“Hell Yeah” or “Hell No” is a terrible decision making heuristic. — Issue #2

… and about every peasant in Mongolia, every waiter in Madrid, and every car-service operator in San Francisco knows that real life happens to have second, third, fourth, nth steps. — Nassim Taleb

One of the most common pieces of advice you’ll hear nowadays says if a decision isn’t a “hell yeah!” then you shouldn’t do it.

It’s a heuristic popular amongst the tech crowd and the self-employed. In 2009, start-up hero Derek Sivers wrote:

Every event you get invited to. Every request to start a new project. If you’re not saying “HELL YEAH!” about it, say “no.”

Look, this framework works very well for low stakes decisions like:

• Do you want to go to In N Out (hellz yes)
• Want to watch 9 hours of the Joe Rogan Podcast on YouTube? (duhhh, Tyler, where you at?)
• Should we get some road beers? (Ummm, hell yea we should get some road beers.)

But this “hell yes” mentality is really bad advice for decisions of consequence. Questions like “should I quit my job” or “should I go to grad school” require more thought and nuance.

It took me a while to realize, but the best decisions only seem obvious to us in hindsight. But if they are truly important, then they’ll rarely seem like no brainers in the moment.

I dropped out of grad school in 2011. Luckily, I withdrew before any scholarships and grants had been dispersed. At the time though, I was torn about what to do. On one hand, I didn’t want to spend $30,000 for another degree and two more years of school. But, I felt like I needed something to separate me from from the job hunting crowd and spending a year in France sounded well, like spending a year in France.

I went back and forth for a whole summer until finally deciding. Now, six years later, I can confidently say it was the right call. But in August of 2011, it was scary to let so many endorsers, administrators and classmates down.

Deciding on large questions should be uncomfortable at best and painful at worst. After all, the root of “decide” is “cide” which derives from the Latin word meaning “to cut.”

A choice is only as valuable as what you give up for it. So if the question is should you go out on Tuesday night, you can pretty quickly come to a conclusion as to whether or not you want to give up a night of solid sleep for a night at the Brooklyn Bowl.

But big picture, big questions, you have to be okay with what YOU’RE WILLING TO SACRIFICE to obtain whatever it is you want.

And that’s why you can’t follow the “hell yes” heuristic for life’s grand questions. If you’re overwhelmed with a looming decision, it’s okay. You’re supposed to. Don’t let the guy who says “hell yes” to a networking mixer tell you otherwise.

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I should note that the only time, in my experience at-least, when a big decision has garnered a “hell yes” response was when I had no other choice.

When you have negative dollars in your bank account, you don’t have time to deliberate a job or negotiate on salary.

As an arrogant 16 year old, I told my dad I couldn’t wait to move out of my boring hometown. Not one of my proudest moments. Not only are those “boring” days what I miss most about Modesto, but that conversation gave me perspective on what causes people to move.

After I said I couldn’t wait to move, my dad just shook his head and said “you kids want to move because you’re bored. We didn’t want to move, we were forced to move for food and work. You really don’t know how good you have it.”

PPS, though a terrible heuristic, “Hell Yeah” is one of my favorite rap songs.

What about you guys? What’s been the toughest decision you’ve had to make?

As in the last issue, I’ll leave you with a few of my favorite articles from this last month.

On the reading front, I’m still working my way through Robert Caro’s brilliant biography series on LBJ. Other than tackling those behemoths, I’ve been re-reading Nassim’s Skin in The Game.

Surgeons Should Not Look Like Surgeons — INCERTO — Medium — medium.com
Literature doesn’t look like literature –Business plans are for suckers — Donaldo Hiring practitioners –the glory of bureaucracy–teach a…

Working class folk may be more empathic, selfless, vigilant and fatalistic, finds new research published in the British Journal of Social Psychology. • r/science — www.reddit.com
5 points and 1 comments so far on reddit

Opinion | Meet the Renegades of the Intellectual Dark Web — www.nytimes.com
An alliance of heretics is making an end run around the mainstream conversation. Should we be listening?