Personal Pre-Mortems

If you are like me you can get into a mindset of negative thinking where you can poke holes in any potential project idea or action. After all, thinking of doomsday scenarios is a marketable skill when you actually take action to prevent them, but in our personal lives having this negative view is very bad for us. It makes us hesitate or not get started on an important project with an uncertain future. It makes us not surprised by failure or neutrality. If you expect the worst you will probably get it.

This same method of thinking can be a powerful ally, however, when used as a weapon.

Defensive Weapon

Think of an important project, relationship, or trajectory in your life. Now imagine the worst that can happen. I call this technique “pre-mortems” and it is not the most fun you will have today. Think of the following scenarios:

• You are divorced
• You are bankrupt
• You have a terrible, but preventable, health issue
• You have lost your job, and are suddenly unable to get another one in the same industry, geographic area, or market due to a damaged reputation.
• All of your shoes have been replaced with pink crocs.

Now ask yourself this question: “How did this happen?” and list the reasons.

Well if I’m divorced it was probably because my wife and I stopped communicating, or stopped making sure that we spent time together and just focused too much on the kids, or maybe I got a wondering eye because of some unresolved problem, or because I stopped trying.

Well if I’ve got diabetes or cancer it might be because I order fried chicken from a car more times than I exercise most weeks. I guess that wouldn’t be a surprise.

If I’m bankrupt it is because I have become disabled and don’t have good coverage in that area. Since I’m the primary breadwinner and we have kids, my wife’s salary wouldn’t cover everything so we would have to lose the house.

If I can’t work in my field this is probably because some really bad scandal was slowly slipped into by a group of people encouraging or ignoring the warning signs.

If I only have pink crocs it is probably because I lost a bet of some form and am being forced to wear them as some sort of shame spectacle.

Now go and avoid those things, establish guardrails against those results, make contingency plans for those things:

• I need to make sure I’m focusing and working on my marriage more.
• I need to get better disability insurance.
• I need to exercise, eat real food, and focus on my health.
• I need to continue to avoid any financial or relational gray areas.
• I should not bet on the New York Jets.

Now take a deep breath – none of these has happened; you still have time. During the life of a project you can apply this same mode of thinking – 60% into a software development project I can sit down and say: “OK this project is late – why?” and list three actions I could take to avoid the most common failure scenarios.

Offensive Weapon

For new projects, you can use the same method without depressing yourself. Let’s imagine something that you want to do but you keep putting it off or convincing yourself that you can’t do it. We all hear a voice that tells us “it won’t work out”, “you will fail and people will see”, “you aren’t good enough”, “your pink crocs are so dumb”, etc.

Maybe you want to write a book, try a new career path, take some time off of work to drive across the country, or audition for American Idol. Pick something you really want to do that you have talked yourself out of a few times.

Let’s listen to the inner voice, really listen for a minute. Give the little hater its chance to make a speech.

OK if you start this project and it fails, then you will have wasted $30,000, which means you would need to sell your crappy car and maybe live with your parents for awhile. As a twenty-eight-year-old man. If you are living with your parents it wouldn’t exactly be a secret, so that would be really embarrassing. Everybody that thought that you had it together would realize that you didn’t, so it would actually erode my reputation in a way that would be hard to crawl out of. From there – living in a basement – it would be really hard to recover emotionally. But I guess since you are not that special it would be what you deserve for trying to be.

Now filter out the emotions, insults, and judgments and just think of the real consequences of failure for your project. Split out how they would make you feel for a moment and just think logistically:

• I would lose a lot of money
• I would be spending time on something that didn’t work out, when I could have been doing other things
• I would trade some of my reputation

Now make some plans to guard against these things being as bad – ways that you can hedge or counter these things – and list them.

• I would lose some money, but I won’t touch a one-month emergency fund. If I got to the point that I touched this I would get a job at Starbucks. I look great in green.
• Yes, there is an opportunity cost, but once I get started I would ignore this thought and really commit. Besides, anything else that I worked on would run into the same obstacles – I’ll be smart with the projects I pick to focus in on.
• My reputation might get hurt, but I might also draw attention and respect for trying something bold – and perhaps I care about those people’s opinions more anyway. Besides, learning from failure means you have to actually fail sometimes.
• Living with my parents would stink, but I wouldn’t have to do my own laundry. Plus my mom will not make fun of my pink crocs.

Now answer the inner critic with a detailed version of “So, what are you going to do about it?”:

I might fail and lose money, time, and face, but I would have really tried, and probably learned something. I would then be able to rebuild my life by taking a regular job and working to save like I have done so far in my life. Since I would have been following what I really wanted to do I wouldn’t regret it and wouldn’t feel “behind” in the years when I was re-establishing my financial stability. I would have failed doing what I want to do, rather than half-failing over the long-term doing something I didn’t care about.

Read some more about this technique at Business Insider and watch some other practical benefits to Pessimism.