Prepare For The Worst Possible Outcome

Learned Living
5 min readMay 11, 2023

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In the book, How To Live: 27 Conflicting Answers and One Weird Conclusion, Derek Sivers maps out several ways to live a good life. These include everything from being independent, to doing nothing, and even pursuing pain. Another way to live a good life is by preparing for the worst.

Of course, this isn’t a wholly unique thought. We can go back thousands of years and read Stoic text that speaks about preparing for the worst possible outcome, so in case that outcome happens, it doesn’t knock us off our feet too badly.

In the same vein, Sivers draws our attention to the fact that our current moment might be as best as it’ll ever get for us, bringing our attention toward gratitude, acceptance, and deliberate action.

So far, you’ve lived in a time of prosperity. You haven’t experienced massive devastation, but you probably will. It’ll be harder to make money. It’ll be harder to be happy. Much of what you love now will be gone. You’ll look back at this year as one of the easiest you ever had.

Sivers adds that with time, we are likely to get sick or injured and lose our ability to see, hear, move, or think.

Some may see this type of thinking and conclude that the person is too negative or pessimistic. That by dwelling on such things, we’re ruining our present state. However, the opposite is true. When we think about the worst possible outcome, we can be grateful for the things we have. For example, how much gratitude would you express toward a loved one if you knew it was the last time you’ll ever see them?

The art of gratitude can be difficult to practice when we are navigating through life. Life is often busy and chaotic and in order to show gratitude, it requires us to take a break, pause for a moment, reflect and be grateful. That’s why the simple fact that we are alive and participating in life can be overlooked by so many people. When in fact, that is something to be grateful for.

As Sivers points out, with time our body will let us down, but in this moment, where we have our senses and ability to move freely, and more importantly, our ability to strengthen our bodies, we should be grateful for it.

There is a possibility that our dreams won’t come true. That we will fail to reach our goals. Reflecting on this possibility brings about gratitude for the time you have had to dedicate to your goals and dreams. Not everyone gets the time to do so. Plus, we can have a Plan B ready, if Plan A doesn’t work.

There is also gratitude in the struggle so far. The challenges and obstacles you have overcome in pursuit of your goals and dreams.

To appreciate something fully, picture losing it. Imagine losing your freedom, reputation, money, and home. Imagine losing your ability to see, hear, walk, or talk. Imagine the people you love dying tomorrow. Never take them for granted.

By reflecting on the worst-case scenario, we also develop a sense of acceptance along with gratitude.

Life right now could be as good as it gets. Part of our health is under our control and we need to do everything in our power to stay healthy. Part of our health isn’t under our control. Bad genetics and accidents are part of life. We accept that.

When it comes to pursuing our goals, we can control our effort, consistency, and iterations, but the result will still be out of our control. We accept that.

With time, we have partial control over how we spend our time and on what. But we don’t know how much time we really have. We accept that.

Do you know what’s behind each mountain of a challenge?

More mountains.

We also have to accept the challenges of life. Behind one obstacle, there lies another.

As we meditate on the worst-case scenario, another thing becomes abundantly clear.

This is how we want to act.

If you think about how you’ve been spending your recent days or sit down and write how you’ve spent the past month of your life or past six months of your life and hold that up against the realistic possibility of the worst-case scenarios, it can but a lot of things in perspective.

Wasting time, wasting moments, wasting days, wasting relationships, and so on have become the norm. The reason is that we assume we will have more time, or another moment, or another day. But that’s not true. So, in the present moment, we need to act deliberately.

We should act in a manner that shows love and appreciation for those who are close to us.

We should act in a manner to appreciate the little joys in life like grabbing coffee with a friend, reading our favourite book, listening to our favourite artist, and eating at our favourite restaurants.

You never know when it’ll be the last time you’ll feel these little joys.

We should also be strict with ourselves. To be disciplined with our time, diet, exercise, and work, but be lenient and flexible with others, as we don’t know what they are going through in their lives and perhaps it will be the last time you’ll interact with that person.

Sivers would also say that we should act in a manner that pursues deeper forms of fulfilment, rather than shallow ones.

Shallow happy is having a donut.

Deep happy is having a fit body.

Shallow happy is what you want now.

Deep happy is what you want most.

Shallow happy serves the present.

Deep happy serves the future.

Shallow happy is trying to conquer the world.

Deep happy is conquering yourself.

Shallow happy is pursuing pleasure.

Deep happy is pursuing fulfillment.

Fulfillment is more fun than fun.

And finally, we should act with gratitude and acceptance.

Grateful for our life. Acceptance of our fate.

Amor fati.

Originally published at http://learnedliving.org on May 11, 2023.

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