What’s the worst thing that can happen?
leostartsup.com
leostartsup.com
I put it to you that the exercise you really do is misleadingly named and that it is actually "what's the best that could happen, given this setback".
The worst that could happen includes losing a paying customer who then finds his business in trouble when he can't get a stable alternative, blames you, sues you under an obscure law which you didn't know of and you lose your company, job and go to jail. Or your site goes down and you can't fix it and your company sinks and your friends ostracize you and your cofounders rubbish your image publically. Or a disgruntled user hunts you down and murders you in your sleep.
You're not doing "worst that could happen", you're doing "least worst that could happen" or maybe "most likely thing that will happen" to get away from the above thinking.
No matter who asks it or at what time or because of what, the literal answer to "what's the worst that can happen" is some variation of either the universe being annihilated instantly, eternal pain and torment, etc, etc. Even your little examples pale in comparison with the worst that could happen.
So maybe that's not really the point that he's trying to make, and instead of quibbling over the semantics, we should think about what the real lesson here is.
To me, the point of this exercise is that we often get incredibly stressed out over little things without stopping to ask whether they're worth the stress we're affording them.
I'm pointing out that what he does, and what he says he does, are opposites.
Perhaps we miss the point because he's not clear about it and isn't describing it accurately?
However, Buddhist mindfulness really does predict that the only way to be happy is to contemplate, and accept, your most secret and horrific fears. Try, "No matter how hard I work, what I make will eventually fail and be replaced." Or maybe "Everyone and everything I love will die and be utterly forgotten in a few hundred years."
This is, in fact, practicing happiness. It seems absurd, but if you can't be happy and productive while accepting these thoughts, you weren't ever really happy; just in denial.
That one isn't really that bad though. Unless you are obsessed with leaving some kind of significant mark on humanity. For most of us, what is remembered and forgotten in a few hundred years is hardly relevant since we will be dead.
Sure, acceptance can lead to happiness. It can also lead to madness.
For an example of "dark buddhism", see Thomas Ligotti's "The Conspiracy against the Human Race".
http://www.amazon.com/Conspiracy-Against-Human-Race-Contriva...
But this has the potential to lead down the path of mediocrity if applied in a company. Just one more lost customer, just another half an hour of down time, just another customer support call missed. They pile on.
The key is to know your core values as a company and be paranoid about them. If your USP is amazing customer service, you should feel like the world ending if one support call is missed. However you may not worry about occasional downtime of half an hour. The situation would be opposite if you offer an infrastructure service and your outage affects your customers' business.
The paranoia in these cases is not rational but that element of irrationality is your edge.
Life is composed of small incremental steps. It's important to keep an open-mind, learn, grow, and tread forward. As long as you do that it doesn't much matter much if you miss some steps, there will be plenty of opportunities to correct course when you stop to introspect.