Permission To Fail

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In this post I’d like to talk about something I’ve struggled with for most of my life and how that affects my work as a software engineer. That is that it’s hard to give myself permission to fail. Said another way:

I’ve never felt that it was ok to fail. I’m afraid to take on new things or say I’m knowledgeable at something for fear of failing.

This happens even though I know in my head that learning from mistakes is critical to our lives and where we make a lot of important progress in learning. Even though I know that the fear isn’t helpful, it is paralyzing when it strikes. I’ve learned some ways over the years to help moderate the fear and paralysis, allow myself to continue forward, and allow myself to learn from a mistake with minimal self deprecation. Though what I’ve learned to do doesn’t always help for me, my hope is that they’ll help somebody on occasion. And if you’ve got ways or resources to help with this, please feel free to leave a comment or contact me (I’ll put contact info at the bottom)

Note: See the section on how I work through this problem for an update.

Why? Where Did This Come From?

Yoda - "No! Try not! Do or Do Not, There is no Try"

I heard this from my father many times during my childhood. I’m sure that he meant to leave me with a willingness to go ahead and try something I’ve been told or shown how to do without delay. It left me, instead, with a fear of messing up what I’m doing and a need to get it right on the first try (regardless of how unreasonable that might be). To me, “do” meant “get it right” and “do not” meant failing either by giving up or not getting it correct. It did not feel like there was permission to fail in a way that I could learn from. What I yearned for was a knowledge that he would show me how to correct an error in the task we were working on if I made a mistake. Note that my dad was a good father and did help me learn how to correct mistakes through the years. This is not meant to disparage my father’s memory in any regard but simply to partly explain where this feeling came from.

How Does This Affect My Work?

The most recent place that this affected my work is my project to make sure I’m learning Ruby on Rails correctly. Because I don’t consider myself knowledgeable yet, I found myself staring at a piece of the automatically generated code knowing that’s where a change has to go, knowing roughly what the change is, and, yet, being afraid to make the change because it would mess up the generated structure of the code. Knowing that Ruby on Rails highly favors convention over configuration and, given that I’m not totally confident in my knowledge of the conventions yet, I look at the code and get paralyzed by fear that I’m going to pick the “wrong way” to implement the change even if it works. In reality, the opinion of those who might take issue with the way I implement the change only matters to the point that they’re no longer willing to teach respectfully and I’ve learned everything I can from them. I know that I’ll end up figuring out how to implement the fix, so keep an eye on the project and, if you have constructive criticism, I’d love to hear from you!

Another way the fear has affected my career is that it has made me afraid to take on big projects or become popular as a contractor/consultant for fear of being offered a big project and failing to deliver. The thought of letting people down or being seen as unreliable sparks the fear of failure in my heart. Because of this, I end up continuing to do little projects that I “know” I can do because I’ve done something almost exactly like them before. Note that specialization and being known to be good at something particular will attract clients and that’s good but this fear still exists because every task varies in its details. One of the only reasons that I’ve been able to start my business is by putting energy into following my plan of attack for overcoming that fear. While I find that some days I have the energy to do so and some days I don’t, I am glad for the growth this is causing in me and the friends I have and will make in the process.

This has also caused fear of estimating how long it will take to do a task. Estimating is a famously hard problem. I usually end up being too optimistic in my estimate because I don’t want to disappoint the person to whom I’m giving an estimate or non-committal because I’ve no idea what a good number for the time to completion looks like. To solve this particular problem, I try to set up a research task to size the project and give the user a better answer after the research is done.

How Do I Work Through This?

The steps I use to work through my panic or unwillingness to make a mistake typically follow this pattern:

  1. Take a break, take a breath, and continue on or distract myself with something else if I need to let the panic in my heart subside.
  2. Come back and recreate the problem
  3. Look at the problem again to see if a solution presents itself given my current knowledge
  4. If a solution doesn’t present itself, find a few examples of how other projects solve the type of problem I’m looking to solve
  5. Double check the appropriate convention regarding how to do what I’d like to do (if I have the time or patience)
  6. Check the expectations of both work to be done and timeline to see if I’m being to hard on myself.

Update: In recent years I have been seeing a therapist and this is one of the issues that we have been working through in our time together. Since I wrote this post, I have also seen a psychotherapist who I’ve worked with to settle on a regimen of medicine that has helped my mental state greatly and that has had a great impact on this specific issue. They have given me the mental and emotional space to follow the above steps.

I do not think that medicine is the right solution for everybody nor do I plan to have to take medicine forever. I do, however, want to encourage you to seek out the help of a therapist and/or psychotherapist if you’re struggling. They are great resources and are a great place to talk through hard feelings.


I’ve spent many years being afraid of making a mistake and looking bad to those whose opinions I care about. This is still a daily issue for me but, through experience and help from others, I’ve started the process of learning to deal with the fear, to choose those whose opinions I care about wisely, and to make sure I’m not assuming what others are feeling about me. I sincerely hope that by being open and honest here I can show you that, if you experience this type of fear, you’re not alone in feeling this and, if you don’t feel this, to inspire you to be patient with others. In the end, I’m learning to give myself permission to fail and learn and am hoping that this will lead me to greater successes than I could have imagined.

Contact Info

Email: [email protected]
Twitter: @TRPriceSoftware

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