Expect the worst and hope…you planned enough!

Just about anyone who has met me, worked with me, or is a friend of mine would likely describe me as “negative” or “always pointing out the worst”. To be honest, I won’t deny such claims. I do focus quite a bit on those things that can go wrong and less on the things I hope go right. It’s also accurate to say that I am not quiet about voicing my concerns.

Am I just a pessimist who can’t be happy with any given situation? Do I have this need to shit on other people’s ideas or potential opportunities?

In short, the answer is a resounding “NO” to both those questions. So what’s up with the bad attitude?

I learned a long time ago, before the startup world, before contracting, before the Army, before I moved out of my parent’s house to expect the worst possible outcome and plan to counter any hurdles that can be identified at the start of an idea, change, or action.

The classic saying goes something like this: Hope for the best but expect the worst. Here’s the thing, if you are hoping for the best then you are likely not putting as much effort or thought into the worst. This sets you up for failure before you even start. In the end, you could probably look back and identify multiple issues that arose which could have been headed off from the beginning with better planning.

Tunnel Rat - WEAPONS COMP - oi (4)
Clearing a drainage tunnel with a 9 MM pistol and flashlight – do you think I had a sunny disposition going in?

In the Army, my thought process was reinforced with life and death situations. When you are a leader taking X number of soldiers on a patrol, ambush, or overwatch, you don’t approach the task with a sunny disposition. The default position is along the lines of: “We are going here to do these things and this, that, and everything else is likely to go wrong…this is how we mitigate risk and reduce the threat preemptively”. Sounds pretty grim, right? Well, it is! Real world combat operations aren’t the party Hollywood makes them out to be.

With a few modifications, this mindset is easily translated to the business world. “If we don’t get Update X out by this date then a high probability of losing 50% of our customer base and having to lay off 75% of the workforce exists.” What do you do? Quit? Hang up your hat, have a fancy cold brew, and let it be? HELL NO! You work with the team to make sure the engineers have what they need to produce Update X; you get the team to volunteer additional time in an effort to extend the deadline; you prep your customer base by setting proper expectations; you get to work.

A lot of people accept the concept of quitting. Life was unfair, I quit. My boss was a dick, I quit. The client wasn’t nice, I quit. It’s too hard, I quit. Here’s the problem, you can’t quit life! Life doesn’t care that you are at rock bottom; life isn’t going to stop while you wipe your tears off your face; life isn’t going to apologize for hurting your delicate sensibilities. Life is going to continue kicking your ass until you realize it’s up to you to change it!

Expecting the worst will help set you up for success. Think about it this way: I’m ready for everything up to and including the worst situation possible, anything short of that is easy.

One last thing, try to tackle the worst possibilities with a smile – it always seems to help the people you’ll end up working with throughout your life.

 

How do you handle planning? Do you start with the best possible situation and work your way to the worst? How do you achieve the end goal? Leave your thoughts in the comments below. Don’t forget to like and share on your favorite social media platform. Thanks for reading!

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