Never ever play the What If game.

A reader on Medium responded to my post yesterday about doing the thing that scares you, and asked, what if you’re scared of death?


Well, I’m not sure if I have any advice about the topic of all topics, but, it might be important to differentiate between fear and worry.

I won’t use the official definitions, but we can try to break it down into casual sets. Let’s define fear as things you can do something about, and worries as things that are just sort of abstract panics about some future state.

I haven’t been able to conquer a lot of my fears, but my worries, those have been pretty easy. As a software developer, I love worries because you can sort of handle them and crush them remotely. You don’t need to go do anything. You just need to modify your internal state.

Worries can include things like:

  • What if I or a loved one dies tomorrow?
  • What if I lose my job?
  • What if my spouse is disloyal?
  • What if my company fails?

I think the common pattern between all worries is that they usually start with “What if”. And I only have one rule in life:

Never, ever play the What If game. Never.

If you play the What If game, you will always lose. Every single time. Because there are an infinite What If’s, and only one of you. You will be outnumbered and out-conquered. Never play the What If game. Simple as that.

Any time I’m speaking with a friend who expresses some sort of What If worry, I tease them and say: Stop right there. Do you realize that I can come up with a hundred what if scenarios to worry your mind after right now? Do you realize there are literally an infinite number of scenarios you can come up with that you can convince yourself are legitimate? Infinite. You’re just toying with one of them. Put it down. Walk away. Don’t play the What If game. You can’t win.

So, in the direction of worries, that’s the first strategy I employ. I never play the What If game. The moment a thought like that enters my mind, I laugh it off. I tell it, I’m not playing with you. Nice try.

Now, if a What If manages to pass through this filter, and seems a lot more credible than other What If’s, and I can’t seem to put it down, then I will employ another strategy. I learned this one from Emerson, and it’s stuck with me ever since. And it’s the realization that nothing can really hurt you. Nothing can leave you better or worse than it found you. The net result of all the events in your life tend to be very close to your average. If your average disposition is congenial, then even the scariest events imaginable, like death, will have a hard time fluctuating you.

Emerson lost both his wife and baby son, and writes:

In the death of my son, now more than two years ago, I seem to have lost a beautiful estate, — no more. I cannot get it nearer to me. If tomorrow I should be informed of the bankruptcy of my principal debtors, the loss of my property would be a great inconvenience to me, perhaps, for many years; but it would leave me as it found me, — neither better nor worse. So is it with this calamity: it does not touch me: some thing which I fancied was a part of me, which could not be torn away without tearing me, nor enlarged without enriching me, falls off from me, and leaves no scar. It was caducous. I grieve that grief can teach me nothing, nor carry me one step into real nature.

He seems to have found that like fear, worry is just another illusion. It’s not real. It’s just as shallow as fear. It leaves him no better or worse than it found him.

Aside from the understanding that nothing can really harm you, and what is scary in thought harms you not, I try to employ another strategy that weakens my worries. It involves befriending them.

I imagine the worst thing that can happen, the thing that worries me the most. I then play out that thing occurring. And I start building a life around it. What if I lose my job tomorrow? Well, that would be pretty great because maybe I’d have a week of bumming around, which may lead me to discovering a new side project. Maybe a little bit of adversity also teaches me a lesson or two? It’s not like I’m going to starve, right? This one’s easy. This one’s so easy, that at some point during actual employment, I began to look forward to this alternate life I built in my head.

What if I or a loved one dies tomorrow? Well, as for me, if I personally die, then I’m dead, and there’s no grief about it. I won’t be alive to be sad about it. I’m sad for my family of course, but I’m dead, so…moving on. What used to get to me more is the thought of the death of a loved one. And while never easy, it’s important to block this one from entering through in the first place using the What If filter. If it gets through, then you can either approach it like Emerson, who has lived to tell the tale that even something as tragic as the death of both his wife and son left him ultimately no better or worse than it found him. Or you can approach it from “building an alternate life” in your head in which you still find meaning in the event of a tragedy.

I think a really good way to sum this all up is:

You’re gonna be fine lol.

The “lol” there is important. It’s sort of like when a naive or younger friend messages you about some worry he or she has, and you, being older or more wise and having been through a hundred similar experiences and lived to tell the tale, respond simply with an omniscient “You’re gonna be fine lol”.

It’s a sort of contentedness with the difficulty of life. It’s going to be ok. Ray Dalio writes in his book Principles that the death of his mother was one of the most tragic events in his life, but when he thinks about her now, he smiles.

That gave me some comfort. From knowing to never play the What If game, to the Emersonian insight of nothing can really harm you, to Dalio’s smiling retrospective, it seems like everything’s going to be just fine.

And if that doesn’t help, then surely this will.

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