Ensure your happiness with a "pre-mortem"

One of the best ways to improve a system is to carefully and objectively analyze its failures. You’re probably familiar with getting a group of engineers together for a “post-mortem” conversation after something went terribly sideways.

A post-mortem, when done correctly, is almost magical in its effectiveness, which is why they have become so common. But when it comes to figuring out what you really want, and what will give you lasting happiness in work and life, well… Waiting until it’s over is too late!

But, interestingly enough, we can use one of the same tools we bring to bear in a post-mortem to create a clearer picture of what our values are and how we want to show up in the world.

Let’s call it a “pre-mortem.”

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I decided to use the term “pre-mortem” deliberately because it reminds us of its purpose: to help you find meaning in your life before it is over.

If you’ve done a few post-mortems before, you’ve probably encountered the “five whys.” If you haven’t, you can watch this video by Dan Milstein at The Lean Startup Conference back in 2012, which is to this day one of my favorite examinations of how to run a “five whys.”

To level set I’ll just quickly describe it: a “five whys” is literally asking why a failure occurred five times. That’s the simplest way to put it, and it works because the first couple of answers are never the root cause. Never, ever. Each time, you ask why the previous answer occurred, and after five, you usually get to the bottom of the stack.

Sometimes three “whys” is enough, but five seems to be the number that most often delivers the best results, so it stuck.

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“Five whys” works because systems are interconnected, sometimes in non-obvious ways. Looking closer at what could have set off each observable event in a production incident gets you closer to the root cause.

Similarly, what we care about and how we express it (even to ourselves) is tangled up in a universe of perception, experience, bias, and even misunderstanding.

By asking more times, you peel those layers back until you get to the essence.

My “five whys”

The way you do this is straightforward (though not necessarily simple): ask yourself “What do I really want?” Answer that question.

Then, ask “why” five times, for each successive response.

Of course there is no hard rule that says you have to do it five times, or that you can’t do it seven times. I did exactly five, then I set it aside and came back to it the next day and considered each response again.

Here’s what I was left with after that process:

What do I really want?

I want to build a self-sustaining coaching practice.

  1. Why? Because I want to set my own hours.

  2. Why? Because I never liked long, busy days; because I only get “lost” in things that are really interesting.

  3. Why? Because I like taking my time on things, I like goofing off.

  4. Why? Because I’m perpetually interested in stuff, and I have many interests, and I like to explore and create things.

  5. Why? Because I am anti-obsessive; I am in my happy place when I can learn many different things and solve different kinds of problems.


Did you spot the crucial turning point in there?

When I went to “I like goofing off,” that was a lazy answer, and it isn’t even true! At that moment, I felt that what I was rebelling against was “too much directed time being forced to do specific tasks.”

But when I’ve taken time off in between jobs for instance, I’ve always had projects going, and I spend a lot of my unstructured time on many different things.

If I’d stopped there, I might have convinced myself that my purpose in life is to do as little as possible, and that’s simply false.

What lights me up is following my curiosity.

Some of this clarity came when I returned to the list the following day and read through it again. I’d suggest giving yourself the space to really examine what feels right for each answer, what feels true for you.

How do you apply this?

Self-awareness is intrinsically valuable because all of your knowledge contributes to your perception. The more you know about yourself, the more true to yourself you will automatically become when you are faced with decisions.

You can make this information more valuable, however, by converting it from static knowledge into an explicit intention.

You can do that by asking yourself some questions. It is tradition around here to end these posts with questions, so I will close with intention questions you can play with.

Let me know how this works out for you!

Questions for you

  1. What do you really want?

  2. How will you show up powerfully in your job and relationships that is in alignment with your purpose?

  3. What must you set aside to make room for what you really want?

Lead image by Midjourney AI