Would you accept a gamble that offers a 10% chance to win $95 and a 90% chance to lose $5?

Would you pay $5 to participate in a lottery that offers a 10% chance to win $100 and a 90% chance to win nothing?

Chances are the second proposition sounded more appealing to you. But look again, both these propositions are identical. The second version attracts more positive answers[1] because it's framed as cost whereas the first version is framed as a loss and who wants to lose?

This is called "framing effects," how something is presented colors how we think about it. Similarly how we interpret the world around us and our situation in it would affect how we feel and act. In fact, there are whole branches of psychotherapy that focus on the art of viewing things differently: "positive reframing", "cognitive reframing", and "cognitive restructuring". However, what I'd like to focus on is dealing with specific set issues, issues that have to do with creating something new in the world, building a business, and all the turmoil that brings.

When you're a startup founder, it's almost like your mood is tied to your metrics. When your company is doing well, you feel great. When you're company isn't doing so hot, you're feeling bad. This, in turn, will affect your productivity and may set you on a vicious cycle of doom where your company isn't doing well, and you don't have the energy to fix it.

So how do you escape this, deal with the stress, take action on it, and have some fun doing it? Well, we can exploit the mental bug that is "framing effects" to bring about a better state of mind. I'll introduce what I call "mental frames"[2] -- I'm not sure if that's a real technical term, but it sounded good to my ears -- that has helped and continues to help me get through tough times.

Before I start, I want to acknowledge that it feels kind of silly that we have to trick ourselves and tell ourselves stories to act the way that we want to act. The reason we have to do this is that more and more we're discovering that we're not just one self, we're multiple ones. Scientists and philosophers, in different contexts, have proposed various theories on the division of the self. There is the momentary vs. the narrating self; there is System 1 vs. System 2; there is the left vs. the right hemisphere; there is the lizard brain vs. the neocortex. All that goes to show that although there is a part of your self that wants to get better at managing your mental states -- the one that's reading this, hi! -- it doesn't automatically mean that all your selves are onboard. So join me on a journey to trick these bastards to do what you want.

Also, I'm not a mental health specialist, see one if you need to.

"Life is a game" mental frame

Once a motherfucker get an understandin' on the game, and what the levels and the rules of the game is, then the world ain't no trick no more, the world is a game to be played.

-- 2Pac in "Starin' Through My Rear View"

Part of the startup game is taking risks, in fact, it's almost the only game in town. If you're not taking risks, then your startup already exists, and you're just copying something else. But if you are creating something new in the world there wouldn't be a week that goes by without feeling anxiety about all the risk that you're taking. Be it your career, other people's times and money, or with your product, users, etc.

The risk anxiety can paralyze you and unless you act you're just making your situation worse. One handy mental frame to adopt in this case is "life is a game, and I'm playing it." If life is a game, then you're there to play it. When you're, for example, playing a video game, although you stop to weigh the pros and cons of every decision you make, in the end, you have to act. Otherwise, nothing will happen, and it's no fun. You'll happily jump from place to place, explore different areas, try different combinations of keys or moves. You're never standing still, always making decisions and executing, learning, failing, restarting and going again.

The "life is a game" mental frame puts you in a fun frame of mind. You just can't wait to see what happens next. Maybe you'll lose, perhaps you'll win -- who cares! As long as it's interesting, keeps you amused, engaged, and learning.

"Time keeps moving forward" mental frame

I was a little bit of a procrastinator and I would be faced with this seemingly insurmountable task. I have final exams, I have massive amounts of work, papers -- there is no way to make it through. At that time -- and this is served me well -- I would say 'well, one way or another time keeps moving forward so even though I'm just three weeks away, whatever happens in three weeks from now I'll be on the other side'. So it seems like a wall that I can't get through but actually time is marching ahead and I will get to that point past that thing automatically and that was helpful to me.

-- Siri, Change.org, and Viv founder Adam Cheyer on the "Finding Mastery" podcast.

When you have an upcoming deadline or a significant date of somesort -- be it a product launch, scoring a deal, hiring someone, or the end of your runway -- there is no real rational reason to feel anxious. All you have to do is perform your best, and the rest is outside your control.

In situations where it's painful, you have to remember that time will go by, nothing lasts forever, and that you'll eventually be on the other side. What's important now is to execute!

"Worst-case scenario" mental frame

You might've used this one before; it's kind of a cliche that's often used out of place: "order the pizza, worst-case scenario we'll eat it in the car" or some such thing.

When correctly used, it can be compelling. Right now, think about a difficult situation in your life, or a tough decision you're pondering, or a risky move you're considering. Now think about the absolute worst thing that can happen as a result of your actions -- like literally the worst thing:

  1. Will someone die?
  2. Will someone get seriously injured?
  3. Will you become homeless and starve on the streets?
  4. Will you lose your house/job/car?
  5. Will you tarnish your reputation?
  6. Will you fail at the startup thing and go back a to a cushy job where they feed and do your laundry?

Etc. Barring #1, #2, and #3 I think everything else can be tolerated. Honestly for most decisions at Silicon Valley startups that may lead to ruin, it's probably going to be #5 that ends up being the worst-case scenario, and you know it's not all that bad.

A excellent technique to couple with the worst-case scenario mental frame is what's called "negative visualization". An age-old technique invented by the Stoics in ancient Greece, you visualize or meditate on the worst. Like, actually imagine it happening. If it does happen, you're already at peace with it, and if good or neutral thing happens then it's ecstatic!

"You're not your job" mental frame

"Founder of [insert sexy startup name]" is what you have on your twitter bio. It seems like this thing is intricately intertwined with your identity. But in reality, you're a lot more than that. You might be a good husband/father/son. You might be a good thinker, writer, or educator. Or you might have hobbies that you're good at.

When failure strikes, you might feel that you, personally you, are a failure -- which is basically depression. When that happens, remind yourself that you're much more than your job -- that you contain multitudes.

It's good to cultivate other interests, hobbies, or anything that you can get good at. Have people that rely on you outside of your work. Mentor someone. Learn a new skill. Find a hobby. Whatever you do try to link it to your identity.

For me, I try to always have someone that I'm mentoring. I read, discuss, and dabble in doing philosophy. I'm currently obsessed with weight-lifting. I also like to get better at writing, public speaking, and storytelling. I love to optimize my health. This year I spent a lot of time enhancing my sleep. Going from an average 5 hours a night to 7.5 hours a night. I also increased my REM sleep, going from less than an hour to 1.5-2.5 hours.

"What did I learn" mental frame

If you're the kind of type A personality that would choose the entrepreneurial path then chances are, you like self-improvement, and chances are, you love learning. So when failure does catch up with you then do yourself a favor and think about everything that you've learned from your experience. Maybe even write about it but, at all costs, avoid titling your post "our wonderful journey."


There is a lot more to this, and I'll try to keep this as a live document. But for now, I need to get back to playing the life game because time won't wait for me, and really, what's the worst that can happen? I want you to remember though, that I'm not only my job, it's true that I learn a lot from it, but I contain multitudes!


[1] Kahneman, Daniel. Thinking, Fast and Slow (p. 364). Farrar, Straus and Giroux. Kindle Edition.

[2] I know of "mental models" but for some reason it didn't quite fit. There is some overlap, however, where mental models is primarily about making intelligent decisions, mental frames is about managing your own psyche.