe that’s just an excuse. As long as I keep trying things and meeting new people I’m sure the confidence will come and the timing will improve. I wish it was all a bit easier to tell what the chances were. Is it 50/50, 70/30, 90/10? It just all seems like a toss up, but even a coin is 50/50. Ugh… Often I feel it’s more like 30/70 though I have no real justification for it. Just don’t sense any attraction on their end based on the information I have to go with, so maybe I just have to talk to them more or something. Even poker seems easier!

Well, at least for now I can say that my work situation is getting better and the whole employment game is getting more clear. Now I just have to take the bets to a different game and take a risk.

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Jacky Tang

A software-psychology guy breaking down the way we think as individuals and collectives