Plan To Fail Or Don’t Expect To Succeed

Plan To Fail Or Don’t Expect To Succeed

Let me share a little secret with you – You are going to fail. You’ll have multiple failures in diverse areas in life. It’s what you do with them that predicts if you’ll be an overall success.

If you are not planning for failure, you aren’t planning for success. My point may sound like a Yogiism, but let’s dissect it a little bit.

This post is a two-part series. Today we’ll introduce the post and talk about the first two angles. Tomorrow or the next day, I’ll post the follow-up with the final two angles and some quotes that serve as good reminders.  Subscribe to my feed to be notified when that posts.


I left the office yesterday for lunch, and I wish I had followed Jon DiPietro‘s great blogger advice and brought my camera phone. One of the landscapers working across the street had himself stuck on a precarious ledge on his lawnmower. His partner came to the rescue as I was getting ready to head over and offer a push. When the partner got there on his own tractor, he pulled out a rope from his cart of tools. He handed the rope off and pulled him up with ease. Now maybe that was actually the plan all along, and it wasn’t really a potential #fail in action, but at the time, I thought it was and remarked in my head, “they were ready for that.”

I know I’ve blogged a bit about this before in posts talking about using checklists, recipes, and algorithms, embracing empirical evidence, or even harnessing paranoia as a DBA. Still, I want to zero in on failure from four angles here.

Angle #1 – Include Failing In Your Planning

The Titanic
An obvious example – Had they planned for failure on the Titanic, would more have survived?

It doesn’t matter what you are doing. Think about the failure scenarios for that task or project. Talk about them with the team; write them out on a project plan even.  The amount of time, energy, and paper you spend on this should change based on the project’s complexity and scope, but even just a quick rundown in your head of a few “what if” scenarios will really help.

If you include failure in your plans, you have three potential outcomes that I can see. Can anyone see any others?

  • You Wasted Some Time – No good came of it. Those scenarios didn’t happen. You wasted time thinking about and discussing the potential failures. (or did you?)
  • You Averted Failure – Through talking out potential failure points and poking theoretical holes in your approach, you actually realized a mistake and changed the plans.
  • You Knew What To Do When You Failed – Because you had discussed some failure paths ahead of time when presented with one that mirrored or was similar to a discussed fail path, you already knew how to handle it. Even if presented with a very different failure path, you still knew what you would do in the event of a failure.

As I survey those outcomes, the benefit of the second two far outweighs the cost of the first. It wasn’t that much time wasted, and even if we didn’t need the plan, what is to say a future project won’t benefit from that discussion?

Angle #2 – Embrace Your Failures (Plan to learn from failure)

On the same day as the lawnmower “rescue mission,” I listened to a radio show and heard the host talking about a time he tried starting a business -he failed. He received a call from an executive recruiter shortly after the failure. Someone wanted him to be CEO of a business in a very similar space. He was confused and asked the recruiter, “doesn’t the company know I just failed to do this same business?” I am paraphrasing the answer but believe it’s worth bolding, “That is why they want to hire you. They know you have the maturity from the failure and know you have that experience.” He decided not to go with the job for various reasons, but that sounds like a brilliant team looking to hire the position. They saw the wisdom gained through failure.

I’ll always remember when I was thrown into the pit with clustering for the first time. It was a new company; they liked my SQL Server DBA experience and felt I would pick up clustering by working with a consultant and introducing the concept to their very young but quickly growing SQL Server environment. The consultant wasn’t actually a clustering expert, so we muddled through together. I read the best practices, documentation, etc., but I got most of my knowledge about clustering where the rubber meets the road. Those first few months were interesting. I learned many things the hard way (pay closer attention to the dialog boxes, don’t remove a dependent resource before clearing the dependency, etc.) I had brought the production cluster down a couple of times while fumbling. I don’t suggest this approach and wouldn’t normally take it, but the timing left us little choice. I had a couple of red-faced moments, but you know what? I learned a ton. I could have got discouraged and said, forget this, I could have let the failures distract me, but I documented where I messed up and gained knowledge (both of clustering and dealing with failures) that helped me on my journey to where I am today.

I want to repeat the secret from my introduction – You are going to fail. You’ll have multiple failures in diverse areas in life. It’s what you do with them that predicts if you’ll be an overall success. If you embrace the failure, learn from it, and move on, was it really a fail? If you flounder and flop after each failure and get gun shy, then it most definitely was.

What Do You Think?

How do you plan for failure? Do you think I’m too paranoid? Have a story of a time you learned through mistakes/failures? Share your thoughts below in the comments; I am sure others would love to see how not alone they are.

Part Two

Check out the follow-up post; it continues the theme with a couple more angles:

  • Angle #3 – Everybody Fails!
  • Angle #4 – Cleanup, Aisle 4

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25 thoughts on “Plan To Fail Or Don’t Expect To Succeed”

  1. >>Do you think I’m being too paranoid?

    Of course not. Measure of true success is by your failures and creating successful futures from them.

    Very good write-up and can’t wait to read the next in the series Mike.

  2. Good post, Mike 🙂 I’ve gotten over failures in the past just because seriously, I really didn’t have that much of a choice. I don’t want to take too much credit for getting over them just because I know that during those times of failure, it wasn’t really like there was any other way to go but up. Life didn’t stop just because I was wallowing in self-deprecation. Oh sure, it felt ironically good to indulge …but mostly, I just got to the point when I just had to say “enough!”, go learn, and move on.

    Looking back, did those events make me better? YES. But does something in me wish that I could have learned things the easy way? YES. The feeling of failure sucks. I can say they’re character-building all I want–but failures are just plain horrible.

    Do I know by now that I’ll learn from failing? Yes. Do I recover from failure quicker now? Yes. Bottomline though, despite the fact that I’ve learned more from my failures than my successes–embracing them will remain a tough thing to do. Failures just feel and look better when they’re over.

    So yes, I totally get paranoia. I totally get planning ahead up to plan Z. I think I get it way too much 😉 I think though that I’d take more pride in myself if the time comes when I can actually say “Bring it on!” both when I plan ahead and when I don’t.

    • Good points 🙂 I don’t mean to suggest we embrace failure over success but, as you point out, it is going to happen – we might as well get used to it and pick the good pieces out of it.

  3. I was listening to the 37signals podcast the other day and they cited research that people who start a business and fail are just as likely to succeed in their next endeavor as people who have never started a business. On the other hand, people who start a business and succeed are much more likely to succeed in their next endeavor. Seems like we don’t learn that well from failure 🙂

    • Interesting perspective there. I’d like to hear more about that research but I have to say I am equally surprised and not surprised, if that is possible. I could see some people who embrace learning opportunities from failures would actually do far better on a second attempt. I can also some people who suffer from the same chronic failure patterns repeating their failures. I would also agree that success is a great teacher also.

      Even with that point perhaps dulled a bit, I still feel that planning to fail can help prevent failures on tasks and projects.

      Thanks for the comment, Jeremiah!

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    • Michael – No apologies necessary! That was a great post where you touch on similar topics. I am sorry I missed it when it first came out but happy to read it now 🙂 You are definitely right, though when you said “In many situations it’s valuable to have the freedom to fail. Especially when the goal is learning.” Great point. I urge anyone reading these comments to go check out his post 🙂

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